Cefotaxime
Grundinformationen
- CAS
60846-21-1- 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- Summenformel
- C16H17N5O7S2
- Durchschnittliche Molmasse
- 455,5 g/mol
- Monoisotopische Masse
- 455,05694025
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 HikmaCephotaximKlaforanPrimafenCHEBI: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 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)-
Eigenschaften
Berechnete Struktureigenschaften
- XLogP
- -1,4
- Polarare Oberfläche (TPSA)
- 227 Ų
- H-Brücken-Donoren
- 3
- H-Brücken-Akzeptoren
- 12
- Frei drehbare Bindungen
- 8
- Schwere Atome
- 30
- Formalladung
- 0
- Komplexität
- 833
Experimentelle und physikochemische Eigenschaften
Drugs
Pharmaceuticals -> Listed in ZINC15
Pharmaceuticals -> Antibiotics
Pharmaceuticals -> Antibiotics
LogP
-0.5
-0.13
Solubility
Soluble
1.46e-01 g/L
Human Drugs
Breast Feeding; Lactation; Milk, Human; Anti-Infective Agents; Antibacterial Agents; Cephalosporins
Medicines for bacterial central nervous system infections
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
Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.
GHS-Klassifizierung
GHS Classification
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 InformationREACH registered substance: Cefotaxime (EC: 264-299-1)
Hazard Classes and CategoriesSkin Irrit. 2 (58.8%)
Toxikologische Informationen
Adverse Effects* Local reaction: pain, swelling
Toxicity Summary
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
Drug-Induced Liver Injury Severity and Toxicity (DILIst)
Chemie und Industrie
Pharmakologische Informationen
ATC Code
J - Antiinfectives for systemic use
QJ - Antiinfectives for systemic use
J01DD01
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 <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
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
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
N2GI8B1GK7
CEFOTAXIME
Established Pharmacologic Class [EPC] - Cephalosporin Antibacterial
Chemical Structure [CS] - Cephalosporins
Cefotaxime is a Cephalosporin Antibacterial.
CEFOTAXIME
MeSH Pharmacological ClassificationSubstances that inhibit the growth or reproduction of BACTERIA.
Absorption, Distribution and Excretion
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