(2S,5R,6R)-6-(1-aminocyclohexaneamido)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid

• ChemBase编号: 873
• 分子式: C15H23N3O4S
• 平均质量: 341.42582
• 单一同位素质量: 341.14092723
• SMILES: S1[C@H]2N([C@H](C1(C)C)C(=O)O)C(=O)[C@H]2NC(=O)C1(N)CCCCC1
• Canonical SMILES: OC(=O)[C@@H]1N2C(=O)[C@H]([C@H]2SC1(C)C)NC(=O)C1(N)CCCCC1
• InChI: InChI=1S/C15H23N3O4S/c1-14(2)9(12(20)21)18-10(19)8(11(18)23-14)17-13(22)15(16)6-4-3-5-7-15/h8-9,11H,3-7,16H2,1-2H3,(H,17,22)(H,20,21)/t8-,9+,11-/m1/s1
• InChIKey: HGBLNBBNRORJKI-WCABBAIRSA-N

名称和登记号

名称

• IUPAC标准名: (2S,5R,6R)-6-(1-aminocyclohexaneamido)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
• IUPAC传统名: (2S,5R,6R)-6-(1-aminocyclohexaneamido)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
• 商标名: Bastcillin; Calthor; Citosarin; Cyclapen; Cyclapen-W; Orfilina; Syngacillin; Ultracillin; Vastcillin; Vipicil; Wyvital
• 别名: Ciclacilline [INN-French]; Ciclacillinum [INN-Latin]; Ciclacilina [INN-Spanish]; Aminocyclohexylpenicillin; Ciclacillin; Ciclacillum; Cyclacillin

登记号

• CAS号: 3485-14-1
• PubChem SID: 160964336; 46508073
• PubChem CID: 19003

理论计算性质

JChem

• Acid pKa: 3.3042057
• 质子受体: 5
• 质子供体: 3
• LogD (pH = 5.5): -1.9151417
• LogD (pH = 7.4): -1.9473974
• Log P: -1.9145718
• 摩尔折射率: 84.2196 cm^3
• 极化性: 33.79713 Å^3
• 极化表面积: 112.73 Å^2
• 可自由旋转的化学键: 3
• 里宾斯基五规则: true

ALOGPS 2.1

• Log P: 0.56
• LOG S: -2.26
• 溶解度: 1.90e+00 g/l

分子性质

理化性质

• 疏水性(logP): 0.4

详细说明

DrugBank - DB01000

• Drug Groups: approved
• Description: A cyclohexylamido analog of penicillanic acid. [PubChem]
• Indication: For the treatment of bacterial infections caused by susceptible organisms.
• Pharmacology: Cyclacillin, a penicillin, is a cyclohexylamido analog of penicillanic acid. Cyclacillin is more resistant to beta-lactamase hydrolysis than ampicillin, is much better absorbed when given by mouth and, as a result, the levels reached in the blood and in the urine are considerably higher than those obtained with the same dose of ampicillin. Cyclacillin has been replaced by newer penicillin treatments.
• Toxicity: Symptoms of overdose include severe diarrhea, nausea and vomiting.
• Affected Organisms: Enteric bacteria and other eubacteria
• Absorption: Moderately absorbed.