Mupirocin

Not to be confused with Miprocin.

Mupirocin
Pseudomonic acid A (PA-A), the principal component of mupirocin
Clinical data
Trade namesBactroban, others
Other namesmuciprocin[1]
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
IUPAC name
  • 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)
SMILES
  • 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
  • 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)

Mupirocin, sold under the brand name Bactroban among others, is a topical antibiotic useful against superficial skin infections such as impetigo or folliculitis.[5][6][7] It may also be used to get rid of methicillin-resistant S. aureus (MRSA) when present in the nose without symptoms.[6] Due to concerns of developing resistance, use for greater than ten days is not recommended.[7] It is used as a cream or ointment applied to the skin.[6]

Common side effects include itchiness and rash at the site of application, headache, and nausea.[6] Long-term use may result in increased growth of fungi.[6] Use during pregnancy and breastfeeding appears to be safe.[6] Mupirocin is chemically a carboxylic acid.[8] It works by blocking a bacteria's ability to make protein, which usually results in bacterial death.[6]

Mupirocin was initially isolated in 1971 from Pseudomonas fluorescens.[9] It is on the World Health Organization's List of Essential Medicines.[10] In 2022, it was the 162nd most commonly prescribed medication in the United States, with more than 3 million prescriptions.[11][12] It is available as a generic medication.[13]

  1. ^ Fleischer AB (2002). Emergency Dermatology: A Rapid Treatment Guide. McGraw Hill Professional. p. 173. ISBN 9780071379953. Archived from the original on 10 September 2017.
  2. ^ "Prescription medicines: registration of new generic medicines and biosimilar medicines, 2017". Therapeutic Goods Administration (TGA). 21 June 2022. Retrieved 30 March 2024.
  3. ^ "Bactroban Product information". Health Canada. 22 October 2009. Archived from the original on 26 February 2023. Retrieved 26 February 2023.
  4. ^ "Bactroban (mupirocin) cream, for topical use Initial U.S. Approval: 1997". DailyMed. Archived from the original on 26 February 2023. Retrieved 26 February 2023.
  5. ^ AlHoufie ST, Foster HA (August 2016). "Effects of sub-lethal concentrations of mupirocin on global transcription in Staphylococcus aureus 8325-4 and a model for the escape from inhibition". Journal of Medical Microbiology. 65 (8): 858–866. doi:10.1099/jmm.0.000270. PMID 27184545.
  6. ^ a b c d e f g "Mupirocin". The American Society of Health-System Pharmacists. Archived from the original on 21 December 2016. Retrieved 8 December 2016.
  7. ^ a b World Health Organization (2009). Stuart MC, Kouimtzi M, Hill SR (eds.). WHO Model Formulary 2008. World Health Organization. p. 298. hdl:10665/44053. ISBN 9789241547659.
  8. ^ Khanna R, Krediet RT (2009). Nolph and Gokal's Textbook of Peritoneal Dialysis (3rd ed.). Springer Science & Business Media. p. 421. ISBN 9780387789408. Archived from the original on 10 September 2017.
  9. ^ Heggers JP, Robson MC, Phillips LG (1990). Quantitative Bacteriology: Its Role in the Armamentarium of the Surgeon. CRC Press. p. 118. ISBN 9780849351297. Archived from the original on 10 September 2017.
  10. ^ World Health Organization (2019). World Health Organization model list of essential medicines: 21st list 2019. Geneva: World Health Organization. hdl:10665/325771. WHO/MVP/EMP/IAU/2019.06. License: CC BY-NC-SA 3.0 IGO.
  11. ^ "The Top 300 of 2022". ClinCalc. Archived from the original on 30 August 2024. Retrieved 30 August 2024.
  12. ^ "Mupirocin Drug Usage Statistics, United States, 2013 - 2022". ClinCalc. Retrieved 30 August 2024.
  13. ^ "Competitive Generic Therapy Approvals". U.S. Food and Drug Administration (FDA). 29 June 2023. Archived from the original on 29 June 2023. Retrieved 29 June 2023.
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