Cefotaxime

HCID 5742673CAS 60846-21-1
Substructure searchFind similar structures

Basic information

Standard SMILES
CO/N=C(\C(=O)N[C@@H]1C(=O)N2C(C(=O)O)=C(COC(C)=O)CS[C@H]12)c1csc(N)n1
InChIKey
GPRBEKHLDVQUJE-QSWIMTSFSA-N
Molecular formula
C16H17N5O7S2
Average molar mass
455.5 g/mol
Monoisotopic mass
455.05693988

Overview

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 an antibacterial drug and a drug allergen. It is a cephalosporin, an oxime O-ether and a member of 1,3-thiazoles. It is a conjugate acid of a cefotaxime(1-).

Names & identifiers

Preferred name
Cefotaxime
IUPAC
(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
English name
(6R,7R)-3-(Acetoxymethyl)-8-oxo-7-[(2-amino-4-thiazolyl)(methoxyimino)acetylamino]-5-thia-1-azabicyclo[4.2.0]octa-2-ene-2-carboxylic acid
Molecular formula
C16H17N5O7S2
Molecular weight
455.47

Names & synonyms

cefotaxime63527-52-6CephotaximeCefotaximaCefotaximumCefotaxim HikmaCHEBI:204928N2GI8B1GK7(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 acidDTXSID6022761Cefotaxim(6R,7R)-3-[(acetyloxy)methyl]-7-[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-(methoxyimino)acetamido]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
Show more names
3-(Acetoxymethyl)-7β-[(2-amino-4-thiazolyl)(methoxyimino)acetylamino]cepham-3-ene-4-carboxylic acid(6R,7R)-3-Acetyloxymethyl-7β-[(2-amino-4-thiazolyl)(methoxyimino)acetylamino]cepham-3-ene-4-carboxylic acid(6R,7R)-3-(Acetoxymethyl)-8-oxo-7-[(2-amino-4-thiazolyl)(methoxyimino)acetylamino]-5-thia-1-azabicyclo[4.2.0]octa-2-ene-2-carboxylic acid(6R,7R)-3-(acetoxymethyl)-7-((Z)-2-(2-aminothiazol-4-yl)-2-(methoxyimino)acetamido)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, 3-[(acetyloxy)methyl]-7-[[2-(2-amino-4-thiazolyl)-2-(methoxyimino)acetyl]amino]-8-oxo-, (6R,7R)-
(6R,7R)-3-Acetoxymethyl-7-{2-(2-amino-thiazol-4-yl)-2-[(Z)-methoxyimino]-acetylamino}-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid(6R,7R,Z)-3-(acetoxymethyl)-7-(2-(2-aminothiazol-4-yl)-2-(methoxyimino)acetamido)-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid5-Thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid, 3-((acetyloxy)methyl)-7-(((2-amino-4-thiazolyl)(methoxyimino)acetyl)amino)-8-oxo-, (6R-(6alpha,7beta(Z)))-CephotaximKlaforanPrimafen(6R,7R)-3-((acetyloxy)methyl)-7-((2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-(methoxyimino)acetamido)-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid(6R,7R)-3-(acetoxymethyl)-7-(((2Z)-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

Database identifiers

CAS
60846-21-1、63527-52-6
PubChem CID
5742673
DTXSID
DTXSID6022761
ChEMBL
CHEMBL1730
ChEBI
CHEBI:204928
UNII
N2GI8B1GK7
EC Number
264-299-1
Nikkaji
J18.743G

Properties

Computed structural properties

XLogP
-1.4
Topological polar surface area
227 Ų
Hydrogen bond donors
3
Hydrogen bond acceptors
12
Rotatable bonds
8
Heavy atoms
30

Experimental & physicochemical properties

Drugs · 3 items

Pharmaceuticals -> Listed in ZINC15

Pharmaceuticals -> Antibiotics

Pharmaceuticals -> Antibiotics

LogP-0.5
Solubility · 2 items

Soluble

1.46e-01 g/L

Human Drugs · 2 items

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

Watch group antibiotics

Physical DescriptionSolid

Physicochemical properties

Density
1.802 · 1.802±0.14 g/cm3(Temp: 25 °C; Press: 760 Torr)(predicted)
pka
2.66 · 2.660±0.50(predicted)

Safety & regulation

GHS classification

GHS Classification · 4 items

Danger

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

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 (click each P-code to see the statement)

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.

Hazard information

Regulatory InformationStatus: Active Update: 18-05-2018 https://echa.europa.eu/registration-dossier/-/registered-dossier/22006
Hazard Classes and CategoriesSkin Irrit. 2 (58.8%)

Toxicology

Adverse Effects* Local reaction: pain, swelling
Toxicity Summary · 1 item

Cefotaxime is metabolized by the liver and excreted through the kidneys, and dysfunctions may result in decreased drug clearance leading to increased plasma concentrations. About 50 to 60% of the agent is excreted unchanged, and 15 to 20% is excreted as a desacetyl metabolite desacetylcefotaxime. Toxicity may result in convulsions, dyspnea, hypothermia, cyanosis, reversible encephalopathy, and death. Mortality has occurred with dosages of 6000 mg/kg/day. Treatment for cefotaxime toxicity requires supportive management.

Drug Induced Liver Injury · 5 items

Drug-Induced Liver Injury Severity and Toxicity (DILIst)

cefotaxime

DILI Positive

Intravenous

DOI:10.1016/j.drudis.2019.09.022

Effects During Pregnancy and Lactation◉ Summary of Use during Lactation

Chemistry & industry

Pharmacology

ATC Code · 3 items

J - Antiinfectives for systemic use

QJ - Antiinfectives for systemic use

J01DD01

Pharmacodynamics · 1 item

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 <i>Pseudomonas aeruginosa</i>. 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.

Mechanism of Action · 1 item

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.

Biological Half-LifeApproximately 1 hour.
Metabolism/Metabolites · 1 item

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.

FDA Pharmacological Classification · 6 items

N2GI8B1GK7

CEFOTAXIME

Established Pharmacologic Class [EPC] - Cephalosporin Antibacterial

Chemical Structure [CS] - Cephalosporins

Cefotaxime is a Cephalosporin Antibacterial.

CEFOTAXIME

Uses & manufacturing

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

Suppliers50 total

北京华美互利生物化工010-56205725 · [email protected]
天津始加生物医药科技有限公司15022261580 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
HubeiwidelychemicaltechnologyCo.,Ltd18627774460 · [email protected]
河北创海生物科技有限公司+86-86-13131129325 · [email protected]
Additional notes · 1 item

DefinitionChEBI: 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-).

Related reactions

19 records
New reaction record

Linked notes

Loading…