1-[(ethoxycarbonyl)oxy]ethyl (2S,5R,6R)-6-[(2R)-2-amino-2-phenylacetamido]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate

• ChemBase编号: 1379
• 分子式: C21H27N3O7S
• 平均质量: 465.51998
• 单一同位素质量: 465.15697122
• SMILES: S1[C@H]2N([C@H](C1(C)C)C(=O)OC(OC(=O)OCC)C)C(=O)[C@H]2NC(=O)[C@H](N)c1ccccc1
• Canonical SMILES: CCOC(=O)OC(OC(=O)[C@@H]1N2C(=O)[C@H]([C@H]2SC1(C)C)NC(=O)[C@@H](c1ccccc1)N)C
• InChI: InChI=1S/C21H27N3O7S/c1-5-29-20(28)31-11(2)30-19(27)15-21(3,4)32-18-14(17(26)24(15)18)23-16(25)13(22)12-9-7-6-8-10-12/h6-11,13-15,18H,5,22H2,1-4H3,(H,23,25)/t11?,13-,14-,15+,18-/m1/s1
• InChIKey: PFOLLRNADZZWEX-FFGRCDKISA-N

名称和登记号

名称

• IUPAC标准名: 1-[(ethoxycarbonyl)oxy]ethyl (2S,5R,6R)-6-[(2R)-2-amino-2-phenylacetamido]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate
• IUPAC传统名: bacampicilline; bacampicillin
• 商标名: Penglobe; Spectrobid
• 别名: Bacampicillin Hydrochloride; Bacampicillin

登记号

• CAS号: 50972-17-3; 37661-08-8
• PubChem SID: 160964839; 46507859
• PubChem CID: 39849; 441397
• CHEBI ID: 2968
• ATC码: J01CA06
• CHEMBL: 1583
• Chemspider ID: 390135
• DrugBank ID: DB01602
• 美国药典/FDA物质标识码: 8GM2J22278
• 维基百科标题: Bacampicillin

理论计算性质

JChem

• Acid pKa: 11.7201185
• 质子受体: 6
• 质子供体: 2
• LogD (pH = 5.5): -0.4384752
• LogD (pH = 7.4): 1.1510522
• Log P: 1.4712881
• 摩尔折射率: 113.7604 cm^3
• 极化性: 45.85553 Å^3
• 极化表面积: 137.26 Å^2
• 可自由旋转的化学键: 10
• 里宾斯基五规则: true

ALOGPS 2.1

• Log P: 1.17
• LOG S: -3.58
• 溶解度: 1.23e-01 g/l

分子性质

药理学性质

• 给药途径: Oral
• 代谢: Rapidly hydrolyzed to ampicillin

详细说明

DrugBank - DB01602

• Drug Groups: approved
• Description: Bacampicillin is a prodrug of ampicillin and is microbiologically inactive. It is absorbed following oral administration. During absorption from the gastrointestinal tract, bacampicillin is hydrolyzed by esterases present in the intestinal wall. It is microbiologically active as ampicillin, and exerts a bactericidal action through the inhibition of the biosynthesis of cell wall mucopeptides. It is used to cure infection of upper and lower respiratory tract; skin and soft tissue; urinary tract and acute uncomplicated gonococcal urethritis etc.
• Indication: For infections at the following sites: upper and lower respiratory tract; skin and soft tissue; urinary tract and acute uncomplicated gonococcal urethritis, when due to sensitive strains of the following organisms: Gram-positive: streptococci (including S. faecalis and S. pneumoniae) and nonpenicillinase-producing staphylococci; Gram-negative: H. influenzae, N. gonorrhoeae, E. coli, P. mirabilis, Salmonellae and Shigellae.
• Pharmacology: Bacampicillin is a prodrug of ampicillin and is microbiologically inactive.
• Affected Organisms: Enteric bacteria and other eubacteria
• Absorption: Absorbed following oral administration.
• External Links: Drugs.com