Mupirocin

Mupirocin, sold under the brand name Bactroban among others, is a topical antibiotic useful against superficial skin infections such as impetigo or folliculitis. It may also be used to get rid of methicillin-resistant S. aureus (MRSA) when present in the nose without symptoms. Due to concerns of developing resistance, use for greater than ten days is not recommended. It is used as a cream or ointment applied to the skin.

Not to be confused with Miprocin.
Mupirocin
Pseudomonic acid A (PA-A), the principal component of mupirocin
Clinical data
Trade namesBactroban, others
Other namesmuciprocin
AHFS/Drugs.comMonograph
MedlinePlusa688004
License data
Pregnancy
category
  • AU: B1
Routes of
administration		Topical
ATC code
Legal status
Legal status
Pharmacokinetic data
Protein binding97%
Elimination half-life20 to 40 minutes
Identifiers
  • 9-[(E)-4-[(2S,3R,4R,5S)-3,4-dihydroxy-5-[[(2S,3S)-3-[(2S,3S)-3-hydroxybutan-2-yl]oxiran-2-yl]methyl]oxan-2-yl]-3-methylbut-2-enoyl]oxynonanoic acid
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.106.215
Chemical and physical data
FormulaC26H44O9
Molar mass500.629 g·mol−1
3D model (JSmol)
Melting point77 to 78 °C (171 to 172 °F)
  • O=C(O)CCCCCCCCOC(=O)\C=C(/C)C[C@@H]2OC[C@H](C[C@@H]1O[C@H]1[C@@H](C)[C@@H](O)C)[C@@H](O)[C@H]2O
  • InChI=1S/C26H44O9/c1-16(13-23(30)33-11-9-7-5-4-6-8-10-22(28)29)12-20-25(32)24(31)19(15-34-20)14-21-26(35-21)17(2)18(3)27/h13,17-21,24-27,31-32H,4-12,14-15H2,1-3H3,(H,28,29)/b16-13+/t17-,18-,19-,20-,21-,24+,25-,26-/m0/s1 Y
  • Key:MINDHVHHQZYEEK-HBBNESRFSA-N Y
 NY (what is this?)  (verify)

Common side effects include itchiness and rash at the site of application, headache, and nausea. Long term use may result in increased growth of fungi. Use during pregnancy and breastfeeding appears to be safe. Mupirocin is chemically a carboxylic acid. It works by blocking a bacteria's ability to make protein, which usually results in bacterial death.

Mupirocin was initially isolated in 1971 from Pseudomonas fluorescens. It is on the World Health Organization's List of Essential Medicines. In 2020, it was the 203rd most commonly prescribed medication in the United States, with more than 2 million prescriptions. It is available as a generic medication.

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