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Identification
NameMupirocin
Accession NumberDB00410  (APRD00162)
TypeSmall Molecule
GroupsApproved, Investigational, Vet 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
Synonyms
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
Bactroban
Centany
Mupirocina
Mupirocine
Mupirocinum
Pseudomonic acid
Pseudomonic acid a
External Identifiers
  • BRL 4910A
  • BRL 4910F
Approved Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Bactrobanointment20 mg/gtopicalGlaxo Smith Kline Llc2000-04-07Not applicableUs
Bactrobanointment20 mg/gtopicalCardinal Health1996-04-10Not applicableUs
Bactrobanointment20 mg/gtopicalLake Erie Medical DBA Quality Care Products LLC1996-04-10Not applicableUs
Bactrobancream20 mg/gtopicalPhysicians Total Care, Inc.2002-07-12Not applicableUs
Bactrobancream20 mg/gtopicalSTAT Rx USA LLC1998-01-23Not applicableUs
Bactrobanointment20 mg/gtopicalPhysicians Total Care, Inc.1996-04-10Not applicableUs
Bactrobancream20 mg/gtopicalGlaxo Smith Kline Llc1998-01-23Not applicableUs
Bactrobancream21.5 mg/gtopicalREMEDYREPACK INC.2013-12-04Not applicableUs
Bactrobanointment20 mg/gtopicalGlaxo Smith Kline Llc1996-04-10Not applicableUs
Bactrobancream21.5 mg/gtopicalLake Erie Medical & Surgical Supply DBA Quality Care Products LLC2012-03-28Not applicableUs
Centanyointment20 mg/gtopicalMedimetriks Pharmaceuticals Inc2009-02-26Not applicableUs
Centany Atointment20 mg/gtopicalMedimetriks Pharmaceuticals, Inc.2010-11-15Not applicableUs
Mupirocin Calciumcream20 mg/gtopicalPrasco Laboratories2013-01-28Not applicableUs
Approved Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Mupirocinointment20 mg/gtopicalREMEDYREPACK INC.2013-11-22Not applicableUs
Mupirocinointment20 mg/gtopicalPreferred Pharmaceuticals, Inc.2015-12-01Not applicableUs
Mupirocinointment20 mg/gtopicalTeva Pharmaceuticals USA Inc2003-11-07Not applicableUs
Mupirocinointment20 mg/gtopicalPreferred Pharmaceuticals, Inc.2014-02-14Not applicableUs
Mupirocinointment20 mg/gtopicalPhysicians Total Care, Inc.2003-12-05Not applicableUs
Mupirocinointment20 mg/gtopicalPerrigo New York Inc2009-10-30Not applicableUs
Mupirocinointment20 mg/gtopicalREMEDYREPACK INC.2013-06-12Not applicableUs
Mupirocincream2 g/100gtopicalGlenmark Pharmaceuticals Inc., Usa2013-01-24Not applicableUs
Mupirocinointment20 mg/gtopicalRebel Distributors Corp2009-10-30Not applicableUs
Mupirocinointment20 mg/gtopicalDIRECT RX2015-01-01Not applicableUs
Mupirocinointment20 mg/gtopicalKeltman Pharmaceuticals Inc.2009-06-22Not applicableUs
Mupirocinointment20 mg/gtopicalTaro Pharmaceuticals U.S.A., Inc.2005-09-23Not applicableUs
Mupirocinointment20 mg/gtopicalDIRECT RX2014-01-01Not applicableUs
Mupirocinointment20 mg/gtopicalRebel Distributors Corp2011-01-11Not applicableUs
Mupirocinointment20 mg/gtopicalProficient Rx LP2003-11-07Not applicableUs
Mupirocinointment20 mg/gtopicalUnit Dose Services2003-11-07Not applicableUs
Mupirocincream2 g/100gtopicalREMEDYREPACK INC.2015-11-12Not applicableUs
Mupirocinointment20 mg/gtopicalRebel Distributors Corp.2005-11-30Not applicableUs
Mupirocinointment20 mg/gtopicalProficient Rx LP2009-10-30Not applicableUs
Mupirocinointment20 mg/gtopicalUnit Dose Services2009-10-30Not applicableUs
Mupirocinointment20 mg/gtopicalAtlantic Biologicals Corps2009-10-30Not applicableUs
Mupirocinointment20 mg/gtopicalClinical Solutions Wholesale2005-09-23Not applicableUs
Mupirocinointment20 mg/gtopicalSTAT RX LLC USA2003-11-07Not applicableUs
Mupirocinointment20 mg/gtopicalUnit Dose Services2005-11-30Not applicableUs
Mupirocinointment20 mg/gtopicalProficient Rx LP2005-09-23Not applicableUs
Mupirocinointment20 mg/gtopicalH.J. Harkins Company, Inc.2009-10-30Not applicableUs
Mupirocinointment20 mg/gtopicalPreferred Pharmaceuticals, Inc.2005-09-23Not applicableUs
Mupirocinointment20 mg/gtopicalE. Fougera & Co. a division of Fougera Pharmaceuticals Inc.2005-11-30Not applicableUs
Mupirocinointment20 mg/gtopicalGlenmark Pharmaceuticals Inc., Usa2011-06-08Not applicableUs
Mupirocinointment20 mg/gtopicalLake Erie Medical DBA Quality Care Products LLC2005-09-23Not applicableUs
Mupirocinointment20 mg/gtopicalMedsource Pharmaceuticals2003-11-07Not applicableUs
Mupirocinointment20 mg/gtopicalProficient Rx LP2011-06-08Not applicableUs
Mupirocin 2%ointment20 mg/gtopicalDIRECT RX2015-01-01Not applicableUs
Approved Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Bactrobanointment2 %topicalGlaxosmithkline Consumer Healthcare Inc.1992-12-31Not applicableCanada
Bactroban Creamcream2 %topicalGlaxosmithkline Consumer Healthcare Inc.1999-04-13Not applicableCanada
Bactroban Nasal Ointmentointment2 %nasalGlaxosmithkline IncNot applicableNot applicableCanada
Taro-mupirocinointment2 %topicalTaro Pharmaceuticals Inc2006-07-10Not applicableCanada
Unapproved/Other Products Not Available
International Brands
NameCompany
Bactroban NasalGlaxoSmithKline
PlasimineGlaxoSmithKline
SpectrodermGlaxoSmithKline
T-BactGlaxoSmithKline
TurixinGlaxoSmithKline
Brand mixturesNot Available
Salts
Name/CASStructureProperties
Mupirocin calcium
ThumbNot applicableDBSALT001049
Categories
UNIID0GX863OA5
CAS number12650-69-0
WeightAverage: 500.6222
Monoisotopic: 500.298533006
Chemical FormulaC26H44O9
InChI KeyInChIKey=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
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[[email protected]](O)[[email protected]](C)[C@@H]1O[[email protected]]1C[[email protected]]1CO[C@@H](C\C(C)=C\C(=O)OCCCCCCCCC(O)=O)[[email protected]](O)[C@@H]1O
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as medium-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 4 and 12 carbon atoms.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acids and conjugates
Direct ParentMedium-chain fatty acids
Alternative Parents
Substituents
  • Medium-chain fatty acid
  • Heterocyclic fatty acid
  • Fatty acid ester
  • Epoxy fatty acid
  • Branched fatty acid
  • Oxane
  • Monosaccharide
  • Dicarboxylic acid or derivatives
  • Saccharide
  • Alpha,beta-unsaturated carboxylic ester
  • Enoate ester
  • Secondary alcohol
  • Carboxylic acid ester
  • 1,2-diol
  • Oxacycle
  • Organoheterocyclic compound
  • Ether
  • Oxirane
  • Dialkyl ether
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Pharmacology
IndicationFor the treatment of Staphylococci nasal carriers.
PharmacodynamicsMupirocin, 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 actionMupirocin 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.
Related Articles
AbsorptionNo measurable systemic absorption
Volume of distributionNot Available
Protein binding97%
Metabolism

Hepatic. Following intravenous or oral administration, mupirocin is rapidly metabolized. The principal metabolite is monic acid, which has no antibacterial activity.

SubstrateEnzymesProduct
Mupirocin
Not Available
Monic acidDetails
Route of eliminationFollowing 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 life20 to 40 minutes
ClearanceNot Available
ToxicityNot Available
Affected organisms
  • Enteric bacteria and other eubacteria
  • Staphylococcus aureus
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption-0.7512
Blood Brain Barrier-0.5988
Caco-2 permeable-0.7665
P-glycoprotein substrateSubstrate0.7774
P-glycoprotein inhibitor INon-inhibitor0.6451
P-glycoprotein inhibitor IINon-inhibitor0.7478
Renal organic cation transporterNon-inhibitor0.8891
CYP450 2C9 substrateNon-substrate0.8948
CYP450 2D6 substrateNon-substrate0.8694
CYP450 3A4 substrateSubstrate0.5877
CYP450 1A2 substrateNon-inhibitor0.8337
CYP450 2C9 inhibitorNon-inhibitor0.8776
CYP450 2D6 inhibitorNon-inhibitor0.9147
CYP450 2C19 inhibitorNon-inhibitor0.8118
CYP450 3A4 inhibitorNon-inhibitor0.7508
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9828
Ames testNon AMES toxic0.7653
CarcinogenicityNon-carcinogens0.9543
BiodegradationNot ready biodegradable0.6731
Rat acute toxicity2.0323 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8815
hERG inhibition (predictor II)Non-inhibitor0.6686
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
Manufacturers
  • Glaxosmithkline
  • Perrigo new york inc
  • Altana inc
  • Taro pharmaceuticals usa inc
  • Teva pharmaceuticals usa inc
Packagers
Dosage forms
FormRouteStrength
Creamtopical20 mg/g
Creamtopical21.5 mg/g
Ointmenttopical2 %
Ointmenttopical20 mg/g
Creamtopical2 %
Ointmentnasal2 %
Creamtopical2 g/100g
Prices
Unit descriptionCostUnit
Bactroban 2% Cream 30 gm Tube92.21USD tube
Bactroban 2% Ointment 22 gm Tube77.01USD tube
Bactroban 2% Cream 15 gm Tube62.17USD tube
Mupirocin powder44.8USD g
Mupirocin 2% Ointment 22 gm Tube44.46USD tube
Bactroban Nasal 2% Ointment 1 gm Tube11.5USD tube
Bactroban nasal 2% ointment10.03USD g
Centany 2% ointment3.98USD g
Bactroban 2% cream3.57USD g
Bactroban 2% ointment3.37USD g
Mupirocin 2% ointment1.94USD g
Bactroban 2 % Cream0.55USD g
Bactroban 2 % Ointment0.55USD g
Taro-Mupirocin 2 % Ointment0.36USD g
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
US6013657 No1998-07-082018-07-08Us
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point77-78 °CNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.0265 mg/mLALOGPS
logP2.25ALOGPS
logP2.45ChemAxon
logS-4.3ALOGPS
pKa (Strongest Acidic)4.83ChemAxon
pKa (Strongest Basic)-2.7ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area146.05 Å2ChemAxon
Rotatable Bond Count17ChemAxon
Refractivity129.39 m3·mol-1ChemAxon
Polarizability55.5 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
References
Synthesis Reference

Harvey Lee Zimmerman, “Pharmaceutical and veterinary compositions of mupirocin and methods for their preparation.” U.S. Patent US6025389, issued January, 1988.

US6025389
General ReferencesNot Available
External Links
ATC CodesD06AX09R01AX06
AHFS Codes
  • 84:04.04
PDB EntriesNot Available
FDA labelDownload (140 KB)
MSDSDownload (47 KB)
Interactions
Drug Interactions
Drug
Picosulfuric acidThe therapeutic efficacy of Sodium picosulfate can be decreased when used in combination with Mupirocin.
Food InteractionsNot Available

Targets

Kind
Protein
Organism
Staphylococcus aureus
Pharmacological action
yes
Actions
inhibitor
General Function:
Zinc ion binding
Specific Function:
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' ed...
Gene Name:
ileS
Uniprot ID:
P41972
Molecular Weight:
104883.78 Da
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:14657089 ]
  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:10212417 ]
  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:11796355 ]
  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:659331 ]
  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:365175 ]
  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:10821672 ]
  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:2496983 ]
  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. doi: 10.1038/nrmicro2278. Epub 2010 Mar 1. [PubMed:20190824 ]
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Drug created on June 13, 2005 07:24 / Updated on July 23, 2016 01:54