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Cefotaxime

PubChem CID
5742673
Structure
Cefotaxime_small.png
Cefotaxime_3D_Structure.png
Molecular Formula
Synonyms
  • cefotaxime
  • Cephotaxime
  • 63527-52-6
  • Cefotaxima
  • Cefotaximum
Molecular Weight
455.5 g/mol
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Dates
  • Create:
    2005-08-01
  • Modify:
    2025-01-18
Description
Cefotaxime is a cephalosporin compound having acetoxymethyl and [2-(2-amino-1,3-thiazol-4-yl)-2-(methoxyimino)acetyl]amino side groups. It has a role as a drug allergen and an antibacterial drug. It is a member of 1,3-thiazoles, an oxime O-ether and a cephalosporin. It is a conjugate acid of a cefotaxime(1-).
Cefotaxime is a third-generation cephalosporin antibiotic. Like other third-generation cephalosporins, it has broad spectrum activity against Gram positive and Gram negative bacteria. In most cases, it is considered to be equivalent to ceftriaxone in terms of safety and efficacy. Cefotaxime sodium is marketed under various trade names including Claforan (Sanofi-Aventis).
Cefotaxime is a Cephalosporin Antibacterial.
See also: Cefotaxime Sodium (has salt form).

1 Structures

1.1 2D Structure

Chemical Structure Depiction
Cefotaxime.png

1.2 3D Conformer

2 Names and Identifiers

2.1 Computed Descriptors

2.1.1 IUPAC Name

(6R,7R)-3-(acetyloxymethyl)-7-[[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-methoxyiminoacetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
Computed by Lexichem TK 2.7.0 (PubChem release 2021.10.14)

2.1.2 InChI

InChI=1S/C16H17N5O7S2/c1-6(22)28-3-7-4-29-14-10(13(24)21(14)11(7)15(25)26)19-12(23)9(20-27-2)8-5-30-16(17)18-8/h5,10,14H,3-4H2,1-2H3,(H2,17,18)(H,19,23)(H,25,26)/b20-9-/t10-,14-/m1/s1
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.3 InChIKey

GPRBEKHLDVQUJE-QSWIMTSFSA-N
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.4 SMILES

CC(=O)OCC1=C(N2[C@@H]([C@@H](C2=O)NC(=O)/C(=N\OC)/C3=CSC(=N3)N)SC1)C(=O)O
Computed by OEChem 2.3.0 (PubChem release 2024.12.12)

2.2 Molecular Formula

C16H17N5O7S2
Computed by PubChem 2.2 (PubChem release 2021.10.14)

2.3 Other Identifiers

2.3.1 CAS

60846-21-1
63527-53-7

2.3.3 Deprecated CAS

69738-42-7

2.3.4 European Community (EC) Number

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 Pharos Ligand ID

2.3.16 RXCUI

2.3.17 Wikidata

2.3.18 Wikipedia

2.4 Synonyms

2.4.1 MeSH Entry Terms

  • Benaxima
  • Biosint
  • Cefotaxim
  • Cefotaxime
  • Cefotaxime Sodium
  • Cefradil
  • Cephotaxim
  • Claforan
  • Fotexina
  • HR 756
  • HR-756
  • HR756
  • Kendrick
  • Klaforan
  • Primafen
  • Ru 24756
  • Ru-24756
  • Ru24756
  • Sodium, Cefotaxime
  • Taporin

2.4.2 Depositor-Supplied Synonyms

3 Chemical and Physical Properties

3.1 Computed Properties

Property Name
Molecular Weight
Property Value
455.5 g/mol
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
XLogP3
Property Value
-1.4
Reference
Computed by XLogP3 3.0 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Donor Count
Property Value
3
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Acceptor Count
Property Value
12
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Rotatable Bond Count
Property Value
8
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Exact Mass
Property Value
455.05694025 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Monoisotopic Mass
Property Value
455.05694025 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Topological Polar Surface Area
Property Value
227 Ų
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Heavy Atom Count
Property Value
30
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
833
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Isotope Atom Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Atom Stereocenter Count
Property Value
2
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
1
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 Solubility

Soluble
1.46e-01 g/L

3.2.3 LogP

-0.5
-0.5

3.3 Chemical Classes

3.3.1 Drugs

Pharmaceuticals -> Antibiotics
S6 | ITNANTIBIOTIC | Antibiotic List from the ITN MSCA ANSWER | DOI:10.5281/zenodo.2621956
S57 | GREEKPHARMA | Suspect Pharmaceuticals from the National Organization of Medicine, Greece | DOI:10.5281/zenodo.3248883
3.3.1.1 Human Drugs
Breast Feeding; Lactation; Milk, Human; Anti-Infective Agents; Antibacterial Agents; Cephalosporins
Human drug -> Discontinued
Watch group antibiotics

5 Chemical Vendors

6 Drug and Medication Information

6.1 Drug Indication

Used to treat gonorrhoea, meningitis, and severe infections including infections of the kidney (pyelonephritis) and urinary system. Also used before an operation to prevent infection after surgery.

6.2 Drug Classes

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

6.3 WHO Essential Medicines

Drug
Drug Classes
Watch group antibiotics
Formulation
(1) Parenteral - General injections - unspecified: 250 mg in vial powder for injection (as sodium salt); (2) Parenteral - General injections - unspecified: 250 mg in vial powder for injection (as sodium salt); 500 mg in vial powder for injection (as sodium salt); 1 g in vial powder for injection (as sodium salt); 2 g in vial powder for injection (as sodium salt)
Indication
(1) Bacterial meningitis; (2) Acute pyelonephritis (severe) [co-prescribed with amikacin]; (3) Inflammatory and other diseases of prostate (severe) [co-prescribed with amikacin]; (4) Bacterial pneumonia (Community-acquired pneumonia - severe) [children]; (5) Bacterial pneumonia (Community-acquired pneumonia - severe) [co-prescribed with clarithromycin]; (6) Other specified pneumonia (Hospital-acquired pneumonia); (7) Peritoneal abscess (mild-moderate) [co-prescribed with metronidazole]; (8) Peritoneal abscess (severe) [co-prescribed with metronidazole]; (9) Peritonitis (mild-moderate) [co-prescribed with metronidazole]; (10) Peritonitis (severe) [co-prescribed with metronidazole]; (11) Sepsis without septic shock; (12) Acute pyelonephritis (mild to moderate); (13) Inflammatory and other diseases of prostate (mild to moderate); (14) Bacterial infection of joint; (15) Osteomyelitis or osteitis; (16) Bacterial infection of unspecified site

6.4 FDA National Drug Code Directory

6.5 Drug Labels

Drug and label

6.6 Clinical Trials

6.6.1 ClinicalTrials.gov

6.6.2 EU Clinical Trials Register

7 Pharmacology and Biochemistry

7.1 Pharmacodynamics

Cefotaxime is a third generation intravenous cephalosporin antibiotic. It has broad spectrum activity against Gram positive and Gram negative bacteria. It does not have activity against Pseudomonas aeruginosa. Cefotaxime works by inhibiting bacterial cell wall biosynthesis. A positive feature of cefotaxime is that it display a resistance to penicillinases and is useful to treat infections that are resistant to penicillin derivatives.

7.2 MeSH Pharmacological Classification

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

7.3 FDA Pharmacological Classification

1 of 2
FDA UNII
N2GI8B1GK7
Active Moiety
CEFOTAXIME
Pharmacological Classes
Established Pharmacologic Class [EPC] - Cephalosporin Antibacterial
Pharmacological Classes
Chemical Structure [CS] - Cephalosporins
FDA Pharmacology Summary
Cefotaxime is a Cephalosporin Antibacterial.
2 of 2
Non-Proprietary Name
CEFOTAXIME
Pharmacological Classes
Cephalosporins [CS]; Cephalosporin Antibacterial [EPC]

7.4 ATC Code

J - Antiinfectives for systemic use

J01 - Antibacterials for systemic use

J01D - Other beta-lactam antibacterials

J01DD - Third-generation cephalosporins

J01DD01 - Cefotaxime

J01DD01

7.5 Absorption, Distribution and Excretion

Absorption
Rapidly absorbed following intramuscular injection.
Route of Elimination
Approximately 20-36% of an intravenously administered dose of 14C-cefotaxime is excreted by the kidney as unchanged cefotaxime and 15-25% as the desacetyl derivative, the major metabolite.

7.6 Metabolism / Metabolites

Approximately 20-36% of an intravenously administered dose of 14C-cefotaxime is excreted by the kidney as unchanged cefotaxime and 15-25% as the desacetyl derivative, the major metabolite. The desacetyl metabolite has been shown to contribute to the bactericidal activity. Two other urinary metabolites (M2 and M3) account for about 20-25%. They lack bactericidal activity.

7.7 Biological Half-Life

Approximately 1 hour.

7.8 Mechanism of Action

The bactericidal activity of cefotaxime results from the inhibition of cell wall synthesis via affinity for penicillin-binding proteins (PBPs). Cefotaxime shows high affinity for penicillin-binding proteins in the cell wall including PBP Ib and PBP III.

7.9 Human Metabolite Information

7.9.1 Cellular Locations

Membrane

8 Use and Manufacturing

8.1 Uses

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

Use (kg; exact) in Germany (2009): 2035

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

Consumption (g per capita; exact) in Germany (2009): 0.0249

Excretion rate: 0.51

Calculated removal (%): 22

9 Safety and Hazards

9.1 Hazards Identification

9.1.1 GHS Classification

Pictogram(s)
Irritant
Health Hazard
Signal
Danger
GHS Hazard Statements

H315 (58.8%): Causes skin irritation [Warning Skin corrosion/irritation]

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

H319 (58.8%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]

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

H335 (58.8%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]

Precautionary Statement Codes

P233, P260, P261, P264, P264+P265, P271, P272, P280, P284, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P333+P317, P337+P317, P342+P316, P362+P364, P403, P403+P233, P405, 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 17 reports by companies from 4 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.

9.1.2 Hazard Classes and Categories

Skin Irrit. 2 (58.8%)

Skin Sens. 1 (100%)

Eye Irrit. 2 (58.8%)

Resp. Sens. 1 (100%)

STOT SE 3 (58.8%)

9.2 Regulatory Information

REACH Registered Substance

10 Toxicity

10.1 Toxicological Information

10.1.1 Drug Induced Liver Injury

Compound
cefotaxime
DILI Annotation
Less-DILI-Concern
Severity Grade
5
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

10.1.2 Effects During Pregnancy and Lactation

◉ Summary of Use during Lactation

Cefotaxime is no longer marketed in the United States. Limited information indicates that cefotaxime produces low levels in milk that are not expected to cause adverse effects in breastfed infants. 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. Cefotaxime is acceptable in nursing mothers.

◉ Effects in Breastfed Infants

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

◉ Effects on Lactation and Breastmilk

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

11 Associated Disorders and Diseases

12 Literature

12.1 Consolidated References

12.2 NLM Curated PubMed Citations

12.3 Springer Nature References

12.4 Thieme References

12.5 Chemical Co-Occurrences in Literature

12.6 Chemical-Gene Co-Occurrences in Literature

12.7 Chemical-Disease Co-Occurrences in Literature

13 Patents

13.1 Depositor-Supplied Patent Identifiers

13.2 WIPO PATENTSCOPE

13.3 Chemical Co-Occurrences in Patents

13.4 Chemical-Disease Co-Occurrences in Patents

13.5 Chemical-Gene Co-Occurrences in Patents

14 Interactions and Pathways

14.1 Protein Bound 3D Structures

14.1.1 Ligands from Protein Bound 3D Structures

PDBe Ligand Code
PDBe Structure Code
PDBe Conformer

14.2 Chemical-Target Interactions

14.3 Drug-Drug Interactions

15 Biological Test Results

15.1 BioAssay Results

16 Taxonomy

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

17 Classification

17.1 MeSH Tree

17.2 NCI Thesaurus Tree

17.3 ChEBI Ontology

17.4 KEGG: ATC

17.5 KEGG: Drug Groups

17.6 KEGG : Antimicrobials

17.7 WHO ATC Classification System

17.8 FDA Pharm Classes

17.9 ChemIDplus

17.10 ChEMBL Target Tree

17.11 UN GHS Classification

17.12 NORMAN Suspect List Exchange Classification

17.13 EPA DSSTox Classification

17.14 LOTUS Tree

17.15 MolGenie Organic Chemistry Ontology

18 Information Sources

  1. 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/
  2. ChemIDplus
    3-(Acetyloxymethyl)-7-(((2E)-2-(2-amino-1,3-thiazol-4-yl)-2-methoxyimino-acetyl)amino)-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid
    https://pubchem.ncbi.nlm.nih.gov/substance/?source=chemidplus&sourceid=0060846211
    ChemIDplus Chemical Information Classification
    https://pubchem.ncbi.nlm.nih.gov/source/ChemIDplus
  3. DrugBank
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    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
  4. EPA DSSTox
    (6R,7R)-3-[(Acetyloxy)methyl]-7-[[(2E)-2-(2-amino-4-thiazolyl)-2-(methoxyimino)acetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
    https://comptox.epa.gov/dashboard/DTXSID501100149
    CompTox Chemicals Dashboard Chemical Lists
    https://comptox.epa.gov/dashboard/chemical-lists/
  5. European Chemicals Agency (ECHA)
    LICENSE
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    https://echa.europa.eu/web/guest/legal-notice
  6. FDA Global Substance Registration System (GSRS)
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    https://www.fda.gov/about-fda/about-website/website-policies#linking
  7. Human Metabolome Database (HMDB)
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    http://www.hmdb.ca/citing
  8. ChEBI
  9. FDA Pharm Classes
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    https://www.fda.gov/about-fda/about-website/website-policies#linking
  10. LOTUS - the natural products occurrence database
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    https://lotus.nprod.net/
  11. NCI Thesaurus (NCIt)
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  12. Open Targets
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  13. ChEMBL
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    http://www.ebi.ac.uk/Information/termsofuse.html
  14. ClinicalTrials.gov
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    https://clinicaltrials.gov/ct2/about-site/terms-conditions#Use
  15. DailyMed
  16. Drug Induced Liver Injury Rank (DILIrank) Dataset
    LICENSE
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    https://www.fda.gov/about-fda/about-website/website-policies#linking
  17. Drugs and Lactation Database (LactMed)
  18. Drugs@FDA
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  19. WHO Model Lists of Essential Medicines
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    https://www.who.int/about/policies/publishing/copyright
  20. EU Clinical Trials Register
  21. National Drug Code (NDC) Directory
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    https://www.fda.gov/about-fda/about-website/website-policies#linking
  22. Japan Chemical Substance Dictionary (Nikkaji)
  23. KEGG
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    https://www.kegg.jp/kegg/legal.html
    Anatomical Therapeutic Chemical (ATC) classification
    http://www.genome.jp/kegg-bin/get_htext?br08303.keg
  24. Natural Product Activity and Species Source (NPASS)
  25. Metabolomics Workbench
  26. NLM RxNorm Terminology
    LICENSE
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    https://www.nlm.nih.gov/research/umls/rxnorm/docs/termsofservice.html
  27. 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/
    Cefotaxime
    NORMAN Suspect List Exchange Classification
    https://www.norman-network.com/nds/SLE/
  28. Therapeutic Target Database (TTD)
  29. Pharos
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    https://pharos.nih.gov/about
  30. Protein Data Bank in Europe (PDBe)
  31. RCSB Protein Data Bank (RCSB PDB)
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  32. Springer Nature
  33. Thieme Chemistry
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  34. WHO Anatomical Therapeutic Chemical (ATC) Classification
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  36. Wikipedia
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    https://www.nlm.nih.gov/copyright.html
  38. PubChem
  39. GHS Classification (UNECE)
  40. MolGenie
    MolGenie Organic Chemistry Ontology
    https://github.com/MolGenie/ontology/
  41. PATENTSCOPE (WIPO)
  42. NCBI
CONTENTS