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Accession NumberDB00410  (APRD00162)
TypeSmall Molecule
GroupsApproved, Investigational, Vet Approved
DescriptionMupirocin (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.
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
Pseudomonic acid
Pseudomonic acid a
External IDs BRL 4910A / BRL 4910F
Product Ingredients
IngredientUNIICASInChI KeyDetails
Mupirocin calciumRG38I2P540 115074-43-6DDHVILIIHBIMQU-YJGQQKNPSA-LDetails
Approved Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
BactrobanCream20 mg/gTopicalStat Rx USA1998-01-23Not applicableUs
BactrobanOintment20 mg/gTopicalPhysicians Total Care, Inc.1996-04-10Not applicableUs
BactrobanOintment20 mg/gTopicalLake Erie Medical Dba Quality Care Produts Llc1996-04-10Not applicableUs
BactrobanCream20 mg/gTopicalPhysicians Total Care, Inc.2002-07-12Not applicableUs
BactrobanOintment20 mg/gTopicalCardinal Health1996-04-10Not applicableUs
BactrobanCream20 mg/gTopicalGlaxosmithkline Inc1998-01-23Not applicableUs
BactrobanCream21.5 mg/gTopicalLake Erie Medical &Surgical Supply Dba Quality Care Products Llc2012-03-28Not applicableUs
BactrobanOintment20 mg/gTopicalGlaxosmithkline Inc1996-04-10Not applicableUs
BactrobanOintment20 mg/gTopicalGlaxosmithkline Inc2000-04-072016-10-13Us
BactrobanCream21.5 mg/gTopicalRemedy Repack2013-12-042017-02-14Us
CentanyOintment20 mg/gTopicalMedimetriks Pharmaceuticals2009-02-26Not applicableUs
Centany AtOintment20 mg/gTopicalMedimetriks Pharmaceuticals2010-11-15Not applicableUs
Mupirocin CalciumCream20 mg/gTopicalPrasco, Laboratories2013-01-282016-11-17Us
Approved Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
MupirocinOintment20 mg/gTopicalAtlantic Biologicals Corps.2009-10-30Not applicableUs
MupirocinCream2 g/100gTopicalBiomes Pharmaceuticals2016-03-22Not applicableUs
MupirocinOintment20 mg/gTopicalA S Medication Solutions2011-06-08Not applicableUs
MupirocinOintment20 mg/gTopicalRemedy Repack2017-03-08Not applicableUs
MupirocinOintment20 mg/gTopicalE. Fougera & CO., A division of Fougera Pharmaceuticals Inc.2005-11-30Not applicableUs
MupirocinOintment20 mg/gTopicalMesource Pharmaceuticals2003-11-07Not applicableUs
MupirocinOintment20 mg/gTopicalProficient Rx LP2011-06-08Not applicableUs
MupirocinOintment20 mg/gTopicalPreferreed Pharmaceuticals Inc.2015-12-01Not applicableUs
MupirocinOintment20 mg/gTopicalClinical Solutions Wholsesale2005-09-23Not applicableUs
MupirocinOintment20 mg/gTopicalBiomes Pharmaceuticals2016-03-22Not applicableUs
MupirocinOintment20 mg/gTopicalPreferreed Pharmaceuticals Inc.2005-09-23Not applicableUs
MupirocinCream2 g/100gTopicalRemedy Repack2015-11-05Not applicableUs
MupirocinOintment20 mg/gTopicalSTAT RX LLC USA2003-11-07Not applicableUs
MupirocinOintment20 mg/gTopicalTaro Pharmaceuticals U.S.A., Inc.2005-09-23Not applicableUs
MupirocinOintment20 mg/gTopicalProficient Rx LP2005-09-23Not applicableUs
MupirocinOintment20 mg/gTopicalGlenmark Pharmaceuticals Inc.,Usa2011-06-08Not applicableUs
MupirocinOintment20 mg/gTopicalA S Medication Solutions2009-10-30Not applicableUs
MupirocinOintment20 mg/gTopicalUnit Dose Services2011-06-08Not applicableUs
MupirocinOintment20 mg/gTopicalPreferreed Pharmaceuticals Inc.2014-02-14Not applicableUs
MupirocinOintment20 mg/gTopicalRebel Distributors2005-11-30Not applicableUs
MupirocinOintment20 mg/gTopicalRemedy Repack2013-06-122017-01-25Us
MupirocinOintment20 mg/gTopicalPhysicians Total Care, Inc.2003-12-05Not applicableUs
MupirocinOintment20 mg/gTopicalProficient Rx LP2009-10-30Not applicableUs
MupirocinOintment20 mg/gTopicalAv Pak2016-09-14Not applicableUs
MupirocinOintment20 mg/gTopicalA S Medication Solutions2003-11-07Not applicableUs
MupirocinOintment20 mg/gTopicalUnit Dose Services2005-11-30Not applicableUs
MupirocinOintment20 mg/gTopicalRebel Distributors2011-01-11Not applicableUs
MupirocinOintment20 mg/gTopicalRemedy Repack2013-11-222017-01-07Us
MupirocinOintment20 mg/gTopicalLake Erie Medical Dba Quality Care Produts Llc2005-09-23Not applicableUs
MupirocinOintment20 mg/gTopicalProficient Rx LP2003-11-07Not applicableUs
MupirocinOintment20 mg/gTopicalLake Erie Medical Dba Quality Care Produts Llc2003-11-07Not applicableUs
MupirocinOintment20 mg/gTopicalDirectrx2014-01-01Not applicableUs
MupirocinOintment20 mg/gTopicalUnit Dose Services2009-10-30Not applicableUs
MupirocinOintment20 mg/gTopicalRebel Distributors2009-10-30Not applicableUs
MupirocinOintment20 mg/gTopicalH.J. Harkins Company2009-10-30Not applicableUs
MupirocinOintment20 mg/gTopicalDirectrx2015-01-01Not applicableUs
MupirocinOintment20 mg/gTopicalKeltman Pharmaceuticals Inc.2009-06-22Not applicableUs
MupirocinOintment20 mg/gTopicalRemedy Repack2016-08-092017-03-09Us
MupirocinOintment20 mg/gTopicalLake Erie Medical Dba Quality Care Produts Llc2009-10-30Not applicableUs
MupirocinOintment20 mg/gTopicalUnit Dose Services2003-11-07Not applicableUs
MupirocinOintment20 mg/gTopicalTeva2003-11-07Not applicableUs
MupirocinOintment20 mg/gTopicalPerrigo New York Inc.2009-10-30Not applicableUs
MupirocinCream2 g/100gTopicalGlenmark Pharmaceuticals Inc.,Usa2013-01-24Not applicableUs
Mupirocin 2%Ointment20 mg/gTopicalDirectrx2015-01-01Not applicableUs
Approved Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
BactrobanOintment2 %TopicalGlaxosmithkline Inc1992-12-31Not applicableCanada
Bactroban CreamCream2 %TopicalGlaxosmithkline Inc1999-04-13Not applicableCanada
Bactroban Nasal OintmentOintment2 %NasalGlaxosmithkline IncNot applicableNot applicableCanada
Taro-mupirocinOintment2 %TopicalTaro Pharmaceuticals, Inc.2006-07-10Not applicableCanada
Unapproved/Other Products Not Available
International Brands
Bactroban NasalGlaxoSmithKline
Brand mixturesNot Available
CAS number12650-69-0
WeightAverage: 500.6222
Monoisotopic: 500.298533006
Chemical FormulaC26H44O9
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
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
IndicationFor the treatment of Staphylococci nasal carriers.
Structured Indications
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.
TargetKindPharmacological actionActionsOrganismUniProt ID
Isoleucine--tRNA ligaseProteinyes
Staphylococcus aureusP41972 details
Related Articles
AbsorptionNo measurable systemic absorption
Volume of distributionNot Available
Protein binding97%

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

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
Pharmacogenomic Effects/ADRs Not Available
Drug Interactions
DrugInteractionDrug group
BCGThe therapeutic efficacy of Bcg can be decreased when used in combination with Mupirocin.Investigational
Picosulfuric acidThe therapeutic efficacy of Picosulfuric acid can be decreased when used in combination with Mupirocin.Approved
Food InteractionsNot Available
Synthesis Reference

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

General ReferencesNot Available
External Links
ATC CodesR01AX06D06AX09
AHFS Codes
  • 84:04.04
PDB EntriesNot Available
FDA labelDownload (140 KB)
MSDSDownload (47 KB)
Clinical Trials
Clinical Trials
1CompletedTreatmentSecondarily Infected Traumatic Skin Lesions1
2Active Not RecruitingTreatmentCystic Fibrosis (CF)1
2CompletedPreventionInfection caused by staphylococci1
2CompletedTreatmentCystic Fibrosis (CF) / Methicillin-Resistant Staphylococcus Aureus (MRSA)1
2CompletedTreatmentImpetigo / Secondarily Infected Traumatic Lesions (SITL)1
2WithdrawnTreatmentInfantile Hemangiomas1
3CompletedPreventionMethicillin Resistant Staphylococcus Aureus Skin Infections1
3CompletedPreventionSurgical Site Infections1
3Not Yet RecruitingTreatmentEpistaxis / Hereditary Haemorrhagic Telangiectasia (HHT)1
4Active Not RecruitingTreatmentMRSA1
4CompletedPreventionCross Infection / Infection caused by staphylococci1
4CompletedPreventionCutaneous Abscess1
4CompletedPreventionSurgical Site Infections1
4CompletedTreatmentChronic Rhinosinusitis1
4CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections / Staphylococcus Aureus1
4CompletedTreatmentInfection caused by staphylococci1
4CompletedTreatmentModerate, refractory Atopic dermatitis1
4RecruitingTreatmentMRSA - Methicillin Resistant Staphylococcus Aureus Infection / Skin and Subcutaneous Tissue Bacterial Infections / Staphylococcus Aureus1
4TerminatedTreatmentMRSA - Methicillin Resistant Staphylococcus Aureus Infection / MRSA Colonization1
4Unknown StatusPreventionRate of Atypical Mycobacterial Infection / Rate of Exit Site Infection / Rate of Peritoneal Dialysis1
4Unknown StatusTreatmentMRSA - Methicillin Resistant Staphylococcus Aureus Infection1
Not AvailableCompletedNot AvailableImpetigo1
Not AvailableCompletedNot AvailableSkin Infections, Bacterial1
Not AvailableCompletedPreventionAbscesses / Cellulitis / Community-Acquired MRSA Infections / Folliculitis1
Not AvailableCompletedPreventionMethicillin Resistant Staphylococcus Aureus Skin Infections1
Not AvailableCompletedPreventionMethicillin-Resistant Staphylococcus Aureus (MRSA)1
Not AvailableCompletedTreatmentAbscesses / Furunculosis / MRSA Infection / Staphylococcal Skin Infections / Staphylococcus Aureus1
Not AvailableCompletedTreatmentAbscesses / Furunculosis / Staphylococcal Skin Infections / Staphylococcus Aureus1
Not AvailableCompletedTreatmentMRSA Colonization1
Not AvailableEnrolling by InvitationPreventionAbscesses / Furunculosis / MRSA Infection / Staphylococcal Skin Infections / Staphylococcus Aureus1
Not AvailableRecruitingPreventionOrthopedic Disorders / Surgical Site Infections1
Not AvailableRecruitingPreventionStaph Aureus Colonization / Staph Aureus Infection1
Not AvailableRecruitingPreventionSurgical Site Infections1
Not AvailableRecruitingTreatmentAntibiotic Resistance / Methicillin-Resistant Staphylococcus Aureus (MRSA) / Recurrences / Staphylococcal Skin Infections1
Not AvailableRecruitingTreatmentThroatcarriers of MRSA1
Not AvailableUnknown StatusPreventionCesarean Section / Infection, Postoperative Wound / Staphylococcus Aureus1
  • Glaxosmithkline
  • Perrigo new york inc
  • Altana inc
  • Taro pharmaceuticals usa inc
  • Teva pharmaceuticals usa inc
Dosage forms
CreamTopical20 mg/g
CreamTopical21.5 mg/g
OintmentTopical2 %
OintmentTopical20 mg/g
CreamTopical2 %
OintmentNasal2 %
CreamTopical2 g/100g
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.
Patent NumberPediatric ExtensionApprovedExpires (estimated)
US6013657 No1998-07-082018-07-08Us
Experimental Properties
melting point77-78 °CNot Available
Predicted Properties
Water Solubility0.0265 mg/mLALOGPS
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
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET features
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
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 )
Mass Spec (NIST)Not Available
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
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
  • Medium-chain fatty acid
  • Branched fatty acid
  • Epoxy fatty acid
  • Fatty acid ester
  • Heterocyclic fatty acid
  • Hydroxy fatty acid
  • Dicarboxylic acid or derivatives
  • Oxane
  • Monosaccharide
  • Enoate ester
  • Alpha,beta-unsaturated carboxylic ester
  • Carboxylic acid ester
  • Secondary alcohol
  • Ether
  • Oxirane
  • Dialkyl ether
  • Carboxylic acid
  • Organoheterocyclic compound
  • Oxacycle
  • Carboxylic acid derivative
  • Carbonyl group
  • Alcohol
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Organooxygen compound
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors


Staphylococcus aureus
Pharmacological action
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:
Uniprot ID:
Molecular Weight:
104883.78 Da
  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 April 25, 2017 04:17