Mupirocin

Mupirocin

Clinical data
Trade names	Bactroban, others
AHFS/Drugs.com	Monograph
MedlinePlus	a688004
License data	US FDA: Bactroban
Pregnancy category	US: B (No risk in non-human studies)
Routes of administration	Topical, nasal
ATC code	D06AX09 (WHO) R01AX06 (WHO)
Legal status
Legal status	US: ℞-only
Pharmacokinetic data
Protein binding	97%
Biological half-life	20 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	12650-69-0 Y
PubChem CID	446596
DrugBank	DB00410 Y
ChemSpider	393914 Y
UNII	D0GX863OA5
KEGG	D01076 Y
ChEBI	CHEBI:7025 N
ChEMBL	CHEMBL719 Y
ECHA InfoCard	100.106.215
Chemical and physical data
Formula	C26H44O9
Molar mass	500.622 g/mol
3D model (Jmol)	Interactive image
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?)

Mupirocin, sold under the brand name Bactroban among others, is an 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.

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 appear to be safe. Mupirocin is in the carbolic acid class of medications. It works by blocking the making of protein by the bacteria 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, the most effective and safe medicines needed in a health system. The wholesale cost in the developing world is about 2.10 USD for a 15 gm tube. In the United States a course of treatment costs 25 to 50 USD.

Mupirocin is used as a topical treatment for bacterial skin infections, for example, furuncle, impetigo, open wounds, etc. It is also useful in the treatment of superficial methicillin-resistant Staphylococcus aureus (MRSA) infections. Mupirocin is inactive for most anaerobic bacteria, mycobacteria, mycoplasma, chlamydia, yeast and fungi.