Oxacillin

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Oxacillin
Oxacillin skeletal.svg
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 monograph
MedlinePlus a685020
Legal status ?
Identifiers
CAS number 66-79-5 YesY
ATC code J01CF04 QJ51CF04
PubChem CID 6196
DrugBank DB00713
ChemSpider 5961 N
UNII UH95VD7V76 YesY
KEGG D08307 YesY
ChEBI CHEBI:49566 N
ChEMBL CHEMBL819 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 (what is this?)  (verify)

Oxacillin sodium (trade name Bactocill) is a narrow spectrum beta-lactam antibiotic of the penicillin class.

It was developed by Beecham.[1]

Uses[edit]

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 oxacillin-resistant Staphylococcus aureus (MRSA/ORSA) have become increasingly prevalent worldwide. MRSA/ORSA is treated using vancomycin.

Adverse effects[edit]

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

References[edit]

  1. ^ David Greenwood (2008). Antimicrobial drugs: chronicle of a twentieth century medical triumph. Oxford University Press US. pp. 124–. ISBN 978-0-19-953484-5. Retrieved 18 November 2010. 
  2. ^ Drugs.com: Bactocill