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Cephalexin

PubChem CID
27447
Structure
Cephalexin_small.png
Cephalexin_3D_Structure.png
Molecular Formula
Synonyms
  • cephalexin
  • Cefalexin
  • 15686-71-2
  • Keflex
  • Cephacillin
Molecular Weight
347.4 g/mol
Computed by PubChem 2.2 (PubChem release 2024.11.20)
Dates
  • Create:
    2005-06-24
  • Modify:
    2025-01-04
Description
Cephalexin is a semisynthetic first-generation cephalosporin antibiotic having methyl and beta-(2R)-2-amino-2-phenylacetamido groups at the 3- and 7- of the cephem skeleton, respectively. It is effective against both Gram-negative and Gram-positive organisms, and is used for treatment of infections of the skin, respiratory tract and urinary tract. It has a role as an antibacterial drug. It is a cephalosporin, a semisynthetic derivative and a beta-lactam antibiotic allergen. It is a conjugate acid of a cephalexin(1-).
Cephalexin is the first of the first generation cephalosporins. This antibiotic contains a beta lactam and a dihydrothiazide. Cephalexin is used to treat a number of susceptible bacterial infections through inhibition of cell wall synthesis. Cephalexin was approved by the FDA on 4 January 1971.
Cephalexin anhydrous is a Cephalosporin Antibacterial.

1 Structures

1.1 2D Structure

Chemical Structure Depiction
Cephalexin.png

1.2 3D Conformer

2 Names and Identifiers

2.1 Computed Descriptors

2.1.1 IUPAC Name

(6R,7R)-7-[[(2R)-2-amino-2-phenylacetyl]amino]-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
Computed by Lexichem TK 2.7.0 (PubChem release 2024.11.20)

2.1.2 InChI

InChI=1S/C16H17N3O4S/c1-8-7-24-15-11(14(21)19(15)12(8)16(22)23)18-13(20)10(17)9-5-3-2-4-6-9/h2-6,10-11,15H,7,17H2,1H3,(H,18,20)(H,22,23)/t10-,11-,15-/m1/s1
Computed by InChI 1.07.0 (PubChem release 2024.11.20)

2.1.3 InChIKey

ZAIPMKNFIOOWCQ-UEKVPHQBSA-N
Computed by InChI 1.07.0 (PubChem release 2024.11.20)

2.1.4 SMILES

CC1=C(N2[C@@H]([C@@H](C2=O)NC(=O)[C@@H](C3=CC=CC=C3)N)SC1)C(=O)O
Computed by OEChem 2.3.0 (PubChem release 2024.12.12)

2.2 Molecular Formula

C16H17N3O4S
Computed by PubChem 2.2 (PubChem release 2024.11.20)

2.3 Other Identifiers

2.3.1 CAS

15686-71-2
1820673-23-1
23325-78-2

2.3.3 Deprecated CAS

14101-75-8, 17692-47-6, 65454-17-3, 82853-18-7

2.3.4 European Community (EC) Number

998-943-4

2.3.5 UNII

2.3.6 ChEBI ID

2.3.7 ChEMBL ID

2.3.8 DrugBank ID

2.3.9 DSSTox Substance ID

2.3.10 HMDB ID

2.3.11 KEGG ID

2.3.12 Metabolomics Workbench ID

2.3.13 NCI Thesaurus Code

2.3.14 Nikkaji Number

2.3.15 PharmGKB ID

2.3.16 RXCUI

2.3.17 Wikidata

2.3.18 Wikipedia

2.4 Synonyms

2.4.1 MeSH Entry Terms

  • 5-Thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid, 7-((aminophenylacetyl)amino)-3-methyl-8-oxo-, (6R-(6alpha,7beta(R*)))-
  • Cefalexin
  • Cephalexin
  • Cephalexin Dihydride
  • Cephalexin Hemihydrate
  • Cephalexin Hydrochloride
  • Cephalexin Monohydrate
  • Cephalexin Monohydrochloride
  • Cephalexin Monohydrochloride, Monohydrate
  • Cephalexin, (6R-(6alpha,7alpha(R*)))-Isomer
  • Cephalexin, (6R-(6alpha,7beta(S*)))-Isomer
  • Cephalexin, (6R-(6alpha,7beta))-Isomer
  • Cephalexin, Monosodium Salt
  • Cephalexin, Monosodium Salt, (6R-(6alpha,7beta))-Isomer
  • Ceporexine
  • Palitrex

2.4.2 Depositor-Supplied Synonyms

3 Chemical and Physical Properties

3.1 Computed Properties

Property Name
Molecular Weight
Property Value
347.4 g/mol
Reference
Computed by PubChem 2.2 (PubChem release 2024.11.20)
Property Name
XLogP3
Property Value
0.6
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
6
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2024.11.20)
Property Name
Rotatable Bond Count
Property Value
4
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2024.11.20)
Property Name
Exact Mass
Property Value
347.09397721 Da
Reference
Computed by PubChem 2.2 (PubChem release 2024.11.20)
Property Name
Monoisotopic Mass
Property Value
347.09397721 Da
Reference
Computed by PubChem 2.2 (PubChem release 2024.11.20)
Property Name
Topological Polar Surface Area
Property Value
138Ų
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2024.11.20)
Property Name
Heavy Atom Count
Property Value
24
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
600
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
3
Reference
Computed by PubChem
Property Name
Undefined Atom Stereocenter Count
Property Value
0
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
Budavari, S. (ed.). The Merck Index - Encyclopedia of Chemicals, Drugs and Biologicals. Rahway, NJ: Merck and Co., Inc., 1989., p. 304
WHITE TO OFF-WHITE, CRYSTALLINE POWDER
Osol, A. and J.E. Hoover, et al. (eds.). Remington's Pharmaceutical Sciences. 15th ed. Easton, Pennsylvania: Mack Publishing Co., 1975., p. 1119

3.2.3 Boiling Point

3.2.4 Melting Point

326.8°C
326.8 °C

3.2.5 Solubility

10mg/mL
SLIGHTLY SOL IN WATER; PRACTICALLY INSOL IN ALC, CHLOROFORM, ETHER
Osol, A. and J.E. Hoover, et al. (eds.). Remington's Pharmaceutical Sciences. 15th ed. Easton, Pennsylvania: Mack Publishing Co., 1975., p. 1119
2.97e-01 g/L

3.2.6 LogP

0.65
HANSCH,C ET AL. (1995)
logP = 0.65
Hansch, C. and A. Leo. The Log P Database. Claremont, CA: Pomona College, 1987.

3.2.7 Stability / Shelf Life

ACID-STABLE
Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 1161

3.2.8 Dissociation Constants

Acidic pKa
2.53
Comparison of the accuracy of experimental and predicted pKa values of basic and acidic compounds. Pharm Res. 2014; 31(4):1082-95. DOI:10.1007/s11095-013-1232-z. PMID:24249037
Basic pKa
7.14
Comparison of the accuracy of experimental and predicted pKa values of basic and acidic compounds. Pharm Res. 2014; 31(4):1082-95. DOI:10.1007/s11095-013-1232-z. PMID:24249037
PKA: 5.2, 7.3
Budavari, S. (ed.). The Merck Index - Encyclopedia of Chemicals, Drugs and Biologicals. Rahway, NJ: Merck and Co., Inc., 1989., p. 304

3.2.9 Collision Cross Section

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

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

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

163.36 Ų [M+H-H2O]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

178.02 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

183.1 Ų [M+Na]+ [CCS Type: TW; Method: calibrated with Waters Major Mix]

186.9 Ų [M+H]+ [CCS Type: TW; Method: calibrated with Waters Major Mix]

179.56 Ų [M-H]-
S61 | UJICCSLIB | Collision Cross Section (CCS) Library from UJI | DOI:10.5281/zenodo.3549476

3.3 Chemical Classes

3.3.1 Drugs

Pharmaceuticals -> Listed in ZINC15
S55 | ZINC15PHARMA | Pharmaceuticals from ZINC15 | DOI:10.5281/zenodo.3247749
Pharmaceuticals -> Antibiotics (Cefalosporins)
S56 | UOATARGPHARMA | Target Pharmaceutical/Drug List from University of Athens | DOI:10.5281/zenodo.3248837
Pharmaceuticals -> Antibiotics
S6 | ITNANTIBIOTIC | Antibiotic List from the ITN MSCA ANSWER | DOI:10.5281/zenodo.2621956
3.3.1.1 Human Drugs
Breast Feeding; Lactation; Milk, Human; Anti-Infective Agents; Antibacterial Agents; Cephalosporins
Human drug -> Discontinued
Human drug -> Prescription; Discontinued; Active ingredient (CEPHALEXIN)
Access group antibiotics
3.3.1.2 Animal Drugs
Active Ingredients (Cephalexin) -> FDA Greenbook
Pharmaceuticals -> Animal Drugs -> Approved in Taiwan
S72 | NTUPHTW | Pharmaceutically Active Substances from National Taiwan University | DOI:10.5281/zenodo.3955664
Pharmaceuticals -> UK Veterinary Medicines Directorate List
S104 | UKVETMED | UK Veterinary Medicines Directorate's List | DOI:10.5281/zenodo.7802119

4 Spectral Information

4.1 1D NMR Spectra

1D NMR Spectra

4.2 Mass Spectrometry

4.2.1 MS-MS

1 of 2
Spectra ID
Instrument Type
LC-ESI-QTOF
Ionization Mode
positive
Top 5 Peaks

158.0278 100

174.0556 56.16

192.0481 19.21

106.0663 11.66

175.0587 9.36

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Notes
instrument=Bruker maXis Impact
2 of 2
Spectra ID
Ionization Mode
Positive
Top 5 Peaks

158.0278 100

174.0556 56.16

192.0481 19.21

106.0663 11.66

175.0587 9.36

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4.2.2 LC-MS

1 of 2
Authors
Nikiforos Alygizakis, Anna Bletsou, Nikolaos Thomaidis, University of Athens
Instrument
Bruker maXis Impact
Instrument Type
LC-ESI-QTOF
MS Level
MS2
Ionization Mode
POSITIVE
Ionization
ESI
Collision Energy
Ramp 22.6-33.8 eV
Fragmentation Mode
CID
Column Name
Acclaim RSLC C18 2.2um, 2.1x100mm, Thermo
Retention Time
4.2 min
Precursor m/z
348.1013
Precursor Adduct
[M+H]+
Top 5 Peaks

158.0278 999

174.0556 561

192.0481 191

106.0663 116

175.0587 93

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License
CC BY
2 of 2
MoNA ID
MS Category
Experimental
MS Type
LC-MS
MS Level
MS2
Precursor Type
[M+H]+
Precursor m/z
348.1013
Instrument
Bruker maXis Impact
Instrument Type
LC-ESI-QTOF
Ionization
ESI
Ionization Mode
positive
Collision Energy
Ramp 22.6-33.8 eV
Retention Time
4.2 min
Top 5 Peaks

158.0278 100

174.0556 56.16

192.0481 19.21

106.0663 11.66

175.0587 9.36

Thumbnail
Thumbnail
License
CC BY

4.2.3 Other MS

1 of 3
View All
MS Category
Experimental
MS Type
Other
MS Level
MS2
Precursor Type
[M-H]-
Precursor m/z
346.087
Instrument
Orbitrap
Ionization Mode
negative
Top 5 Peaks

189.066025 100

173.072189 91.61

142.032211 59.55

268.109863 54.77

109.075684 44.98

Thumbnail
Thumbnail
2 of 3
View All
MS Category
Experimental
MS Type
Other
MS Level
MS2
Precursor Type
[2M-H]-
Precursor m/z
693.182
Instrument
Orbitrap
Ionization Mode
negative
Top 5 Peaks

189.066055 100

135.055939 14.35

166.033615 10.92

268.109741 10.69

173.048538 9.91

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4.3 UV Spectra

MAX ABSORPTION: 260 NM (LOG E= 7750)
Budavari, S. (ed.). The Merck Index - Encyclopedia of Chemicals, Drugs and Biologicals. Rahway, NJ: Merck and Co., Inc., 1989., p. 304

4.4 IR Spectra

4.4.1 ATR-IR Spectra

Instrument Name
Bio-Rad FTS
Technique
ATR-Neat (DuraSamplIR II)
Source of Spectrum
Forensic Spectral Research
Source of Sample
Fluka Vetranal, Sigma-Aldrich Inc.
Catalog Number
33989
Lot Number
8168X
Copyright
Copyright © 2009-2024 John Wiley & Sons, Inc. All Rights Reserved.
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4.5 Raman Spectra

Technique
FT-Raman
Source of Spectrum
Forensic Spectral Research
Source of Sample
Fluka Vetranal, Sigma-Aldrich Inc.
Catalog Number
33989
Lot Number
8168X
Copyright
Copyright © 2012-2024 John Wiley & Sons, Inc. All Rights Reserved.
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6 Chemical Vendors

7 Drug and Medication Information

7.1 Drug Indication

Cephalexin is indicated for the treatment of certain infections caused by susceptible bacteria. These infections include respiratory tract infections, otitis media, skin and skin structure infections, bone infections, and genitourinary tract infections.

7.2 Drug Classes

Breast Feeding; Lactation; Milk, Human; Anti-Infective Agents; Antibacterial Agents; Cephalosporins

7.3 WHO Essential Medicines

Drug
Drug Classes
Access group antibiotics
Formulation
(1) Oral - Liquid: 125 mg per 5 mL (anhydrous) powder for oral liquid; 250 mg per 5 mL (anhydrous) powder for oral liquid; (2) Oral - Solid: 250 mg (as monohydrate); (3) Oral - Solid: 250 mg (as monohydrate); 500 mg (as monohydrate); (4) Oral - Solid - dispersible tablet: 125 mg; 250 mg
Indication
(1) Bacterial cellulitis, erysipelas or lymphangitis; (2) Chronic obstructive pulmonary disease with acute exacerbation; (3) Acute pharyngitis; (4) Bacterial infection of unspecified site

7.4 FDA Approved Drugs

7.5 FDA Orange Book

7.6 FDA National Drug Code Directory

7.7 FDA Green Book

7.8 Drug Labels

Drug and label
Active ingredient and drug

7.9 Clinical Trials

7.9.1 ClinicalTrials.gov

7.9.2 EU Clinical Trials Register

7.9.3 NIPH Clinical Trials Search of Japan

7.10 Therapeutic Uses

Cephalosporins
National Library of Medicine's Medical Subject Headings online file (MeSH, 1999)
/CEPHALEXIN/ HAS ANTIBACTERIAL SPECTRUM SIMILAR TO THAT OF PENICILLINS... AGAINST COCCI & GRAM-POSITIVE BACILLI, PENICILLIN G IS USUALLY MORE EFFECTIVE. ...MOST PENICILLINASES DO NOT AFFECT CEPHALEXIN...
Osol, A. and J.E. Hoover, et al. (eds.). Remington's Pharmaceutical Sciences. 15th ed. Easton, Pennsylvania: Mack Publishing Co., 1975., p. 1119
...CEPHALOSPORINS ARE HIGHLY EFFECTIVE IN THERAPY OF VARIETY OF MILD-TO-SEVERE INFECTIONS DUE TO BOTH GRAM-POSITIVE & GRAM-NEGATIVE MICROORGANISMS. /CEPHALOSPORINS/
Gilman, A.G., T.W. Rall, A.S. Nies and P. Taylor (eds.). Goodman and Gilman's The Pharmacological Basis of Therapeutics. 8th ed. New York, NY. Pergamon Press, 1990., p. 1088
...CEPHALOSPORIN IS...DRUG OF 1ST CHOICE...FOR KLEBSIELLA INFECTIONS. ... THEY ARE...VALUABLE SECONDARY AGENTS, & THEY FREQUENTLY APPEAR AS ALTERNATIVE CHOICES TO PENICILLIN. /CEPHALOSPORINS/
Gilman, A.G., T.W. Rall, A.S. Nies and P. Taylor (eds.). Goodman and Gilman's The Pharmacological Basis of Therapeutics. 8th ed. New York, NY. Pergamon Press, 1990., p. 1091
For more Therapeutic Uses (Complete) data for CEPHALEXIN (9 total), please visit the HSDB record page.

7.11 Drug Warnings

PHYSICIAN MUST ALTER EITHER DRUG DOSAGE OR INTERVAL BETWEEN DOSES WHEN RENAL FUNCTION IS IMPAIRED.
Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 1161
CEPHALOSPORINS SHOULD NOT BE USED TO TREAT BACTERIAL MENINGITIS. THIS IS TRUE FOR ALL CAUSATIVE MICROORGANISMS. ...PENETRATION OF CEPHALOSPORINS INTO CSF IS POOR. /CEPHALOSPORINS/
Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 1164
INFECTIONS DUE TO ENTEROCOCCI ARE USUALLY UNAFFECTED BY THESE CMPD... ENTEROCOCCAL ENDOCARDITIS CANNOT BE CURED WITH CEPHALOSPORIN EVEN WHEN IT IS GIVEN CONCURRENTLY WITH GENTAMICIN OR STREPTOMYCIN. /CEPHALOSPORINS/
Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 1163
ENTEROBACTER (AEROBACTER) INFECTIONS ARE, AS A RULE, RESISTANT TO THESE CMPD. /CEPHALOSPORINS/
Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 1163
For more Drug Warnings (Complete) data for CEPHALEXIN (20 total), please visit the HSDB record page.

8 Pharmacology and Biochemistry

8.1 Pharmacodynamics

Cephalexin (also called Cefalexin) is a first generation cephalosporin antibiotic. It is one of the most widely prescribed antibiotics, often used for the treatment of superficial infections that result as complications of minor wounds or lacerations. It is effective against most gram-positive bacteria through its inihibition of the cross linking reaction between N-acetyl muramicacid and N-acetylglucosamine in the cell wall, leading to cell lysis.

8.2 MeSH Pharmacological Classification

Anti-Bacterial Agents
Substances that inhibit the growth or reproduction of BACTERIA. (See all compounds classified as Anti-Bacterial Agents.)

8.3 FDA Pharmacological Classification

1 of 2
FDA UNII
5SFF1W6677
Active Moiety
CEPHALEXIN ANHYDROUS
Pharmacological Classes
Established Pharmacologic Class [EPC] - Cephalosporin Antibacterial
Pharmacological Classes
Chemical Structure [CS] - Cephalosporins
FDA Pharmacology Summary
Cephalexin anhydrous is a Cephalosporin Antibacterial.
2 of 2
Non-Proprietary Name
CEPHALEXIN
Pharmacological Classes
Cephalosporin Antibacterial [EPC]; Cephalosporins [CS]

8.4 ATC Code

S76 | LUXPHARMA | Pharmaceuticals Marketed in Luxembourg | Pharmaceuticals marketed in Luxembourg, as published by d'Gesondheetskeess (CNS, la caisse nationale de sante, www.cns.lu), mapped by name to structures using CompTox by R. Singh et al. (in prep.). List downloaded from https://cns.public.lu/en/legislations/textes-coordonnes/liste-med-comm.html. Dataset DOI:10.5281/zenodo.4587355

J - Antiinfectives for systemic use

J01 - Antibacterials for systemic use

J01D - Other beta-lactam antibacterials

J01DB - First-generation cephalosporins

J01DB01 - Cefalexin

8.5 Absorption, Distribution and Excretion

Absorption
Well absorbed from the upper gastrointestinal tract with nearly 100% oral bioavailability. Cephalexin is not absorbed in the stomach but is absorbed in the upper intestine. Patients taking 250mg of cephalexin reach a maximum plasma concentration of 7.7mcg/mL and patients taking 500mg reach 12.3mcg/mL.
Route of Elimination
Cephalexin is over 90% excreted in the urine after 6 hours by glomerular filtration and tubular secretion with a mean urinary recovery of 99.3%. Cephalexin is unchanged in the urine.
Volume of Distribution
5.2-5.8L.
Clearance
Clearance from one subject was 376mL/min.
LESS THAN 10 TO 15%...IS BOUND TO PLASMA PROTEIN, & PLASMA DRUG CONCN FALL RAPIDLY... MORE THAN 90%...IS EXCRETED UNALTERED IN URINE WITHIN 6 HR, PRIMARILY BY RENAL TUBULAR SECRETION. ...THERAPEUTICALLY EFFECTIVE CONCN ARE STILL ACHIEVED IN URINE OF PT WITH DECR RENAL FUNCTION.
Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 1161
CEPHALEXIN...IS WELL ABSORBED FROM GI TRACT. PEAK PLASMA CONCN, REACHED @ ABOUT 1 HR AFTER INGESTION OF DRUG, ARE APPROX 9 & 18 UG/ML AFTER ORAL DOSES OF 250 & 500 MG, RESPECTIVELY. INGESTION OF FOOD MAY DELAY ABSORPTION.
Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 1161
CEPHALEXIN IS ALSO EXCRETED INTO BILE.
Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 1162
BOTH ABSORPTION & EXCRETION OF CEPHALEXIN ARE IMPAIRED IN NEW-BORN INFANTS, WHERE 24-HR URINARY RECOVERY OF ANTIBIOTIC ACCOUNTED FOR 5-66% OF DAILY ORAL DOSE.
The Chemical Society. Foreign Compound Metabolism in Mammals Volume 3. London: The Chemical Society, 1975., p. 177
For more Absorption, Distribution and Excretion (Complete) data for CEPHALEXIN (14 total), please visit the HSDB record page.

8.6 Metabolism / Metabolites

Cephalexin is not metabolized in the body.

8.7 Biological Half-Life

The half life of cephalexin is 49.5 minutes in a fasted state and 76.5 minutes with food though these times were not significantly different in the study.
LESS THAN 10 TO 15%...IS BOUND TO PLASMA PROTEIN, & PLASMA DRUG CONCN FALL RAPIDLY, T/2 OF CEPHALEXIN NORMALLY BEING ABOUT 40 MIN.
Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 1161
/IN RATS/ RATIOS OF BONE TO SERUM CONCN AVG...1:9 FOR CEPHALEXIN DURING 0.25-4 HR AFTER /ORAL/ DOSING. DESPITE DIFFERENCES IN CONCN; T/2 IN BONE & SERUM WERE SIMILAR.
The Chemical Society. Foreign Compound Metabolism in Mammals. Volume 2: A Review of the Literature Published Between 1970 and 1971. London: The Chemical Society, 1972., p. 452
PEAK TIME, T/2 OF ELIMINATION, T/2 OF ABSORPTION, & VOL OF DISTRIBUTION WERE ALL SIMILAR FOLOWING ADMIN OF EITHER 1 OR 2 G OF CEPHALEXIN.
CHOW M ET AL; J CLIN PHARMACOL 19 (4): 185-94 (1979)
The serum half-life of cephalexin is 0.5-1.2 hr in adults with normal renal function. The serum half-life of the drug is reported to be about 5 hr in neonates and 2.5 hr in children 3-12 mo of age. In one study, the serum half-life was 7.7 hr in adults with creatinine clearances of 9.2 ml/min and 13.9 hr in adults with creatinine clearances of 4 ml/min.
McEvoy, G.K. (ed.). American Hospital Formulary Service - Drug Information 95. Bethesda, MD: American Society of Hospital Pharmacists, Inc., 1995 (Plus Supplements 1995)., p. 166

8.8 Mechanism of Action

Cephalexin is a first generation cephalosporin antibiotic. Cephalosporins contain a beta lactam and dihydrothiazide. Unlike penicillins, cephalosprins are more resistant to the action of beta lactamase. Cephalexin inhibits bacterial cell wall synthesis, leading breakdown and eventualy cell death.
CEPHALOTHIN & ITS CONGENERS INHIBIT BACTERIAL CELL-WALL SYNTHESIS IN MANNER SIMILAR TO THAT OF PENICILLIN. /CEPHALOSPORINS/
Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 1160
The penicillins and their metabolites are potent immunogens because of their ability to combine with proteins and act as haptens for acute antibody-mediated reactions. The most frequent (about 95 percent) or "major" determinant of penicillin allergy is the penicilloyl determinant produced by opening the beta-lactam ring of the penicillin. This allows linkage of the penicillin to protein at the amide group. "Minor" determinants (less frequent) are the other metabolites formed, including native penicillin and penicilloic acids. /Penicillins/
Haddad, L.M., Clinical Management of Poisoning and Drug Overdose. 2nd ed. Philadelphia, PA: W.B. Saunders Co., 1990., p. 953
Bactericidal; action depends on ability to reach and bind penicillin-binding proteins located in bacterial cytoplasmic membranes; cephalosporins inhibit bacterial septum and cell wall synthesis, probably by acylation of membrane-bound transpeptidase enzymes. This prevents cross-linkage of peptidoglycan chains, which is necessary for bacterial cell wall strength and rigidity. Also, cell division and growth are inhibited, and lysis and elongation of susceptible bacteria frequently occur. Rapidly dividing bacteria are those most susceptible to the action of cephalosporins. /Cephalosporins/
USP Convention. USPDI - Drug Information for the Health Care Professional. 15 th ed. Volume 1. Rockville, MD: United States Pharmacopeial Convention, Inc., 1995. (Plus updates.), p. 679
CEPHALOSPORIN C IS VERY RESISTANT TO ACTION OF PENICILLINASE, FOR WHICH IT IS BOTH COMPETITIVE & NONCOMPETITIVE INHIBITOR, DEPENDING ON SUBSTRATE TESTED... /CEPHALOSPORINS/
Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 1160

8.9 Human Metabolite Information

8.9.1 Cellular Locations

  • Extracellular
  • Membrane

9 Use and Manufacturing

9.1 Uses

EPA CPDat Chemical and Product Categories
The Chemical and Products Database, a resource for exposure-relevant data on chemicals in consumer products, Scientific Data, volume 5, Article number: 180125 (2018), DOI:10.1038/sdata.2018.125
ANTIBIOTIC FOR INFECTIONS OF THE RESPIRATORY & GENITOURINARY TRACTS & OF THE SKIN, EYE, & BONE; ANTIBIOTIC FOR VETERINARY USE
SRI
MEDICATION
MEDICATION (VET):

Use (kg; approx.) in Germany (2009): >1000

Use (kg; exact) in Germany (2009): 2020

Use (kg) in USA (2002): 148000

Consumption (g per capita; approx.) in Germany (2009): 0.0122

Consumption (g per capita; exact) in Germany (2009): 0.0247

Consumption (g per capita) in the USA (2002): 0.525

Excretion rate: 0.8

Calculated removal (%): 22

9.1.1 Use Classification

Animal Drugs -> FDA Approved Animal Drug Products (Green Book) -> Active Ingredients
Human Drugs -> FDA Approved Drug Products with Therapeutic Equivalence Evaluations (Orange Book) -> Active Ingredients
Pharmaceuticals -> Animal Drugs -> Approved in Taiwan
S72 | NTUPHTW | Pharmaceutically Active Substances from National Taiwan University | DOI:10.5281/zenodo.3955664

9.2 Methods of Manufacturing

ACYLATION OF 7-AMINO-3-METHYL-8-OXO-5-THIA-1-AZABICYCLO[4.2.0]OCT-2-ENE-2-CARBOXYLIC ACID (PREPARED FROM CEPHALOSPORIN C) WITH 2-PHENYLGLYCINE IN AN APPROPRIATE DEHYDRATING ENVIRONMENT
SRI
7-AMINO-3-METHYL-8-OXO-5-THIA-1-AZABICYCLO[4.2.0]OCT-2-ENE-2-CARBOXYLIC ACID, WHICH MAY BE PREPD FROM NATURAL ANTIBIOTIC CEPHALOSPORIN C, IS ACYLATED WITH 2-PHENYLGLYCINE IN APPROPRIATE DEHYDRATING ENVIRONMENT.
Osol, A. and J.E. Hoover, et al. (eds.). Remington's Pharmaceutical Sciences. 15th ed. Easton, Pennsylvania: Mack Publishing Co., 1975., p. 1119

9.3 Formulations / Preparations

CEPHALEXIN, USP (KEFLEX), IS MARKETED AS MONOHYDRATE IN SEVERAL FORMS, INCL CAPSULES OF 250 & 500 MG, ORAL SUSPENSIONS PROVIDING, AFTER RECONSTITUTION, 125 MG/5 ML OR 250 MG/5 ML, & PEDIATRIC DROPS, 100 MG/ML.
Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 1162

9.4 Consumption Patterns

ESSENTIALLY 100% AS AN ANTIBIOTIC
SRI

9.5 U.S. Production

(1977) PROBABLY GREATER THAN 4.54X10+5 GRAMS
SRI
(1979) PROBABLY GREATER THAN 4.54X10+5 GRAMS
SRI

9.6 U.S. Imports

(1979) 2.04X10+7 GRAMS (PRINCPL CUSTMS DISTS)
SRI

9.7 General Manufacturing Information

RYAN, ET AL, J MED CHEM 12, 310 (1969); MORIN, JACKSON, US PATENT 3,275,626 (1966 TO LILLY)
Budavari, S. (ed.). The Merck Index - Encyclopedia of Chemicals, Drugs and Biologicals. Rahway, NJ: Merck and Co., Inc., 1989., p. 304
.../CEPHALEXIN/ SEMISYNTHETIC DERIVATIVE OF CEPHALOSPORIN C.
Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 1159

10 Identification

10.1 Analytic Laboratory Methods

FLUOROMETRIC ANALYSIS OF CEPHALOSPORIN ANTIBIOTICS.
YU ABC ET AL; J PHARM SCI 66 (FEB): 213-6 (1977)

10.2 Clinical Laboratory Methods

HIGH SPEED CHROMATOGRAPHIC DETERMINATION OF CEPHALEXIN IN HUMAN PLASMA & URINE.
NAKAGAWA T ET AL; J ANTIBIOT 31 (8): 769-75 (1978)
A rapid, simple, and accurate spectrophotometric method was developed and used for the analysis of cephalexin or cephradinein the urine of volunteers who ingested the drugs.
Abdel-Hamid ME et al; J Clin Pharm Ther 17 (2): 91-5 (1992)

11 Safety and Hazards

11.1 Hazards Identification

11.1.1 GHS Classification

1 of 2
View All
Pictogram(s)
Irritant
Health Hazard
Signal
Danger
GHS Hazard Statements

H317 (100%): May cause an allergic skin reaction [Warning Sensitization, Skin]

H334 (100%): May cause allergy or asthma symptoms or breathing difficulties if inhaled [Danger Sensitization, respiratory]

Precautionary Statement Codes

P233, P260, P261, P271, P272, P280, P284, P302+P352, P304+P340, P321, P333+P317, P342+P316, P362+P364, P403, and P501

(The corresponding statement to each P-code can be found at the GHS Classification page.)

ECHA C&L Notifications Summary

Aggregated GHS information provided per 75 reports by companies from 5 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown.

11.1.2 Hazard Classes and Categories

Skin Sens. 1 (100%)

Resp. Sens. 1 (100%)

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

Cephalexin capsules, tablets, and powder for oral suspension should be stored in tight containers at a temperature less than 40 °C, preferably between 15-30 °C. After reconstitution, cephalexin oral suspensions should be stored at 2-8 °C and discarded if not used within 2 wk.
McEvoy, G.K. (ed.). American Hospital Formulary Service - Drug Information 95. Bethesda, MD: American Society of Hospital Pharmacists, Inc., 1995 (Plus Supplements 1995)., p. 165

11.4 Regulatory Information

New Zealand EPA Inventory of Chemical Status
5-Thia-1-azabicyclo4.2.0oct-2-ene-2-carboxylic acid, 7-(2R)-aminophenylacetylamino-3-methyl-8-oxo-, (6R,7R)-: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right.
New Zealand EPA Inventory of Chemical Status
Cephalexin: Does not have an individual approval but may be used under an appropriate group standard

11.4.1 FDA Requirements

Manufacturers, packers, and distributors of drug and drug products for human use are responsible for complying with the labeling, certification, and usage requirements as prescribed by the Federal Food, Drug, and Cosmetic Act, as amended (secs 201-902, 52 Stat. 1040 et seq., as amended; 21 U.S.C. 321-392).
21 CFR 200-299, 300-499, 820, and 860 (4/1/93)

11.5 Other Safety Information

Chemical Assessment

IMAP assessments - 5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, 7-[(aminophenylacetyl)amino]-3-methyl-8-oxo-, [6R-[6.alpha.,7.beta.(R*)]]-: Human health tier I assessment

IMAP assessments - 5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, 7-[(aminophenylacetyl)amino]-3-methyl-8-oxo-, [6R-[6.alpha.,7.beta.(R*)]]-: Environment tier I assessment

12 Toxicity

12.1 Toxicological Information

12.1.1 Drug Induced Liver Injury

Compound
cephalexin
DILI Annotation
Less-DILI-Concern
Severity Grade
4
Label Section
Adverse reactions
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

12.1.2 Effects During Pregnancy and Lactation

◉ Summary of Use during Lactation

Limited information indicates that maternal cephalexin produces low levels in milk that are usually not expected to cause adverse effects in breastfed infants. Cephalexin is an alternative for the treatment of mastitis. Occasionally disruption of the infant's gastrointestinal flora, resulting in diarrhea or thrush have been reported with cephalosporins, but these effects have not been adequately evaluated. A rare case of a severe allergic reaction occurred in an infant previously exposed to intravenous cefazolin whose mother began taking cephalexin while breastfeeding. Cephalexin is acceptable in nursing mothers.

◉ Effects in Breastfed Infants

In a prospective follow-up study, 7 nursing mothers reported taking cephalexin (dosage not specified). Two mothers reported diarrhea in their infants. No rashes or candidiasis were reported among the exposed infants.

A prospective, controlled study asked mothers who called an information service about adverse reactions experience by their breastfed infants. One of 11 cephalexin-exposed infants reportedly developed diarrhea during maternal cephalexin therapy.

A woman received intravenous cephalothin 1 g every 6 hours for 3 days. Her breastfed infant had a green liquid stool, severe diarrhea, discomfort and crying. The mother's drug regimen was then changed to oral cephalexin 500 mg plus oral probenecid 500 mg 4 times daily for another 16 days. The infant continued to have diarrhea during this time. The authors rated the diarrhea as probably related to cephalexin in milk.

A 4-month-old infant was treated with intravenous cefazolin for a urinary tract infection. Nine days after being discharged and cefazolin discontinuation, the infant developed a blistering rash over most of the body that was diagnosed as toxic epidermal necrolysis (TEN). The infant was being breastfed (extent unspecified) by his mother who had begun cephalexin 2 days prior to the onset of symptoms. A lymphocyte transformation test performed 4 weeks after treatment for TEN was completed found sensitization to both cefazolin and cephalexin. The infant's reaction was probably caused by cephalexin in breastmilk after initial sensitization and subsequent cross-reaction to cefazolin.

◉ Effects on Lactation and Breastmilk

Relevant published information was not found as of the revision date.

◈ What is cephalexin?

Cephalexin is an antibiotic medication that has been used to treat infections such as Staphylococcus aureus (Staph) and Escherichia coli (E. coli). Some brand names for cephalexin are Keflex® and Keftab®.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.Having certain infections (such as a Staph or E. coli infection )during pregnancy can increase the chance for pregnancy-related problems or infections in a newborn baby. MotherToBaby has fact sheets on Staph and E. coli infections here: https://mothertobaby.org/fact-sheets/staphylococcus-aureus-pregnancy/ and https://mothertobaby.org/fact-sheets/e-coli-pregnancy/.

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

Studies have not been done in humans to see if cephalexin can make it harder to get pregnant. In animal studies, cephalexin did not affect fertility (ability to get pregnant).

◈ Does taking cephalexin increase the chance of miscarriage?

Miscarriage is common and can occur in any pregnancy for many different reasons. In a study of 262 people who took cephalexin during pregnancy, there was no increase in miscarriages compared to a similar group of people who did not take cephalexin.

◈ Does taking cephalexin 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. Information on the use of cephalexin in pregnancy is limited. In a study of 262 people who took cephalexin during pregnancy, there was no increased chance for birth defects above the background risk.

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

Studies have not been done to see if cephalexin increases the chance for 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 cephalexin in pregnancy affect future behavior or learning for the child?

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

◈ Breastfeeding while taking cephalexin:

Cephalexin gets into breast milk in small amounts. In reports of 20 babies exposed to cephalexin through breast milk, 4 had diarrhea. There is one report of a baby getting a rash after being breastfed, due to a sensitivity to cephalexin. If you suspect the baby has any symptoms (such as diarrhea or rash), contact the child’s healthcare provider. Be sure to talk to your healthcare provider about all your breastfeeding questions.

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

Studies have not been done to see if cephalexin could affect male fertility (ability to get partner pregnant) or increase the chance of birth defects above the background risk. Some infections, such as Staph or E.coli, might affect male fertility. 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/.

12.1.3 Acute Effects

12.1.4 Interactions

PROBENECID IS EFFECTIVE IN SLOWING URINARY CLEARANCE & ENHANCING DURATION OF SYSTEMIC ANTIMICROBIAL ACTIVITY /OF CEPHALEXIN/.
Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 1161
...CEPHALOSPORINS...MAY BE AFFECTED BY CONCURRENT USE OF...SULFINPYRAZONE. DIMINISHED TUBULAR SECRETION...RESULT IN HIGHER & MORE SUSTAINED SERUM LEVELS & HENCE, INTENSIFICATION OF DRUG ACTIVITY. /CEPHALOSPORINS/
Evaluations of Drug Interactions. 2nd ed. and supplements. Washington, DC: American Pharmaceutical Assn., 1976, 1978., p. 392
FUROSEMIDE MAY ENHANCE NEPHROTOXICITY OF CEPHALOSPORINS. /CEPHALOSPORINS/
Evaluations of Drug Interactions. 2nd ed. and supplements. Washington, DC: American Pharmaceutical Assn., 1976, 1978., p. 391
Hypoprothrombinemia induced by large doses of salicylates and/or cephalosporins, and the gastrointestinal ulcerative or hemorrhagic potential of nonsteroidal anti-inflammatory drugs (NSAIDs), salicylates, or sulfinpyrazone may increase the risk of hemorrhage. /Cephalosporins/
USP Convention. USPDI - Drug Information for the Health Care Professional. 15 th ed. Volume 1. Rockville, MD: United States Pharmacopeial Convention, Inc., 1995. (Plus updates.), p. 680
For more Interactions (Complete) data for CEPHALEXIN (6 total), please visit the HSDB record page.

12.1.5 Antidote and Emergency Treatment

CEPHALEXIN IS EFFICIENTLY REMOVED FROM CIRCULATION BY HEMODIALYSIS OR PERITONEAL DIALYSIS.
Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 1162

12.1.6 Human Toxicity Excerpts

NEUROTOXICITY, SUCH AS HEADACHE, TINNITUS, ATAXIA, & DIPLOPIA, SOMETIMES DEVELOP; THESE EFFECTS ARE REVERSIBLE. CHANGES IN INTESTINAL & VAGINAL FLORA MAY OCCUR; MONILIASIS IS OCCASIONAL, & OVER GROWTH BY PS AERUGINOSA HAS BEEN REPORTED.
Osol, A. and J.E. Hoover, et al. (eds.). Remington's Pharmaceutical Sciences. 15th ed. Easton, Pennsylvania: Mack Publishing Co., 1975., p. 1120
ABOUT 5% OF PATIENTS RECEIVING...SEMISYNTHETIC CEPHALOSPORINS DEVELOP HYPERSENSITIVITY REACTIONS, INCL FEVER, EOSINOPHILIA, SERUM SICKNESS, URTICARIAL OR MORBILLIFORM RASHES, OR ANAPHYLAXIS. TRANSIENT NEUTROPENIA HAS BEEN OBSERVED... /CEPHALOSPORINS/
Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 1162
...CEPHALEXIN, ORALLY ADMIN CEPHALOSPORINS, OCCASIONALLY PRODUCE NAUSEA, VOMITING, & DIARRHEA.
Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 1163
DIRECT POSITIVE COOMBS REACTION IS FREQUENTLY (40%) NOTED WHEN LARGE DOSES OF...CEPHALOSPORINS ARE ADMIN OR WHEN CONVENTIONAL DOSES ARE GIVEN IN PRESENCE OF RENAL DYSFUNCTION. /CEPHALOSPORINS/
Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 1162
For more Human Toxicity Excerpts (Complete) data for CEPHALEXIN (35 total), please visit the HSDB record page.

12.1.7 Non-Human Toxicity Values

LD50 MOUSE ORAL 1.6-4.5 G/KG /MONOHYDRATE/
The Merck Index. 9th ed. Rahway, New Jersey: Merck & Co., Inc., 1976., p. 248
LD50 MOUSE INTRAPERITONEAL 0.4-1.3 G/KG /MONOHYDRATE/
The Merck Index. 9th ed. Rahway, New Jersey: Merck & Co., Inc., 1976., p. 248
LD50 RAT ORAL GREATER THAN 5.0 G/KG /MONOHYDRATE/
The Merck Index. 9th ed. Rahway, New Jersey: Merck & Co., Inc., 1976., p. 248
LD50 RAT INTRAPERITONEAL GREATER THAN 3.7 G/KG /MONOHYDRATE/
The Merck Index. 9th ed. Rahway, New Jersey: Merck & Co., Inc., 1976., p. 248

12.1.8 Protein Binding

Cephalexin is 10-15% bound to serum proteins including serum albumin.

13 Associated Disorders and Diseases

14 Literature

14.1 Consolidated References

14.2 NLM Curated PubMed Citations

14.3 Springer Nature References

14.4 Thieme References

14.5 Wiley References

14.6 Chemical Co-Occurrences in Literature

14.7 Chemical-Gene Co-Occurrences in Literature

14.8 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

Take with or without food.

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: Drug

19.5 KEGG: USP

19.6 KEGG: ATC

19.7 KEGG: JP15

19.8 KEGG: Drug Groups

19.9 KEGG : Antimicrobials

19.10 KEGG: Drug Classes

19.11 WHO ATC Classification System

19.12 FDA Pharm Classes

19.13 ChemIDplus

19.14 ChEMBL Target Tree

19.15 UN GHS Classification

19.16 EPA CPDat Classification

19.17 NORMAN Suspect List Exchange Classification

19.18 CCSBase Classification

19.19 EPA DSSTox Classification

19.20 LOTUS Tree

19.21 MolGenie Organic Chemistry Ontology

20 Information Sources

  1. Australian Industrial Chemicals Introduction Scheme (AICIS)
    5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, 7-[(aminophenylacetyl)amino]-3-methyl-8-oxo-, [6R-[6.alpha.,7.beta.(R*)]]-
    https://services.industrialchemicals.gov.au/search-assessments/
  2. CAS Common Chemistry
    LICENSE
    The data from CAS Common Chemistry is provided under a CC-BY-NC 4.0 license, unless otherwise stated.
    https://creativecommons.org/licenses/by-nc/4.0/
  3. ChemIDplus
    ChemIDplus Chemical Information Classification
    https://pubchem.ncbi.nlm.nih.gov/source/ChemIDplus
  4. DrugBank
    LICENSE
    Creative Common's Attribution-NonCommercial 4.0 International License (http://creativecommons.org/licenses/by-nc/4.0/legalcode)
    https://www.drugbank.ca/legal/terms_of_use
  5. EPA DSSTox
    CompTox Chemicals Dashboard Chemical Lists
    https://comptox.epa.gov/dashboard/chemical-lists/
  6. 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
    Cephalexin hydrate
    https://echa.europa.eu
  7. FDA Global Substance Registration System (GSRS)
    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
  8. Hazardous Substances Data Bank (HSDB)
  9. Human Metabolome Database (HMDB)
    LICENSE
    HMDB is offered to the public as a freely available resource. Use and re-distribution of the data, in whole or in part, for commercial purposes requires explicit permission of the authors and explicit acknowledgment of the source material (HMDB) and the original publication (see the HMDB citing page). We ask that users who download significant portions of the database cite the HMDB paper in any resulting publications.
    http://www.hmdb.ca/citing
  10. New Zealand Environmental Protection Authority (EPA)
    LICENSE
    This work is licensed under the Creative Commons Attribution-ShareAlike 4.0 International licence.
    https://www.epa.govt.nz/about-this-site/general-copyright-statement/
    5-Thia-1-azabicyclo4.2.0oct-2-ene-2-carboxylic acid, 7-(2R)-aminophenylacetylamino-3-methyl-8-oxo-, (6R,7R)-
    https://www.epa.govt.nz/industry-areas/hazardous-substances/guidance-for-importers-and-manufacturers/hazardous-substances-databases/
  11. CCSbase
    CCSbase Classification
    https://ccsbase.net/
  12. 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/
    Cefalexin
    NORMAN Suspect List Exchange Classification
    https://www.norman-network.com/nds/SLE/
  13. ChEBI
  14. FDA Pharm Classes
    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
  15. LOTUS - the natural products occurrence database
    LICENSE
    The code for LOTUS is released under the GNU General Public License v3.0.
    https://lotus.nprod.net/
  16. NCI Thesaurus (NCIt)
    LICENSE
    Unless otherwise indicated, all text within NCI products is free of copyright and may be reused without our permission. Credit the National Cancer Institute as the source.
    https://www.cancer.gov/policies/copyright-reuse
  17. Open Targets
    LICENSE
    Datasets generated by the Open Targets Platform are freely available for download.
    https://platform-docs.opentargets.org/licence
  18. 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
  19. ClinicalTrials.gov
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    https://clinicaltrials.gov/ct2/about-site/terms-conditions#Use
  20. Comparative Toxicogenomics Database (CTD)
    LICENSE
    It is to be used only for research and educational purposes. Any reproduction or use for commercial purpose is prohibited without the prior express written permission of NC State University.
    http://ctdbase.org/about/legal.jsp
  21. Drug Gene Interaction database (DGIdb)
    LICENSE
    The data used in DGIdb is all open access and where possible made available as raw data dumps in the downloads section.
    http://www.dgidb.org/downloads
  22. Therapeutic Target Database (TTD)
  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. WHO Model Lists of Essential Medicines
    LICENSE
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    https://www.who.int/about/policies/publishing/copyright
  29. EPA Chemical and Products Database (CPDat)
  30. EU Clinical Trials Register
  31. FDA Approved Animal Drug Products (Green Book)
    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
  32. FDA Orange Book
    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
  33. National Drug Code (NDC) Directory
    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
  34. Japan Chemical Substance Dictionary (Nikkaji)
  35. 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
    Therapeutic category of drugs in Japan
    http://www.genome.jp/kegg-bin/get_htext?br08301.keg
    Anatomical Therapeutic Chemical (ATC) classification
    http://www.genome.jp/kegg-bin/get_htext?br08303.keg
    Drugs listed in the Japanese Pharmacopoeia
    http://www.genome.jp/kegg-bin/get_htext?br08311.keg
  36. Natural Product Activity and Species Source (NPASS)
  37. MassBank Europe
  38. 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
  39. Metabolomics Workbench
  40. NIPH Clinical Trials Search of Japan
  41. 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
  42. NMRShiftDB
  43. 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/
  44. 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
  45. SpectraBase
  46. Springer Nature
  47. Thieme Chemistry
    LICENSE
    The Thieme Chemistry contribution within PubChem is provided under a CC-BY-NC-ND 4.0 license, unless otherwise stated.
    https://creativecommons.org/licenses/by-nc-nd/4.0/
  48. Wikidata
  49. Wikipedia
  50. Wiley
  51. 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
  52. PubChem
  53. GHS Classification (UNECE)
  54. MolGenie
    MolGenie Organic Chemistry Ontology
    https://github.com/MolGenie/ontology/
  55. PATENTSCOPE (WIPO)
  56. NCBI
CONTENTS