(2S,5R,6R)-6-[3-(2-chloro-6-fluorophenyl)-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: 186
• Molecular Formular: C19H17ClFN3O5S
• Molecular Mass: 453.8717832
• Monoisotopic Mass: 453.05614756
• SMILES: Clc1c(c2noc(c2C(=O)N[C@H]2[C@H]3SC([C@@H](N3C2=O)C(=O)O)(C)C)C)c(F)ccc1
• Canonical SMILES: O=C1[C@@H](NC(=O)c2c(C)onc2c2c(F)cccc2Cl)[C@@H]2N1[C@@H](C(=O)O)C(S2)(C)C
• InChI: InChI=1S/C19H17ClFN3O5S/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: UIOFUWFRIANQPC-JKIFEVAISA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,5R,6R)-6-[3-(2-chloro-6-fluorophenyl)-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: (2S,5R,6R)-6-[3-(2-chloro-6-fluorophenyl)-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: Floxapen; Fluclox; Sesamol
• Synonyms: Flucloxacilina [INN-Spanish]; Flucloxacillin Sodium; Flucloxacillin-Sodium; Flucloxacilline [INN-French]; Flucloxacillinum [INN-Latin]; Floxacillin; Flucloxacillin

Database IDs

• CAS Number: 5250-39-5
• PubChem SID: 160963649; 46508276
• PubChem CID: 21319

CALCULATED PROPERTIES

JChem

• Acid pKa: 3.7475462
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): 0.6915611
• LogD (pH = 7.4): -0.841252
• Log P: 2.4444416
• Molar Refractivity: 106.8535 cm^3
• Polarizability: 41.716312 Å^3
• Polar Surface Area: 112.74 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 2.69
• LOG S: -3.92
• Solubility (Water): 5.45e-02 g/l

PROPERTIES

Physical Property

• Hydrophobicity(logP): 3.2

DETAILS

DrugBank - DB00301

• Drug Groups: approved
• Description: Antibiotic analog of cloxacillin. [PubChem]
• Indication: Used to treat bacterial infection by susceptible microorganisms.
• Pharmacology: Flucloxacillin 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. Flucloxacillin has in vitro activity against gram-positive and gram-negative aerobic and anaerobic bacteria. The bactericidal activity of Flucloxacillin results from the inhibition of cell wall synthesis and is mediated through flucloxacillin binding to penicillin binding proteins (PBPs). Flucloxacillin 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
• Biotransformation: Hepatic.
• Absorption: Bioavailability is 50–70% following oral administration.
• Half Life: 0.75–1 hour
• External Links: Wikipedia