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
Aj-tobramycinLiquid40 mgIntramuscular; IntravenousAgila Jamp Canada IncNot applicableNot applicableCanada
BethkisSolution300 mg/4mLRespiratory (inhalation)Chiesi Pharmaceuticals Inc.2013-04-15Not applicableUs
Jamp-tobramycinLiquid40 mgIntramuscular; IntravenousJamp Pharma Corporation2014-03-11Not applicableCanada
Kitabis PakSolution300 mg/5mLRespiratory (inhalation)Pari Respiratory Equipment2014-12-02Not 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
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Apo-tobramycinSolution0.3 %OphthalmicApotex Corporation2002-09-18Not applicableCanada
TobramycinSolution3 mg/mLOphthalmicRemedy Repack2016-07-192017-03-10Us
TobramycinSolution / drops3 mg/mLOphthalmicRemedy Repack2013-06-132017-01-25Us
TobramycinInjection, solution10 mg/mLIntramuscular; IntravenousFresenius Kabi2004-11-30Not applicableUs
TobramycinInjection, solution40 mg/mLIntramuscular; IntravenousTeva Parenteral Medicines, Inc.1992-02-01Not applicableUs
TobramycinSolution3 mg/mLOphthalmicPreferreed Pharmaceuticals Inc.2012-02-28Not applicableUs
TobramycinInjection, solution40 mg/mLIntramuscular; IntravenousAkorn2014-09-16Not applicableUs
TobramycinInjection40 mg/mLIntramuscular; IntravenousMylan Institutional2008-03-12Not applicableUs
TobramycinSolution / drops3 mg/mLOphthalmicBlenheim Pharmacal, Inc.2015-05-15Not applicableUs
TobramycinSolution3 mg/mLOphthalmicRebel Distributors1993-11-29Not 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)
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
TobraDexTobramycin (3 mg/mL) + Dexamethasone (1 mg/mL)SuspensionOphthalmicRebel Distributors1988-08-18Not applicableUs
TobraDexTobramycin (3 mg/g) + Dexamethasone (1 mg/g)OintmentOphthalmicAlcon, Inc.1988-10-15Not applicableUs
TobraDexTobramycin (0.3 %) + Dexamethasone (0.1 %)SuspensionOphthalmicNovartis1990-12-31Not applicableCanada
TobraDexTobramycin (3 mg/g) + Dexamethasone (1 mg/g)OintmentOphthalmicRebel Distributors1988-09-28Not applicableUs
TobraDexTobramycin (3 mg/mL) + Dexamethasone (1 mg/mL)SuspensionOphthalmicA S Medication Solutions1988-09-152017-06-20Us
TobradexTobramycin (3 mg/mL) + Dexamethasone (1 mg/mL)SuspensionOphthalmicStat Rx USA1988-09-15Not applicableUs
TobraDexTobramycin (3 mg/mL) + Dexamethasone (1 mg/mL)Suspension / dropsOphthalmicAlcon, Inc.1988-09-15Not applicableUs
TobraDexTobramycin (3 mg/mL) + Dexamethasone (1 mg/mL)SuspensionOphthalmicA S Medication Solutions1988-09-152017-06-20Us
TobraDexTobramycin (0.3 %) + Dexamethasone (0.1 %)OintmentOphthalmicNovartis1990-12-31Not applicableCanada
TobraDexTobramycin (3 mg/g) + Dexamethasone (1 mg/g)OintmentOphthalmicA S Medication Solutions1988-10-152017-06-20Us
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

Pharmacology

Indication

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

Structured Indications
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
DrugInteractionDrug group
AceclofenacAceclofenac may decrease the excretion rate of Tobramycin which could result in a higher serum level.Approved, Investigational
AcemetacinAcemetacin may decrease the excretion rate of Tobramycin which could result in a higher serum level.Approved, Experimental, Investigational
AcetyldigitoxinThe serum concentration of Acetyldigitoxin can be decreased when it is combined with Tobramycin.Approved
AcetyldigoxinThe serum concentration of Acetyldigoxin can be decreased when it is combined with Tobramycin.Experimental
Acetylsalicylic acidAcetylsalicylic acid may decrease the excretion rate of Tobramycin which could result in a higher serum level.Approved, Vet Approved
AdapaleneAdapalene may decrease the excretion rate of Tobramycin which could result in a higher serum level.Approved
AlclofenacAlclofenac may decrease the excretion rate of Tobramycin which could result in a higher serum level.Approved, Withdrawn
AlcuroniumTobramycin may increase the respiratory depressant activities of Alcuronium.Experimental
Alendronic acidTobramycin may increase the hypocalcemic activities of Alendronic acid.Approved
AlminoprofenAlminoprofen may decrease the excretion rate of Tobramycin which could result in a higher serum level.Experimental
AmdinocillinThe serum concentration of Tobramycin can be decreased when it is combined with Amdinocillin.Investigational, Withdrawn
AmoxicillinThe serum concentration of Tobramycin can be decreased when it is combined with Amoxicillin.Approved, Vet Approved
Amphotericin BAmphotericin B may increase the nephrotoxic activities of Tobramycin.Approved, Investigational
AmpicillinThe serum concentration of Tobramycin can be decreased when it is combined with Ampicillin.Approved, Vet Approved
AndrographolideAndrographolide may decrease the excretion rate of Tobramycin which could result in a higher serum level.Investigational
AnisodamineAnisodamine may decrease the excretion rate of Tobramycin which could result in a higher serum level.Investigational
AntipyrineAntipyrine may decrease the excretion rate of Tobramycin which could result in a higher serum level.Approved
ApocyninApocynin may decrease the excretion rate of Tobramycin which could result in a higher serum level.Investigational
ApremilastApremilast may decrease the excretion rate of Tobramycin which could result in a higher serum level.Approved, Investigational
AspoxicillinThe serum concentration of Tobramycin can be decreased when it is combined with Aspoxicillin.Experimental
AtracuriumTobramycin may increase the respiratory depressant activities of Atracurium.Experimental, Investigational
Atracurium besylateTobramycin may increase the respiratory depressant activities of Atracurium besylate.Approved
AzapropazoneAzapropazone may decrease the excretion rate of Tobramycin which could result in a higher serum level.Withdrawn
AzelastineAzelastine may decrease the excretion rate of Tobramycin which could result in a higher serum level.Approved
AzidocillinThe serum concentration of Tobramycin can be decreased when it is combined with Azidocillin.Approved
AzlocillinThe serum concentration of Tobramycin can be decreased when it is combined with Azlocillin.Approved
BacampicillinThe serum concentration of Tobramycin can be decreased when it is combined with Bacampicillin.Approved, Investigational
BalsalazideBalsalazide may decrease the excretion rate of Tobramycin which could result in a higher serum level.Approved, Investigational
BCG vaccineThe therapeutic efficacy of BCG vaccine can be decreased when used in combination with Tobramycin.Investigational
BendazacBendazac may decrease the excretion rate of Tobramycin which could result in a higher serum level.Experimental
BenorilateBenorilate may decrease the excretion rate of Tobramycin which could result in a higher serum level.Experimental
BenoxaprofenBenoxaprofen may decrease the excretion rate of Tobramycin which could result in a higher serum level.Withdrawn
Benzathine benzylpenicillinThe serum concentration of Tobramycin can be decreased when it is combined with Benzathine benzylpenicillin.Approved, Vet Approved
BenzydamineBenzydamine may decrease the excretion rate of Tobramycin which could result in a higher serum level.Approved
BenzylpenicillinThe serum concentration of Tobramycin can be decreased when it is combined with Benzylpenicillin.Approved, Vet Approved
Benzylpenicilloyl PolylysineThe serum concentration of Tobramycin can be decreased when it is combined with Benzylpenicilloyl Polylysine.Approved
BevoniumBevonium may decrease the excretion rate of Tobramycin which could result in a higher serum level.Experimental
Botulinum Toxin Type ATobramycin may increase the neuromuscular blocking activities of Botulinum Toxin Type A.Approved, Investigational
Botulinum Toxin Type BTobramycin may increase the neuromuscular blocking activities of Botulinum Toxin Type B.Approved
BromfenacBromfenac may decrease the excretion rate of Tobramycin which could result in a higher serum level.Approved
BucillamineBucillamine may decrease the excretion rate of Tobramycin which could result in a higher serum level.Investigational
BufexamacBufexamac may decrease the excretion rate of Tobramycin which could result in a higher serum level.Experimental
BumadizoneBumadizone may decrease the excretion rate of Tobramycin which could result in a higher serum level.Experimental
BumetanideThe risk or severity of adverse effects can be increased when Bumetanide is combined with Tobramycin.Approved
CapreomycinCapreomycin may increase the neuromuscular blocking activities of Tobramycin.Approved
CarbenicillinThe serum concentration of Tobramycin can be decreased when it is combined with Carbenicillin.Approved, Investigational
Carbenicillin indanylThe serum concentration of Tobramycin can be decreased when it is combined with Carbenicillin indanyl.Approved, Investigational
CarboplatinTobramycin may increase the ototoxic activities of Carboplatin.Approved
CarfecillinThe serum concentration of Tobramycin can be decreased when it is combined with Carfecillin.Experimental
CarprofenCarprofen may decrease the excretion rate of Tobramycin which could result in a higher serum level.Approved, Vet Approved, Withdrawn
CastanospermineCastanospermine may decrease the excretion rate of Tobramycin which could result in a higher serum level.Experimental
CelecoxibCelecoxib may decrease the excretion rate of Tobramycin which could result in a higher serum level.Approved, Investigational
ChloroquineChloroquine may decrease the excretion rate of Tobramycin which could result in a higher serum level.Approved, Vet Approved
Choline magnesium trisalicylateCholine magnesium trisalicylate may decrease the excretion rate of Tobramycin which could result in a higher serum level.Approved
CisatracuriumTobramycin may increase the respiratory depressant activities of Cisatracurium.Approved, Experimental
Cisatracurium besylateTobramycin may increase the respiratory depressant activities of Cisatracurium besylate.Approved
CisplatinCisplatin may increase the nephrotoxic activities of Tobramycin.Approved
Clodronic AcidTobramycin may increase the hypocalcemic activities of Clodronic Acid.Approved, Investigational, Vet Approved
ClonixinClonixin may decrease the excretion rate of Tobramycin which could result in a higher serum level.Approved
CloxacillinThe serum concentration of Tobramycin can be decreased when it is combined with Cloxacillin.Approved, Vet Approved
ColistimethateTobramycin may increase the nephrotoxic activities of Colistimethate.Approved, Vet Approved
CurcuminCurcumin may decrease the excretion rate of Tobramycin which could result in a higher serum level.Investigational
CyclacillinThe serum concentration of Tobramycin can be decreased when it is combined with Cyclacillin.Approved
CyclosporineTobramycin may increase the nephrotoxic activities of Cyclosporine.Approved, Investigational, Vet Approved
CymarinThe serum concentration of Cymarin can be decreased when it is combined with Tobramycin.Experimental
D-LimoneneD-Limonene may decrease the excretion rate of Tobramycin which could result in a higher serum level.Investigational
DecamethoniumTobramycin may increase the respiratory depressant activities of Decamethonium.Approved
DeslanosideThe serum concentration of Deslanoside can be decreased when it is combined with Tobramycin.Approved
DiclofenacDiclofenac may decrease the excretion rate of Tobramycin which could result in a higher serum level.Approved, Vet Approved
DicloxacillinThe serum concentration of Tobramycin can be decreased when it is combined with Dicloxacillin.Approved, Vet Approved
DifenpiramideDifenpiramide may decrease the excretion rate of Tobramycin which could result in a higher serum level.Experimental
DiflunisalDiflunisal may decrease the excretion rate of Tobramycin which could result in a higher serum level.Approved
DigitoxinThe serum concentration of Digitoxin can be decreased when it is combined with Tobramycin.Approved, Investigational
DigoxinThe serum concentration of Digoxin can be decreased when it is combined with Tobramycin.Approved
Digoxin Immune Fab (Ovine)The serum concentration of Digoxin Immune Fab (Ovine) can be decreased when it is combined with Tobramycin.Approved
Domoic AcidTobramycin may increase the respiratory depressant activities of Domoic Acid.Experimental
Doxacurium chlorideTobramycin may increase the respiratory depressant activities of Doxacurium chloride.Approved
DroxicamDroxicam may decrease the excretion rate of Tobramycin which could result in a higher serum level.Approved
DuvelisibDuvelisib may decrease the excretion rate of Tobramycin which could result in a higher serum level.Investigational
E-6201E-6201 may decrease the excretion rate of Tobramycin which could result in a higher serum level.Investigational
EpicillinThe serum concentration of Tobramycin can be decreased when it is combined with Epicillin.Experimental
EpirizoleEpirizole may decrease the excretion rate of Tobramycin which could result in a higher serum level.Approved
Etacrynic acidThe risk or severity of adverse effects can be increased when Etacrynic acid is combined with Tobramycin.Approved
EtanerceptEtanercept may decrease the excretion rate of Tobramycin which could result in a higher serum level.Approved, Investigational
EthenzamideEthenzamide may decrease the excretion rate of Tobramycin which could result in a higher serum level.Experimental
Etidronic acidTobramycin may increase the hypocalcemic activities of Etidronic acid.Approved
EtodolacEtodolac may decrease the excretion rate of Tobramycin which could result in a higher serum level.Approved, Investigational, Vet Approved
EtofenamateEtofenamate may decrease the excretion rate of Tobramycin which could result in a higher serum level.Approved, Investigational
EtoricoxibEtoricoxib may decrease the excretion rate of Tobramycin which could result in a higher serum level.Approved, Investigational
Evening primrose oilEvening primrose oil may decrease the excretion rate of Tobramycin which could result in a higher serum level.Approved, Investigational
exisulindexisulind may decrease the excretion rate of Tobramycin which could result in a higher serum level.Investigational
FelbinacFelbinac may decrease the excretion rate of Tobramycin which could result in a higher serum level.Experimental
FenbufenFenbufen may decrease the excretion rate of Tobramycin which could result in a higher serum level.Approved
FenoprofenFenoprofen may decrease the excretion rate of Tobramycin which could result in a higher serum level.Approved
FentiazacFentiazac may decrease the excretion rate of Tobramycin which could result in a higher serum level.Experimental
FeprazoneFeprazone may decrease the excretion rate of Tobramycin which could result in a higher serum level.Experimental
Ferulic acidFerulic acid may decrease the excretion rate of Tobramycin which could result in a higher serum level.Experimental
FloctafenineFloctafenine may decrease the excretion rate of Tobramycin which could result in a higher serum level.Approved, Withdrawn
FlucloxacillinThe serum concentration of Tobramycin can be decreased when it is combined with Flucloxacillin.Approved, Investigational
FlunixinFlunixin may decrease the excretion rate of Tobramycin which could result in a higher serum level.Vet Approved
FlunoxaprofenFlunoxaprofen may decrease the excretion rate of Tobramycin which could result in a higher serum level.Experimental
FlurbiprofenFlurbiprofen may decrease the excretion rate of Tobramycin which could result in a higher serum level.Approved, Investigational
FoscarnetFoscarnet may increase the nephrotoxic activities of Tobramycin.Approved
FurosemideThe risk or severity of adverse effects can be increased when Furosemide is combined with Tobramycin.Approved, Vet Approved
GallamineTobramycin may increase the respiratory depressant activities of Gallamine.Experimental
Gallamine TriethiodideTobramycin may increase the respiratory depressant activities of Gallamine Triethiodide.Approved
GitoformateThe serum concentration of Gitoformate can be decreased when it is combined with Tobramycin.Experimental
GuacetisalGuacetisal may decrease the excretion rate of Tobramycin which could result in a higher serum level.Experimental
HigenamineHigenamine may decrease the excretion rate of Tobramycin which could result in a higher serum level.Investigational
IbandronateTobramycin may increase the hypocalcemic activities of Ibandronate.Approved, Investigational
IbuprofenIbuprofen may decrease the excretion rate of Tobramycin which could result in a higher serum level.Approved
IbuproxamIbuproxam may decrease the excretion rate of Tobramycin which could result in a higher serum level.Withdrawn
IcatibantIcatibant may decrease the excretion rate of Tobramycin which could result in a higher serum level.Approved
Imidazole salicylateImidazole salicylate may decrease the excretion rate of Tobramycin which could result in a higher serum level.Experimental
IndobufenIndobufen may decrease the excretion rate of Tobramycin which could result in a higher serum level.Investigational
IndomethacinIndomethacin may decrease the excretion rate of Tobramycin which could result in a higher serum level.Approved, Investigational
IndoprofenIndoprofen may decrease the excretion rate of Tobramycin which could result in a higher serum level.Withdrawn
IsoxicamIsoxicam may decrease the excretion rate of Tobramycin which could result in a higher serum level.Withdrawn
KebuzoneKebuzone may decrease the excretion rate of Tobramycin which could result in a higher serum level.Experimental
KetoprofenKetoprofen may decrease the excretion rate of Tobramycin which could result in a higher serum level.Approved, Vet Approved
KetorolacKetorolac may decrease the excretion rate of Tobramycin which could result in a higher serum level.Approved
Lanatoside CThe serum concentration of Lanatoside C can be decreased when it is combined with Tobramycin.Experimental
LeflunomideLeflunomide may decrease the excretion rate of Tobramycin which could result in a higher serum level.Approved, Investigational
LisofyllineLisofylline may decrease the excretion rate of Tobramycin which could result in a higher serum level.Investigational
LonazolacLonazolac may decrease the excretion rate of Tobramycin which could result in a higher serum level.Experimental
LornoxicamLornoxicam may decrease the excretion rate of Tobramycin which could result in a higher serum level.Approved, Investigational
LoxoprofenLoxoprofen may decrease the excretion rate of Tobramycin which could result in a higher serum level.Approved, Investigational
LumiracoxibLumiracoxib may decrease the excretion rate of Tobramycin which could result in a higher serum level.Approved, Investigational
Magnesium salicylateMagnesium salicylate may decrease the excretion rate of Tobramycin which could result in a higher serum level.Approved
MannitolMannitol may increase the nephrotoxic activities of Tobramycin.Approved, Investigational
MasoprocolMasoprocol may decrease the excretion rate of Tobramycin which could result in a higher serum level.Approved, Investigational
MecamylamineTobramycin may increase the neuromuscular blocking activities of Mecamylamine.Approved
Meclofenamic acidMeclofenamic acid may decrease the excretion rate of Tobramycin which could result in a higher serum level.Approved, Vet Approved
Mefenamic acidMefenamic acid may decrease the excretion rate of Tobramycin which could result in a higher serum level.Approved
MeloxicamMeloxicam may decrease the excretion rate of Tobramycin which could result in a higher serum level.Approved, Vet Approved
MesalazineMesalazine may decrease the excretion rate of Tobramycin which could result in a higher serum level.Approved
MetamizoleMetamizole may decrease the excretion rate of Tobramycin which could result in a higher serum level.Investigational, Withdrawn
MetampicillinThe serum concentration of Tobramycin can be decreased when it is combined with Metampicillin.Experimental
MeticillinThe serum concentration of Tobramycin can be decreased when it is combined with Meticillin.Approved, Investigational
MetildigoxinThe serum concentration of Metildigoxin can be decreased when it is combined with Tobramycin.Experimental
MetocurineTobramycin may increase the respiratory depressant activities of Metocurine.Approved
Metocurine IodideTobramycin may increase the respiratory depressant activities of Metocurine Iodide.Withdrawn
MezlocillinThe serum concentration of Tobramycin can be decreased when it is combined with Mezlocillin.Approved, Investigational
MivacuriumTobramycin may increase the respiratory depressant activities of Mivacurium.Approved
MizoribineMizoribine may decrease the excretion rate of Tobramycin which could result in a higher serum level.Investigational
MofebutazoneMofebutazone may decrease the excretion rate of Tobramycin which could result in a higher serum level.Experimental
Mycophenolate mofetilMycophenolate mofetil may decrease the excretion rate of Tobramycin which could result in a higher serum level.Approved, Investigational
Mycophenolic acidMycophenolic acid may decrease the excretion rate of Tobramycin which could result in a higher serum level.Approved
NabumetoneNabumetone may decrease the excretion rate of Tobramycin which could result in a higher serum level.Approved
NafamostatNafamostat may decrease the excretion rate of Tobramycin which could result in a higher serum level.Approved, Investigational
NafcillinThe serum concentration of Tobramycin can be decreased when it is combined with Nafcillin.Approved
NaftifineNaftifine may decrease the excretion rate of Tobramycin which could result in a higher serum level.Approved
NaproxenNaproxen may decrease the excretion rate of Tobramycin which could result in a higher serum level.Approved, Vet Approved
NeosaxitoxinTobramycin may increase the respiratory depressant activities of Neosaxitoxin.Investigational
NepafenacNepafenac may decrease the excretion rate of Tobramycin which could result in a higher serum level.Approved
NifenazoneNifenazone may decrease the excretion rate of Tobramycin which could result in a higher serum level.Experimental
Niflumic AcidNiflumic Acid may decrease the excretion rate of Tobramycin which could result in a higher serum level.Approved
NimesulideNimesulide may decrease the excretion rate of Tobramycin which could result in a higher serum level.Approved, Investigational, Withdrawn
NitroaspirinNitroaspirin may decrease the excretion rate of Tobramycin which could result in a higher serum level.Investigational
OleandrinThe serum concentration of Oleandrin can be decreased when it is combined with Tobramycin.Experimental, Investigational
OlopatadineOlopatadine may decrease the excretion rate of Tobramycin which could result in a higher serum level.Approved
OlsalazineOlsalazine may decrease the excretion rate of Tobramycin which could result in a higher serum level.Approved
OrgoteinOrgotein may decrease the excretion rate of Tobramycin which could result in a higher serum level.Vet Approved
OuabainThe serum concentration of Ouabain can be decreased when it is combined with Tobramycin.Approved
OxacillinThe serum concentration of Tobramycin can be decreased when it is combined with Oxacillin.Approved
OxaprozinOxaprozin may decrease the excretion rate of Tobramycin which could result in a higher serum level.Approved
OxyphenbutazoneOxyphenbutazone may decrease the excretion rate of Tobramycin which could result in a higher serum level.Approved, Withdrawn
PamidronateTobramycin may increase the hypocalcemic activities of Pamidronate.Approved
PancuroniumTobramycin may increase the respiratory depressant activities of Pancuronium.Approved
ParecoxibParecoxib may decrease the excretion rate of Tobramycin which could result in a higher serum level.Approved
ParthenolideParthenolide may decrease the excretion rate of Tobramycin which could result in a higher serum level.Investigational
PenamecillinThe serum concentration of Tobramycin can be decreased when it is combined with Penamecillin.Experimental
PenimepicyclineThe serum concentration of Tobramycin can be decreased when it is combined with Penimepicycline.Experimental
PeruvosideThe serum concentration of Peruvoside can be decreased when it is combined with Tobramycin.Experimental
PhenoxymethylpenicillinThe serum concentration of Tobramycin can be decreased when it is combined with Phenoxymethylpenicillin.Approved, Vet Approved
PhenylbutazonePhenylbutazone may decrease the excretion rate of Tobramycin which could result in a higher serum level.Approved, Vet Approved
Picosulfuric acidThe therapeutic efficacy of Picosulfuric acid can be decreased when used in combination with Tobramycin.Approved
PimecrolimusPimecrolimus may decrease the excretion rate of Tobramycin which could result in a higher serum level.Approved, Investigational
PipecuroniumTobramycin may increase the respiratory depressant activities of Pipecuronium.Approved
PiperacillinThe serum concentration of Tobramycin can be decreased when it is combined with Piperacillin.Approved
PiretanideThe risk or severity of adverse effects can be increased when Piretanide is combined with Tobramycin.Experimental
PirfenidonePirfenidone may decrease the excretion rate of Tobramycin which could result in a higher serum level.Approved, Investigational
PiroxicamPiroxicam may decrease the excretion rate of Tobramycin which could result in a higher serum level.Approved, Investigational
PirprofenPirprofen may decrease the excretion rate of Tobramycin which could result in a higher serum level.Experimental
PivampicillinThe serum concentration of Tobramycin can be decreased when it is combined with Pivampicillin.Approved
PivmecillinamThe serum concentration of Tobramycin can be decreased when it is combined with Pivmecillinam.Approved
PranoprofenPranoprofen may decrease the excretion rate of Tobramycin which could result in a higher serum level.Experimental, Investigational
Procaine benzylpenicillinThe serum concentration of Tobramycin can be decreased when it is combined with Procaine benzylpenicillin.Approved, Vet Approved
ProglumetacinProglumetacin may decrease the excretion rate of Tobramycin which could result in a higher serum level.Experimental
PropacetamolPropacetamol may decrease the excretion rate of Tobramycin which could result in a higher serum level.Approved, Investigational
PropicillinThe serum concentration of Tobramycin can be decreased when it is combined with Propicillin.Experimental
PropyphenazonePropyphenazone may decrease the excretion rate of Tobramycin which could result in a higher serum level.Experimental
ProquazoneProquazone may decrease the excretion rate of Tobramycin which could result in a higher serum level.Experimental
ProscillaridinThe serum concentration of Proscillaridin can be decreased when it is combined with Tobramycin.Experimental
PTC299PTC299 may decrease the excretion rate of Tobramycin which could result in a higher serum level.Investigational
PyrantelTobramycin may increase the respiratory depressant activities of Pyrantel.Approved, Vet Approved
RapacuroniumTobramycin may increase the respiratory depressant activities of Rapacuronium.Withdrawn
ResveratrolResveratrol may decrease the excretion rate of Tobramycin which could result in a higher serum level.Approved, Experimental, Investigational
RisedronateTobramycin may increase the hypocalcemic activities of Risedronate.Approved, Investigational
RocuroniumTobramycin may increase the respiratory depressant activities of Rocuronium.Approved
RofecoxibRofecoxib may decrease the excretion rate of Tobramycin which could result in a higher serum level.Investigational, Withdrawn
SalicylamideSalicylamide may decrease the excretion rate of Tobramycin which could result in a higher serum level.Approved
Salicylic acidSalicylic acid may decrease the excretion rate of Tobramycin which could result in a higher serum level.Approved, Vet Approved
SalsalateSalsalate may decrease the excretion rate of Tobramycin which could result in a higher serum level.Approved
SemapimodSemapimod may decrease the excretion rate of Tobramycin which could result in a higher serum level.Investigational
SeratrodastSeratrodast may decrease the excretion rate of Tobramycin which could result in a higher serum level.Approved
SerrapeptaseSerrapeptase may decrease the excretion rate of Tobramycin which could result in a higher serum level.Investigational
SRT501SRT501 may decrease the excretion rate of Tobramycin which could result in a higher serum level.Investigational
SuccinylcholineTobramycin may increase the respiratory depressant activities of Succinylcholine.Approved
SulbactamThe serum concentration of Tobramycin can be decreased when it is combined with Sulbactam.Approved
SulbenicillinThe serum concentration of Tobramycin can be decreased when it is combined with Sulbenicillin.Experimental
SulfasalazineSulfasalazine may decrease the excretion rate of Tobramycin which could result in a higher serum level.Approved
SulindacSulindac may decrease the excretion rate of Tobramycin which could result in a higher serum level.Approved
SultamicillinThe serum concentration of Tobramycin can be decreased when it is combined with Sultamicillin.Investigational
SuprofenSuprofen may decrease the excretion rate of Tobramycin which could result in a higher serum level.Approved, Withdrawn
SuxibuzoneSuxibuzone may decrease the excretion rate of Tobramycin which could result in a higher serum level.Experimental
TalampicillinThe serum concentration of Tobramycin can be decreased when it is combined with Talampicillin.Experimental
TarenflurbilTarenflurbil may decrease the excretion rate of Tobramycin which could result in a higher serum level.Investigational
TazobactamThe serum concentration of Tobramycin can be decreased when it is combined with Tazobactam.Approved
Technetium Tc-99m etidronateTobramycin may increase the hypocalcemic activities of Technetium Tc-99m etidronate.Approved
Technetium Tc-99m medronateTobramycin may increase the hypocalcemic activities of Technetium Tc-99m medronate.Approved
TenidapTenidap may decrease the excretion rate of Tobramycin which could result in a higher serum level.Experimental
Tenofovir disoproxilThe serum concentration of Tobramycin can be increased when it is combined with Tenofovir disoproxil.Approved, Investigational
TenoxicamTenoxicam may decrease the excretion rate of Tobramycin which could result in a higher serum level.Approved
TepoxalinTepoxalin may decrease the excretion rate of Tobramycin which could result in a higher serum level.Vet Approved
TeriflunomideTeriflunomide may decrease the excretion rate of Tobramycin which could result in a higher serum level.Approved
Tiaprofenic acidTiaprofenic acid may decrease the excretion rate of Tobramycin which could result in a higher serum level.Approved
TicarcillinThe serum concentration of Tobramycin can be decreased when it is combined with Ticarcillin.Approved, Investigational, Vet Approved
Tiludronic acidTobramycin may increase the hypocalcemic activities of Tiludronic acid.Approved, Investigational, Vet Approved
TinoridineTinoridine may decrease the excretion rate of Tobramycin which could result in a higher serum level.Investigational
Tolfenamic AcidTolfenamic Acid may decrease the excretion rate of Tobramycin which could result in a higher serum level.Approved
TolmetinTolmetin may decrease the excretion rate of Tobramycin which could result in a higher serum level.Approved
TorasemideThe risk or severity of adverse effects can be increased when Torasemide is combined with Tobramycin.Approved
TranilastTranilast may decrease the excretion rate of Tobramycin which could result in a higher serum level.Approved, Investigational
TribenosideTribenoside may decrease the excretion rate of Tobramycin which could result in a higher serum level.Experimental
TriptolideTriptolide may decrease the excretion rate of Tobramycin which could result in a higher serum level.Investigational
TubocurarineTobramycin may increase the respiratory depressant activities of Tubocurarine.Approved
ValdecoxibValdecoxib may decrease the excretion rate of Tobramycin which could result in a higher serum level.Investigational, Withdrawn
VancomycinVancomycin may increase the nephrotoxic activities of Tobramycin.Approved
VecuroniumTobramycin may increase the respiratory depressant activities of Vecuronium.Approved
ZaltoprofenZaltoprofen may decrease the excretion rate of Tobramycin which could result in a higher serum level.Approved, Investigational
ZileutonZileuton may decrease the excretion rate of Tobramycin which could result in a higher serum level.Approved, Investigational, Withdrawn
Zoledronic acidTobramycin may increase the hypocalcemic activities of Zoledronic acid.Approved
ZomepiracZomepirac may decrease the excretion rate of Tobramycin which could result in a higher serum level.Withdrawn
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
HMDB14822
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, 2Unknown StatusTreatmentCystic Fibrosis (CF)1
2CompletedPreventionCystic Fibrosis (CF) / Pulmonary Disease, Chronic Obstructive1
2CompletedTreatmentChronic Rhinosinusitis1
2CompletedTreatmentCystic Fibrosis (CF)1
2CompletedTreatmentCystic Fibrosis (CF) / Pseudomonas Aeruginosa1
2, 3RecruitingTreatmentNon-CF Bronchiectasis1
3Active Not RecruitingTreatmentCystic Fibrosis (CF)1
3CompletedTreatmentBacterial Infections / Cystic Fibrosis (CF)1
3CompletedTreatmentCataracts1
3CompletedTreatmentConjunctivitis, Bacterial1
3CompletedTreatmentBacterial blepharitis / Conjunctivitis / Corneal Inflammation1
3CompletedTreatmentCystic Fibrosis (CF)7
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
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
4Not Yet RecruitingPreventionSurgical Site Infections1
4RecruitingTreatmentCystic Fibrosis (CF)1
4RecruitingTreatmentVentilator-associated Bacterial Pneumonia1
4Unknown StatusTreatmentBronchiectasis1
4Unknown StatusTreatmentCystic Fibrosis (CF)1
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 / Cyanide Poisoning / 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) / Hospital-acquired bacterial pneumonia / Hypercholesterolaemia / 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 / 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 / Thrombosis / Trachoma / Treatment-resistant Schizophrenia / Tularemia / Typhus Fever / Uncomplicated Skin and Skin Structure Infections / Uncomplicated Urinary Tract Infections / Urinary Tract Infections (UTIs) / Vomiting / Withdrawal1
Not AvailableRecruitingNot AvailablePseudomonas Aeruginosa in Cystic Fibrosis1
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
Dosage forms
FormRouteStrength
SolutionRespiratory (inhalation)300 mg/4mL
SolutionRespiratory (inhalation)300 mg/5mL
LiquidIntramuscular; Intravenous1.2 g
LiquidIntravenous10 mg
LiquidIntramuscular; Intravenous60 mg
LiquidIntramuscular; Intravenous80 mg
SolutionOphthalmic0.3 %
SolutionRespiratory (inhalation)60 mg
SolutionOral300 mg/5mL
SolutionRespiratory (inhalation)300 mg
CapsuleOral; Respiratory (inhalation)28 mg/1
CapsuleRespiratory (inhalation)28 mg
OintmentOphthalmic
InjectionIntramuscular; Intravenous40 mg/mL
InjectionIntravenous1200 mg/30mL
Injection, powder, for solutionIntravenous1200 mg/30mL
Injection, powder, lyophilized, for solutionIntravenous1.2 g/30mL
Injection, solutionIntramuscular; Intravenous10 mg/mL
Injection, solutionIntramuscular; Intravenous40 mg/mL
Injection, solutionIntravenous40 mg/mL
SolutionOphthalmic3 mg/mL
SolutionOral3 mg/mL
Solution / dropsOphthalmic3 mg/mL
SuspensionOphthalmic
Suspension / dropsOphthalmic
Powder, for solutionIntravenous1.2 g
Injection, solutionIntravenous.8 mg/mL
SolutionIntramuscular; Intravenous10 mg
SolutionIntramuscular; Intravenous40 mg
LiquidIntramuscular; Intravenous10 mg
LiquidIntramuscular; Intravenous40 mg
LiquidOphthalmic3 mg
OintmentOphthalmic0.3 %
OintmentOphthalmic3 mg/g
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)
US5508269No1994-10-192014-10-19Us
US5149694No1992-09-222009-09-22Us
CA2414737No2009-01-062021-06-26Canada
US7795316No2008-08-032028-08-03Us
US8101582No2007-12-192027-12-19Us
US8450287No2007-12-192027-12-19Us
US7368102No2002-12-192022-12-19Us
US8715623No2002-12-192022-12-19Us
US7559325No2005-10-272025-10-27Us
US7442388No2000-05-102020-05-10Us
US7097827No1996-04-162016-04-16Us
US8349294No2000-05-102020-05-10Us
US8069851No2004-09-242024-09-24Us
US7516741No2004-01-112024-01-11Us
US7939502No2002-06-142022-06-14Us
US6987094No2002-09-222022-09-22Us
US7696178No2003-03-172023-03-17Us

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 December 10, 2017 17:18