Mupirocin

Title: Mupirocin
CAS Registry Number: 12650-69-0
CAS Name: (2E)-5,9-Anhydro-2,3,4,8-tetradeoxy-8-[[(2S,3S)-3-[(1S,2S)-2-hydroxy-1-methylpropyl]oxiranyl]methyl]-3-methyl-L-talo-non-2-enonic acid, 8-carboxyoctyl ester
Additional Names: pseudomonic acid A; trans-pseudomonic acid
Manufacturers' Codes: BRL-4910A
Trademarks: Bactoderm (Pfizer); Bactroban (GSK); Turixin (GSK)
Molecular Formula: C26H44O9
Molecular Weight: 500.62
Percent Composition: C 62.38%, H 8.86%, O 28.76%
Literature References: Major component of the pseudomonic acids, q.v., an antibiotic complex produced by Pseudomonas fluorescens NCIB 10586. Isoln and characterization: A. T. Fuller et al., Nature 234, 416 (1971); K. D. Barrow, G. Mellows, DE 2227739; eidem, US 3977943; eidem, US 4071536 (1973, 1976, 1978 all to Beecham). Purification: P. J. O'Hanlon et al., DE 2842358; eidem, US 4222942 (1979, 1980 both to Beecham). Structure: E. B. Chain, G. Mellows, Chem. Commun. 1974, 847; eidem, J. Chem. Soc. Perkin Trans. 1 1977, 294. Absolute configuration: R. G. Alexander et al., ibid. 1978, 561. Prepn from methyl pseudomonate C: eidem, Tetrahedron Lett. 22, 2059 (1981). Total syntheses of (±)-form: B. B. Snider, G. B. Phillips, J. Am. Chem. Soc. 104, 1113 (1982); B. B. Snider et al., J. Org. Chem. 48, 3003 (1983). Biosynthesis: T. C. Feline et al., J. Chem. Soc. Perkin Trans. 1 1977, 309. Effect of pH on chemical stability and antibacterial activity: J. P. Clayton et al., ibid. 1979, 838. Inhibition of bacterial protein synthesis: J. Hughes, G. Mellows, J. Antibiot. 31, 330 (1978); of isoleucyl-tRNA synthetase: eidem, Biochem. J. 176, 305 (1978); eidem, ibid. 191, 209 (1980). In vitro antibacterial spectrum: R. Sutherland et al., Antimicrob. Agents Chemother. 27, 495 (1985); M. W. Casewell, R. L. R. Hill, J. Antimicrob. Chemother. 15, 523 (1985). Antimycoplasmal activity in vitro: R. M. Banks et al., J. Antibiot. 41, 609 (1988). Clinical evaluations: G. D. Reilly, R. C. Spencer, ibid. 13, 295 (1984); M. W. Casewell, R. L. R. Hill, ibid. 17, 365 (1986). Reviews: A. Ward, D. M. Campoli-Richards, Drugs 32, 425-444 (1986); M. W. Casewell, R. L. R. Hill, J. Antimicrob. Chemother. 19, 1-5 (1987).
Properties: Crystals from ether, mp 77-78°. [a]D20 -19.3° (c = 1 in methanol). uv max (ethanol): 222 nm (e 14500).
Melting point: mp 77-78°
Optical Rotation: [a]D20 -19.3° (c = 1 in methanol)
Absorption maximum: uv max (ethanol): 222 nm (e 14500)
Therap-Cat: Topical antibacterial.
Therap-Cat-Vet: Topical antibacterial.
Keywords: Antibacterial (Antibiotics).
Muraglitazar Muramic Acid Muramyl Dipeptide Murexide Murexine

Mupirocin
Systematic (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
Clinical data
Trade names Bactroban
AHFS/Drugs.com monograph
MedlinePlus a688004
Licence data US FDA:link
Pregnancy cat. B (US)
Legal status Rx Only (US)
Routes topical,nasal
Pharmacokinetic data
Protein binding 97%
Half-life 20 to 40 minutes
Identifiers
CAS number 12650-69-0 YesY
ATC code D06AX09 R01AX06
PubChem CID 446596
DrugBank DB00410
ChemSpider 393914 YesY
UNII D0GX863OA5 N
KEGG D01076 YesY
ChEMBL CHEMBL719 YesY
Chemical data
Formula C26H44O9 
Mol. mass 500.622 g/mol
 N (what is this?)  (verify)

Mupirocin (Bactroban or Centany) is an antibiotic of the monoxycarbolic acid class.[1] It was originally isolated from Pseudomonas fluorescens NCIMB 10586,[2] developed by Beecham.

Mupirocin is bacteriostatic at low concentrations and bactericidal at high concentrations.[3] It is used topically and is effective against Gram-positive bacteria, including MRSA.[4] Mupirocin is a mixture of several pseudomonic acids, with pseudomonic acid A (PA-A) constituting greater than 90% of the mixture. Also present in mupirocin are pseudomonic acid B with an additional hydroxyl group at C8,[5] pseudomonic acid C with a double bond between C10 and C11, instead of the epoxide of PA-A,[6] and pseudomonic acid D with a double bond at C4` and C5` in the 9-hydroxy-nonanoic acid portion of mupirocin.[7]