Fexofenadine
- fexofenadine
- 83799-24-0
- Carboxyterfenadine
- Terfenadine carboxylate
- Terfenadine-COOH
- Create:2005-03-25
- Modify:2025-01-18
- alpha-(4-(1-carboxy-1-methylethyl)phenyl)-4-hydroxydiphenylmethyl-1-piperidinebutanol
- fexofenadine
- fexofenadine hydrochloride
- MDL 16,455A
- MDL 16.455
- MDL 16455
- MDL-16455
- fexofenadine
- 83799-24-0
- Carboxyterfenadine
- Terfenadine carboxylate
- Terfenadine-COOH
- Terfenadine acid metabolite
- Allegra
- Telfast
- MDL 16455
- Fexofenadina
- HSDB 7486
- 2-(4-{1-HYDROXY-4-[4-(HYDROXYDIPHENYLMETHYL)PIPERIDIN-1-YL]BUTYL}PHENYL)-2-METHYLPROPANOIC ACID
- UNII-E6582LOH6V
- Fexofendine
- Fexofenadine (INN)
- CHEBI:5050
- E6582LOH6V
- 2-(4-(1-Hydroxy-4-(4-(hydroxydiphenylmethyl)piperidin-1-yl)butyl)phenyl)-2-methylpropanoic acid
- 4-(1-Hydroxy-4-(4-(hydroxydiphenylmethyl)-1-piperidinyl)butyl)-alpha,alpha-dimethylbenzeneacetic acid
- 2-[4-[1-hydroxy-4-[4-[hydroxy(diphenyl)methyl]piperidin-1-yl]butyl]phenyl]-2-methylpropanoic acid
- MDL-16455
- CHEMBL914
- DTXSID00861411
- EC 801-893-7
- 83799-24-0 (free base)
- MDL-16455; Terfenadine carboxylate
- 138452-21-8
- FEXOFENADINE [INN]
- Benzeneacetic acid,4-[1-hydroxy-4-[4-(hydroxydiphenylmethyl)-1-piperidinyl]butyl]-a,a-dimethyl-
- Fexofenadine [INN:BAN]
- 2-[4-(1-hydroxy-4-{4-[hydroxy(diphenyl)methyl]piperidin-1-yl}butyl)phenyl]-2-methylpropanoic acid
- Benzeneacetic acid, 4-(1-hydroxy-4-(4-(hydroxydiphenylmethyl)-1-piperidinyl)butyl)-alpha,alpha-dimethyl-
- FEXOFENADINE (USP-RS)
- FEXOFENADINE [USP-RS]
- Fexofenidine hydrochloride
- MDL 16455 hydrochloride
- Telfast (TN)
- Terfenidine carboxylate hydrochloride
- NCGC00015453-05
- fexofenadinum
- SR-01000075889
- piperidin-1-yl)
- MFCD00871892
- Terfenidine carboxylate, MDL 16455
- Spectrum_001914
- Spectrum2_001179
- Spectrum3_001921
- Spectrum4_000204
- Spectrum5_001474
- FEXOFENADINE [MI]
- F 9427
- FEXOFENADINE [HSDB]
- SCHEMBL4900
- FEXOFENADINE [VANDF]
- Lopac0_000488
- BSPBio_003521
- KBioGR_000807
- KBioSS_002456
- FEXOFENADINE [WHO-DD]
- SPBio_001197
- GTPL4819
- butyl)phenyl)-2-methylpropanoic
- BDBM22874
- KBio2_002449
- KBio2_005017
- KBio2_007585
- KBio3_002742
- DTXCID50197277
- R06AX26
- HMS3261B17
- HMS3370C16
- BCP11806
- HY-B0801
- Tox21_500488
- BBL029080
- STK624102
- AKOS005557315
- BCP9000683
- CCG-204579
- DB00950
- LP00488
- SDCCGSBI-0050472.P003
- alpha-(4-(1-carboxy-1-methylethyl)phenyl)-4-hydroxydiphenylmethyl-1-piperidinebutanol
- NCGC00015453-03
- NCGC00015453-04
- NCGC00015453-06
- NCGC00015453-10
- NCGC00015453-19
- NCGC00092389-02
- NCGC00092389-03
- NCGC00092389-04
- NCGC00261173-01
- (+/-)-4-(1-Hydroxy-4-(4-(hydroxydiphenyl-methyl)-1- piperidinyl)butyl)-alpha-dimethylbenzeneacetic acid
- 2-(4-(1-Hydroxy-4-(4-(hydroxydiphenylmethyl)-piperidin-1-yl)butyl)phenyl)-2-methylpropanoic acid
- 2-[4-[1-hydroxy-4-[4-[hydroxy(diphenyl)methyl]-1-piperidyl]butyl]phenyl]-2-methyl-propanoic acid
- AS-35188
- SBI-0050472.P002
- DB-016658
- DB-226998
- CS-0012429
- EU-0100488
- NS00010515
- EN300-58439
- C06999
- D07958
- 2-(4-(1-hydroxy-4-(4-(hydroxydiphenylmethyl)
- AB00876239_06
- AB00876239_07
- L000869
- Q415122
- Q-201113
- SR-01000075889-1
- BRD-A73368467-003-02-8
- BRD-A73368467-003-07-7
- BRD-A73368467-003-16-8
- BRD-A73368467-003-17-6
- BRD-A73368467-003-18-4
- (+)-4-[4-[4-(hydroxydiphenylmethyl)-1-piperidinyl]-1-hydroxybutyl]-alpha,alpha-dimethylbenzeneacetic-acid
- (+/-)-4-(1-Hydroxy-4-(4-(hydroxydiphenyl-methyl)-1-piperidinyl)butyl)-alpha-dimethylbenzeneacetic acid
- (+/-)-P-(1-HYDROXY-4-(4-(HYDROXYDIPHENYLMETHYL)PIPERIDINO)BUTYL)-.ALPHA.-METHYLHYDRATROPIC ACID
- (+/-)-P-(1-HYDROXY-4-(4-(HYDROXYDIPHENYLMETHYL)PIPERIDINO)BUTYL)-alpha-METHYLHYDRATROPIC ACID
- 1319714-86-7
- 2-[4-(1-Hydroxy-4-{4-[hydroxy(diphenyl)methyl]-1-piperidinyl}butyl)phenyl]-2-methylpropanoic acid
- 2-[4-[1-hydroxy-4-[4-(hydroxydiphenylmethyl)-1-piperidyl]butyl]phenyl]-2-methyl-propanoic acid
- 4-[1-Hydroxy-4-[4-(hydroxydiphenylmethyl)-1-piperidinyl]butyl]-alpha,alpha-dimethyl-benzene-acetic Acid
- 4-[4-(4-(Hydroxydiphenylmethyl)-1-piperidinyl]-1-hydroxybutyl]-alpha, alpha-dimethylbenzeneacetic acid
- 4-[4-[4-(hydroxydiphenylmethyl)-1-piperidinyl]-1-hydroxybutyl] -alpha,alpha-dimethylbenzeneacetic acid
- 4-[4-[4-(Hydroxydiphenylmethyl)-1-piperidinyl]-1-hydroxybutyl]-alpha,alpha-dimethylbenzeneacetic acid
- 4-[4-[4-(hydroxydiphenylmethyl)-1-piperidinyl]-1-hydroxybutyl]-alpha,alpha-dimethylphenylacetic acid
- 4-[4[4-(hydroxydiphenylmethyl)-1-piperidinyl]-1-hydroxybutyl]-alpha,alpha-dimethylbenzeneacetic acid
- alpha,alpha-Dimethyl-4-(1-hydroxy-4-(4-(hydroxydiphenylmethyl)-1-piperidinyl)butyl)-benzeneacetic acid
- BENZENEACETIC ACID, 4-(1-HYDROXY-4-(4-(HYDROXYDIPHENYLMETHYL)-1-PIPERIDINYL)BUTYL)-.ALPHA.,.ALPHA.-DIMETHYL-, (+/-)-
- BENZENEACETIC ACID, 4-(1-HYDROXY-4-(4-(HYDROXYDIPHENYLMETHYL)-1-PIPERIDINYL)BUTYL)-alpha,alpha-DIMETHYL-, (+/-)-
- racemic 4-[4-[4-(hydroxydiphenylmethyl)-1-piperidinyl]-1-hydroxybutyl]-alpha,alpha-dimethylbenzeneacetic acid
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]
258.15 100
378.2438 75.26
188.1081 10.85
230.1549 5.62
145.0659 3.82
258.15 100
188.1081 30.81
145.0659 15.20
110.0612 12.99
112.0768 11.87
466.2577 999
484.275 500
502.2952 252
171.1161 128
467.2727 96
502.2953 999
484.2849 39
466.2733 12
171.1167 1
- Brain
- Epidermis
- Kidney
- Liver
- Cytoplasm
- Membrane
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
Not Classified
Reported as not meeting GHS hazard criteria by 1 of 1 companies. For more detailed information, please visit ECHA C&L website.
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
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
◉ 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/.
Patents are available for this chemical structure:
https://patentscope.wipo.int/search/en/result.jsf?inchikey=RWTNPBWLLIMQHL-UHFFFAOYSA-N
- 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.
- BindingDBLICENSEAll data curated by BindingDB staff are provided under the Creative Commons Attribution 3.0 License (https://creativecommons.org/licenses/by/3.0/us/).https://www.bindingdb.org/rwd/bind/info.jsp2-(4-{1-hydroxy-4-[4-(hydroxydiphenylmethyl)piperidin-1-yl]butyl}phenyl)-2-methylpropanoic acidhttps://www.bindingdb.org/rwd/bind/chemsearch/marvin/MolStructure.jsp?monomerid=22874
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- ChEBI
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- LiverTox
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- EU Clinical Trials Register
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- Metabolomics Workbench
- NIPH Clinical Trials Search of Japan
- SpectraBaseFexofenadine breakdown (439)https://spectrabase.com/spectrum/GvJT248vkd2Fexofenadine breakdown (439)https://spectrabase.com/spectrum/JUk7SfiQG9AFEXOFENADINE;ALPHA,ALPHA-DIMETHYL-4-[1-HYDROXY-4-[4-(HYDROXYDIPHENYL-METHYL)-1-PIPERIDINYL]-BUTYL]-BENZENE_ACETIC_ACIDhttps://spectrabase.com/spectrum/GWdnmUGSRqLFEXOFENADINEhttps://spectrabase.com/spectrum/KdYIGnCC8dG
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- WikipediaBumetanidehttps://en.wikipedia.org/wiki/BumetanideFexofenadinehttps://en.wikipedia.org/wiki/Fexofenadine
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