Oxacillin

History

Oxacillin, a derivative of methicillin, was first synthesized in the early 1960s by Peter Doyle and John Naylor of Beecham in consort with Bristol-Myers. It belongs to the isoxazolyl penicillin family, which also includes cloxacillin and dicloxacillin, developed to counter penicillin-resistant Staphylococcus aureus. Unlike methicillin, oxacillin could be given orally or by injection. Beecham retained rights to cloxacillin in the UK, while Bristol-Myers received marketing rights for oxacillin in the US.

Medical uses

Oxacillin is a penicillinase-resistant β-lactam similar to methicillin, which it has replaced in clinical use. It is used in the US to treat penicillin-resistant Staphylococcus aureus due to its resistance to penicillinase enzymes. However, methicillin-resistant and oxacillin-resistant Staphylococcus aureus (MRSA/ORSA) have become increasingly prevalent worldwide and may require treatment with vancomycin or other new antibiotics.

Adverse effects

Common adverse effects of oxacillin include skin rash, diarrhea, nausea, vomiting, hematuria, agranulocytosis, eosinophilia, leukopenia, neutropenia, thrombocytopenia, hepatotoxicity, acute interstitial nephritis, and fever. High doses may cause renal, hepatic, and nervous system toxicity. As a penicillin, it can cause acute or delayed hypersensitivity reactions, and injection may cause redness, swelling, and itching at the site.

Society and culture

Multiple pharmaceutical companies have received approval for oxacillin products in the US. Sandoz obtained approval for Oxacillin Sodium Injectable in 1971 and for Oxacillin Sodium Powder in 1986. GlaxoSmithKline received approval for Bactocill Capsule in 1973 and Bactocill for Solution in 1981.

Other applicants include Ani Pharms Inc, TEVA, Watson Labs Inc, Baxter Healthcare, Sagent Pharms, Aurobindo Pharma LTD, Mylan Labs LTD, Hospira Inc, and Wockhardt Bio/Ag. The average wholesale price for Bactocill in Dextrose Intravenous is $20.37 for 1 g/50 mL and $32.48 for 2 g/50 mL. Oxacillin Sodium Injection prices are $17.52 for 1 g, $33.99 for 2 g, and $138.77 for 10 g.

Did You Know?

• Oxacillin is contraindicated in individuals with hypersensitivity to any penicillin antibiotic, and cross-allergenicity has been documented with cephalosporins and cephamycins.
• Oxacillin works by covalently binding to penicillin-binding proteins, inhibiting peptidoglycan synthesis and bacterial cell wall integrity.
• The chemical structure of oxacillin features a 6-aminopenicillanic acid nucleus with a thiazolidine ring attached to a β-lactam ring.