Structure via PubChem · Public domain (PubChem)
mupirocin
Sign in to saveAlso known as pseudomonic acid, 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, pseudomonic acid A, C26H44O9, BRL-4910A
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. Out of 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.
Key facts
- Drug.Verifiedfields
- changed
- Drug.verifiedrevid
- 408766144
- Drug.image
- Mupirocin structure.png
- Drug.image_class
- skin-invert-image
- Drug.width
- 320
- Drug.alt
- Structural formula of pseudomonic acid A (PA-A), the principal component of mupirocin
- Drug.image2
- Mupirocin molecule ball.png
- Drug.image_class2
- bg-transparent
- Drug.alt2
- Ball-and-stick model of the pseudomonic acid A molecule, the principal component of mupirocin
- Drug.caption
- Pseudomonic acid A (PA-A), the principal component of mupirocin
- Drug.tradename
- Bactroban, others
- Drug.MedlinePlus
- a688004
- Drug.DailyMedID
- Mupirocin
- Drug.pregnancy_AU
- B1
- Drug.routes_of_administration
- Topical
- Drug.ATC_prefix
- D06
- Drug.ATC_suffix
- AX09
- Drug.legal_AU
- S4
via Wikipedia infobox
Chemical data
- Formula
- C26H44O9
- Molecular weight
- 500.6 g/mol
- 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
- 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
- InChIKey
- MINDHVHHQZYEEK-HBBNESRFSA-N
- XLogP
- 3
- Polar surface area
- 146 Ų
- H-bond donors
- 4
- H-bond acceptors
- 9
- Formal charge
- 0
via PubChem
~12 min read
Encyclopedic overview
9 sectionsContents
- Medical uses
- Resistance
- Mechanism of action
- Biosynthesis
- Biosynthesis of pseudomonic acid A
- Monic acid biosynthesis
- Post-PKS tailoring
- 9-Hydroxy-nonanoic acid biosynthesis
- References
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. Out of 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 appears to be safe. Mupirocin is chemically a carboxylic acid. It works by blocking a bacterium's ability to make protein, which usually results in bacterial death.
Excerpted from Wikipedia’s “mupirocin” article, available under the CC BY-SA 4.0 licence.