Mupirocin
[CAS# 12650-69-0]

Identification

• Classification: API >> Antibiotics >> Other antibiotics
• Name: Mupirocin
• Synonyms: 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
• Molecular Formula: C₂₆H₄₄O₉
• Molecular Weight: 500.62
• CAS Registry Number: 12650-69-0
• EC Number: 603-145-3
• 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

Properties

• Solubility: 35 mg/mL (DMSO)

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H302-H315-H317-H319
• Safety Statements: P261-P264-P264+P265-P270-P272-P280-P301+P317-P302+P352-P305+P351+P338-P321-P330-P332+P317-P333+P317-P337+P317-P362+P364-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Acute toxicity	Acute Tox.	4	H302
Skin sensitization	Skin Sens.	1	H317

Discovery and Applications

Mupirocin, a potent antibiotic, was discovered in the late 1970s by researchers at Beecham Pharmaceuticals (now GlaxoSmithKline). The discovery stemmed from efforts to find new antimicrobial agents derived from naturally occurring compounds. Mupirocin is produced by fermentation of the bacterium Pseudomonas fluorescens, which was isolated from soil samples. Its unique mechanism of action involves inhibition of bacterial isoleucyl-tRNA synthetase, disrupting protein synthesis in susceptible bacteria. Mupirocin's discovery represented a significant breakthrough in antibiotic research.

Mupirocin is primarily used as a topical antibiotic for the treatment of bacterial skin infections, including impetigo, folliculitis, and infected wounds. Its broad-spectrum activity against Gram-positive bacteria, including MRSA, makes it effective in controlling and eliminating bacterial colonization on the skin. Mupirocin inhibits bacterial growth by interfering with protein synthesis, thereby preventing the proliferation of susceptible bacteria and promoting wound healing.

Mupirocin is also employed for nasal decolonization to eradicate methicillin-resistant Staphylococcus aureus (MRSA) carriage in patients, particularly those at high risk of infection, such as healthcare workers and surgical patients. Nasal application of mupirocin reduces the bacterial load in the nasal passages, minimizing the risk of MRSA transmission and subsequent infections.

In addition to treatment, mupirocin is used prophylactically to prevent skin infections in certain populations, such as athletes and military personnel. Application of mupirocin to areas prone to bacterial colonization, such as the nostrils and skin folds, reduces the risk of infection transmission and outbreaks.

Mupirocin is effective in preventing and treating secondary bacterial infections in dermatological conditions, such as eczema, psoriasis, and atopic dermatitis. Topical application of mupirocin helps control bacterial growth, reduce inflammation, and prevent exacerbations of underlying skin conditions.

Mupirocin is utilized in veterinary medicine for the treatment of bacterial skin infections in companion animals and livestock. Its topical formulation allows for targeted application to affected areas, facilitating wound healing and preventing the spread of bacterial infections within animal populations.

References

2000. Mupirocin Prophylaxis in Peritoneal Dialysis. Peritoneal Dialysis International, 20(5).
URL: https://pubmed.ncbi.nlm.nih.gov/11117244/

2007. Transient Loss of High-Level Mupirocin Resistance in Staphylococcus aureus Due to MupA Polymorphism. Antimicrobial Agents and Chemotherapy, 51(6).
DOI: 10.1128/AAC.01297-06

2003. Subinhibitory Mupirocin Inhibits Pseudomonas aeruginosa Flagella. Microbiology and Immunology, 47(1).
DOI: 10.1111/j.1348-0421.2003.tb02786.x