Flucloxacillin

(CC) Image: David E. Volk
flucloxacillin
IUPAC name: see chemistry section Synonyms: see below Formula: C19H17ClFN3O5S
Uses:	antibiotic drug
Properties:	beta-lactam
Hazards:	see drug interactions
Mass (g/mol): CAS #: 453.8718 5250-39-5

Flucloxacillin is a pencillin-like beta-lactam antibiotic that is an analog of cloxacillin. It is used to treat bacterial infections, mostly from aerobic Gram-positive bacteria. Flucloxacillin, and all penicillin-like drugs, may cause anaphylactic shock.

Mechanism of action

Like other penicillin drugs, it inhibits the last stage of bacterial cell wall synthesis by binding to penicillin binding proteins, which inhibits the cross-linking needed to form stable cell walls. This leads to autolysis of the bacteria by autolysins.

Chemistry

Its IUPAC chemical name is (2S,5R,6R)-6-[[3-(2-chloro-6-fluorophenyl)-5-methyl1,2-oxazole-4-carbonyl]amino]-3, 3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid and it has molecular formula C₁₉H₁₇ClFN₃O₅S, giving it a molecular mass of 453.8718 g/mol. Flucloxacillin is stable against degradation by beta-lactamases, including penicillinases, and cephalosporinases.

Drug interactions

Several drugs, including demeclocycline, doxyclycline, methacycline, minocycline. oxytetracycline, rolitetracycline and tetracycline may be antagonists of flucloxacillin. Flucloxacillin may decrease the effects of the contraceptive drugs ethinyl estradiol and mestranol.

Synonyms and brand names

Synonyms Flucloxacilina Flucloxacillin Flucloxacillin Flucloxacilline Flucloxacillinum Floxacillin

Brand names Floxapen® Fluclox® Sesamol®

External links

The most up-to-date information about Flucloxacillin and other drugs can be found at the following sites.

• Flucloxacillin - FDA approved drug information (drug label) from DailyMed (U.S. National Library of Medicine).
• Flucloxacillin - Drug information for consumers from MedlinePlus (U.S. National Library of Medicine).
• Flucloxacillin - Detailed information from DrugBank.