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

• ChemBase编号: 594
• 分子式: C19H19N3O5S
• 平均质量: 401.43626
• 单一同位素质量: 401.10454172
• SMILES: S1[C@H]2N([C@H](C1(C)C)C(=O)O)C(=O)[C@H]2NC(=O)c1c(noc1C)c1ccccc1
• Canonical SMILES: OC(=O)[C@@H]1N2C(=O)[C@H]([C@H]2SC1(C)C)NC(=O)c1c(C)onc1c1ccccc1
• InChI: InChI=1S/C19H19N3O5S/c1-9-11(12(21-27-9)10-7-5-4-6-8-10)15(23)20-13-16(24)22-14(18(25)26)19(2,3)28-17(13)22/h4-8,13-14,17H,1-3H3,(H,20,23)(H,25,26)/t13-,14+,17-/m1/s1
• InChIKey: UWYHMGVUTGAWSP-JKIFEVAISA-N

名称和登记号

名称

• IUPAC标准名: (2S,5R,6R)-3,3-dimethyl-6-(5-methyl-3-phenyl-1,2-oxazole-4-amido)-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
• IUPAC传统名: (2S,5R,6R)-3,3-dimethyl-6-(5-methyl-3-phenyl-1,2-oxazole-4-amido)-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
• 商标名: Bactocill
• 别名: Oxacillin Sodium; Oxacillin

登记号

• CAS号: 66-79-5
• PubChem SID: 46505710; 160964057
• PubChem CID: 6196

理论计算性质

JChem

• Acid pKa: 3.7509665
• 质子受体: 5
• 质子供体: 2
• LogD (pH = 5.5): -0.05194399
• LogD (pH = 7.4): -1.5865542
• Log P: 1.697695
• 摩尔折射率: 101.8323 cm^3
• 极化性: 39.999657 Å^3
• 极化表面积: 112.74 Å^2
• 可自由旋转的化学键: 4
• 里宾斯基五规则: true

ALOGPS 2.1

• Log P: 2.05
• LOG S: -3.67
• 溶解度: 8.62e-02 g/l

分子性质

理化性质

• 溶解度: 13.9 mg/L
• 疏水性(logP): 2.4

详细说明

DrugBank - DB00713

• Drug Groups: approved
• Description: An antibiotic similar to flucloxacillin used in resistant staphylococci infections. [PubChem]
• Indication: Used in the treatment of resistant staphylococci infections.
• Pharmacology: Oxacillin is a penicillin beta-lactam antibiotic used in the treatment of bacterial infections caused by susceptible, usually gram-positive, organisms. The name "penicillin" can either refer to several variants of penicillin available, or to the group of antibiotics derived from the penicillins. Oxacillin has in vitro activity against gram-positive and gram-negative aerobic and anaerobic bacteria. The bactericidal activity of Oxacillin results from the inhibition of cell wall synthesis and is mediated through Oxacillin binding to penicillin binding proteins (PBPs). Oxacillin is stable against hydrolysis by a variety of beta-lactamases, including penicillinases, and cephalosporinases and extended spectrum beta-lactamases.
• Affected Organisms: Enteric bacteria and other eubacteria
• Half Life: 20 to 30 minutes
• Protein Binding: 94.2 +/- 2.1% (binds to serum protein, mainly albumin)
• Elimination: Oxacillin Sodium is rapidly excreted as unchanged drug in the urine by glomerular filtration and active tubular secretion.
• External Links: Wikipedia; RxList; Drugs.com