(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

• ChemBase ID: 376
• Molecular Formular: C16H17N5O7S2
• Molecular Mass: 455.46548
• Monoisotopic Mass: 455.05693991
• SMILES: S1[C@H]2N(C(=O)[C@H]2NC(=O)/C(=N/OC)/c2nc(sc2)N)C(=C(C1)COC(=O)C)C(=O)O
• Canonical SMILES: CO/N=C(\c1csc(n1)N)/C(=O)N[C@@H]1C(=O)N2[C@@H]1SCC(=C2C(=O)O)COC(=O)C
• 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)/t10-,14-/m1/s1
• InChIKey: GPRBEKHLDVQUJE-QMTHXVAHSA-N

NAMES AND DATABASE IDS

Names

• 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; claforan
• Brand Name: Claforan
• Synonyms: Cefotaxime sodium; Cephotaxime; Cefotaxime

Database IDs

• CAS Number: 63527-52-6
• PubChem SID: 160963839
• PubChem CID: 5479527
• ATC CODE: J01DD01
• CHEMBL: 102
• Chemspider ID: 4586392
• DrugBank ID: DB00493
• KEGG ID: D07647
• Unique Ingredient Identifier: N2GI8B1GK7
• Wikipedia Title: Cefotaxime
• Medline Plus: a682765

CALCULATED PROPERTIES

JChem

• Acid pKa: 3.1773155
• H Acceptors: 9
• H Donor: 3
• LogD (pH = 5.5): -2.9842594
• LogD (pH = 7.4): -4.1677856
• Log P: -1.9052299
• Molar Refractivity: 105.1083 cm^3
• Polarizability: 40.078896 Å^3
• Polar Surface Area: 173.51 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 0.14
• LOG S: -3.49
• Solubility (Water): 1.46e-01 g/l

PROPERTIES

Physical Property

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

Pharmacology Properties

• Admin Routes: Intravenous
• Bioavailability: n/a
• Excretion: 50–85% renal
• Half Life: 0.8–1.4 hours
• Metabolism: Hepatic
• Legal Status: S4 (Australia)
• Pregnancy Category: B (US); B1 (Australia)

DETAILS

DrugBank - DB00493

• 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.
• External Links: Wikipedia; RxList; Drugs.com