Oxacillin

(CC) Image: David E. Volk
oxacillin
IUPAC name: see chemistry section Synonyms: Bactocill® Formula: C19H19N3O5S
Uses:	antibiotic drug
Properties:	beta-lactam
Hazards:	see drug interactions
Mass (g/mol): CAS #: 401.4363 66-79-5

Oxacillin, sold under the brand name Bactocill®, is a penicillin beta-lactam type of antibiotic similar to flucloxacillin used in resistant staphylococci infections. It is active against Gram-positive bacteria and some Gram-negative bacteria. Like other penicillin-like antibiotics, it functions by interfering with the last stage of bacterial cell wall synthesis and leads to autolysis of the bacteria cells. It is stable against hydrolysis from beta-lactamases, including penicillinases, and cephalosporinases.

Chemistry

Its IUPAC chemical name is (2S,5R,6R)-3,3-dimethyl-6-[(5-methyl-3-phenyl1,2-oxazole-4-carbonyl)amino]-7-oxo-4- thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid and it has molecular formula C₁₉H₁₉N₃O₅S, giving it a molecular mass of 401.4363 g/mol. It is susceptible do degradation in bacteria which express beta-lactamase.