Mupirocin

Identification

Name
Mupirocin
Accession Number
DB00410
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.7 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.7 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.

Type
Small Molecule
Groups
Approved, Investigational, Vet approved
Structure
Thumb
Weight
Average: 500.6222
Monoisotopic: 500.298533006
Chemical Formula
C26H44O9
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

Pharmacology

Indication

Indicated for the treatment of impetigo and secondary skin infections, leading to traumatic skin lesions, due to Staphylococcus aureus and Streptococcus pyogenes.7

Associated Conditions
Contraindications & Blackbox Warnings
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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).7 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.7 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.7

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
Absorption

Systemic or percutaneous absorption of mupirocin following dermal application is expected to be minimal in adults and children.7 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%.7

Metabolism

Following intravenous or oral administration, mupirocin undergoes rapid hepatic metabolism to form the principal metabolite monic acid, which has no antibacterial activity.7

Hover over products below to view reaction partners

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.7

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.

Adverse Effects
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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. In reproduction studies using male and female rats, there were no signs of impaired fertility upon subcutaneous administration of mupirocin.7

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.7

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
AcenocoumarolThe risk or severity of bleeding can be increased when Mupirocin is combined with Acenocoumarol.
DicoumarolThe risk or severity of bleeding can be increased when Mupirocin is combined with Dicoumarol.
FluindioneThe risk or severity of bleeding can be increased when Mupirocin is combined with Fluindione.
PhenindioneThe risk or severity of bleeding can be increased when Mupirocin is combined with Phenindione.
PhenprocoumonThe risk or severity of bleeding can be increased when Mupirocin is combined with Phenprocoumon.
Vibrio cholerae CVD 103-HgR strain live antigenThe therapeutic efficacy of Vibrio cholerae CVD 103-HgR strain live antigen can be decreased when used in combination with Mupirocin.
WarfarinThe risk or severity of bleeding can be increased when Mupirocin is combined with Warfarin.
Additional Data Available
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Food Interactions
No interactions found.

Products

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Product Ingredients
IngredientUNIICASInChI Key
Mupirocin calciumRG38I2P540115074-43-6DDHVILIIHBIMQU-YJGQQKNPSA-L
International/Other Brands
Bactroban Nasal (GlaxoSmithKline) / Plasimine (GlaxoSmithKline) / Spectroderm (GlaxoSmithKline) / T-Bact (GlaxoSmithKline) / Turixin (GlaxoSmithKline)
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
BactrobanCream20 mg/1gTopicalGlaxoSmithKline LLC1998-01-23Not applicableUS flag
BactrobanCream20 mg/1gTopicalLake Erie Medical &Surgical Supply Dba Quality Care Products Llc2012-03-282015-12-31US flag
BactrobanCream20 mg/1gTopicalStat Rx USA1998-01-23Not applicableUS flag
BactrobanOintment20 mg/1gTopicalGlaxoSmithKline LLC1996-04-10Not applicableUS flag
BactrobanOintment20 mg/1gTopicalLake Erie Medical Dba Quality Care Produts Llc1996-04-102016-12-31US flag
BactrobanCream20 mg/1gTopicalPhysicians Total Care, Inc.2002-07-12Not applicableUS flag
BactrobanOintment20 mg/1gTopicalGlaxosmithkline Inc2000-04-072016-08-31US flag
BactrobanOintment20 mg/1gTopicalCardinal Health1996-04-102017-11-30US flag
BactrobanOintment20 mg/1gTopicalGlaxo Opoerations UK Ltd1996-04-102018-01-04US flag
BactrobanOintment20 mg/1gTopicalPhysicians Total Care, Inc.1996-04-10Not applicableUS flag
Additional Data Available
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Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
MupirocinOintment20 mg/1gTopicalPreferred Pharmaceuticals, Inc.2005-09-23Not applicableUS flag
MupirocinOintment20 mg/1gTopicalUnit Dose Services2003-11-07Not applicableUS flag
MupirocinOintment20 mg/1gTopicalNucare Pharmaceuticals,inc.2009-10-30Not applicableUS flag
MupirocinOintment20 mg/1gTopicalDirectrx2015-01-01Not applicableUS flag
MupirocinOintment20 mg/1gTopicalUnit Dose Services2011-06-08Not applicableUS flag
MupirocinOintment20 mg/1gTopicalUnit Dose Services2005-11-302017-12-31US flag
MupirocinCream2 g/100gTopicalGlenmark Pharmaceuticals Inc., USA2013-01-24Not applicableUS flag
MupirocinOintment20 mg/1gTopicalAtlantic Biologicals Corps2009-10-30Not applicableUS flag
MupirocinOintment20 mg/1gTopicalRebel Distributors2009-10-30Not applicableUS flag
MupirocinOintment20 mg/1gTopicalUnit Dose Services2009-10-30Not applicableUS flag
Additional Data Available
  • Application Number
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  • Product Code
    Product Code
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Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
BactrobanOintment2 %TopicalGlaxosmithkline Consumer Healthcare Ulc1992-12-312020-07-24Canada flag
Bactroban CreamCreamTopicalGlaxosmithkline Consumer Healthcare Ulc1999-04-132020-07-24Canada flag
Bactroban Nasal OintmentOintmentNasalGlaxosmithkline IncNot applicableNot applicableCanada flag
StramucinCreamTopicalGlenmark Pharmaceuticals, Inc2019-06-05Not applicableCanada flag
Taro-mupirocinOintmentTopicalTaro Pharmaceuticals, Inc.2006-07-10Not applicableCanada flag
Additional Data Available
  • Application Number
    Application Number
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    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

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  • Product Code
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Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
Dermawerx Surgical Plus PakMupirocin (20 mg/1g) + Chlorhexidine gluconate (4 g/100mL) + Dimethicone (50 mg/1mL)KitTopicalPatchwerx Labs2015-10-21Not applicableUS flag
NuSurgePak Surgical Prep/CarePakMupirocin (20 mg/1g) + Chlorhexidine gluconate (4 g/100mL) + Dimethicone (50 mg/1mL)KitTopicalNucare Pharmaceuticals Inc2016-07-29Not applicableUS flag
NuSurgePak Surgical Prep/CarePakMupirocin (20 mg/1g) + Chlorhexidine gluconate (4 g/100mL) + Dimethicone (50 ug/1mg)KitTopicalNucare Pharmaceuticals Inc2011-06-08Not applicableUS flag
WhyteDerm SurgiPakMupirocin (20 mg/1g) + Chlorhexidine gluconate (4 g/100mL) + Dimethicone (20 mg/1mL)KitTopicalWhyteman Labs Llc2015-10-212016-04-04US flag
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
DermacinRx ClorhexacinMupirocin (20 mg/1g) + Chlorhexidine gluconate (4 g/100mL) + Dimethicone (50 mg/1mL)KitTopicalPureTek Corporation2016-06-02Not applicableUS flag
DermacinRx Surgical PharmaPakMupirocin (20 mg/1g) + Chlorhexidine gluconate (4 g/100mL) + Dimethicone (50 mg/1mL)KitTopicalPureTek Corporation2015-08-27Not applicableUS flag
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 flag
Lidocaine 2% / Mupirocin 2%Mupirocin (2 g/100g) + Lidocaine (2 g/100g)OintmentTopicalSincerus Florida, LLC2019-05-15Not applicableUS flag
Metronidazole 1% / Mupirocin 2%Mupirocin (2 g/100g) + Metronidazole (1 g/100g)OintmentTopicalSincerus Florida, LLC2019-05-15Not applicableUS flag
Metronidazole 1% / Mupirocin 2%Mupirocin (2 g/100g) + Metronidazole (1 g/100g)OintmentTopicalSincerus Florida, LLC2019-05-15Not applicableUS flag
Metronidazole 1% / Mupirocin 2% /Mupirocin (2 g/100g) + Metronidazole (1 g/100g)OintmentTopicalSincerus Florida, LLC2019-05-14Not applicableUS flag
Pre and Post Sx PouchMupirocin (20 mg/1g) + Chlorhexidine gluconate (4 g/100mL) + Dimethicone (5 g/100mL)KitTopicalTerrain Pharmaceuticals2018-01-19Not applicableUS flag

Categories

ATC Codes
R01AX06 — MupirocinD06AX09 — Mupirocin
Drug Categories
Chemical TaxonomyProvided by Classyfire
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
Alcohol / Aliphatic heteromonocyclic compound / Alpha,beta-unsaturated carboxylic ester / Branched fatty acid / Carbonyl group / Carboxylic acid / Carboxylic acid derivative / Carboxylic acid ester / Dialkyl ether / Dicarboxylic acid or derivatives
show 17 more
Molecular Framework
Aliphatic heteromonocyclic compounds
External Descriptors
monocarboxylic acid, secondary alcohol, epoxide, triol, alpha,beta-unsaturated carboxylic ester, oxanes (CHEBI:7025)

Chemical Identifiers

UNII
D0GX863OA5
CAS number
12650-69-0
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

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]
  7. MUPIROCIN OINTMENT - FDA Label [Link]
  8. BACTROBAN (mupirocin) ointment, for topical use - FDA Label [Link]
Human Metabolome Database
HMDB0014554
KEGG Drug
D01076
KEGG Compound
C11758
PubChem Compound
446596
PubChem Substance
46505594
ChemSpider
393914
BindingDB
50290686
RxNav
42372
ChEBI
7025
ChEMBL
CHEMBL719
ZINC
ZINC000004102194
Therapeutic Targets Database
DAP000711
PharmGKB
PA164764568
PDBe Ligand
MRC
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Mupirocin
AHFS Codes
  • 84:04.04 — Antibiotics
MSDS
Download (184 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4Active Not RecruitingPreventionStaphylococcus Aureus1
4CompletedHealth Services ResearchHuman Microbiome2
4CompletedPreventionCross Infection / Infection caused by staphylococci1
4CompletedPreventionCutaneous Abscess1
4CompletedPreventionEnd Stage Renal Disease (ESRD)1
4CompletedPreventionInfection caused by staphylococci1
4CompletedPreventionOrthopaedic Surgery / Prevention / Staphylococcus Aureus / Surgical Site Infections1
4CompletedPreventionSurgical Site Infections1
4CompletedTreatmentAtopic Dermatitis (AD)1
4CompletedTreatmentChronic Rhinosinusitis1

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
Ointment2 g/100g
CreamTopical2 %
OintmentTopical2 %
CreamTopical20 mg/1g
CreamTopical21.5 mg/1g
OintmentTopical2 g/100g
OintmentNasal2 %
CreamTopical
OintmentNasal
OintmentTopical20 mg/1g
CreamTopical1 g
KitTopical
OintmentTopical20 mg/g
CreamTopical
OintmentTopical
OintmentTopical2 g
CreamTopical2 g/100g
CreamTopical20 MG/G
PowderNot applicable1 g/1g
Ointment2 %
Ointment
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)Region
US6013657No2000-01-112018-07-08US flag
Additional Data Available
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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

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]
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Drug created on June 13, 2005 07:24 / Updated on November 23, 2020 09:08

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