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M7694

Sigma-Aldrich

Mupirocin

≥92% (HPLC), powder

Synonym(s):

5,9-Anhydro-2,3,4,8-tetradeoxy-8-[[3-(2-hydroxy-1-methylpropyl)oxiranyl]methyl]-3-methyl-[2E,8[2S,3S(1S,2S)]]-L-talonon-2-enonic acid 8-carboxyoctyl ester, BRL 4910A, Pseudomonic acid

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About This Item

Empirical Formula (Hill Notation):
C26H44O9
CAS Number:
12650-69-0
Molecular Weight:
500.62
MDL number:
MFCD01711620
UNSPSC Code:
12352200
PubChem Substance ID:
24724542
NACRES:
NA.77

Quality Level

100

Assay

≥92% (HPLC)

form

powder

optical activity

[α]/D -15.7 to -20°, c = 1 in methanol

color

white to tan

solubility

DMSO: ≥10 mg/mL

antibiotic activity spectrum

fungi

Mode of action

enzyme | inhibits
protein synthesis | interferes

originator

GlaxoSmithKline

storage temp.

room temp

SMILES string

[H][C@@]1(CO[C@@H](C\C(C)=C\C(=O)OCCCCCCCCC(O)=O)[C@H](O)[C@@H]1O)C[C@@H]2O[C@@]2([H])[C@@H](C)[C@H](C)O

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

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General description

Mupirocin is produced by Pseudomonas fluorescens. Mupirocin is used to treat impetigo and skin infections.

Application

Mupirocin has been used:
  • for kinetic assay
  • to assess its resistance by performing turbidity assay
  • to determine its antimicrobial susceptibility

Biochem/physiol Actions

Antibiotic; inhibits isoleucyl-tRNA synthetase (IRS).

Features and Benefits

This compound was developed by GlaxoSmithKline. To browse the list of other pharma-developed compounds and Approved Drugs/Drug Candidates, click here.

WGK

WGK 2

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

监管及禁止进口产品

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Eduardo Pérez-Roth et al.
Antimicrobial agents and chemotherapy, 54(5), 2252-2257 (2010-03-10)
We have sequenced the conjugative plasmid pPR9, which carries the ileS2 gene, which had contributed to the dissemination of high-level mupirocin resistance at our institution. The plasmid backbone shows extensive genetic conservation with plasmids belonging to the pSK41/pGO1 family, but
Mupirocin: a topical antibiotic with a unique structure and mechanism of action.
Parenti MA, et al.
Clinical Pharmacy, 6(10), 761-770 (1987)
Canine and Feline Dermatology Drug Handbook (2012)
Methods for detecting microbial methane production and consumption by gas chromatography
Aldridge JT, et al.
Bio-protocol, 6(7), 761-770 (2016)
Efficacy of topically delivered moxifloxacin against wound infection by Pseudomonas aeruginosa and methicillin-resistant Staphylococcus aureus
Jacobsen F, et al.
Antimicrobial Agents and Chemotherapy, 55(5), 2325-2334 (2011)
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