Compound ID | 2489

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Mupirocin

Synonym(s): Pseudomonic acid

Class: Natural product antibiotic

Spectrum of activity: Gram-positive
Details of activity: Active against Staphylococcus aureus, Staphylococcus epidermidis, and Streptococcus pyogenes
Propensity to select resistant mutants: Yes
Description: Natural product from Pseudomonas fluorescens; used topically but not systemically (compound is rapidly hydrolysed to inactive metabolites in the latter case)
Year first mentioned: 1971
Highest developmental phase: Approved for topical use by FDA in 1997
Development status: Approved
Chemical structure(s):
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Molecular weight: 500.62
Iso. 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
InChI Key: MINDHVHHQZYEEK-HBBNESRFSA-N
Can. SMILES: C/C(=C\C(=O)OCCCCCCCCC(=O)O)/C[C@H]1[C@@H]([C@@H]([C@@H](C[C@H]2[C@H]([C@@H](C)[C@H](C)O)O2)CO1)O)O
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
External links:
PubChem link: https://pubchem.ncbi.nlm.nih.gov/compound/446596
Guide to Pharmacology: mupirocin
Citation: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC1162199/
Patent: US6013657A

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