Mupirocin
| Subclass of | epoxide, triol, tetrahydropyran, carboxylate ester, monocarboxylic acid  |
|---|---|
| Get use | Medication |
| Stereoisomer of | 9-[4-[(2S,3R,4R,5S)-3,4-dihydroxy-5-[[(2S,3S)-3-[(2S,3S)-3-hydroxybutan-2-yl]-2-oxiranyl]methyl]-2-oxanyl]-3-methyl-1-oxobut-2-enoxy]nonanoic acid |
| Chemical formula | C₂₆H₄₄O₉ |
| Canonical SMILES | CC(C1C(O1)CC2COC(C(C2O)O)CC(=CC(=O)OCCCCCCCCC(=O)O)C)C(C)O |
| Isomeric SMILES | C[C@H]([C@H]1[C@@H](O1)C[C@H]2CO[C@H]([C@@H]([C@@H]2O)O)C/C(=C/C(=O)OCCCCCCCCC(=O)O)/C)[C@H](C)O |
| Active ingredient in | Bactroban, Centany, Muricin |
| World Health Organisation international non-proprietary name | mupirocin |
| Found insyd taxon | Pseudomonas fluorescens |
| Medical condition treated | impetigo, staphylococcal infection |
| Pregnancy category | US pregnancy category B |
| Subject has role | antibiotic, protein synthesis inhibitor, essential medicine, bactericide |
Mupirocin, dem sell under de brand name Bactroban among odas, be a topical antibiotic useful against superficial skin infections such as impetigo anaa folliculitis.[1][2][3] E sanso fi be used to get rid of methicillin-resistant S. aureus (MRSA) wen present insyd de nose widout symptoms.[2] Out of concerns of developing resistance, use for greater dan ten days no be recommended.[3] Dem dey use am as a cream anaa ointment dem apply to de skin.[2]
Common side effects dey include itchiness den rash at de site of application, headache, den nausea.[2] Long-term use fi result in increased growth of fungi.[2] Use during pregnancy den breastfeeding appear to be safe.[2] Mupirocin chemically be a carboxylic acid.[4] E dey work by blocking a bacterium ein ability to make protein, wich usually dey result in bacterial death.[2]
Na dem initially isolate mupirocin insyd 1971 from Pseudomonas fluorescens.[5] E dey on de World Health Organization's List of Essential Medicines.[6] Insyd 2023, na e be de 171st most commonly prescribed medication insyd de United States, plus more dan 2 million prescriptions.[7][8] E be available as a generic medication.[9]
Biosynthesis
[edit | edit source]Biosynthesis of pseudomonic acid A
[edit | edit source]| Gene | Function |
|---|---|
| mupA | FMNH2 dependent oxygenase |
| mmpA | KS ACP KS KR ACP KS ACP ACP |
| mupB | 3-oxoacyl-ACP synthase |
| mmpB | KS DH KR ACP ACP ACP TE |
| mmpC | AT AT |
| mmpD | KS DH KR MeT ACP KS DH KR ACP KS DH KR MeT ACP KS KR ACP |
| mupC | NADH/NADPH oxidoreductase |
| macpA | ACP |
| mupD | 3-oxoacyl-ACP reductase |
| mupE | enoyl reductase |
| macpB | ACP |
| mupF | KR |
| macpC | ACP |
| mupG | 3-oxoacyl-ACP synthase I |
| mupH | HMG-CoA synthase |
| mupJ | enoyl-CoA hydratase |
| mupK | enoyl-CoA hydratase |
| mmpE | KS hydrolase |
| mupL | putative hydrolase |
| mupM | isoleucyl-tRNA synthase |
| mupN | phosphopantetheinyl transferase |
| mupO | cytochrome P450 |
| mupP | unknown |
| mupQ | acyl-CoA synthase |
| mupS | 3-oxoacyl-ACP reductase |
| macpD | ACP |
| mmpF | KS |
| macpE | ACP |
| mupT | ferredoxin dioxygenase |
| mupU | acyl-CoA synthase |
| mupV | oxidoreductase |
| mupW | dioxygenase |
| mupR | N-AHL-responsive transcriptional activator |
| mupX | amidase/hydrolase |
| mupI | N-AHL synthase |
References
[edit | edit source]- ↑ 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.
- 1 2 3 4 5 6 7 "Mupirocin". The American Society of Health-System Pharmacists. Archived from the original on 21 December 2016. Retrieved 8 December 2016.
- 1 2 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.
- ↑ Khanna R, Krediet RT (2009). Nolph and Gokal's Textbook of Peritoneal Dialysis (in English) (3rd ed.). Springer Science & Business Media. p. 421. ISBN 9780387789408. Archived from the original on 10 September 2017.
- ↑ Heggers JP, Robson MC, Phillips LG (1990). Quantitative Bacteriology: Its Role in the Armamentarium of the Surgeon (in English). CRC Press. p. 118. ISBN 9780849351297. Archived from the original on 10 September 2017.
- ↑ 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.
- ↑ "Top 300 of 2023". ClinCalc. Archived from the original on 12 August 2025. Retrieved 12 August 2025.
- ↑ "Mupirocin Drug Usage Statistics, United States, 2013 - 2023". ClinCalc. Retrieved 19 August 2025.
- ↑ "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.
External links
[edit | edit source]