(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 ID: 594
• Molecular Formular: C19H19N3O5S
• Molecular Mass: 401.43626
• Monoisotopic Mass: 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

NAMES AND DATABASE IDS

Names

• IUPAC name: (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 Traditional name: (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
• Brand Name: Bactocill
• Synonyms: Oxacillin Sodium; Oxacillin

Database IDs

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

CALCULATED PROPERTIES

JChem

• Acid pKa: 3.7509665
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): -0.05194399
• LogD (pH = 7.4): -1.5865542
• Log P: 1.697695
• Molar Refractivity: 101.8323 cm^3
• Polarizability: 39.999657 Å^3
• Polar Surface Area: 112.74 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 2.05
• LOG S: -3.67
• Solubility (Water): 8.62e-02 g/l

PROPERTIES

Physical Property

• Solubility: 13.9 mg/L
• Hydrophobicity(logP): 2.4

DETAILS

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