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

• ChemBase ID: 1018
• Molecular Formular: C19H18ClN3O5S
• Molecular Mass: 435.88132
• Monoisotopic Mass: 435.06556937
• SMILES: Clc1c(c2noc(c2C(=O)N[C@H]2[C@H]3SC([C@@H](N3C2=O)C(=O)O)(C)C)C)cccc1
• Canonical SMILES: OC(=O)[C@@H]1N2C(=O)[C@H]([C@H]2SC1(C)C)NC(=O)c1c(C)onc1c1ccccc1Cl
• InChI: InChI=1S/C19H18ClN3O5S/c1-8-11(12(22-28-8)9-6-4-5-7-10(9)20)15(24)21-13-16(25)23-14(18(26)27)19(2,3)29-17(13)23/h4-7,13-14,17H,1-3H3,(H,21,24)(H,26,27)/t13-,14+,17-/m1/s1
• InChIKey: LQOLIRLGBULYKD-JKIFEVAISA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,5R,6R)-6-[3-(2-chlorophenyl)-5-methyl-1,2-oxazole-4-amido]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
• IUPAC Traditional name: cloxacillin; (2S,5R,6R)-6-[3-(2-chlorophenyl)-5-methyl-1,2-oxazole-4-amido]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
• Brand Name: Cloxapen; Novo-Cloxin; Nu-Cloxi
• Synonyms: Cloxacillin Sodium; Cloxacillin

Database IDs

• CAS Number: 61-72-3
• PubChem SID: 160964481; 46507109
• PubChem CID: 6098
• CHEBI ID: 49566
• ATC CODE: QJ51CF02; QS01AA90; J01CF02
• CHEMBL: 891
• Chemspider ID: 5873
• DrugBank ID: DB01147
• KEGG ID: D07733
• Unique Ingredient Identifier: O6X5QGC2VB
• Wikipedia Title: Cloxacillin

CALCULATED PROPERTIES

JChem

• Acid pKa: 3.7497845
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): 0.55099535
• LogD (pH = 7.4): -0.9830029
• Log P: 2.3017397
• Molar Refractivity: 106.6371 cm^3
• Polarizability: 41.93821 Å^3
• Polar Surface Area: 112.74 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 2.61
• LOG S: -3.91
• Solubility (Water): 5.32e-02 g/l

PROPERTIES

Physical Property

• Solubility: 13.9 mg/L
• Hydrophobicity(logP): 3

Pharmacology Properties

• Admin Routes: Oral, IM
• Bioavailability: 37 to 90%
• Excretion: Renal and biliary
• Half Life: 30 minutes to 1 hour
• Protein Bound: 95%
• Pregnancy Category: B (US)

DETAILS

DrugBank - DB01147

• Drug Groups: approved
• Description: A semi-synthetic antibiotic that is a chlorinated derivative of oxacillin. [PubChem]
• Indication: Used to treat infections caused by penicillinase-producing staphylococci, including pneumococci, group A beta-hemolytic streptococci, and penicillin G-sensitive and penicillin G-resistant staphylococci.
• Pharmacology: Cloxacillin is a semisynthetic antibiotic in the same class as penicillin. Cloxacillin is for use against staphylococci that produce beta-lactamase.
• Toxicity: Oral LD₅₀ in rat and mouse is 5000 mg/kg. Intravenous LD₅₀ in rat is 1660 mg/kg. Symptoms of overdose include wheezing, tightness in the chest, fever, itching, bad cough, blue skin color, fits, and swelling of face, lips, tongue, or throat.
• Affected Organisms: Enteric bacteria and other eubacteria
• Absorption: Well absorbed from the gastrointestinal tract.
• Protein Binding: 95%
• External Links: Wikipedia; Drugs.com