Mupirocin (BRL-4910A)

Alias:
Cat No.:V1438 Purity: ≥98%
Mupirocin (formerly BRL-4910A; BRL 4910A;Pseudomonic acid;Mupirocin, Bactroban, Centany) is a potent and orally bioactiveisoleucyl t-RNA synthetase inhibitor and a naturally occuring antibiotic isolated fromPseudomonas fluorescens.
Mupirocin (BRL-4910A) Chemical Structure CAS No.: 12650-69-0
Product category: DNA(RNA) Synthesis
This product is for research use only, not for human use. We do not sell to patients.
Size Price Stock Qty
10mg
25mg
50mg
100mg
250mg
500mg
1g
Other Sizes

Other Forms of Mupirocin (BRL-4910A):

  • Mupirocin lithium (BRL-4910A lithium; Pseudomonic acid lithium)
  • Mupirocin calcium hydrate
  • Mupirocin calcium
Official Supplier of:
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Purity & Quality Control Documentation

Purity: ≥98%

Product Description

Mupirocin (formerly BRL-4910A; BRL 4910A; Pseudomonic acid; Mupirocin, Bactroban, Centany) is a potent and orally bioactive isoleucyl t-RNA synthetase inhibitor and a naturally occuring antibiotic isolated from Pseudomonas fluorescens. It is authorized for use in the management of skin infections caused by bacteria. One member of the monoxycarbolic acid class of antibiotics is mupirocin. Mupirocin has concentration-dependent effects; at low concentrations, it has bacteriostatic effects, while at high concentrations, it has bactericidal effects. It works well as a topical antibiotic against MRSA and other Gram-positive bacteria. More than 90% of the mixture in mupirocin is made up of pseudomonic acid A (PA-A), one of several pseudomonic acids that are present in the mixture.

Biological Activity I Assay Protocols (From Reference)
Targets
isoleucyl t-RNA synthetase
ln Vitro

Mupirocin (BRL-4910A, Pseudomonic acid) (0-100 μM; 48 h) exhibits antibacterial activity against certain gram-negative bacteria, streptococci, and staphylococci; its MIC values range from 0.06-0.25 μg/mL (MIC50 = 0.12 μg/mL, MIC90 = 0.25 μg/mL)[1].
Mupirocin is 95% bound to the protein found in human serum, which causes activity inhibition when human serum is present[1].
Mupirocin appears to work against bacteria by reversibly blocking isoleucyl-transfer RNA, which stops the synthesis of bacterial proteins and RNA[2].
Mupirocin (2% ointment) decreases the expression of tumor necrosis factor-alpha (TNF-α), increases the leavel of vascular endothelial growth factor (VEGF), and decreases the levels of pro-inflammatory cytokines IL-1β and IL-17[4].
Mupirocin has minimum inhibitory concentrations (MICs) of 0.25, 1.26, and 1.59 mg/L for MS (S. epidermidis ATCC 12228), MR (S. epidermidis (Se56-99)), and VIR (S. epidermidis (Se43-98))[5].
Note: MIC, the minimum inhibition concentration.

ln Vivo
MRSA: Meticillin-resistant Staphylococcus aureus.
Mupirocin (BRL-4910A, pseudomononic acid) is well absorbed when administered orally and parenterally; however, the prolonged breakdown of the antibiotic to the antibacterially inactive metabolite monic acid A resulted in a brief duration of antibiotic concentrations in the serum[1].
Mupirocin (2% ointment; external administration; twice daily; 3-6 d) reduces the overall bacterial loads in the skin lesions with either topical treatment[3].
Mupirocin (2% ointment; external administration; 4 d) reduces pressure ulcers in mice that are infected with MRSA[4].
Mupirocin (100 mg/mL; s.c.; 7 d) has a preventive effect against Staphylococcus epidermidis-related vascular prosthetic graft infection[5].
Cell Assay
Cell Line: Staphylococcus aureus
Concentration: 0-100 μM/mL
Incubation Time: 24, 48 hours
Result: Resulted in a 90 to 99% reduction at 24 h, with MIC values ranged from 0.12-1.0 μM/mL and MBC values ranged from 4.0-32 μM/mL at 48 h.
Animal Protocol
MRSA skin infection model in mice (10-12 weeks old)
2% ointment
External administration; twice daily; 3-6 days
References

[1]. Antibacterial activity of mupirocin (pseudomonic acid), a new antibiotic for topical use. Antimicrob Agents Chemother. 1985 Apr;27(4):495-8.

[2]. Mupirocin: a topical antibiotic with a unique structure and mechanism of action. Clin Pharm. 1987 Oct;6(10):761-70.

[3]. Efficacy of topical and systemic antibiotic treatment of meticillin-resistant Staphylococcus aureus in a murine superficial skin wound infection model. Int J Antimicrob Agents. 2013 Sep. 42(3):272-5.

[4]. Investigating auranofin for the treatment of infected diabetic pressure ulcers in mice and dermal toxicity in pigs. Sci Rep. 2021 May 25;11(1):10935.

[5]. Mupirocin prophylaxis against methicillin-susceptible, methicillin-resistant, or vancomycin-intermediate Staphylococcus epidermidis vascular-graft infection. Antimicrob Agents Chemother. 2000 Oct. 44(10):2842-4.

These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C26H44O9
Molecular Weight
500.62
Exact Mass
500.3
Elemental Analysis
C, 62.38; H, 8.86; O, 28.76
CAS #
12650-69-0
Appearance
Solid powder
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
InChi Code
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
Chemical 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
Synonyms

BRL4910A; Pseudomonic acid; BRL-4910A; BRL 4910A; Mupirocin; Bactroban; Centany

HS Tariff Code
2934.99.9001
Storage

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Shipping Condition
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
Solubility Data
Solubility (In Vitro)
DMSO: ~100 mg/mL (~199.8 mM)
Water: ~46 mg/mL warmed (91.9 mM)
Ethanol: ~100 mg/mL (~199.8 mM)
Solubility (In Vivo)

Chemical 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

InChi Key:MINDHVHHQZYEEK-HBBNESRFSA-N

InChi Code: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

SMILES Code:O=C(O)CCCCCCCCOC(/C=C(C)/C[C@@H]1OC[C@H](C[C@@H]2O[C@H]2[C@H]([C@@H](O)C)C)[C@@H](O)[C@H]1O)=O

 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 1.9975 mL 9.9876 mL 19.9752 mL
5 mM 0.3995 mL 1.9975 mL 3.9950 mL
10 mM 0.1998 mL 0.9988 mL 1.9975 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.

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Calculation results

Working concentration mg/mL;

Method for preparing DMSO stock solution mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.

Method for preparing in vivo formulation:Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O,mix and clarify.

(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
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Clinical Trial Information
NCT Number Recruitment interventions Conditions Sponsor/Collaborators Start Date Phases
NCT03140423 Active
Recruiting
Drug: Arm 1. Routine Care
(Mupirocin/CHG)
Drug: Arm 2. Iodophor/CHG
Decolonization
Staphylococcus Aureus Harvard Pilgrim Health Care May 1, 2017 Phase 4
NCT02967432 Completed Drug: Mupirocin Topical Ointment
Drug: Petroleum Jelly
Staphylococcus Crouse Hospital October 2016 Phase 2
NCT04287777 Completed Drug: Mupirocin gel
Drug: Placebo
Impetigo Reig Jofre Group February 2014 Phase 3
NCT01949935 Completed Drug: Mupirocin Surgical Site Infections Horizon Health Network March 2009 Phase 3
NCT00156377 Completed Drug: Mupirocin Staphylococcal Infections
Cross Infection
University Hospital Muenster November 2002 Phase 4
Biological Data
  • Histopathology of murine pressure ulcers infected with MRSA and given vehicle control or topical mupirocin treatment. Sci Rep . 2021 May 25;11(1):10935.
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