Identification

Name
Tobramycin
Accession Number
DB00684
Description

An aminoglycoside, broad-spectrum antibiotic produced by Streptomyces tenebrarius. It is effective against gram-negative bacteria, especially the pseudomonas species. It is a 10% component of the antibiotic complex, nebramycin, produced by the same species.

Type
Small Molecule
Groups
Approved, Investigational
Structure
Thumb
Weight
Average: 467.5145
Monoisotopic: 467.259127807
Chemical Formula
C18H37N5O9
Synonyms
  • 3'-Deoxykanamycin B
  • Nebramycin 6
  • O-3-Amino-3-deoxy-alpha-D-glucopyranosyl-(1-4)-O-(2,6-diamino-2,3,6-trideoxy-alpha-D-ribohexopyranosyl-(1-4))-2-deoxy-D-streptamine
  • Tobramicina
  • Tobramycin
  • Tobramycine
  • Tobramycinum
External IDs
  • 47663
  • Lilly 47663
  • SPRC-AB01

Pharmacology

Indication

For the treatment of pseudomonas aeruginosa lung infections. Also being investigated for use in the treatment of sinus infections.

Associated Conditions
Contraindications & Blackbox Warnings
Learn about our commercial Contraindications & Blackbox Warnings data.
Learn More
Pharmacodynamics

Tobramycin, an aminoglycoside antibiotic obtained from cultures of Streptomyces tenebrarius, is used in combination with other antibiotics to treat urinary tract infections, gynecologic infections, peritonitis, endocarditis, pneumonia, bacteremia and sepsis, respiratory infections including those associated with cystic fibrosis, osteomyelitis, and diabetic foot and other soft-tissue infections. It acts primarily by disrupting protein synthesis, leading to altered cell membrane permeability, progressive disruption of the cell envelope, and eventual cell death. Tobramycin has in vitro activity against a wide range of gram-negative organisms including Pseudomonas aeruginosa.

Mechanism of action

Tobramycin binds irreversibly to one of two aminoglycoside binding sites on the 30 S ribosomal subunit, inhibiting bacterial protein synthesis. Tobramycin may also destabilize bacterial memebrane by binding to 16 S 16 S r-RNA. An active transport mechanism for aminoglycoside uptake is necessary in the bacteria in order to attain a significant intracellular concentration of tobramycin.

TargetActionsOrganism
A30S ribosomal protein S12
inhibitor
Escherichia coli (strain K12)
U16S ribosomal RNA
inhibitor
Enteric bacteria and other eubacteria
Absorption

The bioavailability of tobramycin may vary because of individual differences in nebulizer performance and airway pathology.

Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination
Not Available
Half-life

The elimination half-life of tobramycin from serum is approximately 2 hours after intravenous (IV) administration.

Clearance
Not Available
Adverse Effects
Learn about our commercial Adverse Effects data.
Learn More
Toxicity

LD50=441mg/kg (s.c. in mice)

Affected organisms
  • Enteric bacteria and other eubacteria
Pathways
PathwayCategory
Tobramycin Action PathwayDrug action
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
AbacavirTobramycin may decrease the excretion rate of Abacavir which could result in a higher serum level.
AcarboseTobramycin may decrease the excretion rate of Acarbose which could result in a higher serum level.
AceclofenacAceclofenac may decrease the excretion rate of Tobramycin which could result in a higher serum level.
AcemetacinAcemetacin may decrease the excretion rate of Tobramycin which could result in a higher serum level.
AcenocoumarolThe risk or severity of bleeding can be increased when Tobramycin is combined with Acenocoumarol.
AcetaminophenTobramycin may decrease the excretion rate of Acetaminophen which could result in a higher serum level.
AcetylcholineThe therapeutic efficacy of Acetylcholine can be decreased when used in combination with Tobramycin.
AcetyldigitoxinThe risk or severity of adverse effects can be increased when Tobramycin is combined with Acetyldigitoxin.
Acetylsalicylic acidAcetylsalicylic acid may decrease the excretion rate of Tobramycin which could result in a higher serum level.
AclidiniumTobramycin may decrease the excretion rate of Aclidinium which could result in a higher serum level.
Additional Data Available
  • Extended Description
    Extended Description
    Available for Purchase

    Extended description of the mechanism of action and particular properties of each drug interaction.

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  • Severity
    Severity
    Available for Purchase

    A severity rating for each drug interaction, from minor to major.

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  • Evidence Level
    Evidence Level
    Available for Purchase

    A rating for the strength of the evidence supporting each drug interaction.

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  • Action
    Action
    Available for Purchase

    An effect category for each drug interaction. Know how this interaction affects the subject drug.

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Food Interactions
No interactions found.

Products

Product Ingredients
IngredientUNIICASInChI Key
Tobramycin hydrochloride01IX3OU16895188-93-5CVDADWBWFLWJNQ-TWDWGCDDSA-N
Tobramycin sulfateHJT0RXD7JK49842-07-1ZEUUPKVZFKBXPW-TWDWGCDDSA-N
International/Other Brands
Aktob (Akorn) / Alveoterol (Tetrafarm) / Amgy (Kobec) / Bactob (Solitaire) / Belbarmicina (Quimica Luar) / Bideon Biotic (Fecofar) / Bioptic (Bausch & Lomb) / Bramitob (Torrex) / Gernebcin (Infectopharm) / Nebcin (Lilly) / Obracin (EuroCept) / Tobracin (Opso Saline) / Tobramaxin (Alcon)
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
BethkisSolution300 mg/4mLRespiratory (inhalation)Chiesi USA, Inc.2013-04-15Not applicableUS flag
Kitabis PakSolution300 mg/5mLRespiratory (inhalation)Pari Respiratory Equipment, Inc.2015-02-19Not applicableUS flag
Kitabis PakSolution300 mg/5mLRespiratory (inhalation)Catalent Pharma Solutions,Llc2015-02-192018-03-22US flag
Nebcin Inj 1.2gm/30mlLiquidIntramuscular; IntravenousEli Lilly & Co. Ltd.1986-12-312003-05-12Canada flag
Nebcin Inj 10mg/mlLiquidIntramuscular; IntravenousEli Lilly & Co. Ltd.1975-12-312003-05-12Canada flag
Nebcin Inj 10mg/ml (vantage Vial)LiquidIntravenousEli Lilly & Co. Ltd.1989-12-311997-05-20Canada flag
Nebcin Inj 40mg/mlLiquidIntramuscular; IntravenousEli Lilly & Co. Ltd.1975-12-312003-05-12Canada flag
Nebcin Inj 60mgLiquidIntramuscular; IntravenousEli Lilly & Co. Ltd.1978-12-311998-08-04Canada flag
Nebcin Inj 80mgLiquidIntramuscular; IntravenousEli Lilly & Co. Ltd.1978-12-311998-08-04Canada flag
TobiSolution300 mg/5mLOralNovartis Pharmaceuticals Corporation1997-12-22Not applicableUS flag
Additional Data Available
  • Application Number
    Application Number
    Available for Purchase

    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
    Available for Purchase

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

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Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Aj-tobramycinLiquidIntramuscular; IntravenousAgila Jamp Canada IncNot applicableNot applicableCanada flag
Apo-tobramycinSolutionOphthalmicApotex Corporation2002-09-18Not applicableCanada flag
Jamp-tobramycinSolutionIntramuscular; IntravenousJamp Pharma Corporation2014-03-11Not applicableCanada flag
PMS-tobramycin 0.3% Ophthalmic SolutionLiquidOphthalmicPharmascience Inc1999-02-182017-09-30Canada flag
Sandoz TobramycinSolutionOphthalmicSandoz Canada Incorporated2000-08-21Not applicableCanada flag
Teva-tobramycinSolutionRespiratory (inhalation)TEVA Canada Limited2016-02-03Not applicableCanada flag
TobramycinSolution / drops3.0 mg/1mLOphthalmicA-S Medication Solutions2017-07-05Not applicableUS flag
TobramycinSolution3 mg/1mLOphthalmicRemedy Repack2016-07-192017-03-06US flag
TobramycinSolution / drops3.0 mg/1mLOphthalmicRpk Pharmaceuticals, Inc.2017-06-28Not applicableUS flag
TobramycinSolution / drops3 mg/1mLOphthalmicStat Rx USA1996-01-31Not applicableUS flag
Additional Data Available
  • Application Number
    Application Number
    Available for Purchase

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

    Learn more
  • Product Code
    Product Code
    Available for Purchase

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

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Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
TobraDexTobramycin (3 mg/1g) + Dexamethasone (1 mg/1g)OintmentOphthalmicRebel Distributors1988-09-28Not applicableUS flag
TobraDexTobramycin (3 mg/1mL) + Dexamethasone (1 mg/1mL)SuspensionOphthalmicA S Medication Solutions1988-09-15Not applicableUS flag
TobraDexTobramycin (3 mg/1mL) + Dexamethasone (1 mg/1mL)Suspension / dropsOphthalmicALCON LABORATORIES, INC.1988-09-15Not applicableUS flag
TobraDexTobramycin (0.3 %) + Dexamethasone (0.1 %)SuspensionOphthalmicNovartis1990-12-31Not applicableCanada flag
TobraDexTobramycin (3 mg/1mL) + Dexamethasone (1 mg/1mL)SuspensionOphthalmicRebel Distributors1988-08-18Not applicableUS flag
TobraDexTobramycin (3 mg/1g) + Dexamethasone (1 mg/1g)OintmentOphthalmicNovartis Pharmaceuticals Corporation1988-10-15Not applicableUS flag
TobraDexTobramycin (3 mg/1g) + Dexamethasone (1 mg/1g)OintmentOphthalmicPhysicians Total Care, Inc.1988-10-152010-06-30US flag
TobraDexTobramycin (3 mg/1mL) + Dexamethasone (1 mg/1mL)SuspensionOphthalmicA S Medication Solutions1988-09-15Not applicableUS flag
TobraDexTobramycin (3 mg/1g) + Dexamethasone (1 mg/1g)OintmentOphthalmicALCON LABORATORIES, INC.1988-10-15Not applicableUS flag
TobraDexTobramycin (0.3 %) + Dexamethasone (0.1 %)OintmentOphthalmicNovartis1990-12-31Not applicableCanada flag

Categories

ATC Codes
S01AA12 — TobramycinJ01GB01 — Tobramycin
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as 4,6-disubstituted 2-deoxystreptamines. These are 2-deoxystreptamine aminoglycosides that a glycosidically linked to a pyranose of furanose unit at the C4- and C6-positions.
Kingdom
Organic compounds
Super Class
Organic oxygen compounds
Class
Organooxygen compounds
Sub Class
Carbohydrates and carbohydrate conjugates
Direct Parent
4,6-disubstituted 2-deoxystreptamines
Alternative Parents
O-glycosyl compounds / Aminocyclitols and derivatives / Cyclohexylamines / Cyclohexanols / Oxanes / Monosaccharides / 1,2-aminoalcohols / Oxacyclic compounds / Acetals / Primary alcohols
show 3 more
Substituents
1,2-aminoalcohol / 4,6-disubstituted 2-deoxystreptamine / Acetal / Alcohol / Aliphatic heteromonocyclic compound / Amine / Aminocyclitol or derivatives / Cyclic alcohol / Cyclitol or derivatives / Cyclohexanol
show 15 more
Molecular Framework
Aliphatic heteromonocyclic compounds
External Descriptors
amino cyclitol glycoside (CHEBI:28864)

Chemical Identifiers

UNII
VZ8RRZ51VK
CAS number
32986-56-4
InChI Key
NLVFBUXFDBBNBW-PBSUHMDJSA-N
InChI
InChI=1S/C18H37N5O9/c19-3-9-8(25)2-7(22)17(29-9)31-15-5(20)1-6(21)16(14(15)28)32-18-13(27)11(23)12(26)10(4-24)30-18/h5-18,24-28H,1-4,19-23H2/t5-,6+,7+,8-,9+,10+,11-,12+,13+,14-,15+,16-,17+,18+/m0/s1
IUPAC Name
(2S,3R,4S,5S,6R)-4-amino-2-{[(1S,2S,3R,4S,6R)-4,6-diamino-3-{[(2R,3R,5S,6R)-3-amino-6-(aminomethyl)-5-hydroxyoxan-2-yl]oxy}-2-hydroxycyclohexyl]oxy}-6-(hydroxymethyl)oxane-3,5-diol
SMILES
NC[C@H]1O[C@H](O[C@@H]2[C@@H](N)C[C@@H](N)[C@H](O[C@H]3O[C@H](CO)[C@@H](O)[C@H](N)[C@H]3O)[C@H]2O)[C@H](N)C[C@@H]1O

References

Synthesis Reference

Istvan Bakondi-Kovacs, "Metabolic controlled fermentation process for carbamoyl tobramycin production." U.S. Patent US20020197683, issued December 26, 2002.

US20020197683
General References
Not Available
Human Metabolome Database
HMDB0014822
KEGG Drug
D00063
KEGG Compound
C00397
PubChem Compound
36294
PubChem Substance
46507662
ChemSpider
33377
BindingDB
50366778
RxNav
10627
ChEBI
28864
ChEMBL
CHEMBL1747
ZINC
ZINC000008214692
Therapeutic Targets Database
DAP000110
PharmGKB
PA451704
PDBe Ligand
TOY
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Tobramycin
AHFS Codes
  • 08:12.02 — Aminoglycosides
  • 52:04.04 — Antibacterials
PDB Entries
1lc4 / 1m4d / 3sg8 / 3vet / 4ebk / 4evy / 4jd6 / 4lfc / 4xje / 5cfs
show 1 more
FDA label
Download (414 KB)
MSDS
Download (73.3 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4Active Not RecruitingTreatmentCystic Fibrosis (CF)1
4CompletedTreatmentAntibotics in Cementless Knees1
4CompletedTreatmentBlepharokeratoconjunctivitis1
4CompletedTreatmentCataracts / Pseudoexfoliation Syndrome1
4CompletedTreatmentChalazion / Hordeolum1
4CompletedTreatmentConjunctivitis1
4CompletedTreatmentCystic Fibrosis (CF)4
4CompletedTreatmentFever / Malignancies / Neutropenia1
4CompletedTreatmentInflammatory Reaction1
4CompletedTreatmentKnee Replacement Surgery1

Pharmacoeconomics

Manufacturers
  • Alcon laboratories inc
  • Akorn inc
  • Alcon universal ltd
  • Altana inc
  • Bausch and lomb pharmaceuticals inc
  • Novex pharma
  • Falcon pharmaceuticals ltd
  • Novartis pharmaceuticals corp
  • Eli lilly and co
  • Akorn strides llc
  • Apothecon inc div bristol myers squibb
  • App pharmaceuticals llc
  • Astrazeneca lp
  • Baxter healthcare corp anesthesia and critical care
  • Hospira inc
  • Marsam pharmaceuticals llc
  • Teva parenteral medicines inc
  • X gen pharmaceuticals inc
Packagers
  • Advanced Pharmaceutical Services Inc.
  • Akorn Inc.
  • Alcon Laboratories
  • Apotex Inc.
  • APP Pharmaceuticals
  • A-S Medication Solutions LLC
  • Bausch & Lomb Inc.
  • Bristol-Myers Squibb Co.
  • Cardinal Health
  • Clipper Distributing Co. LLC
  • Darby Dental Supply Co. Inc.
  • Dispensing Solutions
  • Diversified Healthcare Services Inc.
  • E.R. Squibb and Sons LLC
  • Eye Care and Cure Corp.
  • Falcon Pharmaceuticals Ltd.
  • H.J. Harkins Co. Inc.
  • Hospira Inc.
  • Innoviant Pharmacy Inc.
  • Keltman Pharmaceuticals Inc.
  • Lake Erie Medical and Surgical Supply
  • Major Pharmaceuticals
  • Medical Ophthalmics
  • Medisca Inc.
  • MWI Veterinary Supply Co.
  • Novartis AG
  • Novex Pharma
  • Nucare Pharmaceuticals Inc.
  • Ocusoft
  • Palmetto Pharmaceuticals Inc.
  • PD-Rx Pharmaceuticals Inc.
  • Pharmedix
  • Physicians Total Care Inc.
  • Preferred Pharmaceuticals Inc.
  • Rebel Distributors Corp.
  • Redpharm Drug
  • Rx Veterinary Products
  • Stat Rx Usa
  • Strides Arcolab Limited
  • Taylor Pharmaceuticals
  • Teva Pharmaceutical Industries Ltd.
  • Vedco Inc.
  • Wilson Ophthalmic Corp.
  • X-Gen Pharmaceuticals
Dosage Forms
FormRouteStrength
PowderRespiratory (inhalation)300 mg
SolutionRespiratory (inhalation)300 mg/4mL
Solution100 MG/2ML
Solution150 MG/2ML
SprayRespiratory (inhalation)300 MG/4ML
SolutionOphthalmic300 MG/5ML
Solution / dropsAuricular (otic)0.1 %
SuspensionOphthalmic3 mg/ml
Solution / dropsIntraocular0.3 %
SolutionConjunctival; Ophthalmic1 mg
SolutionConjunctival; Ophthalmic0.05 mg
OintmentConjunctival; Ophthalmic; Topical0.3 g
Solution / dropsOphthalmic15 MG/5ML
SolutionRespiratory (inhalation)300 mg/5mL
Suspension / dropsOphthalmic0.5 %
SuspensionConjunctival; Ophthalmic5 mg
Suspension / dropsOphthalmic1 MG/ML
LiquidIntramuscular; Intravenous
LiquidIntravenous
Injection, solutionIntramuscular; Intravenous100 MG/2ML
Injection, solutionIntramuscular; Intravenous150 MG/2ML
Injection, solutionIntramuscular; Intravenous300 mg/4ml
Injection, solutionIntramuscular; Intravenous80 MG
Injection, solutionParenteral20 MG/2ML
Injection, solutionParenteral40 MG/ML
SolutionConjunctival; Ophthalmic0.3 g
Solution / dropsOphthalmic0.1 %
OintmentConjunctival; Ophthalmic0.3 g
Solution / dropsOphthalmic100 mg/100mL
Solution / dropsOphthalmic0.3 %
OintmentOphthalmic0.3 %
SolutionOphthalmic4.4 mg
OintmentOphthalmic0.1 g
SuspensionAuricular (otic)1 mg
Suspension / dropsAuricular (otic)0.1 %
Solution / dropsOphthalmic5 ml
SolutionOphthalmic
SolutionRespiratory (inhalation)
Solution / dropsConjunctival0.3 %
InjectionIntramuscular; Intravenous20 mg/2mL
InjectionIntramuscular; Intravenous80 mg/2mL
SolutionOral300 mg/5mL
CapsuleOral; Respiratory (inhalation)28 mg/1
CapsuleRespiratory (inhalation)28 mg
Powder, meteredRespiratory (inhalation)28 MG
Capsule, coatedOral28 mg
SolutionRespiratory (inhalation)300 mg
OintmentOphthalmic
OintmentOphthalmic0.1 %
SuspensionOphthalmic
Suspension / dropsOphthalmic0.1 %
Suspension / dropsOphthalmic100 mg/100mL
OintmentConjunctival; Ophthalmic0.1 g
OintmentOphthalmic3 mg
Solution / dropsOphthalmic3 mg
OintmentOphthalmic1 mg/g
SuspensionOphthalmic1 mg
Solution / drops0.3 %
Suspension / dropsOphthalmic5 mg/mL
Solution300 MG/5ML
Injection, solution1 MG/ML
Injection, solution3 MG/ML
Suspension / dropsIntraocular3 MG/ML
Injection, solutionParenteral100 MG/2ML
Injection, solutionParenteral150 MG/2ML
SolutionRespiratory (inhalation)60 mg
OintmentOphthalmic; Topical0.3 g
Injection, solution100 MG/2ML
Injection, solution150 MG/2ML
OintmentConjunctival; Ophthalmic1 mg
InjectionIntramuscular; Intravenous40 mg/1mL
InjectionIntravenous1200 mg/30mL
Injection, powder, for solutionIntravenous1200 mg/30mL
Injection, powder, lyophilized, for solutionIntravenous1.2 g/30mL
Injection, solutionIntramuscular; Intravenous10 mg/1mL
Injection, solutionIntramuscular; Intravenous40 mg/1mL
Injection, solutionIntravenous40 mg/1mL
Injection, solution, concentrateIntravenous10 mg/1mL
SolutionOphthalmic3 mg/1mL
SolutionOphthalmic3.0 mg/1mL
SolutionOral3 mg/1mL
SolutionRespiratory (inhalation)60 mg/1mL
Solution / dropsOphthalmic3 mg/1mL
Solution / dropsOphthalmic3.0 mg/1mL
Solution / dropsOphthalmic300 mg/100mL
Suspension / dropsOphthalmic
SolutionParenteral1 mg/ml
SolutionParenteral3 mg/ml
Powder, for solutionIntravenous
Injection, solutionIntravenous0.8 mg/1mL
Injection, solutionIntravenous1.2 mg/1mL
InhalantRespiratory (inhalation)300 mg/5mL
SolutionIntramuscular; Intravenous
LiquidOphthalmic
SolutionOphthalmic; Topical3 mg
Injection, solution, concentrateIntravenous160 mg/2ml
SuspensionConjunctival; Ophthalmic1 mg
Suspension / dropsOphthalmic0.3 %
OintmentOphthalmic3 mg/1g
OintmentOphthalmic300 mg/100g
SolutionOphthalmic0.3 %
OintmentOphthalmic3 mg/g
Solution / dropsOphthalmic3 mg/ml
SolutionConjunctival; Ophthalmic3 mg
OintmentOphthalmic1 mg
Solution170 MG
Suspension / dropsOphthalmic5 mg/1mL
Prices
Unit descriptionCostUnit
Tobi (1 Box = 56, 5ml Ampules = 280ml Total) 280ml Plastic Container4461.42USD plastic
Tobramycin 1.2 gm vial338.25USD vial
TobraDex 0.3-0.1% Suspension 10ml Bottle200.43USD bottle
TobraDex 0.3-0.1% Ointment 3.5 gm Tube126.67USD tube
TobraDex 0.3-0.1% Suspension 5ml Bottle98.11USD bottle
Tobrex 0.3% Ointment 3.5 gm Tube80.02USD tube
Tobrex 0.3% Solution 5ml Bottle67.58USD bottle
TobraDex 0.3-0.1% Suspension 2.5ml Bottle54.99USD bottle
Tobramycin sulfate powder53.55USD g
Tobradex eye drops19.27USD ml
Tobi 300 mg/5 ml solution17.58USD ml
Tobramycin Sulfate 0.3% Solution 5ml Bottle15.99USD bottle
Tobrex 0.3% eye drops13.0USD ml
Tobi 60 mg/ml Solution11.4USD ml
Tobramycin Sulfate 40 mg/ml Solution3.6USD ml
Tobramycin 40 mg/ml3.14USD ml
Tobramycin 0.3% eye drops2.99USD ml
Aktob 0.3% eye drops2.85USD ml
Tobrex 0.3 % Ointment2.66USD g
Tobramycin 10 mg/ml2.26USD ml
Tobrex 0.3 % Solution1.88USD ml
Pms-Tobramycin 0.3 % Solution1.05USD ml
Sandoz Tobramycin 0.3 % Solution1.05USD ml
Tobramycin 60 mg/50 ml ns0.19USD ml
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)Region
US5508269No1996-04-162014-10-19US flag
US5149694No1992-09-222009-09-22US flag
CA2414737No2009-01-062021-06-26Canada flag
US7795316No2010-09-142028-08-03US flag
US8101582No2012-01-242027-12-19US flag
US8450287No2013-05-282027-12-19US flag
US7368102No2008-05-062022-12-19US flag
US8715623No2014-05-062022-12-19US flag
US7559325No2009-07-142025-10-27US flag
US7442388No2008-10-282020-05-10US flag
US7097827No2006-08-292016-04-16US flag
US8349294No2013-01-082020-05-10US flag
US8069851No2011-12-062024-09-24US flag
US7516741No2009-04-142024-01-11US flag
US7939502No2011-05-102022-06-14US flag
US6987094No2006-01-172022-09-22US flag
US7696178No2010-04-132023-03-17US flag
US10207066No2019-02-192030-11-04US flag
US8664187No2014-03-042025-06-20US flag
US8869794No2014-10-282028-09-12US flag
US9421166No2016-08-232022-12-19US flag
USRE47526No2004-04-092024-04-09US flag
Additional Data Available
  • Filed On
    Filed On
    Available for Purchase

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

    Learn more

Properties

State
Solid
Experimental Properties
PropertyValueSource
water solubility1E+003 mg/mlNot Available
logP-5.8Not Available
Predicted Properties
PropertyValueSource
Water Solubility53.7 mg/mLALOGPS
logP-3ALOGPS
logP-6.5ChemAxon
logS-0.94ALOGPS
pKa (Strongest Acidic)12.54ChemAxon
pKa (Strongest Basic)9.83ChemAxon
Physiological Charge5ChemAxon
Hydrogen Acceptor Count14ChemAxon
Hydrogen Donor Count10ChemAxon
Polar Surface Area268.17 Å2ChemAxon
Rotatable Bond Count6ChemAxon
Refractivity106.69 m3·mol-1ChemAxon
Polarizability47.18 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption-0.9313
Blood Brain Barrier-0.9794
Caco-2 permeable-0.759
P-glycoprotein substrateSubstrate0.5933
P-glycoprotein inhibitor INon-inhibitor0.7579
P-glycoprotein inhibitor IINon-inhibitor0.9086
Renal organic cation transporterNon-inhibitor0.8412
CYP450 2C9 substrateNon-substrate0.8361
CYP450 2D6 substrateNon-substrate0.8333
CYP450 3A4 substrateNon-substrate0.6662
CYP450 1A2 substrateNon-inhibitor0.9052
CYP450 2C9 inhibitorNon-inhibitor0.9359
CYP450 2D6 inhibitorNon-inhibitor0.923
CYP450 2C19 inhibitorNon-inhibitor0.9117
CYP450 3A4 inhibitorNon-inhibitor0.9728
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9398
Ames testNon AMES toxic0.7537
CarcinogenicityNon-carcinogens0.9469
BiodegradationNot ready biodegradable0.9052
Rat acute toxicity1.7638 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9695
hERG inhibition (predictor II)Non-inhibitor0.7522
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

Targets

Kind
Protein
Organism
Escherichia coli (strain K12)
Pharmacological action
Yes
Actions
Inhibitor
General Function
Trna binding
Specific Function
With S4 and S5 plays an important role in translational accuracy.Interacts with and stabilizes bases of the 16S rRNA that are involved in tRNA selection in the A site and with the mRNA backbone. Lo...
Gene Name
rpsL
Uniprot ID
P0A7S3
Uniprot Name
30S ribosomal protein S12
Molecular Weight
13736.995 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]
  3. Gill AE, Amyes SG: The contribution of a novel ribosomal S12 mutation to aminoglycoside resistance of Escherichia coli mutants. J Chemother. 2004 Aug;16(4):347-9. [PubMed:15332709]
  4. Yang G, Trylska J, Tor Y, McCammon JA: Binding of aminoglycosidic antibiotics to the oligonucleotide A-site model and 30S ribosomal subunit: Poisson-Boltzmann model, thermal denaturation, and fluorescence studies. J Med Chem. 2006 Sep 7;49(18):5478-90. [PubMed:16942021]
Kind
Nucleotide
Organism
Enteric bacteria and other eubacteria
Pharmacological action
Unknown
Actions
Inhibitor
In prokaryotes, the 16S rRNA is essential for recognizing the 5' end of mRNA and hence positioning it correctly on the ribosome. The 16S rRNA has a characteristic secondary structure in which half of the nucleotides are base-paired. The 16S rRNA sequence has been highly conserved and is often used for evolutionary and species comparative analysis.
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]
  3. Doi Y, de Oliveira Garcia D, Adams J, Paterson DL: Coproduction of novel 16S rRNA methylase RmtD and metallo-beta-lactamase SPM-1 in a panresistant Pseudomonas aeruginosa isolate from Brazil. Antimicrob Agents Chemother. 2007 Mar;51(3):852-6. Epub 2006 Dec 11. [PubMed:17158944]
  4. Bogaerts P, Galimand M, Bauraing C, Deplano A, Vanhoof R, De Mendonca R, Rodriguez-Villalobos H, Struelens M, Glupczynski Y: Emergence of ArmA and RmtB aminoglycoside resistance 16S rRNA methylases in Belgium. J Antimicrob Chemother. 2007 Mar;59(3):459-64. Epub 2007 Jan 15. [PubMed:17224412]
  5. Chen SY, Lin TH: A molecular dynamics study on binding recognition between several 4,5 and 4,6-linked aminoglycosides with A-site RNA. J Mol Recognit. 2010 Sep-Oct;23(5):423-34. doi: 10.1002/jmr.1008. [PubMed:20029836]

Enzymes

Kind
Protein
Organism
Mycobacterium tuberculosis
Pharmacological action
Unknown
Actions
Substrate
General Function
May catalyze the coenzyme A-dependent acetylation of the 2' hydroxyl or amino group of a broad spectrum of aminoglycosides and confer resistance to aminoglycosides (By similarity). In vitro assays show no significant increase of resistance to aminoglycosides, possibly due to low expression in a heterologous system (PubMed:9159528).
Specific Function
Aminoglycoside 2'-n-acetyltransferase activity
Gene Name
aac
Uniprot ID
P9WQG9
Uniprot Name
Aminoglycoside 2'-N-acetyltransferase
Molecular Weight
20037.53 Da
References
  1. Vetting MW, Hegde SS, Javid-Majd F, Blanchard JS, Roderick SL: Aminoglycoside 2'-N-acetyltransferase from Mycobacterium tuberculosis in complex with coenzyme A and aminoglycoside substrates. Nat Struct Biol. 2002 Sep;9(9):653-8. [PubMed:12161746]

Drug created on June 13, 2005 07:24 / Updated on January 16, 2021 12:52

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