(6R,7R)-7-[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-(methoxyimino)acetamido]-3-(methoxymethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

• ChemBase编号: 1225
• 分子式: C15H17N5O6S2
• 平均质量: 427.45538
• 单一同位素质量: 427.06202529
• SMILES: S1[C@H]2N(C(=O)[C@H]2NC(=O)/C(=N\OC)/c2nc(sc2)N)C(=C(C1)COC)C(=O)O
• Canonical SMILES: CO/N=C(/c1csc(n1)N)\C(=O)N[C@H]1[C@H]2SCC(=C(N2C1=O)C(=O)O)COC
• InChI: InChI=1S/C15H17N5O6S2/c1-25-3-6-4-27-13-9(12(22)20(13)10(6)14(23)24)18-11(21)8(19-26-2)7-5-28-15(16)17-7/h5,9,13H,3-4H2,1-2H3,(H2,16,17)(H,18,21)(H,23,24)/b19-8-/t9-,13-/m1/s1
• InChIKey: WYUSVOMTXWRGEK-HBWVYFAYSA-N

名称和登记号

名称

• IUPAC标准名: (6R,7R)-7-[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-(methoxyimino)acetamido]-3-(methoxymethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
• IUPAC传统名: cefpodoxime
• 商标名: Vantin; Banan; Doxef
• 别名: (6R,7R)-7-[[(2Z)-2-(2-Amino-4-thiazolyl)-2-(methoxyimino)acetyl]amino]-3-(methoxymethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid; Cefpodoxime; R 3763; Cefpodoxime Acid; Cefpodoxime proxetil; CPDX-PR; RU 51807; Cefpodoxime

登记号

• CAS号: 80210-62-4; 82619-04-3
• PubChem SID: 46504897; 160964685
• PubChem CID: 6335986

理论计算性质

JChem

• Acid pKa: 3.217438
• 质子受体: 9
• 质子供体: 3
• LogD (pH = 5.5): -2.7401698
• LogD (pH = 7.4): -3.9569473
• Log P: -1.6657981
• 摩尔折射率: 100.708 cm^3
• 极化性: 38.09914 Å^3
• 极化表面积: 156.44 Å^2
• 可自由旋转的化学键: 7
• 里宾斯基五规则: true

ALOGPS 2.1

• Log P: 0.05
• LOG S: -3.36
• 溶解度: 1.85e-01 g/l

分子性质

理化性质

• 溶解度: DMSO
• 外观: Pale Yellow to Beige Solid
• 熔点: 200-202°C (dec.)

安全信息

• 保存条件: -20°C Freezer

详细说明

DrugBank - DB01416

• Drug Groups: approved
• Description: Cefpodoxime is an oral third generation cephalosporin antibiotic. It is active against most Gram positive and Gram negative bacteria. It is commonly used to treat acute otitis media, pharyngitis, and sinusitis. Cefpodoxime proxetil is a prodrug which is absorbed and de-esterified by the intestinal mucosa to Cefpodoxime.
• Indication: For the treatment of patients with mild to moderate infections caused by susceptible strains of the designated microorganisms.
• Pharmacology: Cefpodoxime is an oral third generation cephalosporin antibiotic. It is active against most Gram positive and Gram negative bacteria. Notable exceptions include Pseudomonas aeruginosa, Enterococcus, and Bacteroides fragilis.
• Affected Organisms: Enteric bacteria and other eubacteria
• Absorption: Cefpodoxime proxetil is a prodrug that is absorbed from the gastrointestinal tract and de-esterified to its active metabolite, cefpodoxime. Following oral administration of 100 mg of cefpodoxime proxetil to fasting subjects, approximately 50% of the administered cefpodoxime dose was absorbed systemically.
• Half Life: 2.09 to 2.84 hours
• Protein Binding: 22 to 33% in serum and from 21 to 29% in plasma.
• Elimination: Over the recommended dosing range (100 to 400 mg), approximately 29 to 33% of the administered cefpodoxime dose was excreted unchanged in the urine in 12 hours.
• External Links: Wikipedia; RxList; Drugs.com

Toronto Research Chemicals - C243850

A metabolite of Cefpodoxime Proxetil (C243860). An antibacterial.

参考文献

• Fujimoto, K., et al.: J. Antibiot., 40, 370 (1987)
• Utsui, Y., et al.: Antimicrob. Agents Chemother., 31, 1085 (1987)