Oxacillin

Table of contents

  • Brand Names
  • Drug Combinations
  • Chemistry
  • Pharmacologic Category
  • Mechanism of Action
  • Therapeutic Use
  • Pregnancy and Lactation Implications
  • Contraindications
  • Warnings and Precautions
  • Adverse Reactions
  • Drug Interactions
  • Dosage
  • Pharmacokinetics and Pharmacodynamics
  • Special Considerations

Brand Names

Europe

Belgium: Penstapho; Estonia: Prostaphlin; France: Bristopen, Oxacilline; Germany: Infectostaph, Masteet, Oxacillin, Totocillin; Greece: Prostaphlin; Italy: Penstapho; Lithuania: Oxacillin; Romania: Oxacilina, Oxalin-Europharm; Slovakia: Oxacilin, Prostaphlin.

North America

USA: Bactocill.

Latin America

Brazil: Oxacilina, Oxanon, Oxapen, Prodoxacilina, Staficilin.

Asia

Japan: Bactocill, Oxacilina.

Drug combinations

Oxacillin and Ampicillin

Chemistry

Oxacillin Sodium: C~19~H~18~N~3~NaO~5~S H~2~O. Mw: 441.43. (1) 4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, 3,3-dimethyl-6-[[(5-methyl-3-phenyl-4-isoxazolyl)carbonyl]amino]-7-oxo-, monosodium salt, monohydrate, [2S-(2α,5α,6β)]-; (2) Monosodium (2S,5R,6R)-3,3-dimethyl-6-(5-methyl-3-phenyl-4-isoxazolecarboxamido)-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate monohydrate. CAS-7240-38-2; CAS-1173-88-2 (anhydrous); CAS-66-79-5 (oxacillin)(1962).

Pharmacologic Category

Penicillinase-resistant Penicillins. (ATC-Code: J01CF04).

Mechanism of action

Usually bactericidal. Like other β-lactam antibiotics, antibacterial activity results from inhibition of bacterial cell wall synthesis by binding to one or more penicillin-binding proteins and so inhibiting final transpeptidation step of peptidoglycan synthesis in bacterial cell walls. Spectrum of activity includes many Gram-positive aerobic cocci, some Gram-positive bacilli, and a few Gram-negative aerobic cocci. Active in vitro against penicillinase-producing and nonpenicillinase-producing Gram-positive aerobes such as Staphylococcus aureus and S. epidermidis, S. pyogenes (group A β-hemolytic Streptococci), S. agalactiae (group B Streptococci), groups C and G Streptococci, S. pneumoniae, and some viridans Streptococci. Enterococci (including E. faecalis) usually resistant. Complete cross-resistance occurs among penicillinase-resistant penicillins (dicloxacillin, nafcillin, oxacillin).

Therapeutic use

Osteomyelitis, septicemia, endocarditis, and CNS infections caused by susceptible strains of Staphylococcus.

Pregnancy and lactiation implications

Adverse events not observed in animals. Oxacillin is distributed into amniotic fluid and detected in cord blood. No increased risk of teratogenic effects with oxacillin in humans observed. Enters breast milk (use caution).

Unlabeled use

Contraindications

Hypersensitivity to oxacillin or other penicillins or any component of the formulation.

Warnings and precautions

Serious and occasionally severe or fatal hypersensitivity (anaphylactoid) reactions reported in patients on penicillin therapy, especially with history of β-lactam hypersensitivity, history of sensitivity to multiple allergens, or previous IgE-mediated reactions (caution in asthmatic patients). Prolonged use may result in fungal or bacterial superinfection, including C. difficile-associated diarrhea and pseudomembranous colitis. Use with caution in renal impairment, in the elderly, and in neonates (elimination of drug is slow). May interfere with urinary glucose tests using cupric sulfate. May inactivate aminoglycosides in vitro. May produce false-positive urinary and serum proteins.

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