Cefotaxime (HCID 5742673)

Überblick

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-).

Namen und Bezeichner

Bevorzugter 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
Englischer 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
Summenformel: C16H17N5O7S2
Molmasse: 455.47

Namen und Synonyme

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

Weitere Namen anzeigen

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

Datenbank-Bezeichner

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

Eigenschaften

Berechnete Struktureigenschaften

XLogP: -1,4
Polarare Oberfläche (TPSA): 227 Å²
H-Brücken-Donoren: 3
H-Brücken-Akzeptoren: 12
Frei drehbare Bindungen: 8
Schwere Atome: 30
Formalladung: 0
Komplexität: 833

Experimentelle und physikochemische Eigenschaften

Drugs · 3 Einträge

Pharmaceuticals -> Listed in ZINC15

Pharmaceuticals -> Antibiotics

LogP-0.5

Solubility · 2 Einträge

Soluble

1.46e-01 g/L

Human Drugs · 2 Einträge

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

Watch group antibiotics

Physical DescriptionSolid

Physikochemische Eigenschaften

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

Sicherheit und Regulatorisches

GHS-Klassifizierung

GHS Classification · 4 Einträge

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.

Gefahrenhinweise

Regulatory InformationStatus: Active Update: 18-05-2018 https://echa.europa.eu/registration-dossier/-/registered-dossier/22006

Hazard Classes and CategoriesSkin Irrit. 2 (58.8%)

Toxikologische Informationen

Adverse Effects* Local reaction: pain, swelling

Toxicity Summary · 1 Eintrag

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 Einträge

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

Chemie und Industrie

Pharmakologische Informationen

ATC Code · 3 Einträge

J - Antiinfectives for systemic use

QJ - Antiinfectives for systemic use

J01DD01

Pharmacodynamics · 1 Eintrag

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 Eintrag

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 Eintrag

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 Einträge

N2GI8B1GK7

CEFOTAXIME

Established Pharmacologic Class [EPC] - Cephalosporin Antibacterial

Chemical Structure [CS] - Cephalosporins

Cefotaxime is a Cephalosporin Antibacterial.

CEFOTAXIME