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Merck

M7694

Sigma-Aldrich

Mupirocin

≥92% (HPLC), isoleucyl-tRNA synthetase (IRS) inhibitor, 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

Key Documents

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Product Name

Mupirocin, 920-1020 μg/mg (HPLC), crystalline

Quality Level

100

Assay

920-1020 μg/mg (HPLC)

form

crystalline

color

white to yellow

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.

Preparation Note

Mupirocin is poorly soluble in water (26 mg/L), but highly soluble in DMSO (≥10 mg/mL). If sterilization is required, it is advisable to use filter sterilization with a 0.22 µm PTFE, Polypropylene, or Nylon filter membrane.

Storage Class Code

11 - Combustible Solids

WGK

WGK 2

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
106M4733V
071M4705V
101M4750V
120M4711V
021M4718V

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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)
Gaston H M Vondenhoff et al.
European journal of medicinal chemistry, 46(11), 5227-5236 (2011-10-05)
Increasing resistance to antibiotics is a major problem worldwide and provides the stimulus for development of new bacterial inhibitors with preferably different modes of action. In search for new leads, several new bacterial targets are being exploited beside the use
Evaluation of the pig-tailed macaque (Macaca nemestrina) as a model of human Staphylococcus aureus nasal carriage
Cole AL, et al.
Infection and Immunity, 86(6), e00043-e00018 (2018)
Mupirocin: a topical antibiotic with a unique structure and mechanism of action.
Parenti MA, et al.
Clinical Pharmacy, 6(10), 761-770 (1987)
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