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

• ChemBase编号: 489
• 分子式: C21H22N2O5S
• 平均质量: 414.47478
• 单一同位素质量: 414.12494281
• SMILES: S1[C@H]2N([C@H](C1(C)C)C(=O)O)C(=O)[C@H]2NC(=O)c1c2c(ccc1OCC)cccc2
• Canonical SMILES: CCOc1ccc2c(c1C(=O)N[C@@H]1C(=O)N3[C@@H]1SC([C@@H]3C(=O)O)(C)C)cccc2
• InChI: InChI=1S/C21H22N2O5S/c1-4-28-13-10-9-11-7-5-6-8-12(11)14(13)17(24)22-15-18(25)23-16(20(26)27)21(2,3)29-19(15)23/h5-10,15-16,19H,4H2,1-3H3,(H,22,24)(H,26,27)/t15-,16+,19-/m1/s1
• InChIKey: GPXLMGHLHQJAGZ-JTDSTZFVSA-N

名称和登记号

名称

• IUPAC标准名: (2S,5R,6R)-6-(2-ethoxynaphthalene-1-amido)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
• IUPAC传统名: (2S,5R,6R)-6-(2-ethoxynaphthalene-1-amido)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
• 商标名: Nafcilin-1; Nafcillin sodium for injection; Nallpen; Nallpen In Plastic Container; Naphcillin; Unipen
• 别名: Nafcilina [INN-Spanish]; Nafcillin Sodium; Nafcillin sodium salt; Nafcilline [INN-French]; Nafcillinum [INN-Latin]; Nafcillin

登记号

• CAS号: 985-16-0
• PubChem SID: 46508100; 160963952
• PubChem CID: 8982

理论计算性质

JChem

• Acid pKa: 3.3094113
• 质子受体: 5
• 质子供体: 2
• LogD (pH = 5.5): 0.11520102
• LogD (pH = 7.4): -1.1349657
• Log P: 2.289126
• 摩尔折射率: 108.1384 cm^3
• 极化性: 43.10996 Å^3
• 极化表面积: 95.94 Å^2
• 可自由旋转的化学键: 5
• 里宾斯基五规则: true

ALOGPS 2.1

• Log P: 3.21
• LOG S: -4.38
• 溶解度: 1.72e-02 g/l

分子性质

理化性质

• 溶解度: Soluble
• 疏水性(logP): 3.3

详细说明

DrugBank - DB00607

• Drug Groups: approved
• Description: A semi-synthetic antibiotic related to penicillin. [PubChem]
• Indication: For the treatment of infections caused by penicillinase-producing staphylococci which have demonstrated susceptibility to the drugs.
• Pharmacology: Nafcillin is a semisynthetic antibiotic substance derived from 6-amino-penicillanic acid. The drugs in this class are highly resistant to inactivation by staphylococcal penicillinase and are active against penicillinase-producing and non penicillinase-producing strains of Staphylococcus aureus. The penicillinase- resistant penicillins are active in vitro against a variety of other bacteria.
• Toxicity: Serious toxicity is unlikely following large doses of nafcillin. Acute ingestion of large doses of nafcillin may cause nausea, vomiting, diarrhea and abdominal pain. Acute oliguric renal failure and hematuria may occur following large doses.
• Affected Organisms: Enteric bacteria and other eubacteria
• Biotransformation: Hepatic metabolism accounts for less than 30% of the biotransformation of most penicillins.
• Half Life: The serum half-life of nafcillin administered by the intravenous route ranged from 33 to 61 minutes as measured in three separate studies.
• Protein Binding: 89.9 ±1.5%
• Elimination: Nafcillin is primarily eliminated by nonrenal routes, namely hepatic inactivation and excretion in the bile.
• External Links: Wikipedia; RxList; Drugs.com