Mupirocin

Synonym(s): Pseudomonic acid

Class: Aminoacyl-tRNA synthetase inhibitor (isoleucyl-tRNA synthetase [Ile-RS] inhibitor)

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):
Canonical 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
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
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
InChI Key:	MINDHVHHQZYEEK-HBBNESRFSA-N
Structure link:	https://pubchem.ncbi.nlm.nih.gov/compound/446596

External links:
Guide to Pharmacology:	mupirocin
Main Source:	https://www.ncbi.nlm.nih.gov/pmc/articles/PMC1162199/
Patent:	US6013657A