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

• ChemBase编号: 368
• 分子式: C19H17Cl2N3O5S
• 平均质量: 470.32638
• 单一同位素质量: 469.02659702
• SMILES: Clc1c(c2noc(c2C(=O)N[C@H]2[C@H]3SC([C@@H](N3C2=O)C(=O)O)(C)C)C)c(Cl)ccc1
• Canonical SMILES: OC(=O)[C@@H]1N2C(=O)[C@H]([C@H]2SC1(C)C)NC(=O)c1c(C)onc1c1c(Cl)cccc1Cl
• InChI: InChI=1S/C19H17Cl2N3O5S/c1-7-10(12(23-29-7)11-8(20)5-4-6-9(11)21)15(25)22-13-16(26)24-14(18(27)28)19(2,3)30-17(13)24/h4-6,13-14,17H,1-3H3,(H,22,25)(H,27,28)/t13-,14+,17-/m1/s1
• InChIKey: YFAGHNZHGGCZAX-JKIFEVAISA-N

名称和登记号

名称

• IUPAC标准名: (2S,5R,6R)-6-[3-(2,6-dichlorophenyl)-5-methyl-1,2-oxazole-4-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-[3-(2,6-dichlorophenyl)-5-methyl-1,2-oxazole-4-amido]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
• 商标名: Dycill; Dynapen; Maclicine; Pathocil
• 别名: Diclossacillina [DCIT]; Dicloxacilina [INN-Spanish]; Dicloxacillin Sodium; Dicloxacilline [INN-French]; Dicloxacillinum [INN-Latin]; Dicloxacilin; Dicloxacycline; Dicloxacillin

登记号

• CAS号: 3116-76-5
• PubChem SID: 160963831; 46508182
• PubChem CID: 18381

理论计算性质

JChem

• Acid pKa: 3.7486086
• 质子受体: 5
• 质子供体: 2
• LogD (pH = 5.5): 1.1539227
• LogD (pH = 7.4): -0.3794561
• Log P: 2.9057844
• 摩尔折射率: 111.4419 cm^3
• 极化性: 43.893353 Å^3
• 极化表面积: 112.74 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: 3.19
• LOG S: -4.2
• 溶解度: 2.96e-02 g/l

分子性质

理化性质

• 溶解度: 3.63 mg/L
• 疏水性(logP): 3.7

详细说明

DrugBank - DB00485

• Drug Groups: approved
• Description: One of the penicillins which is resistant to penicillinase. [PubChem]
• Indication: Used to treat infections caused by penicillinase-producing staphylococci which have demonstrated susceptibility to the drug.
• Pharmacology: Dicloxacillin is a beta-lactamase resistant penicillin similar to oxacillin. Dicloxacillin has in vitro activity against gram-positive and gram-negative aerobic and anaerobic bacteria. The bactericidal activity of dicloxacillin results from the inhibition of cell wall synthesis and is mediated through dicloxacillin binding to penicillin binding proteins (PBPs). Dicloxacillin is stable against hydrolysis by a variety of beta-lactamases, including penicillinases, and cephalosporinases and extended spectrum beta-lactamases.
• Toxicity: Oral LD₅₀ in rat is 3579 mg/kg. Symptoms of overexposure include irritation, rash, labored breathing, hives, itching, wheezing, nausea, chills, and fever.
• Affected Organisms: Enteric bacteria and other eubacteria
• Absorption: Absorption of the isoxazolyl penicillins after oral administration is rapid but incomplete: peak blood levels are achieved in 1-1.5 hours. Oral absorption of cloxacillin, dicloxacillin, oxacillin and nafcillin is delayed when the drugs are administered after meals.
• Half Life: The elimination half-life for dicloxacillin is about 0.7 hour.
• Protein Binding: Binds to serum protein, mainly albumin.
• Elimination: Dicloxacillin sodium is rapidly excreted as unchanged drug in the urine by glomerular filtration and active tubular secretion.
• External Links: Wikipedia; RxList; Drugs.com