Cefotaxime

• Catalog No.: DB00493
• CAS Number: 63527-52-6
• M. F.: C16H17N5O7S2
• M. W.: 455.46548

SYNONYMS

• IUPAC name: (6R,7R)-3-[(acetyloxy)methyl]-7-[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
• IUPAC Traditional name: cefotaxim
• Brand Name: Claforan
• Synonyms: Cefotaxime sodium; Cephotaxime

DATABASE IDS

• CAS Number: 63527-52-6

PROPERTIES

• Hydrophobicity(logP): -0.5
• Solubility: Soluble

DETAILS

Description (English)

• Drug Groups: approved
• Description: 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).
• 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.
• Pharmacology: 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.
• Toxicity: Adverse effects following overdosage include nausea, vomiting, epigastric distress, diarrhea, and convulsions. Oral rat LD₅₀ is over 20,000 mg/kg while intravenous rat LD₅₀ is over 7,000 mg/kg.
• Affected Organisms: Enteric bacteria and other eubacteria
• Biotransformation: 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.
• Absorption: Rapidly absorbed following intramuscular injection.
• Half Life: Approximately 1 hour.
• 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.
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