(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编号: 376
• 分子式: C16H17N5O7S2
• 平均质量: 455.46548
• 单一同位素质量: 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

名称和登记号

名称

• IUPAC标准名: (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传统名: cefotaxim; claforan
• 商标名: Claforan
• 别名: Cefotaxime sodium; Cephotaxime; Cefotaxime

登记号

• CAS号: 63527-52-6
• PubChem SID: 160963839
• PubChem CID: 5479527
• ATC码: J01DD01
• CHEMBL: 102
• Chemspider ID: 4586392
• DrugBank ID: DB00493
• KEGG ID: D07647
• 美国药典/FDA物质标识码: N2GI8B1GK7
• 维基百科标题: Cefotaxime
• Medline Plus: a682765

理论计算性质

JChem

• Acid pKa: 3.1773155
• 质子受体: 9
• 质子供体: 3
• LogD (pH = 5.5): -2.9842594
• LogD (pH = 7.4): -4.1677856
• Log P: -1.9052299
• 摩尔折射率: 105.1083 cm^3
• 极化性: 40.078896 Å^3
• 极化表面积: 173.51 Å^2
• 可自由旋转的化学键: 8
• 里宾斯基五规则: true

ALOGPS 2.1

• Log P: 0.14
• LOG S: -3.49
• 溶解度: 1.46e-01 g/l

分子性质

理化性质

• 溶解度: Soluble
• 疏水性(logP): -0.5

药理学性质

• 给药途径: Intravenous
• 生物利用度: n/a
• 排泄: 50–85% renal
• 半衰期: 0.8–1.4 hours
• 代谢: Hepatic
• 法定药品分级: S4 (Australia)
• 妊娠期药物分类: B (US); B1 (Australia)

详细说明

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