Identification

Name
Tobramycin
Accession Number
DB00684  (APRD00582)
Type
Small Molecule
Groups
Approved, Investigational
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. [PubChem]

Structure
Thumb
Synonyms
  • 3'-Deoxykanamycin b
  • Nebramycin 6
  • Nebramycin factir 6
  • Nebramycin-Faktor 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
  • Tobracin (tn)
  • Tobramicina
  • Tobramycin
  • Tobramycine
  • Tobramycinum
  • Tobrex (tn)
External IDs
47663 / Lilly 47663 / SPRC-AB01
Product Ingredients
IngredientUNIICASInChI Key
Tobramycin hydrochloride01IX3OU16895188-93-5CVDADWBWFLWJNQ-TWDWGCDDSA-N
Tobramycin SulfateHJT0RXD7JK49842-07-1ZEUUPKVZFKBXPW-TWDWGCDDSA-N
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
BethkisSolution300 mg/4mLRespiratory (inhalation)Chiesi USA, Inc.2013-04-15Not applicableUs
Kitabis PakSolution300 mg/5mLRespiratory (inhalation)Catalent Pharma Solutions,Llc2015-02-192018-03-22Us
Kitabis PakSolution300 mg/5mLRespiratory (inhalation)Pari Respiratory Equipment2015-02-19Not applicableUs
Nebcin Inj 1.2gm/30mlLiquid1.2 gIntramuscular; IntravenousEli Lilly & Co. Ltd.1986-12-312003-05-12Canada
Nebcin Inj 10mg/mlLiquid10 mgIntramuscular; IntravenousEli Lilly & Co. Ltd.1975-12-312003-05-12Canada
Nebcin Inj 10mg/ml (vantage Vial)Liquid10 mgIntravenousEli Lilly & Co. Ltd.1989-12-311997-05-20Canada
Nebcin Inj 40mg/mlLiquid40 mgIntramuscular; IntravenousEli Lilly & Co. Ltd.1975-12-312003-05-12Canada
Nebcin Inj 60mgLiquid60 mgIntramuscular; IntravenousEli Lilly & Co. Ltd.1978-12-311998-08-04Canada
Nebcin Inj 80mgLiquid80 mgIntramuscular; IntravenousEli Lilly & Co. Ltd.1978-12-311998-08-04Canada
Sandoz Tobramycin 0.3%Solution0.3 %OphthalmicSandoz Canada Incorporated2000-08-21Not applicableCanada
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Aj-tobramycinLiquid40 mgIntramuscular; IntravenousAgila Jamp Canada IncNot applicableNot applicableCanada
Apo-tobramycinSolution0.3 %OphthalmicApotex Corporation2002-09-18Not applicableCanada
Jamp-tobramycinLiquid40 mgIntramuscular; IntravenousJamp Pharma Corporation2014-03-11Not applicableCanada
PMS-tobramycin 0.3% Ophthalmic SolutionLiquid3 mgOphthalmicPharmascience Inc1999-02-18Not applicableCanada
Teva-tobramycinSolution60 mgRespiratory (inhalation)Teva2016-02-03Not applicableCanada
TobramycinSolution300 mg/5mLRespiratory (inhalation)Teva Pharmaceuticals USA, Inc.2013-11-19Not applicableUs
TobramycinSolution / drops3 mg/1mLOphthalmicBlenheim Pharmacal, Inc.2015-05-15Not applicableUs
TobramycinInjection, solution40 mg/1mLIntravenousHospira, Inc.2006-02-172012-07-01Us
TobramycinSolution / drops3 mg/1mLOphthalmicHenry Schein2015-05-13Not applicableUs
TobramycinInjection40 mg/1mLIntramuscular; IntravenousMylan Institutional2011-05-10Not applicableUs
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
TobraDexTobramycin (3 mg/1mL) + Dexamethasone (1 mg/1mL)SuspensionOphthalmicRebel Distributors1988-08-18Not applicableUs
TobraDexTobramycin (3 mg/1mL) + Dexamethasone (1 mg/1mL)Suspension / dropsOphthalmicAlcon, Inc.1988-09-15Not applicableUs
TobraDexTobramycin (0.3 %) + Dexamethasone (0.1 %)OintmentOphthalmicNovartis1990-12-31Not applicableCanada
TobraDexTobramycin (3 mg/1g) + Dexamethasone (1 mg/1g)OintmentOphthalmicPhysicians Total Care, Inc.1988-10-152010-06-30Us
TobraDexTobramycin (3 mg/1mL) + Dexamethasone (1 mg/1mL)SuspensionOphthalmicA S Medication Solutions1988-09-15Not applicableUs
TobraDexTobramycin (3 mg/1mL) + Dexamethasone (1 mg/1mL)Suspension / dropsOphthalmicA-S Medication Solutions1988-09-152017-01-31Us
TobraDexTobramycin (3 mg/1g) + Dexamethasone (1 mg/1g)OintmentOphthalmicA S Medication Solutions1988-10-15Not applicableUs
TobradexTobramycin (3 mg/1mL) + Dexamethasone (1 mg/1mL)SuspensionOphthalmicStat Rx USA1988-09-15Not applicableUs
TobraDexTobramycin (3 mg/1g) + Dexamethasone (1 mg/1g)OintmentOphthalmicRebel Distributors1988-09-28Not applicableUs
TobraDexTobramycin (3 mg/1g) + Dexamethasone (1 mg/1g)OintmentOphthalmicAlcon, Inc.1988-10-15Not applicableUs
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)
Categories
UNII
VZ8RRZ51VK
CAS number
32986-56-4
Weight
Average: 467.5145
Monoisotopic: 467.259127807
Chemical Formula
C18H37N5O9
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

Pharmacology

Indication

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

Associated Conditions
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 rRNA
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
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
DrugInteraction
(R)-warfarinThe risk or severity of bleeding can be increased when Tobramycin is combined with (R)-warfarin.
(S)-WarfarinThe risk or severity of bleeding can be increased when Tobramycin is combined with (S)-Warfarin.
1,10-PhenanthrolineThe therapeutic efficacy of 1,10-Phenanthroline can be decreased when used in combination with Tobramycin.
4-hydroxycoumarinThe risk or severity of bleeding can be increased when Tobramycin is combined with 4-hydroxycoumarin.
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.
AceclofenacThe risk or severity of nephrotoxicity can be increased when Aceclofenac is combined with Tobramycin.
AcemetacinThe risk or severity of nephrotoxicity can be increased when Acemetacin is combined with Tobramycin.
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.
Food Interactions
Not Available

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
External Links
Human Metabolome Database
HMDB0014822
KEGG Drug
D00063
KEGG Compound
C00397
PubChem Compound
36294
PubChem Substance
46507662
ChemSpider
33377
BindingDB
50366778
ChEBI
28864
ChEMBL
CHEMBL1747
Therapeutic Targets Database
DAP000110
PharmGKB
PA451704
HET
TOY
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Tobramycin
ATC Codes
S01AA12 — TobramycinJ01GB01 — Tobramycin
AHFS Codes
  • 08:12.02 — Aminoglycosides
  • 52:04.04 — Antibacterials
PDB Entries
1lc4 / 1m4d / 3sg8 / 3vet / 4ebk / 4evy / 4jd6 / 4lfc / 4xje / 5cfs
FDA label
Download (414 KB)
MSDS
Download (73.3 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
0RecruitingTreatmentOsteomyelitis1
1CompletedBasic ScienceCystic Fibrosis (CF)1
1CompletedTreatmentBurkholderia Cepacia Infection / Cystic Fibrosis (CF)1
1CompletedTreatmentCystic Fibrosis (CF)4
1CompletedTreatmentEye Dryness1
1Unknown StatusTreatmentHealthy Volunteers1
1, 2CompletedBasic ScienceInfection NOS / Minor burns1
1, 2CompletedTreatmentBronchiectasis1
1, 2RecruitingTreatmentCystic Fibrosis (CF)1
1, 2Unknown StatusTreatmentCystic Fibrosis (CF)1
2CompletedPreventionCystic Fibrosis (CF) / Pulmonary Disease, Chronic Obstructive1
2CompletedTreatmentChronic Rhinosinusitis1
2CompletedTreatmentCystic Fibrosis (CF)1
2CompletedTreatmentCystic Fibrosis (CF) / Pseudomonas Aeruginosa1
2Not Yet RecruitingTreatmentProsthetic Joint Infection1
2, 3RecruitingTreatmentNon-CF Bronchiectasis1
3CompletedTreatmentBacterial Infections / Cystic Fibrosis (CF)1
3CompletedTreatmentCataracts1
3CompletedTreatmentConjunctivitis, Bacterial1
3CompletedTreatmentBacterial blepharitis / Conjunctivitis / Corneal Inflammation1
3CompletedTreatmentCystic Fibrosis (CF)8
3CompletedTreatmentEye Infections / Postoperative Complications1
3CompletedTreatmentMultiple Myeloma (MM)1
3CompletedTreatmentOcular Inflammation Associated With Blepharaconjunctivitis1
3CompletedTreatmentPseudomonas Aeruginosa Infection1
3CompletedTreatmentPseudomonas Infections1
3CompletedTreatmentPurulent Bacterial Conjunctivitis1
3CompletedTreatmentTreatment of Early Pulmonary Infections With P. Aeruginosa in Cystic Fibrosis Patients1
3CompletedTreatmentBacterial blepharitis1
3RecruitingPreventionCritical Illness / Sepsis / Shock, Septic / Ventilator-associated Bacterial Pneumonia1
3RecruitingTreatmentAcute maxillary sinusitis caused by M. catarrhalis / Chronic Lung Diseases / Cystic Fibrosis (CF)1
3RecruitingTreatmentCystic Fibrosis (CF)1
3RecruitingTreatmentFractures, Open1
3Unknown StatusTreatmentAcute Bacterial Conjunctivitis1
3WithdrawnTreatmentPost-surgical Inflammation1
4Active Not RecruitingTreatmentMeibomian Gland Dysfunction (MGD) / Posterior Blepharitis1
4Active Not RecruitingTreatmentOpen-angle Glaucoma (OAG)1
4CompletedTreatmentBlepharokeratoconjunctivitis1
4CompletedTreatmentChalazion / Hordeolum1
4CompletedTreatmentConjunctivitis1
4CompletedTreatmentCystic Fibrosis (CF)3
4CompletedTreatmentInflammatory Reaction1
4CompletedTreatmentOcular Hypertension / Open-angle Glaucoma (OAG)1
4CompletedTreatmentPneumonia Ventilator Associated1
4RecruitingPreventionSurgical Site Infections1
4RecruitingTreatmentCystic Fibrosis (CF)1
4RecruitingTreatmentVentilator-associated Bacterial Pneumonia1
4Unknown StatusTreatmentBronchiectasis1
4Unknown StatusTreatmentCystic Fibrosis (CF)1
Not AvailableActive Not RecruitingNot AvailablePseudomonas Aeruginosa in Cystic Fibrosis1
Not AvailableCompletedNot AvailableCystic Fibrosis (CF)1
Not AvailableCompletedNot AvailableOcular Hypertension1
Not AvailableCompletedNot AvailableOrthopedic Operations1
Not AvailableCompletedTreatmentCataracts1
Not AvailableCompletedTreatmentChalazion Both Eyes / Chalazion Left Eye, Unspecified Eyelid / Chalazion Right Eye, Unspecified Eyelid / Chalazion Unspecified Eye, Unspecified Eyelid1
Not AvailableCompletedTreatmentChronic Bronchitis / Cystic Fibrosis (CF)1
Not AvailableNot Yet RecruitingTreatmentDry Eye Syndrome (DES)1
Not AvailableRecruitingNot AvailableAcute Bacterial Exacerbation of Chronic Bronchitis (ABECB) / Acute Bacterial Sinusitis (ABS) / Acute Decompensated Heart Failure (ADHF) / Acute Pyelonephritis / Adenovirus / Adjunct to general anesthesia therapy / Adrenal Insufficiency / Airway Swelling / Anaesthesia therapy / Anxiolysis / Arterial Hypotension / Autism, Early Infantile / Autistic Disorder / Bartonellosis / Benzodiazepine Withdrawal / Benzodiazepines / Bipolar Disorder (BD) / Bloodstream Infections / Bone and Joint Infections / Brain Swelling / Bronchospasm / Brucellosis / Cardiac Arrest / Central Nervous System Infections / Cholera / Chronic Bacterial Prostatitis / Community Acquired Pneumonia (CAP) / Complicated Urinary Tract Infections / Convulsions / Cytomegalovirus Retinitis / Drug hypersensitivity reaction / Early-onset Schizophrenia Spectrum Disorders / Edema / Epilepsies / Feeling Anxious / Flu caused by Influenza / Gastroparesis / Gynaecological infection / Headaches / Herpes Simplex Virus / High Blood Pressure (Hypertension) / High Cholesterol / Hospital-acquired bacterial pneumonia / Hyperlipidemias / Infantile Hemangiomas / Infection NOS / Inflammatory Conditions / Inflammatory Reaction / Influenza Treatment or Prophylaxis / Inhalational Anthrax (Post-Exposure) / Intra-Abdominal Infections / Life-threatening Fungal Infections / Lower Respiratory Tract Infection (LRTI) / Meningitis, Bacterial / Migraines / Muscle Spasms / Nausea / Opioid Addiction / Pain NOS / Plague / Pneumonia / Prophylaxis / Psittacosis / Q Fever / Reflux / Relapsing Fever / Rocky Mountain Spotted Fever / Schizophrenic Disorders / Sedation therapy / Seizures / Sepsis / Skeletal Muscle Spasms / Skin and Subcutaneous Tissue Bacterial Infections / Skin Structures and Soft Tissue Infections / Stable Angina (SA) / Thromboprophylaxis / Thrombotic events / Toxic effect of hydrocyanic acid and cyanides / Trachoma / Treatment-resistant Schizophrenia / Tularemia / Typhus Fever / Uncomplicated Skin and Skin Structure Infections / Uncomplicated Urinary Tract Infections / Urinary Tract Infections (UTIs) / Vomiting / Withdrawal1
Not AvailableRecruitingDiagnosticCystic Fibrosis (CF)1
Not AvailableRecruitingTreatmentAge-related Cataract1
Not AvailableRecruitingTreatmentBacterial Keratitis1
Not AvailableRecruitingTreatmentCystic Fibrosis (CF)1
Not AvailableRecruitingTreatmentMyopia / Refractive Errors1
Not AvailableUnknown StatusTreatmentBronchiectasis With Chronic Infection With Pseudomonas Aeruginosa1

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
SolutionRespiratory (inhalation)300 mg/4mL
LiquidIntramuscular; Intravenous1.2 g
LiquidIntravenous10 mg
LiquidIntramuscular; Intravenous60 mg
LiquidIntramuscular; Intravenous80 mg
SolutionOphthalmic0.3 %
SolutionRespiratory (inhalation)60 mg
SolutionRespiratory (inhalation)300 mg
CapsuleOral; Respiratory (inhalation)28 mg/1
CapsuleRespiratory (inhalation)28 mg
OintmentOphthalmic
SuspensionOphthalmic
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
SolutionOral300 mg/5mL
SolutionRespiratory (inhalation)60 mg/1mL
Solution / dropsOphthalmic3 mg/1mL
Suspension / dropsOphthalmic
Powder, for solutionIntravenous1.2 g
Injection, solutionIntravenous0.8 mg/1mL
Injection, solutionIntravenous1.2 mg/1mL
SolutionRespiratory (inhalation)300 mg/5mL
SolutionIntramuscular; Intravenous10 mg
SolutionIntramuscular; Intravenous40 mg
LiquidIntramuscular; Intravenous10 mg
LiquidIntramuscular; Intravenous40 mg
LiquidOphthalmic3 mg
OintmentOphthalmic0.3 %
OintmentOphthalmic3 mg/1g
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)
US5508269No1996-04-162014-10-19Us
US5149694No1992-09-222009-09-22Us
CA2414737No2009-01-062021-06-26Canada
US7795316No2010-09-142028-08-03Us
US8101582No2012-01-242027-12-19Us
US8450287No2013-05-282027-12-19Us
US7368102No2008-05-062022-12-19Us
US8715623No2014-05-062022-12-19Us
US7559325No2009-07-142025-10-27Us
US7442388No2008-10-282020-05-10Us
US7097827No2006-08-292016-04-16Us
US8349294No2013-01-082020-05-10Us
US8069851No2011-12-062024-09-24Us
US7516741No2009-04-142024-01-11Us
US7939502No2011-05-102022-06-14Us
US6987094No2006-01-172022-09-22Us
US7696178No2010-04-132023-03-17Us

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

Taxonomy

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
4,6-disubstituted 2-deoxystreptamine / Glycosyl compound / O-glycosyl compound / Aminocyclitol or derivatives / Cyclohexanol / Cyclohexylamine / Cyclitol or derivatives / Monosaccharide / Oxane / Cyclic alcohol
show 15 more
Molecular Framework
Aliphatic heteromonocyclic compounds
External Descriptors
amino cyclitol glycoside (CHEBI:28864)

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]
2. 16S rRNA
Kind
Nucleotide
Organism
Enteric bacteria and other eubacteria
Pharmacological action
Unknown
Actions
Inhibitor
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 November 17, 2018 07:11