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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
Identifiers
CAS number 66-79-5
ATC code J01CF04 QJ51CF04
PubChem 6196
Chemical data
Formula C19H19N3O5S 
Mol. mass 401.436 g/mol
Therapeutic considerations
Pregnancy cat.  ?
Legal status
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Oxacillin sodium (trade name Bactocill) is a narrow spectrum beta-lactam antibiotic of the penicillin class.

Uses

Oxacillin is a penicillinase resistant β-lactam. It is similar to methicillin, and has replaced methicillin in clinical use since it has better properties. 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, resistant strains called oxacillin-resistant Staphylococcus aureus (MRSA/ORSA) are highly prevalent in the U.S. and the U.K. According to a CDC study, about 94,000 cases of invasive MRSA infection occurred in 2005 in the US and an estimated 19,000 cases resulted in death.[1]. Thus, more deaths are due to MRSA than HIV in the US. A new strain of MRSA (called USA300) has widely disseminated in the US and causes mainly Skin and soft tissue infection but it also causes necrotizing disease, and severe sepsis. Different strains of MRSA cause Healthcare associated and Community-associated disease. USA300 is a community-associated strain.

References

  1. ^ (Klevens, R. M., M. A. Morrison, J. Nadle, S. Petit, K. Gershman, S. Ray, L. H. Harrison, R. Lynfield, G. Dumyati, J. M. Townes, A. S. Craig, E. R. Zell, G. E. Fosheim, L. K. McDougal, R. B. Carey, and S. K. Fridkin. 2007. Invasive methicillin-resistant Staphylococcus aureus infections in the United States. Jama 298:1763-71.
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