Oxacillin
Systematic (IUPAC) name
(2S,5R,6R)-3,3-dimethyl-6-[(5-methyl-3-phenyl-
1,2-oxazole-4-carbonyl)amino]-7-oxo-4-thia-1-
azabicyclo[3.2.0]heptane-2-carboxylic acid
Clinical data
Trade names Bactocill
AHFS/Drugs.com
MedlinePlus
Legal status
?
Identifiers
CAS number  YesY
ATC code J01 QJ51
PubChem
DrugBank
ChemSpider  N
UNII  YesY
KEGG  YesY
ChEBI  N
ChEMBL  N
Chemical data
Formula C19H19N3O5S 
Mol. mass 401.436 g/mol
Physical data
Density 1.49 g/cm³
Boiling point 686.8 °C (1268 °F)
 N   

Oxacillin sodium (trade name Bactocill) is a narrow-spectrum beta-lactam antibiotic of the penicillin class developed by Beecham.[1]

Uses

Oxacillin is a penicillinase-resistant β-lactam. It is similar to methicillin, and has replaced methicillin in clinical use. Another related compound is nafcillin. Since it is resistant to penicillinase enzymes, such as that produced by Staphylococcus aureus, it is widely used clinically in the US to treat penicillin-resistant Staphylococcus aureus. However, with the introduction and widespread use of both oxacillin and methicillin, antibiotic-resistant strains called methicillin-resistant and oxacillin-resistant Staphylococcus aureus (MRSA/ORSA) have become increasingly prevalent worldwide. MRSA/ORSA is treated using vancomycin.

Adverse effects

Side effects include hypersensitivity and local reactions. In high doses, renal, hepatic, or nervous system effects can occur.[2]

References

  • ChemBank
  1. ^ David Greenwood (2008). Antimicrobial drugs: chronicle of a twentieth century medical triumph. Oxford University Press US. pp. 124–.  
  2. ^ Drugs.com: Bactocill