Identification

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Name
Mupirocin
Accession Number
DB00410  (APRD00162)
Type
Small Molecule
Groups
Approved, Investigational, Vet approved
Description

Mupirocin, formerly termed pseudomonic acid A,1 is a novel antibacterial agent with a unique chemical structure and mode of action apart from other antibiotic agents. Produced by fermentation using the organism Pseudomonas fluorescens, mupirocin is a naturally-occurring antibiotic that displays a broad-specturm activity against many gram-positive bacteria and certain gram-negative bacteria in vitro.Label It primarily works by inhibiting bacterial protein synthesis. Due to its unique mode of action of inhibiting the activity of bacterial isoleucyl-tRNA synthetase, mupirocin does not demonstrate cross-resistance with other classes of antimicrobial agents, giving it a therapeutic advantage.Label It is available in topical formulations only due to extensive systemic metabolism1 and is used in the treatment of impetigo caused by Staphylococcus aureus and Streptococcus pyogenes and traumatic skin lesions due to secondary skin infections caused by S. aureus and S. pyogenes. There is also some clinical evidence that suggests the potential role of mupirocin in eradicating nasal carriage of Staphylococci when administered intranasally.1,3 Mupirocin is commonly marketed under the brand name Bactroban.

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
  • Mupirocin
  • 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
BactrobanCream20 mg/1gTopicalPhysicians Total Care, Inc.2002-07-12Not applicableUs
BactrobanCream20 mg/1gTopicalLake Erie Medical &Surgical Supply Dba Quality Care Products Llc2012-03-282015-12-31Us
BactrobanOintment20 mg/1gTopicalGlaxosmithkline Inc2000-04-072016-08-31Us
BactrobanCream20 mg/1gTopicalGlaxoSmithKline LLC1998-01-23Not applicableUs
BactrobanOintment20 mg/1gTopicalLake Erie Medical Dba Quality Care Produts Llc1996-04-102016-12-31Us
BactrobanCream21.5 mg/1gTopicalRemedy Repack2014-10-292015-10-29Us
BactrobanOintment20 mg/1gTopicalGlaxoSmithKline LLC1996-04-10Not applicableUs
BactrobanOintment20 mg/1gTopicalPhysicians Total Care, Inc.1996-04-10Not applicableUs
BactrobanOintment20 mg/1gTopicalCardinal Health1996-04-102018-05-02Us
BactrobanCream20 mg/1gTopicalStat Rx USA1998-01-23Not applicableUs
Additional Data Available
  • Application Number
    Application Number

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

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  • Product Code
    Product Code

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
MupirocinOintment20 mg/1gTopicalRpk Pharmaceuticals, Inc.2011-06-08Not applicableUs
MupirocinOintment20 mg/1gTopicalLohxa2018-05-26Not applicableUs
MupirocinOintment20 mg/1gTopicalRebel Distributors2005-11-30Not applicableUs
MupirocinOintment20 mg/1gTopicalClinical Solutions Wholsesale2005-09-232017-06-22Us
MupirocinCream2 g/100gTopicalBIOMES PHARMACEUTICALS LLC2016-03-22Not applicableUs
MupirocinOintment20 mg/1gTopicalUnit Dose Services2003-11-07Not applicableUs
MupirocinOintment20 mg/1gTopicalREMEDYREPACK INC.2019-01-21Not applicableUs
MupirocinOintment20 mg/1gTopicalPerrigo New York Inc2009-10-30Not applicableUs
MupirocinOintment20 mg/1gTopicalRebel Distributors2011-01-11Not applicableUs
MupirocinOintment20 mg/1gTopicalCentral Texas Community Health Centers2011-06-08Not applicableUs
Additional Data Available
  • Application Number
    Application Number

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

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  • Product Code
    Product Code

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
BactrobanOintment2 %TopicalGlaxosmithkline Inc1992-12-31Not applicableCanada
Bactroban CreamCreamTopicalGlaxosmithkline Inc1999-04-13Not applicableCanada
Bactroban Nasal OintmentOintmentNasalGlaxosmithkline IncNot applicableNot applicableCanada
StramucinCreamTopicalGlenmark Pharmaceuticals, Inc2019-06-05Not applicableCanada
Taro-mupirocinOintmentTopicalTaro Pharmaceuticals, Inc.2006-07-10Not applicableCanada
Additional Data Available
  • Application Number
    Application Number

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

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  • Product Code
    Product Code

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
DermacinRx ClorhexacinMupirocin (20 mg/1g) + Chlorhexidine gluconate (4 g/100mL) + Dimethicone (50 mg/1mL)KitTopicalPureTek Corporation2016-06-02Not applicableUs
DermacinRx Surgical PharmaPakMupirocin (20 mg/1g) + Chlorhexidine gluconate (4 g/100mL) + Dimethicone (50 mg/1mL)KitTopicalPureTek Corporation2015-08-27Not applicableUs
Dermawerx Surgical Plus PakMupirocin (20 mg/1g) + Chlorhexidine gluconate (4 g/100mL) + Dimethicone (50 mg/1mL)KitTopicalPatchwerx Labs2015-10-21Not applicableUs
NuSurgePak Surgical Prep/CarePakMupirocin (20 mg/1g) + Chlorhexidine gluconate (4 g/100mL) + Dimethicone (50 mg/1mL)KitTopicalNucare Pharmaceuticals Inc2016-07-29Not applicableUs
WhyteDerm SurgiPakMupirocin (20 mg/1g) + Chlorhexidine gluconate (4 g/100mL) + Dimethicone (20 mg/1mL)KitTopicalWhyteman Labs Llc2015-10-212016-04-04Us
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
Levocetirizine Dihydrochloride 2% / Mupirocin 2% / Triamcinolone Acetonide 0.025%Mupirocin (2 g/100g) + Levocetirizine dihydrochloride (2 g/100g) + Triamcinolone acetonide (0.025 g/100g)CreamTopicalSincerus Florida, LLC2019-05-15Not applicableUs
Lidocaine 2% / Mupirocin 2%Mupirocin (2 g/100g) + Lidocaine (2 g/100g)OintmentTopicalSincerus Florida, LLC2019-05-15Not applicableUs
Metronidazole 1% / Mupirocin 2%Mupirocin (2 g/100g) + Metronidazole (1 g/100g)OintmentTopicalSincerus Florida, LLC2019-05-15Not applicableUs
Metronidazole 1% / Mupirocin 2%Mupirocin (2 g/100g) + Metronidazole (1 g/100g)OintmentTopicalSincerus Florida, LLC2019-05-15Not applicableUs
Metronidazole 1% / Mupirocin 2% /Mupirocin (2 g/100g) + Metronidazole (1 g/100g)OintmentTopicalSincerus Florida, LLC2019-05-14Not applicableUs
Pre and Post Sx PouchMupirocin (20 mg/1g) + Chlorhexidine gluconate (4 g/100mL) + Dimethicone (5 g/100mL)KitTopicalTerrain Pharmaceuticals2018-01-19Not applicableUs
International/Other Brands
Bactroban Nasal (GlaxoSmithKline) / Plasimine (GlaxoSmithKline) / Spectroderm (GlaxoSmithKline) / T-Bact (GlaxoSmithKline) / Turixin (GlaxoSmithKline)
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
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

Pharmacology

Indication

Indicated for the treatment of impetigo and secondary skin infections, leading to traumatic skin lesions, due to Staphylococcus aureus and Streptococcus pyogenes.Label

Associated Conditions
Pharmacodynamics

Mupirocin is reported to be active against susceptible aerobic gram-positive cocci, such as Staphylococcus aureus, Staphylococcus epidermidis, and other beta-hemolytic streptococciStreptococcus pyogenes.4 It mediates its antibacterial activity by inhibiting the bacterial protein synthesis and formation of bacterial proteins essential for survival. The minimum bactericidal concentration (MBC) against relevant pathogens is generally eight-fold to thirty-fold higher than the minimum inhibitory concentration (MIC).Label In one clinical study investigating the therapeutic effectiveness of topical mupirocin in impetigo, the therapeutic response rate was about 94 to 98% after one week following the end of therapy.Label In clinical studies of patients with primary and secondary skin infections, both elimination of the bacterial pathogen and clinical cure or improvement hav been demonstrated in over 90% of patients receiving topical mupirocin.3 Mupirocin resistance as high as 81% has been reported previously.5 Resistance to mupirocin, which occurs more frequently in methicillin-resistant than methicillin-susceptible staphylococci, may occur with the production of a modified isoleucyl-tRNA synthetase, or the acquisition of, by genetic transfer, a plasmid mediating a new isoleucyl-tRNA synthetase.Label

Mechanism of action

Mupirocin specifically and reversibly binds to bacterial isoleucyl transfer-RNA (tRNA) synthetase, which is an enzyme that promotes the conversion of isoleucine and tRNA to isoleucyl-tRNA. Inhibition of this enzyme subsequently leads to the inhibition of the bacterial protein and RNA synthesis.1 Mupirocin is bacteriostatic at lower concentrations but it exerts bactericidal effects with prolonged exposure, killing 90-99% of susceptible bacteria over a 24 hour period.2

TargetActionsOrganism
AIsoleucine--tRNA ligase
inhibitor
Staphylococcus aureus
Additional Data Available
Adverse Effects

Comprehensive structured data on known drug adverse effects with statistical prevalence. MedDRA and ICD10 ids are provided for adverse effect conditions and symptoms.

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Additional Data Available
Contraindications

Structured data covering drug contraindications. Each contraindication describes a scenario in which the drug is not to be used. Includes restrictions on co-administration, contraindicated populations, and more.

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Additional Data Available
Blackbox Warnings

Structured data representing warnings from the black box section of drug labels. These warnings cover important and dangerous risks, contraindications, or adverse effects.

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Absorption

Systemic or percutaneous absorption of mupirocin following dermal application is expected to be minimal in adults and children.Label Occlusive dressings do not significantly enhance drug absorption, but damaged skin may allow enhanced penetration of the drug across the skin barrier.2

Volume of distribution

No information available.

Protein binding

The protein binding of mupirocin is reported to be over 95%.Label

Metabolism

Following intravenous or oral administration, mupirocin undergoes rapid hepatic metabolism to form the principal metabolite monic acid, which has no antibacterial activity.Label

Route of elimination

Any mupirocin reaching the systemic circulation is rapidly metabolized to form the inactive monic acid, which is eliminated by renal excretion. 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.Label

Half life

In healthy male volunteers, the elimination half-life of mupirocin was about 20 to 40 minutes following intravenous administration. The elimination half-life of monic acid was about 30 to 80 minutes.6

Clearance

No information available.

Toxicity

LD50 and Nonclinical Toxicity

The oral LD50 value in rats is 5000 mg/kg.MSDS Studies evaluating the carcinogenic potential of mupirocin have not been performed. In various in vivo animal and in vitro bacterial assays, there was no evidence of genotoxicity caused by mupirocin.Label In reproduction studies using male and female rats, there were no signs of impaired fertility upon subcutaneous administration of mupirocin.Label

Use in special populations

Mupirocin was found to be excreted in human milk. As there is limited data on the use of topical mupirocin in pregnant women, the use of this drug in these patients should be undertaken with caution. Based on the findings in clinical trials, topical mupirocin was shown to be safe and effective in pediatric patients aged 2 months to 16 years.

Affected organisms
  • Enteric bacteria and other eubacteria
  • Streptococcus pyogenes
  • Staphylococcus aureus
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
(R)-warfarinThe risk or severity of bleeding can be increased when Mupirocin is combined with (R)-warfarin.
(S)-WarfarinThe risk or severity of bleeding can be increased when Mupirocin is combined with (S)-Warfarin.
4-hydroxycoumarinThe risk or severity of bleeding can be increased when Mupirocin is combined with 4-hydroxycoumarin.
AcenocoumarolThe risk or severity of bleeding can be increased when Mupirocin is combined with Acenocoumarol.
ClorindioneThe risk or severity of bleeding can be increased when Mupirocin is combined with Clorindione.
CoumarinThe risk or severity of bleeding can be increased when Mupirocin is combined with Coumarin.
DicoumarolThe risk or severity of bleeding can be increased when Mupirocin is combined with Dicoumarol.
DiphenadioneThe risk or severity of bleeding can be increased when Mupirocin is combined with Diphenadione.
Ethyl biscoumacetateThe risk or severity of bleeding can be increased when Mupirocin is combined with Ethyl biscoumacetate.
FluindioneThe risk or severity of bleeding can be increased when Mupirocin is combined with Fluindione.
Additional Data Available
  • Extended Description
    Extended Description

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  • Severity
    Severity

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  • Evidence Level
    Evidence Level

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  • Action
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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
  1. Parenti MA, Hatfield SM, Leyden JJ: Mupirocin: a topical antibiotic with a unique structure and mechanism of action. Clin Pharm. 1987 Oct;6(10):761-70. [PubMed:3146455]
  2. Putnam CD, Reynolds MS: Mupirocin: a new topical therapy for impetigo. J Pediatr Health Care. 1989 Jul-Aug;3(4):224-7. [PubMed:2502615]
  3. Lamb YJ: Overview of the role of mupirocin. J Hosp Infect. 1991 Sep;19 Suppl B:27-30. [PubMed:1684188]
  4. Pappa KA: The clinical development of mupirocin. J Am Acad Dermatol. 1990 May;22(5 Pt 1):873-9. [PubMed:2112164]
  5. Poovelikunnel T, Gethin G, Humphreys H: Mupirocin resistance: clinical implications and potential alternatives for the eradication of MRSA. J Antimicrob Chemother. 2015 Oct;70(10):2681-92. doi: 10.1093/jac/dkv169. Epub 2015 Jul 3. [PubMed:26142407]
  6. MUPIROCIN OINTMENT USP, 2% - DailyMed [Link]
External Links
Human Metabolome Database
HMDB0014554
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 (184 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
0RecruitingTreatmentOsteomyelitis1
1CompletedTreatmentSecondarily Infected Traumatic Skin Lesions1
1Unknown StatusTreatmentImpetigo1
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
2RecruitingTreatmentCystic Fibrosis (CF)1
2WithdrawnTreatmentInfantile Hemangiomas1
2, 3RecruitingPreventionRadiation Dermatitis1
3CompletedPreventionMethicillin Resistant Staphylococcus Aureus Skin Infections1
3CompletedPreventionSurgical Site Infections1
3Not Yet RecruitingTreatmentChronic Rhinosinusitis (Diagnosis)1
3Not Yet RecruitingTreatmentEpistaxis / Hereditary Haemorrhagic Telangiectasia (HHT)1
3RecruitingTreatmentSecondarily Infected Traumatic Skin Lesions1
4Active Not RecruitingPreventionDecolonization / Orthopaedic Surgery / Prevention / Staphylococcus Aureus / Surgical Site Infections1
4Active Not RecruitingPreventionStaphylococcus Aureus1
4CompletedPreventionCross Infection / Infection caused by staphylococci1
4CompletedPreventionCutaneous Abscess1
4CompletedPreventionEnd Stage Renal Disease (ESRD)1
4CompletedPreventionInfection caused by staphylococci1
4CompletedPreventionSurgical Site Infections1
4CompletedTreatmentAtopic Dermatitis (AD)1
4CompletedTreatmentChronic Rhinosinusitis1
4CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections / Staphylococcus Aureus1
4CompletedTreatmentInfection caused by staphylococci1
4CompletedTreatmentMRSA1
4RecruitingTreatmentAntibiotic Resistance, Bacterial / 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 AvailableCompletedNot AvailableImpetigo1
Not AvailableCompletedNot AvailableMethicillin Resistant Staphylococcus Aureus (MRSA) / MRSA - Methicillin Resistant Staphylococcus Aureus Infection1
Not AvailableCompletedNot AvailableSkin Infections, Bacterial1
Not AvailableCompletedPreventionAbscesses / Cellulitis / Community-Acquired MRSA Infections / Folliculitis1
Not AvailableCompletedPreventionAbscesses / Furunculosis / MRSA Infection / Staphylococcal Skin Infections / Staphylococcus Aureus1
Not AvailableCompletedPreventionCataract operation / Endophthalmitis / Prophylaxis1
Not AvailableCompletedPreventionHepatobiliary Diseases / Inflammatory Bowel Diseases (IBD) / Pancreas Diseases1
Not AvailableCompletedPreventionMethicillin Resistant Staphylococcus Aureus Skin Infections1
Not AvailableCompletedPreventionMethicillin-Resistant Staphylococcus Aureus (MRSA)1
Not AvailableCompletedPreventionOrthopedic Disorders / Surgical Site Infections1
Not AvailableCompletedTreatmentAbscesses / Furunculosis / MRSA Infection / Staphylococcal Skin Infections / Staphylococcus Aureus1
Not AvailableCompletedTreatmentAbscesses / Furunculosis / Staphylococcal Skin Infections / Staphylococcus Aureus1
Not AvailableCompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections / Infection caused by staphylococci1
Not AvailableCompletedTreatmentMRSA Colonization1
Not AvailableCompletedTreatmentThroatcarriers of MRSA1
Not AvailableRecruitingPreventionMotility Disorders / Staphylococcus Aureus1
Not AvailableRecruitingPreventionStaph Aureus Colonization / Staph Aureus Infection1
Not AvailableRecruitingPreventionSurgical Site Infections1
Not AvailableUnknown StatusPreventionCesarean Section / Postoperative Wound Infection / Staphylococcus Aureus1
Not AvailableWithdrawnTreatmentMethicillin-Resistant Staphylococcus Aureus (MRSA)1

Pharmacoeconomics

Manufacturers
  • Glaxosmithkline
  • Perrigo new york inc
  • Altana inc
  • Taro pharmaceuticals usa inc
  • Teva pharmaceuticals usa inc
Packagers
  • A-S Medication Solutions LLC
  • Atlantic Biologicals Corporation
  • Dispensing Solutions
  • Diversified Healthcare Services Inc.
  • E. Fougera and Co.
  • Gallipot
  • GlaxoSmithKline Inc.
  • Innoviant Pharmacy Inc.
  • Lake Erie Medical and Surgical Supply
  • Medimetriks Pharmaceuticals Inc.
  • Nycomed Inc.
  • Ortho Mcneil Janssen Pharmaceutical Inc.
  • Palmetto Pharmaceuticals Inc.
  • Perrigo Co.
  • Pharmedix
  • Physicians Total Care Inc.
  • Preferred Pharmaceuticals Inc.
  • Rebel Distributors Corp.
  • Stat Scripts LLC
  • Taro Pharmaceuticals USA
  • Teva Pharmaceutical Industries Ltd.
Dosage forms
FormRouteStrength
CreamTopical20 mg/1g
CreamTopical21.5 mg/1g
OintmentTopical2 %
CreamTopical
OintmentNasal
OintmentTopical20 mg/1g
KitTopical
CreamTopical
OintmentTopical
CreamTopical2 g/100g
PowderNot applicable1 g/1g
OintmentTopical
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)
US6013657No2000-01-112018-07-08Us
Additional Data Available
  • Filed On
    Filed On

    The date on which a patent was filed with the relevant government.

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Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)77-78MSDS
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 November 20, 2019 12:15