Identification

Name
Mupirocin
Accession Number
DB00410  (APRD00162)
Type
Small Molecule
Groups
Approved, 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
  • Mupirocina
  • Mupirocine
  • Mupirocinum
  • Pseudomonic acid
  • Pseudomonic acid a
External IDs
BRL 4910A / BRL 4910F / BRL-4910A
Product Ingredients
IngredientUNIICASInChI Key
Mupirocin calciumRG38I2P540115074-43-6DDHVILIIHBIMQU-YJGQQKNPSA-L
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
BactrobanOintment20 mg/gTopicalGlaxosmithkline Inc2000-04-072016-10-13Us
BactrobanOintment20 mg/gTopicalCardinal Health1996-04-10Not applicableUs
BactrobanCream21.5 mg/gTopicalRemedy Repack2013-12-042017-02-14Us
BactrobanOintment20 mg/gTopicalGlaxosmithkline Inc1996-04-10Not applicableUs
BactrobanCream20 mg/gTopicalPhysicians Total Care, Inc.2002-07-12Not applicableUs
BactrobanCream21.5 mg/gTopicalLake Erie Medical &Surgical Supply Dba Quality Care Products Llc2012-03-28Not applicableUs
BactrobanCream20 mg/gTopicalStat Rx USA1998-01-23Not applicableUs
BactrobanOintment20 mg/gTopicalLake Erie Medical Dba Quality Care Produts Llc1996-04-102017-10-04Us
BactrobanOintment20 mg/gTopicalPhysicians Total Care, Inc.1996-04-10Not applicableUs
BactrobanCream20 mg/gTopicalGlaxosmithkline Inc1998-01-23Not applicableUs
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
DermacinRx ClorhexacinKitPure Tek Corporation2016-06-02Not applicableUs
DermacinRx Surgical PharmaPakKitPure Tek Corporation2015-08-27Not applicableUs
Dermawerx Surgical Plus PakKitTopicalPatchwerx Labs2015-10-21Not applicableUs
MupirocinOintment20 mg/gTopicalA S Medication Solutions2003-11-072017-06-20Us
MupirocinOintment20 mg/gTopicalNu Care Pharmaceuticals,inc.2011-06-08Not applicableUs
MupirocinOintment20 mg/gTopicalRebel Distributors2011-01-11Not applicableUs
MupirocinOintment20 mg/gTopicalUnit Dose Services2003-11-07Not applicableUs
MupirocinOintment20 mg/gTopicalProficient Rx LP2009-10-30Not applicableUs
MupirocinOintment20 mg/gTopicalLake Erie Medical Dba Quality Care Produts Llc2005-09-23Not applicableUs
MupirocinOintment20 mg/gTopicalLake Erie Medical Dba Quality Care Produts Llc2003-11-07Not applicableUs
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
International/Other Brands
Bactroban / Bactroban Nasal (GlaxoSmithKline) / Centany / Plasimine (GlaxoSmithKline) / Spectroderm (GlaxoSmithKline) / T-Bact (GlaxoSmithKline) / Turixin (GlaxoSmithKline)
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
NuSurgePak Surgical Prep/CarePakMupirocin (20 mg/1g) + Chlorhexidine gluconate (4 g/100mL) + Dimethicone (50 mg/1mL)KitNucare Pharmaceuticals Inc2016-07-29Not applicableUs
Categories
UNII
D0GX863OA5
CAS number
12650-69-0
Weight
Average: 500.6222
Monoisotopic: 500.298533006
Chemical Formula
C26H44O9
InChI Key
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

Pharmacology

Indication

For the treatment of Staphylococci nasal carriers.

Structured Indications
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.

TargetActionsOrganism
AIsoleucine--tRNA ligase
inhibitor
Staphylococcus aureus
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
  • Staphylococcus aureus
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteractionDrug group
Picosulfuric acidThe therapeutic efficacy of Picosulfuric acid can be decreased when used in combination with Mupirocin.Approved
Food Interactions
Not 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 References
Not Available
External Links
Human Metabolome Database
HMDB14554
KEGG Drug
D01076
KEGG Compound
C11758
PubChem Compound
446596
PubChem Substance
46505594
ChemSpider
393914
BindingDB
50290686
ChEBI
7025
ChEMBL
CHEMBL719
Therapeutic Targets Database
DAP000711
PharmGKB
PA164764568
HET
MRC
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Mupirocin
ATC Codes
R01AX06 — MupirocinD06AX09 — Mupirocin
AHFS Codes
  • 84:04.04 — Antibiotics
FDA label
Download (140 KB)
MSDS
Download (47 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
0RecruitingTreatmentOsteomyelitis1
1CompletedTreatmentSecondarily Infected Traumatic Skin Lesions1
2CompletedPreventionInfection caused by staphylococci1
2CompletedTreatmentCystic Fibrosis (CF)1
2CompletedTreatmentCystic Fibrosis (CF) / Methicillin-Resistant Staphylococcus Aureus (MRSA)1
2CompletedTreatmentImpetigo / Secondarily Infected Traumatic Lesions (SITL)1
2RecruitingPreventionStaphylococcus1
2WithdrawnTreatmentInfantile Hemangiomas1
3CompletedPreventionMethicillin Resistant Staphylococcus Aureus Skin Infections1
3CompletedPreventionSurgical Site Infections1
3Not Yet RecruitingTreatmentChronic Rhinosinusitis (Diagnosis)1
3Not Yet RecruitingTreatmentHereditary Haemorrhagic Telangiectasia (HHT) / Nasal Bleeding1
4Active Not RecruitingTreatmentMRSA1
4CompletedPreventionCross Infection / Infection caused by staphylococci1
4CompletedPreventionCutaneous Abscess1
4CompletedPreventionSurgical Site Infections1
4CompletedTreatmentAtopic Dermatitis (AD)1
4CompletedTreatmentChronic Rhinosinusitis1
4CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections / Staphylococcus Aureus1
4CompletedTreatmentInfection caused by staphylococci1
4CompletedTreatmentMethicillin Resistant Staphylococcus Aureus (MRSA) / MRSA - Methicillin Resistant Staphylococcus Aureus Infection1
4RecruitingPreventionStaphylococcus Aureus1
4RecruitingTreatmentAntibiotic Resistance / Methicillin-Resistant Staphylococcus Aureus (MRSA) / Recurrences / Staphylococcal Skin Infections1
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
Not AvailableActive Not RecruitingPreventionOrthopedic Disorders / Surgical Site Infections1
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 AvailableCompletedTreatmentThroatcarriers of MRSA1
Not AvailableEnrolling by InvitationPreventionAbscesses / Furunculosis / MRSA Infection / Staphylococcal Skin Infections / Staphylococcus Aureus1
Not AvailableRecruitingPreventionMotility Disorders / Staphylococcus Aureus1
Not AvailableRecruitingPreventionStaph Aureus Colonization / Staph Aureus Infection1
Not AvailableRecruitingPreventionSurgical Site Infections1
Not AvailableUnknown StatusPreventionCesarean Section / Infection, Postoperative Wound / Staphylococcus Aureus1

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 %
Kit
KitTopical
CreamTopical2 g/100g
Kit
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)
US6013657No1998-07-082018-07-08Us

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)77-78 °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 FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
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)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSNot Available
MS/MS Spectrum - , positiveLC-MS/MSsplash10-056r-1976100000-dfa28e3b7efa7b734a99
MS/MS Spectrum - , positiveLC-MS/MSsplash10-0bwa-3920000000-b910c0ca6dcc91904891

Taxonomy

Description
This 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.
Kingdom
Organic compounds
Super Class
Lipids and lipid-like molecules
Class
Fatty Acyls
Sub Class
Fatty acids and conjugates
Direct Parent
Medium-chain fatty acids
Alternative Parents
Branched fatty acids / Epoxy fatty acids / Fatty acid esters / Hydroxy fatty acids / Dicarboxylic acids and derivatives / Oxanes / Monosaccharides / Enoate esters / Secondary alcohols / Oxacyclic compounds
show 6 more
Substituents
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
show 17 more
Molecular Framework
Aliphatic heteromonocyclic compounds
External Descriptors
monocarboxylic acid, secondary alcohol, epoxide, triol, alpha,beta-unsaturated carboxylic ester, oxanes (CHEBI:7025)

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 d...
Gene Name
ileS
Uniprot ID
P41972
Uniprot Name
Isoleucine--tRNA ligase
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]

Drug created on June 13, 2005 07:24 / Updated on January 14, 2018 10:04