mupirocin
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| mupirocin | |
|---|---|
| IUPAC name | (2S,3R,4R,5S)-5-[(2S,3S,4S,5S)-2,3-Epoxy-5-hydroxy-4-methylhexyl]tetrahydro-3,4-dihydroxy-β-methyl-2H-pyran-2-crotonic acid, ester with 9-hydroxynonanoic acid |
| Tradename | Bactroban, Centany, others |
| Drugs.com | Monograph |
| MedlinePlus | a688004 |
| Pregnancy AU | B1 |
| Routes of administration | Topical |
| ATC prefix | D06 |
| ATC suffix | AX09 |
| CAS number | 12650-69-0 |
| PubChem | 446596 |
| DrugBank | DB00410 |
| ChemSpiderID | 393912 |
| UNII | D0GX863OA5 |
| ChEBI | 50672 |
| ChEMBL | 177 |
| Chemical formula | C26H44O9 |
| Molecular weight | 500.629 g/mol |
mupirocin is a topical antibiotic primarily used to treat infections caused by Staphylococcus aureus and Streptococcus pyogenes. It is particularly effective against methicillin-resistant Staphylococcus aureus and is a key agent for decolonization prior to surgery. The compound is produced naturally by the bacterium Pseudomonas fluorescens.
Medical uses
It is indicated for the topical treatment of impetigo, folliculitis, and other primary skin infections. Clinicians at the Mayo Clinic often prescribe it for secondary infection of traumatic lesions like lacerations or abrasions. A significant application, supported by guidelines from the Centers for Disease Control and Prevention, is the eradication of MRSA carriage in the anterior nares to prevent surgical site infection. This use is standard in protocols at institutions like the National Health Service and the Cleveland Clinic before major procedures such as cardiac surgery or orthopedic surgery.
Adverse effects
Local reactions such as burning, stinging, or pruritus at the application site are most common. Cases of contact dermatitis and angioedema have been reported to regulatory bodies like the Food and Drug Administration and the European Medicines Agency. Rare instances of anaphylaxis and systemic effects like nausea have been documented in the British National Formulary. Use on large open wounds or burns may increase systemic absorption and the risk of adverse events.
Mechanism of action
It acts by selectively and reversibly binding to bacterial isoleucyl-tRNA synthetase, an enzyme critical for protein synthesis. This inhibition prevents the incorporation of isoleucine into polypeptide chains, leading to the cessation of bacterial growth. Its unique target, distinct from those of macrolides, tetracyclines, and aminoglycosides, means there is no cross-resistance with these common classes. The specificity for bacterial over mammalian enzymes, a focus of research at Scripps Research, accounts for its selective toxicity.
Pharmacology
Following topical application to intact skin, systemic absorption is minimal. When applied to damaged epidermis, absorption increases but plasma concentrations remain low. Metabolism occurs rapidly in the skin to the inactive metabolite monic acid, which is then eliminated. Studies conducted by GlaxoSmithKline and published in the British Journal of Clinical Pharmacology confirm its localized pharmacokinetic profile. It is formulated in a polyethylene glycol base for the ointment and as a calcium salt in the nasal preparation.
History
The antibiotic was first isolated in the 1970s from Pseudomonas fluorescens strain NCIB 10586 by researchers at Beecham Research Laboratories in the United Kingdom. Its development name was pseudomonic acid A. Following clinical trials, it was approved for medical use under the trade name Bactroban by the Food and Drug Administration in the late 1980s. Its role expanded significantly during the global rise of MRSA in the 1990s, becoming a cornerstone of infection control strategies in hospitals from Johns Hopkins Hospital to Singapore General Hospital.
Society and culture
It is marketed globally under various brand names including Bactroban by GlaxoSmithKline and Centany by Ortho Dermatologics. Its inclusion on the World Health Organization's List of Essential Medicines underscores its public health importance. High-profile cases, such as its use in preventing outbreaks in professional sports leagues like the National Football League, have been covered by media outlets like ESPN. Debates on antimicrobial stewardship, often highlighted in journals like The Lancet, focus on balancing its critical decolonization use against the potential for developing resistance.
Category:World Health Organization essential medicines Category:Topical antibiotics Category:GlaxoSmithKline