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Identification
Name Mupirocin
Accession Number DB00410 (APRD00162)
Type small molecule
Groups approved
Description

Mupirocin (pseudomonic acid A, or Bactroban or Centany) is an antibiotic originally isolated from Pseudomonas fluorescens. It is used topically, and is primarily effective against Gram-positive bacteria. Mupirocin is bacteriostatic at low concentrations and bactericidal at high concentrations.
Mupirocin has a unique mechanism of action, which is selective binding to bacterial isoleucyl-tRNA synthetase, which halts the incorporation of isoleucine into bacterial proteins. Because this mechanism of action is not shared with any other antibiotic, mupirocin has few problems of antibiotic cross-resistance.
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  • MRC
  • mupirocin
  • Mupirocine
  • Pseudomonic acid
Brand names
  • Bactoderm
  • Bactroban
  • Bactroban Nasal
  • Centany
  • Turixin
Brand name mixtures Not Available
Categories
  • Anti-Bacterial Agents
  • Antibiotics
  • Protein Synthesis Inhibitors
CAS number 12650-69-0
Weight Average: 500.6222
Monoisotopic: 500.298533006
Chemical Formula C26H44O9
InChI Key InChIKey=MINDHVHHQZYEEK-HBBNESRFSA-N
InChI
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
Plain Text
IUPAC Name
9-{[(2E)-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]oxy}nonanoic acid
SMILES
C[C@H](O)[C@H](C)[C@@H]1O[C@H]1C[C@H]1CO[C@@H](C\C(C)=C\C(=O)OCCCCCCCCC(O)=O)[C@H](O)[C@@H]1O
Plain Text
Mass Spec Not Available
Taxonomy
Kingdom Organic
Classes
  • Fatty Acids
Substructures
  • Carboxylic Acids and Derivatives
  • Glycerol and Derivatives
  • Hydroxy Compounds
  • Alkanes and Alkenes
  • Pyrans
  • Acetates
  • Ethers
  • Alcohols and Polyols
  • Heterocyclic compounds
  • Epoxides
  • Fatty Acids
Pharmacology
Indication For the treatment of Staphylococci nasal carriers.
Pharmacodynamics Mupirocin, an antibiotic produced from Pseudomonas fluorescens, is structurally unrelated to any other topical or systemic antibiotics. Mupirocin is used to treat infection caused by Staphylococcus aureus and beta-hemolytic streptococci including Streptococcus pyogenes. This antibiotic has little, if any, potential for cross-resistance with other antibiotics.
Mechanism of action Mupirocin reversibly binds to bacterial isoleucyl-tRNA synthetase, an enzyme which promotes the conversion of isoleucine and tRNA to isoleucyl-tRNA. Prevention of this enzymes from functioning properly results in the inhibition of bacterial protein and RNA synthesis.
Absorption No measurable systemic absorption
Volume of distribution Not Available
Protein binding 97%
Metabolism

Hepatic. Following intravenous or oral administration, mupirocin is rapidly metabolized. The principal metabolite is monic acid, which has no antibacterial activity.
Route of elimination Following the application of Centany (mupirocin ointment),2% to a 400 cm2 area on the back of 23 healthy volunteers once daily for 7 days, the mean (range) cumulative urinary excretion of monic acid over 24 hrs following the last administration was 1.25% (0.2% to 3.0%) of the administered dose of mupirocin.
Half life 20 to 40 minutes
Clearance Not Available
Toxicity Not Available
Affected organisms
  • Enteric bacteria and other eubacteria
Pathways Not Available
Pharmacoeconomics
Manufacturers
  • Glaxosmithkline
  • Perrigo new york inc
  • Altana inc
  • Taro pharmaceuticals usa inc
  • Teva pharmaceuticals usa inc
Packagers
Dosage forms
Form Route Strength
Cream Topical
Ointment Topical
Prices
Unit description Cost Unit
Bactroban 2% Cream 30 gm Tube 92.21 USD tube
Bactroban 2% Ointment 22 gm Tube 77.01 USD tube
Bactroban 2% Cream 15 gm Tube 62.17 USD tube
Mupirocin powder 44.8 USD g
Mupirocin 2% Ointment 22 gm Tube 44.46 USD tube
Bactroban Nasal 2% Ointment 1 gm Tube 11.5 USD tube
Bactroban nasal 2% ointment 10.03 USD g
Centany 2% ointment 3.98 USD g
Bactroban 2% cream 3.57 USD g
Bactroban 2% ointment 3.37 USD g
Mupirocin 2% ointment 1.94 USD g
Bactroban 2 % Cream 0.55 USD g
Bactroban 2 % Ointment 0.55 USD g
Taro-Mupirocin 2 % Ointment 0.36 USD g
Patents
Country Patent Number Approved Expires
United States 6013657 1998-07-08 2018-07-08
Properties
State solid
Melting point 77-78oC
Experimental Properties Not Available
Predicted Properties
Property Value Source
water solubility 2.65e-02 g/l ALOGPS
logP 2.25 ALOGPS
logP 2.45 ChemAxon Molconvert
logS -4.28 ALOGPS
pKa 13.10 ChemAxon Molconvert
hydrogen acceptor count 8 ChemAxon Molconvert
hydrogen donor count 4 ChemAxon Molconvert
polar surface area 146.05 ChemAxon Molconvert
rotatable bond count 17 ChemAxon Molconvert
refractivity 129.39 ChemAxon Molconvert
polarizability 55.50 ChemAxon Molconvert
References
Synthesis Reference Not Available
General Reference Not Available
External Links
Resource Link
KEGG Drug D01076 Link_out
KEGG Compound C11758 Link_out
PubChem Compound 446596 Link_out
PubChem Substance 46505594 Link_out
ChemSpider 393914 Link_out
Therapeutic Targets Database DAP000711 Link_out
PharmGKB PA450563 Link_out
HET MRC Link_out
Drug Product Database 2239757 Link_out
RxList http://www.rxlist.com/cgi/generic/mupi.htm Link_out
Drugs.com http://www.drugs.com/cdi/mupirocin-cream.html Link_out
Wikipedia http://en.wikipedia.org/wiki/Mupirocin Link_out
ATC Codes
  • D06AX09
  • R01AX06
AHFS Codes
  • 84:04.04
PDB Entries Not Available
FDA label show (140 KB)
MSDS show (47 KB)
Interactions
Drug Interactions
Drug Interaction
Food Interactions Not Available
Targets

1. Isoleucyl-tRNA synthetase

Pharmacological action: yes
Actions: inhibitor

Catalyzes the attachment of isoleucine to tRNA(Ile). As IleRS can inadvertently accommodate and process structurally similar amino acids such as valine, to avoid such errors it has two additional distinct tRNA(Ile)-dependent editing activities. One activity is designated as 'pretransfer' editing and involves the hydrolysis of activated Val-AMP. The other activity is designated 'posttransfer' editing and involves deacylation of mischarged Val-tRNA(Ile)

Organism class: bacterial
UniProt ID: P41972 Link_out
Gene: ileS
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Hurdle JG, O’Neill AJ, Chopra I: The isoleucyl-tRNA synthetase mutation V588F conferring mupirocin resistance in glycopeptide-intermediate Staphylococcus aureus is not associated with a significant fitness burden. J Antimicrob Chemother. 2004 Jan;53(1):102-4. Epub 2003 Dec 4. Pubmed
  2. Thomas DG, Wilson JM, Day MJ, Russell AD: Mupirocin resistance in staphylococci: development and transfer of isoleucyl-tRNA synthetase-mediated resistance in vitro. J Appl Microbiol. 1999 Apr;86(4):715-22. Pubmed
  3. Antonio M, McFerran N, Pallen MJ: Mutations affecting the Rossman fold of isoleucyl-tRNA synthetase are correlated with low-level mupirocin resistance in Staphylococcus aureus. Antimicrob Agents Chemother. 2002 Feb;46(2):438-42. Pubmed
  4. Hughes J, Mellows G: On the mode of action of pseudomonic acid: inhibition of protein synthesis in Staphylococcus aureus. J Antibiot (Tokyo). 1978 Apr;31(4):330-5. Pubmed
  5. Hughes J, Mellows G: Inhibition of isoleucyl-transfer ribonucleic acid synthetase in Escherichia coli by pseudomonic acid. Biochem J. 1978 Oct 15;176(1):305-18. Pubmed
  6. Brown MJ, Mensah LM, Doyle ML, Broom NJ, Osbourne N, Forrest AK, Richardson CM, O’Hanlon PJ, Pope AJ: Rational design of femtomolar inhibitors of isoleucyl tRNA synthetase from a binding model for pseudomonic acid-A. Biochemistry. 2000 May 23;39(20):6003-11. Pubmed
  7. Rechsteiner T, Leisinger T: Purification of isoleucyl-tRNA synthetase from Methanobacterium thermoautotrophicum by pseudomonic acid affinity chromatography. Eur J Biochem. 1989 Apr 15;181(1):41-6. Pubmed
  8. Thomas CM, Hothersall J, Willis CL, Simpson TJ: Resistance to and synthesis of the antibiotic mupirocin. Nat Rev Microbiol. 2010 Apr;8(4):281-9. Epub 2010 Mar 1. Pubmed
Comments
Drug created on June 13, 2005 07:24 / Updated on November 10, 2010 13:39

This project is supported by Genome Alberta & Genome Canada, a not-for-profit organization that is leading Canada's national genomics strategy with $600 million in funding from the federal government. This project is also supported in part by GenomeQuest, Inc., an enterprise genomic information company serving the life science community.