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Fexofenadine

PubChem CID
3348
Structure
Fexofenadine_small.png
Fexofenadine_3D_Structure.png
Molecular Formula
Synonyms
  • fexofenadine
  • 83799-24-0
  • Carboxyterfenadine
  • Terfenadine carboxylate
  • Terfenadine-COOH
Molecular Weight
501.7 g/mol
Computed by PubChem 2.2 (PubChem release 2024.11.20)
Dates
  • Create:
    2005-03-25
  • Modify:
    2025-01-18
Description
Fexofenadine is a piperidine-based anti-histamine compound. It has a role as a H1-receptor antagonist and an anti-allergic agent. It is a member of piperidines and a tertiary amine. It is functionally related to an isobutyric acid.
Fexofenadine is an over-the-counter second-generation antihistamine used in the treatment of various allergic symptoms. It is selective for the H1 receptor, carries little-to-no activity at off-targets, and does not cross the blood-brain barrier - this is in contrast to previous first-generation antihistamines, such as [diphenhydramine], which readily bind to off-targets that contribute to side effects such as sedation. Fexofenadine is the major active metabolite of [terfenadine] and is administered as a racemic mixture in which both enantiomers display approximately equivalent antihistamine activity.
Fexofenadine is a Histamine-1 Receptor Antagonist. The mechanism of action of fexofenadine is as a Histamine H1 Receptor Antagonist.

1 Structures

1.1 2D Structure

Chemical Structure Depiction
Fexofenadine.png

1.2 3D Conformer

2 Names and Identifiers

2.1 Computed Descriptors

2.1.1 IUPAC Name

2-[4-[1-hydroxy-4-[4-[hydroxy(diphenyl)methyl]piperidin-1-yl]butyl]phenyl]-2-methylpropanoic acid
Computed by Lexichem TK 2.7.0 (PubChem release 2024.11.20)

2.1.2 InChI

InChI=1S/C32H39NO4/c1-31(2,30(35)36)25-17-15-24(16-18-25)29(34)14-9-21-33-22-19-28(20-23-33)32(37,26-10-5-3-6-11-26)27-12-7-4-8-13-27/h3-8,10-13,15-18,28-29,34,37H,9,14,19-23H2,1-2H3,(H,35,36)
Computed by InChI 1.07.0 (PubChem release 2024.11.20)

2.1.3 InChIKey

RWTNPBWLLIMQHL-UHFFFAOYSA-N
Computed by InChI 1.07.0 (PubChem release 2024.11.20)

2.1.4 SMILES

CC(C)(C1=CC=C(C=C1)C(CCCN2CCC(CC2)C(C3=CC=CC=C3)(C4=CC=CC=C4)O)O)C(=O)O
Computed by OEChem 2.3.0 (PubChem release 2024.12.12)

2.2 Molecular Formula

C32H39NO4
Computed by PubChem 2.2 (PubChem release 2024.11.20)

2.3 Other Identifiers

2.3.1 CAS

2.3.2 Deprecated CAS

159389-12-5, 76815-58-2

2.3.3 European Community (EC) Number

2.3.4 UNII

2.3.5 ChEBI ID

2.3.6 ChEMBL ID

2.3.7 DrugBank ID

2.3.8 DSSTox Substance ID

2.3.9 HMDB ID

2.3.10 KEGG ID

2.3.11 Metabolomics Workbench ID

2.3.12 NCI Thesaurus Code

2.3.13 Nikkaji Number

2.3.14 PharmGKB ID

2.3.15 Pharos Ligand ID

2.3.16 RXCUI

2.3.17 Wikidata

2.3.18 Wikipedia

2.4 Synonyms

2.4.1 MeSH Entry Terms

  • alpha-(4-(1-carboxy-1-methylethyl)phenyl)-4-hydroxydiphenylmethyl-1-piperidinebutanol
  • fexofenadine
  • fexofenadine hydrochloride
  • MDL 16,455A
  • MDL 16.455
  • MDL 16455
  • MDL-16455

2.4.2 Depositor-Supplied Synonyms

3 Chemical and Physical Properties

3.1 Computed Properties

Property Name
Molecular Weight
Property Value
501.7 g/mol
Reference
Computed by PubChem 2.2 (PubChem release 2024.11.20)
Property Name
XLogP3-AA
Property Value
3
Reference
Computed by XLogP3 3.0 (PubChem release 2024.11.20)
Property Name
Hydrogen Bond Donor Count
Property Value
3
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2024.11.20)
Property Name
Hydrogen Bond Acceptor Count
Property Value
5
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2024.11.20)
Property Name
Rotatable Bond Count
Property Value
10
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2024.11.20)
Property Name
Exact Mass
Property Value
501.28790873 Da
Reference
Computed by PubChem 2.2 (PubChem release 2024.11.20)
Property Name
Monoisotopic Mass
Property Value
501.28790873 Da
Reference
Computed by PubChem 2.2 (PubChem release 2024.11.20)
Property Name
Topological Polar Surface Area
Property Value
81 Ų
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2024.11.20)
Property Name
Heavy Atom Count
Property Value
37
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
678
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2024.11.20)
Property Name
Isotope Atom Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Atom Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Undefined Atom Stereocenter Count
Property Value
1
Reference
Computed by PubChem
Property Name
Defined Bond Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Undefined Bond Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Covalently-Bonded Unit Count
Property Value
1
Reference
Computed by PubChem
Property Name
Compound Is Canonicalized
Property Value
Yes
Reference
Computed by PubChem (release 2021.10.14)

3.2 Experimental Properties

3.2.1 Physical Description

Solid

3.2.2 Color / Form

Crystals from methanol-butanone
O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. 13th Edition, Whitehouse Station, NJ: Merck and Co., Inc., 2001., p. 718

3.2.3 Melting Point

142.5 °C
PhysProp
195-197 °C
O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. 13th Edition, Whitehouse Station, NJ: Merck and Co., Inc., 2001., p. 718
142.5 °C

3.2.4 Solubility

Slightly soluble
Canadian Label

3.2.5 Stability / Shelf Life

Commercially available fexofenadine hydrochloride capsules have an expiration date of 18 or 24 months after the date of manufacture when packaged in the manufacturer's unopened blister packages or high-density polyethylene bottles, respectively. Commercially available fexofenadine hydrochloride 30-mg conventional tablets have an expiration date of 18 months after the date of manufacture when packaged either in the manufacturer's unopened blister packages or high-density polyethylene bottles, whereas the commercially available fexofenadine hydrochloride 60-mg conventional tablets have an expiration date of 30 months after the date of manufacture when packaged either in the manufacturer's unopened blister packages or high-density polyethylene bottles. In addition, fexofenadine hydrochloride 180-mg conventional tablets have an expiration date of 18 or 30 months after the date of manufacture when packaged either in the manufacturer's unopened blister packages or high-density polyethylene bottles, respectively.
McEvoy, G.K. (ed.). American Hospital Formulary Service. AHFS Drug Information. American Society of Health-System Pharmacists, Bethesda, MD. 2006., p. 37

3.2.6 Collision Cross Section

226.9 Ų [M+H]+ [CCS Type: TW; Method: Major Mix IMS/Tof Calibration Kit (Waters)]

225.55 Ų [M+K]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

217.69 Ų [M+Na]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

222.76 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

Ross et al. JASMS 2022; 33; 1061-1072. DOI:10.1021/jasms.2c00111

3.2.7 Other Experimental Properties

Molecular weight is 538.13. Fexofenadine hydrochloride is a white to off-white crystalline powder. It is freely soluble in methanol and ethanol, slightly soluble in chloroform and water, and insoluble in hexane. Fexofenadine hydrochloride is a racemate and exists as a zwitterion in aqueous media at physiological pH /Hydrochloride/
Physicians Desk Reference 60th ed, Thomson PDR, Montvale, NJ 2006., p. 2857

3.3 Chemical Classes

Pharmaceutical

3.3.1 Drugs

Pharmaceuticals
S10 | SWISSPHARMA | Pharmaceutical List with Consumption Data | DOI:10.5281/zenodo.2623484
Pharmaceuticals -> unsed in Switzerland 2014-2016
S113 | SWISSPHARMA24 | 2024 Swiss Pharmaceutical List with Metabolites | DOI:10.5281/zenodo.10501043
3.3.1.1 Human Drugs
Breast Feeding; Lactation; Antihistamines; Nonsedating Antihistamines
Human drug -> Discontinued
Pharmaceuticals
S72 | NTUPHTW | Pharmaceutically Active Substances from National Taiwan University | DOI:10.5281/zenodo.3955664
Antiallergics and medicines used in anaphylaxis

4 Spectral Information

4.1 1D NMR Spectra

4.1.1 13C NMR Spectra

1 of 2
Copyright
Copyright © 2016-2024 W. Robien, Inst. of Org. Chem., Univ. of Vienna. All Rights Reserved.
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2 of 2
Copyright
Copyright © 2016-2024 W. Robien, Inst. of Org. Chem., Univ. of Vienna. All Rights Reserved.
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4.2 Mass Spectrometry

4.2.1 GC-MS

1 of 3
View All
NIST Number
335271
Library
Main library
Total Peaks
32
m/z Top Peak
280
m/z 2nd Highest
105
m/z 3rd Highest
131
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2 of 3
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Source of Spectrum
Mass Spectrometry Committee of the Toxicology Section of the American Academy of Forensic Sciences
Copyright
Copyright © 2012-2024 John Wiley & Sons, Inc. Portions provided by AAFS, Toxicology Section. All Rights Reserved.
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4.2.2 MS-MS

1 of 8
View All
Spectra ID
Ionization Mode
Negative
Top 5 Peaks

258.15 100

378.2438 75.26

188.1081 10.85

230.1549 5.62

145.0659 3.82

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2 of 8
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Spectra ID
Ionization Mode
Negative
Top 5 Peaks

258.15 100

188.1081 30.81

145.0659 15.20

110.0612 12.99

112.0768 11.87

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4.2.3 LC-MS

1 of 16
View All
Authors
Kevin S. Jewell; Björn Ehlig; Arne Wick
Instrument
TripleTOF 5600 SCIEX
Instrument Type
LC-ESI-QTOF
MS Level
MS2
Ionization Mode
POSITIVE
Ionization
ESI
Collision Energy
35
Fragmentation Mode
CID
Column Name
Zorbax Eclipse Plus C18 2.1 mm x 150 mm, 3.5 um, Agilent
Retention Time
8.7 min
Precursor m/z
502.2952
Precursor Adduct
[M+H]+
Top 5 Peaks

466.2577 999

484.275 500

502.2952 252

171.1161 128

467.2727 96

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License
dl-de/by-2-0
2 of 16
View All
Authors
Beck B, Stravs M, Schymanski E, Singer H, Department of Environmental Chemistry, Eawag
Instrument
Q Exactive Orbitrap Thermo Scientific
Instrument Type
LC-ESI-QFT
MS Level
MS2
Ionization Mode
POSITIVE
Ionization
ESI
Collision Energy
15 (nominal)
Fragmentation Mode
HCD
Column Name
XBridge C18 3.5um, 2.1x50mm, Waters
Retention Time
8.2 min
Precursor m/z
502.2952
Precursor Adduct
[M+H]+
Top 5 Peaks

502.2953 999

484.2849 39

466.2733 12

171.1167 1

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License
CC BY

6 Chemical Vendors

7 Drug and Medication Information

7.1 Drug Indication

In the United States, fexofenadine is indicated for the symptomatic treatment of allergic rhinitis in patients ≥2 years old and chronic idiopathic urticaria in patients ≥6 months old. In Canada, fexofenadine carries the same indications but is approved only for patients ≥12 years old. Fexofenadine is also available in combination with [pseudoephedrine] for the symptomatic treatment of season allergic rhinitis in patients ≥12 years old.

7.2 LiverTox Summary

Fexofenadine is a second generation antihistamine that is used for the treatment of allergic rhinitis, angioedema and chronic urticaria. Fexofenadine has not been linked to serum enzyme elevations during therapy or to instances of clinically apparent acute liver injury.

7.3 Drug Classes

Breast Feeding; Lactation; Antihistamines; Nonsedating Antihistamines
Antihistamines

7.4 WHO Essential Medicines

Drug
Drug Classes
Antiallergics and medicines used in anaphylaxis
Formulation
Indication
Allergic or hypersensitivity conditions of unspecified type

7.5 Drug Labels

Drug and label

7.6 Clinical Trials

7.6.1 ClinicalTrials.gov

7.6.2 EU Clinical Trials Register

7.6.3 NIPH Clinical Trials Search of Japan

7.7 Therapeutic Uses

Histamine H1 antagonists
National Library of Medicine's Medical Subject Headings online file (MeSH, 2006)
Antihistaminic
O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. 13th Edition, Whitehouse Station, NJ: Merck and Co., Inc., 2001., p. 718
Fexofenadine is indicated to relieve symptoms that are associated with seasonal allergic rhinitis, such as sneezing;rhinorrhea; itchy eyes, nose and throt; and red watery eyes. /Included in US product label/
Thomson/Micromedex. Drug Information for the Health Care Professional. Volume 1, Greenwood Village, CO. 2006., p. 1470
Fexofenadine is indicated for the treatment of uncomplicated skin manifestations of chronic idiopathic urticaria. It significantly reduces pruritus and the number of wheals. /Included in US product label/
Thomson/Micromedex. Drug Information for the Health Care Professional. Volume 1, Greenwood Village, CO. 2006., p. 1470

7.8 Drug Warnings

In controlled clinical studies in patients 12 years of age and older with allergic rhinitis receiving oral fexofenadine hydrochloride dosages of 60 mg twice daily or placebo, drowsiness or fatigue occurred in 1.3% of patients, compared with 0.9% of those receiving placebo. In these studies in patients receiving fexofenadine hydrochloride dosages of 180 mg once daily (as conventional tablets) or placebo, headache was reported in 10.6 or 7.5% of patients, respectively. In controlled studies in children 6-11 years of age with seasonal allergic rhinitis receiving fexofenadine hydrochloride dosages of 30 mg twice daily or placebo, headache was reported in 7.2 or 6.6% of patients, respectively, while pain was reported in 2.4 or 0.4% of patients, respectively.
McEvoy, G.K. (ed.). American Hospital Formulary Service. AHFS Drug Information. American Society of Health-System Pharmacists, Bethesda, MD. 2006., p. 33
Sleep disorder, insomnia, or paroniria has occurred in patients receiving fexofenadine hydrochloride.
McEvoy, G.K. (ed.). American Hospital Formulary Service. AHFS Drug Information. American Society of Health-System Pharmacists, Bethesda, MD. 2006., p. 33
During controlled clinical studies, nausea and dyspepsia were reported in 1.6 and 1.3%, respectively, of patients receiving oral fexofenadine hydrochloride dosages of 60 mg twice daily versus 1.5 and 0.6%, respectively, of those receiving placebo.
McEvoy, G.K. (ed.). American Hospital Formulary Service. AHFS Drug Information. American Society of Health-System Pharmacists, Bethesda, MD. 2006., p. 33
Clinical data from over 2000 patients indicate that fexofenadine hydrochloride lacks the cardiotoxic potential of its parent drug terfenadine. In 714 patients with seasonal allergic rhinitis, fexofenadine hydrochloride dosages of 60-240 mg twice daily were not associated with statistically significant mean increases in the QT interval corrected for rate (QTc) in controlled clinical studies. In addition, in 231 healthy individuals, fexofenadine hydrochloride dosages of 240 mg given once daily for 1 year also were not associated with statistically significant increases in the mean QTc. Even at dosages exceeding these (e.g., up to 400 mg twice daily for 6 days in 40 patients, up to 690 mg twice daily for about 1 month in 32 patients, up to 800 mg given in a single dose in 87 patients), statistically significant mean increases in the QTc or other ECG abnormalities have not been reported in healthy adults or patients with seasonal allergic rhinitis.
McEvoy, G.K. (ed.). American Hospital Formulary Service. AHFS Drug Information. American Society of Health-System Pharmacists, Bethesda, MD. 2006., p. 33
For more Drug Warnings (Complete) data for FEXOFENADINE (15 total), please visit the HSDB record page.

7.9 Drug Tolerance

There was no evidence of tolerance to these effects (tachyphylaxis) after 28 days of therapy /with fexofenadine/...
McEvoy, G.K. (ed.). American Hospital Formulary Service. AHFS Drug Information. American Society of Health-System Pharmacists, Bethesda, MD. 2006., p. 36

8 Pharmacology and Biochemistry

8.1 Pharmacodynamics

Fexofenadine relieves allergy symptoms by antagonizing the actions of histamine, an endogenous compound predominantly responsible for allergic symptomatology. The relatively long duration of action of fexofenadine (approximately 24 hours) allows for once or twice daily dosing, and its rapid absorption allows for an onset of action within 1-3 hours. Fexofenadine should not be taken with fruit juice, as this may impair its absorption.

8.2 MeSH Pharmacological Classification

Anti-Allergic Agents
Agents that are used to treat allergic reactions. Most of these drugs act by preventing the release of inflammatory mediators or inhibiting the actions of released mediators on their target cells. (From AMA Drug Evaluations Annual, 1994, p475) (See all compounds classified as Anti-Allergic Agents.)
Histamine H1 Antagonists, Non-Sedating
A class of non-sedating drugs that bind to but do not activate histamine receptors (DRUG INVERSE AGONISM), thereby blocking the actions of histamine or histamine agonists. These antihistamines represent a heterogenous group of compounds with differing chemical structures, adverse effects, distribution, and metabolism. Compared to the early (first generation) antihistamines, these non-sedating antihistamines have greater receptor specificity, lower penetration of BLOOD-BRAIN BARRIER, and are less likely to cause drowsiness or psychomotor impairment. (See all compounds classified as Histamine H1 Antagonists, Non-Sedating.)

8.3 FDA Pharmacological Classification

FDA UNII
E6582LOH6V
Active Moiety
FEXOFENADINE
Pharmacological Classes
Mechanisms of Action [MoA] - Histamine H1 Receptor Antagonists
Pharmacological Classes
Established Pharmacologic Class [EPC] - Histamine-1 Receptor Antagonist
FDA Pharmacology Summary
Fexofenadine is a Histamine-1 Receptor Antagonist. The mechanism of action of fexofenadine is as a Histamine H1 Receptor Antagonist.

8.4 ATC Code

R - Respiratory system

R06 - Antihistamines for systemic use

R06A - Antihistamines for systemic use

R06AX - Other antihistamines for systemic use

R06AX26 - Fexofenadine

8.5 Absorption, Distribution and Excretion

Absorption
Fexofenadine is rapidly absorbed following oral administration and its absolute bioavailability is approximately 33%. The Tmax following oral administration is approximately 1-3 hours. The steady-state AUCss(0-12h) and Cmax following twice daily dosing of 60mg are 1367 ng/mL.h and 299 ng/mL, respectively. Fexofenadine AUC is decreased by >20% when coadministered with fruit juices (e.g. apple, orange, grapefruit) due to their inhibition of OATP transporters - for this reason, prescribing information recommends administering fexofenadine only with water. Similarly, coadministration of fexofenadine with a high-fat meal appears to decrease AUC and Cmax by >20%.
Route of Elimination
Approximately 80% of an ingested dose is eliminated in the feces, likely largely unchanged due to fexofenadine's limited metabolism, and 11% is eliminated in the urine. The principal pathways of fexofenadine elimination are biliary and renal.
Volume of Distribution
The volume of distribution is approximately 5.4-5.8 L/kg.
Clearance
The oral clearance of fexofenadine is approximately 50.6 L/h and the renal clearance is approximately 4.32 L/h.
Fexofenadine hydrochloride is rapidly absorbed from the GI tract following oral administration. Following oral administration of two 60-mg fexofenadine hydrochloride capsules, peak plasma concentrations are achieved in about 2.6 hours. Following oral administration of a single 60-mg capsule or 60- or 180-mg conventional tablet in healthy individuals, mean peak plasma concentrations were 131, 142, and 494 ng/mL, respectively. In healthy men, peak plasma concentrations of 167 ng/mL were achieved within 1.42 hours following oral administration of 60-mg fexofenadine hydrochloride doses every 12 hours for 9 doses.
McEvoy, G.K. (ed.). American Hospital Formulary Service. AHFS Drug Information. American Society of Health-System Pharmacists, Bethesda, MD. 2006., p. 35
Following oral administration of fexofenadine hydrochloride capsules in fasting children (mean age: 8-11.6 years) with a history of allergic rhinitis with or without mild asthma, peak plasma fexofenadine concentrations of about 178 or 286 ng/mL were attained in approximately 2.4 hours after a 30- or 60-mg dose, respectively.
McEvoy, G.K. (ed.). American Hospital Formulary Service. AHFS Drug Information. American Society of Health-System Pharmacists, Bethesda, MD. 2006., p. 36
Following oral administration of a 60-mg dose of fexofenadine hydrochloride, the AUC was 56% greater in children 7-12 years of age with allergic rhinitis than in healthy adults. Plasma exposure in children receiving 30 mg of fexofenadine hydrochloride is similar to that of adults receiving 60 mg of the drug. Limited data indicate that peak plasma fexofenadine concentrations in adolescents (12-16 years of age) were similar to those in adults, while peak plasma concentrations in geriatric adults (65 years of age and older) were 99% greater than in healthy individuals younger than 65 years of age. AUC also was higher in geriatric adults (65-80 years of age) than in younger adults (19-45 years of age)...
McEvoy, G.K. (ed.). American Hospital Formulary Service. AHFS Drug Information. American Society of Health-System Pharmacists, Bethesda, MD. 2006., p. 36
Peak plasma concentrations of fexofenadine were 87 and 111% higher in patients with mild (creatinine clearance of 41-80 mL/minute) to severe (creatinine clearance of 11-40 mL/minute) renal impairment, respectively, compared with those observed in healthy adults. In patients undergoing dialysis (creatinine clearance of 10 mL/minute or less), peak plasma concentrations of fexofenadine were 82% higher than in healthy adults.
McEvoy, G.K. (ed.). American Hospital Formulary Service. AHFS Drug Information. American Society of Health-System Pharmacists, Bethesda, MD. 2006., p. 36
For more Absorption, Distribution and Excretion (Complete) data for FEXOFENADINE (12 total), please visit the HSDB record page.

8.6 Metabolism / Metabolites

Fexofenadine is very minimally metabolized, with only 5% of an ingested dose undergoing hepatic metabolism. The only identified metabolites are a methyl ester of fexofenadine (3.6% of the total dose) and MDL 4829 (1.5% of the total dose). The enzymes responsible for this metabolism have not been elucidated.
About 5% of a single oral dose of fexofenadine is metabolized.
McEvoy, G.K. (ed.). American Hospital Formulary Service. AHFS Drug Information. American Society of Health-System Pharmacists, Bethesda, MD. 2006., p. 36
Negligible amounts of fexofenadine (about 0.5-1.5% of a dose) are metabolized in the liver by the cytochrome P-450 microsomal enzyme system to an inactive metabolite, while about 3.5% of a fexofenadine dose is metabolized by a second metabolic pathway (unrelated to the cytochrome P-450 microsomal enzyme system) to the methyl ester derivative of fexofenadine. The methyl ester metabolite of fexofenadine is found only in feces, and it has been suggested that the intestinal flora probably are involved in this metabolism.
McEvoy, G.K. (ed.). American Hospital Formulary Service. AHFS Drug Information. American Society of Health-System Pharmacists, Bethesda, MD. 2006., p. 36
Approximately 5% of the total dose is metabolized, by cytochrome P450 3A4 and by intestinal microflora. Half Life: 14.4 hours

8.7 Biological Half-Life

The terminal elimination half-life is approximately 11-15 hours.
Following oral administration of 60 mg of fexofenadine hydrochloride twice daily in healthy individuals, the mean elimination half-life of the drug at steady state reportedly is about 14.4-14.6 hours; mean elimination half-life reportedly was similar in geriatric adults (65 years of age or older) who received a single 80-mg oral dose of fexofenadine hydrochloride.
McEvoy, G.K. (ed.). American Hospital Formulary Service. AHFS Drug Information. American Society of Health-System Pharmacists, Bethesda, MD. 2006., p. 36
... Elimination half-life was about 18 hours in fasting children (mean age: 8-11.6 years) who received single oral 30- or 60-mg doses of fexofenadine hydrochloride as capsules.
McEvoy, G.K. (ed.). American Hospital Formulary Service. AHFS Drug Information. American Society of Health-System Pharmacists, Bethesda, MD. 2006., p. 36
In patients with mild (creatinine clearance of 41-80 mL/minute) to severe (creatinine clearance of 11-40 mL/minute) renal impairment, mean elimination half-lives were 59 and 72% longer than those observed in healthy individuals, respectively.
McEvoy, G.K. (ed.). American Hospital Formulary Service. AHFS Drug Information. American Society of Health-System Pharmacists, Bethesda, MD. 2006., p. 36
In patients undergoing dialysis (creatinine clearance of 10 mL/minute or less), elimination half-life was 31% longer than in healthy individuals.
McEvoy, G.K. (ed.). American Hospital Formulary Service. AHFS Drug Information. American Society of Health-System Pharmacists, Bethesda, MD. 2006., p. 36

8.8 Mechanism of Action

The H1 histamine receptor is responsible for mediating hypersensitivity and allergic reactions. Exposure to an allergen results in degranulation of mast cells and basophils, which then release histamine and other inflammatory mediators. Histamine binds to, and activates, H1 receptors, which results in the further release of pro-inflammatory cytokines, such as interleukins, from basophils and mast cells. These downstream effects of histamine binding are responsible for a wide variety of allergic symptoms, such as pruritus, rhinorrhea, and watery eyes. Fexofenadine is considered an “inverse agonist” of the H1 receptor because it binds to and stabilizes the inactive form of the receptor, preventing its activation and subsequent downstream effects. It has a potent and selective affinity for H1 receptors, and there is no evidence that it carries antidopaminergic, antiserotonergic, anticholinergic, sedative, or adrenergic blocking activity. Fexofenadine does not cross the blood-brain barrier and thus is unlikely to cause significant CNS effects.
Fexofenadine is a specific, selective, histamine H1-receptor antagonist. ... Fexofenadine has been shown to inhibit histamine release from peritoneal mast cells in rats. Unlike terfenadine, fexofenadine does not block the potassium channel involved in repolarization of cardiac cells (i.e., blockade of the delayed rectifier potassium current IK). As a result, fexofenadine lacks the cardiotoxic potential of terfenadine. Fexofenadine also does not possess appreciable anticholinergic, antidopaminergic, or alpha- or beta-adrenergic blocking effects at usual antihistaminic doses in pharmacologic studies.
McEvoy, G.K. (ed.). American Hospital Formulary Service. AHFS Drug Information. American Society of Health-System Pharmacists, Bethesda, MD. 2006., p. 35
It has been suggested that the increased safety profile of fexofenadine compared with the parent drug results from the lack of fexofenadine-induced cardiotoxicity in addition to only minimal metabolism of fexofenadine in the liver by the cytochrome P-450 microsomal enzyme system. Evidence from animal models using fexofenadine have suggested that the apparent lack of cardiotoxic effects of the drug may have resulted at least in part from lack of blockade of the potassium channel involved in repolarization of cardiac cells (ie, blockade of the delayed rectifier potassium current IK). Prolongations in the QTc interval were not reported in dogs receiving oral fexofenadine hydrochloride dosages of 10 mg/kg daily for 5 days or in rabbits receiving an IV fexofenadine hydrochloride dose of 10 mg/kg (resulting in plasma fexofenadine concentrations 28 or 63 times the therapeutic plasma concentrations in humans, respectively, based on a dosage of 60 mg of fexofenadine hydrochloride given twice daily). In addition, no effect was observed on calcium-channel current, delayed potassium-channel current, or action potential duration in guinea pig myocytes, sodium current in rat neonatal myocytes, or on the delayed rectifier potassium channel cloned from human heart at fexofenadine concentrations up to 1.0 X10-5 M (approximately equivalent to 32 times the therapeutic plasma concentrations in humans, based on a dosage of 60 mg of fexofenadine hydrochloride given twice daily).
McEvoy, G.K. (ed.). American Hospital Formulary Service. AHFS Drug Information. American Society of Health-System Pharmacists, Bethesda, MD. 2006., p. 33
In vitro, terfenadine exhibits a similar affinity for histamine H1-receptors from brain and peripheral tissues; however, in vivo, unlike first generation antihistamines, terfenadine and fexofenadine do not readily cross the blood-brain barrier and therefore do not appear to interact appreciably with H1-receptors within the CNS at usual doses.
McEvoy, G.K. (ed.). American Hospital Formulary Service. AHFS Drug Information. American Society of Health-System Pharmacists, Bethesda, MD. 2006., p. 35

8.9 Human Metabolite Information

8.9.1 Tissue Locations

  • Brain
  • Epidermis
  • Kidney
  • Liver

8.9.2 Cellular Locations

  • Cytoplasm
  • Membrane

8.9.3 Metabolite Pathways

9 Use and Manufacturing

9.1 Uses

THERAP CAT: Antihistaminic
O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. 13th Edition, Whitehouse Station, NJ: Merck and Co., Inc., 2001., p. 718

Use (kg; approx.) in Germany (2009): >2500

Use (kg) in USA (2002): 123000

Consumption (g per capita; approx.) in Germany (2009): 0.0305

Consumption (g per capita) in the USA (2002): 0.436

Excretion rate: 0.1

Calculated removal (%): 12.6

An antihistamine drug used in the treatment of hayfever and similar allergy symptoms.

9.1.1 Use Classification

Pharmaceuticals
S72 | NTUPHTW | Pharmaceutically Active Substances from National Taiwan University | DOI:10.5281/zenodo.3955664

9.2 Formulations / Preparations

Oral, Capsules, 60 mg, Allegra, Sanofi-Aventis; Tablets, film-coated, 30 mg, Allegra ( with povidone), Sanofi-Aventis 60 mg, Allegra ( with povidone), Sanofi-Aventis 180 mg, Allegra ( with povidone), Sanofi-Aventis
McEvoy, G.K. (ed.). American Hospital Formulary Service. AHFS Drug Information. American Society of Health-System Pharmacists, Bethesda, MD. 2006., p. 37

10 Identification

10.1 Analytic Laboratory Methods

Analyte: fexofenadine hydrochloride; matrix: chemical identification; procedure: infrared absorption spectrophotometry with comparison to standards /fexofenadine hydrochloride/
U.S. Pharmacopeia. The United States Pharmacopeia, USP 29/The National Formulary, NF 24; Rockville, MD: U.S. Pharmacopeial Convention, Inc., p905 (2006)
Analyte: fexofenadine hydrochloride; matrix: chemical identification; procedure: retention time of the major peak of the liquid chromatogram with comparison to standards /fexofenadine hydrochloride/
U.S. Pharmacopeia. The United States Pharmacopeia, USP 29/The National Formulary, NF 24; Rockville, MD: U.S. Pharmacopeial Convention, Inc., p905 (2006)
Analyte: fexofenadine hydrochloride; matrix: chemical identification; procedure: differential scanning calorimetry with analysis between 25 °C and 225 °C; sample exhibits single endotherm between 193 °C and 199 °C /fexofenadine hydrochloride/
U.S. Pharmacopeia. The United States Pharmacopeia, USP 29/The National Formulary, NF 24; Rockville, MD: U.S. Pharmacopeial Convention, Inc., p905 (2006)
Analyte: fexofenadine hydrochloride; matrix: chemical purity; procedure: liquid chromatography with detection at 220 nm and comparison to standards /fexofenadine hydrochloride/
U.S. Pharmacopeia. The United States Pharmacopeia, USP 29/The National Formulary, NF 24; Rockville, MD: U.S. Pharmacopeial Convention, Inc., p905 (2006)
For more Analytic Laboratory Methods (Complete) data for FEXOFENADINE (7 total), please visit the HSDB record page.

11 Safety and Hazards

11.1 Hazards Identification

11.1.1 GHS Classification

GHS Hazard Statements

Not Classified

Reported as not meeting GHS hazard criteria by 1 of 1 companies. For more detailed information, please visit ECHA C&L website.

11.1.2 Hazard Classes and Categories

Not Classified

11.2 Accidental Release Measures

11.2.1 Disposal Methods

SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.

11.3 Handling and Storage

11.3.1 Storage Conditions

Fexofenadine hydrochloride capsules, conventional tablets, and the extended-release tablets containing fexofenadine hydrochloride in fixed combination with pseudoephedrine hydrochloride should be stored at controlled room temperature between 20-25 °C; foil-backed blister packages containing the drug should be protected from excessive moisture.
McEvoy, G.K. (ed.). American Hospital Formulary Service. AHFS Drug Information. American Society of Health-System Pharmacists, Bethesda, MD. 2006., p. 36

11.4 Regulatory Information

REACH Registered Substance

11.4.1 FDA Requirements

The Approved Drug Products with Therapeutic Equivalence Evaluations List identifies currently marketed prescription drug products, incl fexofenadine hydrochloride, approved on the basis of safety and effectiveness by FDA under sections 505 of the Federal Food, Drug, and Cosmetic Act. /fexofenadine hydrochloride/
DHHS/FDA; Electronic Orange Book-Approved Drug Products with Therapeutic Equivalence Evaluations. Available from, as of November 15, 2006: https://www.fda.gov/cder/ob/

12 Toxicity

12.1 Toxicological Information

12.1.1 Toxicity Summary

Like other H1-blockers, Fexofenadine competes with free histamine for binding at H1-receptors in the GI tract, large blood vessels, and bronchial smooth muscle. This blocks the action of endogenous histamine, which subsequently leads to temporary relief of the negative symptoms (eg. nasal congestion, watery eyes) brought on by histamine. Fexofenadine exhibits no anticholinergic, antidopaminergic, alpha1-adrenergic or beta-adrenergic-receptor blocking effects.

12.1.2 USGS Health-Based Screening Levels for Evaluating Water-Quality

Chemical
Fexofenadine
Chemical Classes
Pharmaceutical
Reference
Smith, C.D. and Nowell, L.H., 2024. Health-Based Screening Levels for evaluating water-quality data (3rd ed.). DOI:10.5066/F71C1TWP

12.1.3 Hepatotoxicity

Fexofenadine use is not generally associated with liver enzyme elevations but terfenadine, a second generation antihistamine that is metabolized in part to fexofenadine, was the attributed cause of several reported cases of clinically apparent liver injury. Terfenadine was also linked to cardiac arrhythmias and prolongation of the QTc interval for which reason it was withdrawn from use in 1997, just as fexofenadine was introduced. Liver injury from terfenadine typically arose after 1 to 5 months and was associated with a hepatocellular pattern of liver enzyme abnormalities without immunoallergic or autoimmune features. Fexofenadine has not been linked to similar cases of cardiac arrhythmias or liver injury.

Likelihood score: E (unlikely cause of clinically apparent liver injury).

References on the safety and potential hepatotoxicity of antihistamines are given together after the Overview section on Antihistamines.

Drug Class: Antihistamines

12.1.4 Drug Induced Liver Injury

Compound
fexofenadine
DILI Annotation
No-DILI-Concern
Label Section
No match
References

M Chen, V Vijay, Q Shi, Z Liu, H Fang, W Tong. FDA-Approved Drug Labeling for the Study of Drug-Induced Liver Injury, Drug Discovery Today, 16(15-16):697-703, 2011. PMID:21624500 DOI:10.1016/j.drudis.2011.05.007

M Chen, A Suzuki, S Thakkar, K Yu, C Hu, W Tong. DILIrank: the largest reference drug list ranked by the risk for developing drug-induced liver injury in humans. Drug Discov Today 2016, 21(4): 648-653. PMID:26948801 DOI:10.1016/j.drudis.2016.02.015

12.1.5 Carcinogen Classification

Carcinogen Classification
No indication of carcinogenicity to humans (not listed by IARC).

12.1.6 Effects During Pregnancy and Lactation

◉ Summary of Use during Lactation

Because of its lack of sedation and low milk levels, maternal use of fexofenadine would not be expected to cause any adverse effects in breastfed infants. Fexofenadine might have a negative effect on lactation, especially in combination with a sympathomimetic agent such as pseudoephedrine.

◉ Effects in Breastfed Infants

In one telephone follow-up study of 25 infants exposed to the fexofenadine's parent drug terfenadine, 3 mothers reported irritability in their infants. None of the reactions required medical attention.

◉ Effects on Lactation and Breastmilk

Antihistamines in relatively high doses given by injection can decrease basal serum prolactin in nonlactating women and in early postpartum women. However, suckling-induced prolactin secretion is not affected by antihistamine pretreatment of postpartum mothers. Whether lower oral doses of antihistamines have the same effect on serum prolactin or whether the effects on prolactin have any consequences on breastfeeding success have not been studied. The prolactin level in a mother with established lactation may not affect her ability to breastfeed.

◈ What is fexofenadine?

Fexofenadine is an over-the-counter antihistamine that has been used to treat and prevent allergy symptoms such as sneezing, runny nose, watery eyes, itching, and hives. Some brand names are Allegra® and Aller-Ease®.Sometimes when people find out they are pregnant, they think about changing how they take their medication, or stopping their medication altogether. However, it is important to talk with your healthcare providers before making any changes to how you take your medication. Your healthcare providers can talk with you about the benefits of treating your condition and the risks of untreated illness during pregnancy.

◈ I take fexofenadine. Can it make it harder for me to get pregnant?

Studies have not been done in humans to see if taking fexofenadine could make it harder to get pregnant. Animal studies have not shown that taking fexofenadine would affect fertility (ability to get pregnant).

◈ Does taking fexofenadine increase the chance of miscarriage?

Miscarriage is common and can occur in any pregnancy for many different reasons. One study that compared the use of fexofenadine to other common allergy medications during pregnancy found no difference in the chance of miscarriage in those who took fexofenadine.

◈ Does taking fexofenadine increase the chance of birth defects?

Every pregnancy starts out with a 3-5% chance of having a birth defect. This is called the background risk. Studies on fexofenadine have not found an increased chance of birth defects.

◈ Does taking fexofenadine in pregnancy increase the chance of other pregnancy-related problems?

A study that compared the use of fexofenadine to other similar antihistamines did not find an increased chance for other pregnancy-related problems, such as preterm delivery (birth before week 37) or low birth weight (weighing less than 5 pounds, 8 ounces [2500 grams] at birth).

◈ Does taking fexofenadine in pregnancy affect future behavior or learning for the child?

Studies have not been done to see if fexofenadine can cause behavior or learning issues for the child.

◈ Breastfeeding while taking fexofenadine:

Fexofenadine gets into breastmilk in small amounts. This amount is likely too low to cause problems for the baby. Be sure to talk to your healthcare provider about all your breastfeeding questions.

◈ If a male takes fexofenadine, could it affect fertility or increase the chance of birth defects?

Studies have not been done to see if fexofenadine could affect male fertility (ability to get partner pregnant) or increase the chance of birth defects. In general, exposures that fathers or sperm donors have are unlikely to increase risks to a pregnancy. For more information, please see the MotherToBaby fact sheet Paternal Exposures at https://mothertobaby.org/fact-sheets/paternal-exposures-pregnancy/.

12.1.7 Exposure Routes

Oral. 33%

12.1.8 Symptoms

Side effects include dizziness, drowsiness, and dry mouth.

12.1.9 Acute Effects

12.1.10 Treatment

In the event of overdose, consider standard measures to remove any unabsorbed drug. Symptomatic and supportive treatment is recommended. (L1712)
L1712: RxList: The Internet Drug Index (2009). http://www.rxlist.com/

12.1.11 Interactions

Increased concentrations of fexofenadine have been reported in 2 controlled drug interaction studies in healthy individuals receiving 120 mg of fexofenadine hydrochloride twice daily concomitantly with erythromycin dosages of 500 mg every 8 hours or ketoconazole 400 mg once daily. In these studies, area under the plasma-concentration time curve (AUC) of fexofenadine increased by 109 or 164% following concomitant administration with erythromycin or ketoconazole, respectively, while peak plasma concentrations of fexofenadine increased by 82 or 135%, respectively. However, no clinically important adverse effects or changes in the QT interval corrected for rate (QTc) were reported after concomitant administration of erythromycin or ketoconazole with fexofenadine.
McEvoy, G.K. (ed.). American Hospital Formulary Service. AHFS Drug Information. American Society of Health-System Pharmacists, Bethesda, MD. 2006., p. 35
Administration of a single 120-mg dose (2 capsules of 60 mg) of fexofenadine hydrochloride within 15 minutes of administration of an aluminum and magnesium hydroxides antacid (Maalox) decreased the AUC and peak plasma concentration of fexofenadine by 41 and 43%, respectively. Therefore, the manufacturer states that fexofenadine (alone or in fixed combination with pseudoephedrine hydrochloride) should not be taken closely in time with antacids containing aluminum and magnesium.
McEvoy, G.K. (ed.). American Hospital Formulary Service. AHFS Drug Information. American Society of Health-System Pharmacists, Bethesda, MD. 2006., p. 35
Fruit (grapefruit, orange, apple) juices may reduce bioavailability and systemic exposure of fexofenadine. In clinical studies, the size of wheal and flare was substantially larger when fexofenadine hydrochloride was administered with grapefruit juice or orange juice compared with water; based on literature reports, the same effects may be extrapolated to other fruit juices such as apple juice. The clinical importance of these observations is unknown. Based on a population pharmacokinetic analysis of combined data from the studies using concomitant grapefruit juice or orange juice with data from a bioequivalence study, bioavailability of fexofenadine was reduced by 36%. Therefore, to maximize the effects of fexofenadine, the manufacturer recommends that the drug be administered with water.
McEvoy, G.K. (ed.). American Hospital Formulary Service. AHFS Drug Information. American Society of Health-System Pharmacists, Bethesda, MD. 2006., p. 35

12.1.12 Antidote and Emergency Treatment

For the treatment of fexofenadine overdosage, usual measures to remove unabsorbed drug from the GI tract, and supportive and symptomatic treatment should be initiated. Experience with terfenadine (no longer commercially available in the US), the parent drug, indicates that fexofenadine is not effectively removed by hemodialysis.
McEvoy, G.K. (ed.). American Hospital Formulary Service. AHFS Drug Information. American Society of Health-System Pharmacists, Bethesda, MD. 2006., p. 35
Basic treatment: Establish a patent airway (oropharyngeal or nasopharyngeal airway, if needed). Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if needed. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... . Monitor for shock and treat if necessary ... . Anticipate seizures and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with 0.9% saline (NS) during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 ml/kg up to 200 ml of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool ... . Cover skin burns with dry sterile dressings after decontamination ... . /Poisons A and B/
Currance, P.L. Clements, B., Bronstein, A.C. (Eds).; Emergency Care For Hazardous Materials Exposure. 3Rd edition, Elsevier Mosby, St. Louis, MO 2005, p. 160
Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in severe respiratory distress. Positive-pressure ventilation techniques with a bag valve mask device may be beneficial. Consider drug therapy for pulmonary edema ... . Consider administering a beta agonist such as albuterol for severe bronchospasm ... . Monitor cardiac rhythm and treat arrhythmias as necessary ... . Start IV administration of D5W /SRP: "To keep open", minimal flow rate/. Use 0.9% saline (NS) or lactated Ringer's if signs of hypovolemia are present. For hypotension with signs of hypovolemia, administer fluid cautiously. Watch for signs of fluid overload ... . Treat seizures with diazepam or lorazepam ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Poisons A and B/
Currance, P.L. Clements, B., Bronstein, A.C. (Eds).; Emergency Care For Hazardous Materials Exposure. 3Rd edition, Elsevier Mosby, St. Louis, MO 2005, p. 160-1

12.1.13 Non-Human Toxicity Excerpts

/LABORATORY ANIMALS: Chronic Exposure or Carcinogenicity/ No evidence of carcinogenesis was seen in mice and rats receiving oral terfenadine (the parent drug of fexofenadine; no longer commercially available in the US) dosages up to 150 mg/kg daily for 18 and 24 months, respectively, resulting in fexofenadine exposure levels calculated to be of 2-3 times the maximum recommended daily oral human dosage.[McEvoy, G.K. (ed.). American Hospital Formulary Service. AHFS Drug Information. American Society of Health-System Pharmacists, Bethesda, MD. 2006., p. 34]
/LABORATORY ANIMALS: Developmental or Reproductive Toxicity/ Reproduction studies in rats and rabbits using oral terfenadine dosages up to 300 mg/kg resulting in fexofenadine exposure levels calculated to be about 3-4 and 25-31 times, respectively, those resulting from the maximum recommended daily oral human dosage of fexofenadine hydrochloride in adults have not revealed evidence of teratogenicity.[McEvoy, G.K. (ed.). American Hospital Formulary Service. AHFS Drug Information. American Society of Health-System Pharmacists, Bethesda, MD. 2006., p. 34]
/LABORATORY ANIMALS: Developmental or Reproductive Toxicity/ Reproduction studies in mice receiving fexofenadine doses up to 3730 mg/kg (approximately 10-15 times the maximum recommended daily oral human dosage of fexofenadine hydrochloride in adults) have not revealed evidence of adverse or teratogenic effects during gestation.[McEvoy, G.K. (ed.). American Hospital Formulary Service. AHFS Drug Information. American Society of Health-System Pharmacists, Bethesda, MD. 2006., p. 34]
/LABORATORY ANIMALS: Developmental or Reproductive Toxicity/ Reproduction studies in male and female mice receiving fexofenadine doses up to 4438 mg/kg (approximately 10-15 times the maximum recommended daily oral human dosage of fexofenadine hydrochloride in adults) have not revealed evidence of impaired fertility. Reproduction studies in rats using terfenadine dosages of 150 mg/kg (resulting in fexofenadine exposure levels calculated to be about 3-4 times those resulting from the maximum recommended daily oral human dosage of fexofenadine hydrochloride), revealed dose-related decreases in implantation and an increased incidence of postimplantation losses.[McEvoy, G.K. (ed.). American Hospital Formulary Service. AHFS Drug Information. American Society of Health-System Pharmacists, Bethesda, MD. 2006., p. 34]
For more Non-Human Toxicity Excerpts (Complete) data for FEXOFENADINE (6 total), please visit the HSDB record page.

12.1.14 Populations at Special Risk

Safety and efficacy of fexofenadine hydrochloride have not been established in children younger than 6 years of age.
McEvoy, G.K. (ed.). American Hospital Formulary Service. AHFS Drug Information. American Society of Health-System Pharmacists, Bethesda, MD. 2006., p. 34

12.1.15 Protein Binding

Fexofenadine is 60-70% bound to plasma proteins, primarily to albumin and α1-acid glycoprotein. The extent of protein binding is decreased to 56-68% and 56-75% in patients with renal and hepatic impairment, respectively.

12.2 Ecological Information

12.2.1 Environmental Water Concentrations

While data specific to fexofenadine were not located(SRC, 2006), the literature suggests that some pharmaceutically active compounds originating from human and veterinary therapy are not eliminated completely in municipal sewage treatment plants and are therefore discharged into receiving waters(1). Wastewater treatment processes often were not designed to remove them from the effluent(2). Selected organic waste compounds may be degrading to new and more persistent compounds that may be released instead of or in addition to the parent compound(2).
(1) Heberer T; Tox Lett 131: 5-17 (2002)
(2) Koplin DW et al; Environ Sci Toxicol 36: 1202-211 (2002)

12.2.2 Milk Concentrations

It is not known if fexofenadine hydrochloride is distributed into breast milk
McEvoy, G.K. (ed.). American Hospital Formulary Service. AHFS Drug Information. American Society of Health-System Pharmacists, Bethesda, MD. 2006., p. 35

13 Associated Disorders and Diseases

14 Literature

14.1 Consolidated References

14.2 NLM Curated PubMed Citations

14.3 Springer Nature References

14.4 Chemical Co-Occurrences in Literature

14.5 Chemical-Gene Co-Occurrences in Literature

14.6 Chemical-Disease Co-Occurrences in Literature

15 Patents

15.1 Depositor-Supplied Patent Identifiers

15.2 WIPO PATENTSCOPE

15.3 Chemical Co-Occurrences in Patents

15.4 Chemical-Disease Co-Occurrences in Patents

15.5 Chemical-Gene Co-Occurrences in Patents

16 Interactions and Pathways

16.1 Chemical-Target Interactions

16.2 Drug-Drug Interactions

16.3 Drug-Food Interactions

  • Avoid fruit juice. Fruit juices like grapefruit, orange, and apple may reduce bioavailability and overall exposure to the medication.
  • Take with or without food. Co-administration with food does not significantly affect absorption.

16.4 Pathways

17 Biological Test Results

17.1 BioAssay Results

18 Taxonomy

The LOTUS Initiative for Open Natural Products Research: frozen dataset union wikidata (with metadata) | DOI:10.5281/zenodo.5794106

19 Classification

19.1 MeSH Tree

19.2 NCI Thesaurus Tree

19.3 ChEBI Ontology

19.4 KEGG: ATC

19.5 KEGG: Target-based Classification of Drugs

19.6 KEGG: Risk Category of Japanese OTC Drugs

19.7 KEGG: Drug Groups

19.8 WHO ATC Classification System

19.9 FDA Pharm Classes

19.10 ChemIDplus

19.11 IUPHAR / BPS Guide to PHARMACOLOGY Target Classification

19.12 ChEMBL Target Tree

19.13 UN GHS Classification

19.14 NORMAN Suspect List Exchange Classification

19.15 CCSBase Classification

19.16 EPA DSSTox Classification

19.17 LOTUS Tree

19.18 MolGenie Organic Chemistry Ontology

20 Information Sources

  1. BindingDB
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    https://www.bindingdb.org/rwd/bind/info.jsp
    2-(4-{1-hydroxy-4-[4-(hydroxydiphenylmethyl)piperidin-1-yl]butyl}phenyl)-2-methylpropanoic acid
    https://www.bindingdb.org/rwd/bind/chemsearch/marvin/MolStructure.jsp?monomerid=22874
  2. Comparative Toxicogenomics Database (CTD)
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    http://ctdbase.org/about/legal.jsp
  3. DrugBank
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    https://www.drugbank.ca/legal/terms_of_use
  4. IUPHAR/BPS Guide to PHARMACOLOGY
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    https://www.guidetopharmacology.org/about.jsp#license
    Guide to Pharmacology Target Classification
    https://www.guidetopharmacology.org/targets.jsp
  5. Therapeutic Target Database (TTD)
  6. Toxin and Toxin Target Database (T3DB)
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    http://www.t3db.ca/downloads
  7. CAS Common Chemistry
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    https://creativecommons.org/licenses/by-nc/4.0/
  8. ChemIDplus
    ChemIDplus Chemical Information Classification
    https://pubchem.ncbi.nlm.nih.gov/source/ChemIDplus
  9. EPA DSSTox
    CompTox Chemicals Dashboard Chemical Lists
    https://comptox.epa.gov/dashboard/chemical-lists/
  10. European Chemicals Agency (ECHA)
    LICENSE
    Use of the information, documents and data from the ECHA website is subject to the terms and conditions of this Legal Notice, and subject to other binding limitations provided for under applicable law, the information, documents and data made available on the ECHA website may be reproduced, distributed and/or used, totally or in part, for non-commercial purposes provided that ECHA is acknowledged as the source: "Source: European Chemicals Agency, http://echa.europa.eu/". Such acknowledgement must be included in each copy of the material. ECHA permits and encourages organisations and individuals to create links to the ECHA website under the following cumulative conditions: Links can only be made to webpages that provide a link to the Legal Notice page.
    https://echa.europa.eu/web/guest/legal-notice
    (+/-)-4-(1-Hydroxy-4-(4-(hydroxydiphenyl-methyl)-1- piperidinyl)butyl)-alpha-dimethylbenzeneacetic acid
    https://chem.echa.europa.eu/100.228.648
    (+/-)-4-(1-Hydroxy-4-(4-(hydroxydiphenyl-methyl)-1- piperidinyl)butyl)-alpha-dimethylbenzeneacetic acid (EC: 801-893-7)
    https://echa.europa.eu/information-on-chemicals/cl-inventory-database/-/discli/details/235192
  11. FDA Global Substance Registration System (GSRS)
    LICENSE
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    https://www.fda.gov/about-fda/about-website/website-policies#linking
  12. Hazardous Substances Data Bank (HSDB)
  13. Human Metabolome Database (HMDB)
    LICENSE
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    http://www.hmdb.ca/citing
  14. CCSbase
    CCSbase Classification
    https://ccsbase.net/
  15. ChEBI
  16. FDA Pharm Classes
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    https://www.fda.gov/about-fda/about-website/website-policies#linking
  17. LiverTox
  18. LOTUS - the natural products occurrence database
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  19. NCI Thesaurus (NCIt)
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  20. Open Targets
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    https://platform-docs.opentargets.org/licence
  21. ChEMBL
    LICENSE
    Access to the web interface of ChEMBL is made under the EBI's Terms of Use (http://www.ebi.ac.uk/Information/termsofuse.html). The ChEMBL data is made available on a Creative Commons Attribution-Share Alike 3.0 Unported License (http://creativecommons.org/licenses/by-sa/3.0/).
    http://www.ebi.ac.uk/Information/termsofuse.html
  22. ClinicalTrials.gov
    LICENSE
    The ClinicalTrials.gov data carry an international copyright outside the United States and its Territories or Possessions. Some ClinicalTrials.gov data may be subject to the copyright of third parties; you should consult these entities for any additional terms of use.
    https://clinicaltrials.gov/ct2/about-site/terms-conditions#Use
  23. DailyMed
  24. Drug Induced Liver Injury Rank (DILIrank) Dataset
    LICENSE
    Unless otherwise noted, the contents of the FDA website (www.fda.gov), both text and graphics, are not copyrighted. They are in the public domain and may be republished, reprinted and otherwise used freely by anyone without the need to obtain permission from FDA. Credit to the U.S. Food and Drug Administration as the source is appreciated but not required.
    https://www.fda.gov/about-fda/about-website/website-policies#linking
  25. Drugs and Lactation Database (LactMed)
  26. Mother To Baby Fact Sheets
    LICENSE
    Copyright by OTIS. This work is available under the Creative Commons Attribution-NonCommercial-NoDerivs 3.0 Unported license (CC BY-NC-ND 3.0).
    https://www.ncbi.nlm.nih.gov/books/about/copyright/
  27. Drugs@FDA
    LICENSE
    Unless otherwise noted, the contents of the FDA website (www.fda.gov), both text and graphics, are not copyrighted. They are in the public domain and may be republished, reprinted and otherwise used freely by anyone without the need to obtain permission from FDA. Credit to the U.S. Food and Drug Administration as the source is appreciated but not required.
    https://www.fda.gov/about-fda/about-website/website-policies#linking
  28. NORMAN Suspect List Exchange
    LICENSE
    Data: CC-BY 4.0; Code (hosted by ECI, LCSB): Artistic-2.0
    https://creativecommons.org/licenses/by/4.0/
    FEXOFENADINE
    NORMAN Suspect List Exchange Classification
    https://www.norman-network.com/nds/SLE/
  29. WHO Model Lists of Essential Medicines
    LICENSE
    Permission from WHO is not required for the use of WHO materials issued under the Creative Commons Attribution-NonCommercial-ShareAlike 3.0 Intergovernmental Organization (CC BY-NC-SA 3.0 IGO) license.
    https://www.who.int/about/policies/publishing/copyright
  30. EU Clinical Trials Register
  31. NIST Mass Spectrometry Data Center
    LICENSE
    Data covered by the Standard Reference Data Act of 1968 as amended.
    https://www.nist.gov/srd/public-law
  32. Japan Chemical Substance Dictionary (Nikkaji)
  33. KEGG
    LICENSE
    Academic users may freely use the KEGG website. Non-academic use of KEGG generally requires a commercial license
    https://www.kegg.jp/kegg/legal.html
    Anatomical Therapeutic Chemical (ATC) classification
    http://www.genome.jp/kegg-bin/get_htext?br08303.keg
    Target-based classification of drugs
    http://www.genome.jp/kegg-bin/get_htext?br08310.keg
    Risk category of Japanese OTC drugs
    http://www.genome.jp/kegg-bin/get_htext?br08312.keg
  34. MassBank Europe
  35. MassBank of North America (MoNA)
    LICENSE
    The content of the MoNA database is licensed under CC BY 4.0.
    https://mona.fiehnlab.ucdavis.edu/documentation/license
  36. Metabolomics Workbench
  37. NIPH Clinical Trials Search of Japan
  38. SpectraBase
    FEXOFENADINE;ALPHA,ALPHA-DIMETHYL-4-[1-HYDROXY-4-[4-(HYDROXYDIPHENYL-METHYL)-1-PIPERIDINYL]-BUTYL]-BENZENE_ACETIC_ACID
    https://spectrabase.com/spectrum/GWdnmUGSRqL
  39. NLM RxNorm Terminology
    LICENSE
    The RxNorm Terminology is created by the National Library of Medicine (NLM) and is in the public domain and may be republished, reprinted and otherwise used freely by anyone without the need to obtain permission from NLM. Credit to the U.S. National Library of Medicine as the source is appreciated but not required. The full RxNorm dataset requires a free license.
    https://www.nlm.nih.gov/research/umls/rxnorm/docs/termsofservice.html
  40. PharmGKB
    LICENSE
    PharmGKB data are subject to the Creative Commons Attribution-ShareALike 4.0 license (https://creativecommons.org/licenses/by-sa/4.0/).
    https://www.pharmgkb.org/page/policies
  41. Pharos
    LICENSE
    Data accessed from Pharos and TCRD is publicly available from the primary sources listed above. Please respect their individual licenses regarding proper use and redistribution.
    https://pharos.nih.gov/about
  42. Springer Nature
  43. USGS Health-Based Screening Levels for Evaluating Water-Quality Data
  44. WHO Anatomical Therapeutic Chemical (ATC) Classification
    LICENSE
    Use of all or parts of the material requires reference to the WHO Collaborating Centre for Drug Statistics Methodology. Copying and distribution for commercial purposes is not allowed. Changing or manipulating the material is not allowed.
    https://www.whocc.no/copyright_disclaimer/
  45. Wikidata
  46. Wikipedia
  47. PubChem
  48. Medical Subject Headings (MeSH)
    LICENSE
    Works produced by the U.S. government are not subject to copyright protection in the United States. Any such works found on National Library of Medicine (NLM) Web sites may be freely used or reproduced without permission in the U.S.
    https://www.nlm.nih.gov/copyright.html
    Histamine H1 Antagonists, Non-Sedating
    https://www.ncbi.nlm.nih.gov/mesh/68039563
  49. GHS Classification (UNECE)
  50. MolGenie
    MolGenie Organic Chemistry Ontology
    https://github.com/MolGenie/ontology/
  51. PATENTSCOPE (WIPO)
  52. NCBI
CONTENTS