Identification

Name
Gentamicin
Accession Number
DB00798  (APRD00214)
Type
Small Molecule
Groups
Approved, Vet Approved
Description

A complex of three different closely related aminoglycoside sulfates, Gentamicins C1, C2, and C1a, obtained from Micromonospora purpurea and related species. They are broad-spectrum antibiotics, but may cause ear and kidney damage. They act to inhibit protein synthesis (genetic translation).

Structure
Thumb
Synonyms
Not Available
Product Ingredients
IngredientUNIICASInChI Key
Gentamicin sulfate8X7386QRLV1405-41-0Not applicable
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Alcomicin Oph Sol 3mg/mlLiquid3 mgOphthalmicAlcon, Inc.1983-12-312009-04-24Canada
Cidomycin Inj 10mg/mlLiquid10 mgIntramuscular; IntravenousHoechst Roussel Canada Inc.1995-12-312000-07-28Canada
Cidomycin Inj 40mg/mlLiquid40 mgIntramuscular; IntravenousHoechst Roussel Canada Inc.1995-12-311999-08-20Canada
Cidomycin Inj 40mg/mlLiquid40 mgIntramuscular; IntravenousRoussel Canada Inc.1979-12-311997-08-05Canada
Cidomycin Inj Pediatric 10mgLiquid10 mgIntramuscular; IntravenousRoussel Canada Inc.1972-12-311997-08-05Canada
Garamycin Cream 0.1%Cream.1 %TopicalSchering Plough1966-12-312007-08-03Canada
Garamycin Inj 10mg/ml PediatricSolution10 mgIntramuscular; IntravenousSchering Plough1970-12-312004-07-21Canada
Garamycin Inj 40mg/mlSolution40 mgIntramuscular; IntravenousSchering Plough1966-12-312004-07-21Canada
Garamycin Ont 0.1%Ointment1 mgTopicalSchering Plough1966-12-312007-08-03Canada
Garamycin Ophthalmic Drops 0.3%Solution / drops3 mgOphthalmicMerck Ltd.1981-12-312014-09-02Canada
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
GaramycinOintment3 mg/gOphthalmicFera Pharmaceuticals2010-10-082016-11-18Us
GaramycinSolution / drops3 mg/mLOphthalmicFera Pharmaceuticals2011-05-152016-11-16Us
Garamycin Gentamicin SulfateSolution3 mg/mLOphthalmicPaddock Laboratories, Inc.2014-06-052017-01-18Us
GentakOintment3 mg/gOphthalmicAkorn2013-03-11Not applicableUs
GentakOintment3 mg/gOphthalmicA S Medication Solutions2006-05-082017-06-20Us
GentakOintment3 mg/gOphthalmicRemedy Repack2017-07-24Not applicableUs
GentakOintment3 mg/gOphthalmicLake Erie Medical &Surgical Supply Dba Quality Care Products Llc2012-03-27Not applicableUs
GentakOintment3 mg/gOphthalmicA S Medication Solutions2006-05-082017-06-20Us
GentakOintment3 mg/gOphthalmicAkorn2006-05-08Not applicableUs
GentakOintment3 mg/gOphthalmicRemedy Repack2013-06-242017-04-14Us
International/Other Brands
Alcomicin / Bristagen / G-Mycin / Genoptic (Allergan) / Gentacidin / Gentafair / Gentamar / Jenamicin / Ocu-Mycin / Spectro-Genta / U-gencin (U-Liang)
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
Betamycin Ophthalmic/otic SolutionGentamicin (3 mg) + Betamethasone (1 mg)SolutionAuricular (otic); OphthalmicSterimax IncNot applicableNot applicableCanada
Diprogen CreamGentamicin (0.1 %) + Betamethasone (0.05 %)CreamTopicalMerck Ltd.1980-12-312017-03-13Canada
Diprogen OintmentGentamicin (0.1 %) + Betamethasone (0.05 %)OintmentTopicalMerck Ltd.1980-12-312017-03-13Canada
Dom-gentamicin-betamethasoneGentamicin (3 mg) + Betamethasone (1 mg)LiquidAuricular (otic); OphthalmicDominion PharmacalNot applicableNot applicableCanada
Garasone Ophthalmic and Otic SolutionGentamicin (3 mg) + Betamethasone (1 mg)SolutionAuricular (otic); OphthalmicMerck Ltd.1987-12-312014-04-01Canada
Garasone Ophthalmic OintmentGentamicin (3 mg) + Betamethasone (1 mg)OintmentOphthalmicMerck Ltd.1983-12-312013-07-15Canada
Gentamicin Sulfate In 0.9% Sodium Chloride InjectionGentamicin (0.8 mg) + Sodium Chloride (9 mg)SolutionIntravenousHospira, Inc.1991-12-31Not applicableCanada
Gentamicin Sulfate In Nacl 0.9% InjGentamicin (1.2 mg) + Sodium Chloride (9 mg)SolutionIntravenousHospira, Inc.1991-12-312011-08-05Canada
Gentamicin Sulfate In Nacl 0.9% InjGentamicin (1 mg) + Sodium Chloride (9 mg)SolutionIntravenousHospira, Inc.1994-12-312011-08-05Canada
Gentamicin Sulfate In Nacl O.9% InjGentamicin (0.8 mg) + Sodium Chloride (9 mg)SolutionIntravenousHospira, Inc.1991-12-312014-08-01Canada
Categories
UNII
T6Z9V48IKG
CAS number
1403-66-3
Weight
Average: 477.5954
Monoisotopic: 477.316248755
Chemical Formula
C21H43N5O7
InChI Key
CEAZRRDELHUEMR-UHFFFAOYSA-N
InChI
InChI=1S/C21H43N5O7/c1-9(25-3)13-6-5-10(22)19(31-13)32-16-11(23)7-12(24)17(14(16)27)33-20-15(28)18(26-4)21(2,29)8-30-20/h9-20,25-29H,5-8,22-24H2,1-4H3
IUPAC Name
2-{[4,6-diamino-3-({3-amino-6-[1-(methylamino)ethyl]oxan-2-yl}oxy)-2-hydroxycyclohexyl]oxy}-5-methyl-4-(methylamino)oxane-3,5-diol
SMILES
CNC(C)C1CCC(N)C(OC2C(N)CC(N)C(OC3OCC(C)(O)C(NC)C3O)C2O)O1

Pharmacology

Indication

For treatment of serious infections caused by susceptible strains of the following microorganisms: P. aeruginosa, Proteus species (indole-positive and indole-negative), E. coli, Klebsiella-Enterobactor-Serratia species, Citrobacter species and Staphylococcus species (coagulase-positive and coagulase-negative).

Structured Indications
Pharmacodynamics

Gentamicin is a broad spectrum aminoglycoside antibiotic. Aminoglycosides work by binding to the bacterial 30S ribosomal subunit, causing misreading of t-RNA, leaving the bacterium unable to synthesize proteins vital to its growth. Aminoglycosides are useful primarily in infections involving aerobic, Gram-negative bacteria, such as Pseudomonas, Acinetobacter, and Enterobacter. In addition, some mycobacteria, including the bacteria that cause tuberculosis, are susceptible to aminoglycosides. Infections caused by Gram-positive bacteria can also be treated with aminoglycosides, but other types of antibiotics are more potent and less damaging to the host. In the past the aminoglycosides have been used in conjunction with penicillin-related antibiotics in streptococcal infections for their synergistic effects, particularly in endocarditis. Aminoglycosides are mostly ineffective against anaerobic bacteria, fungi and viruses.

Mechanism of action

Aminoglycosides like gentamicin "irreversibly" bind to specific 30S-subunit proteins and 16S rRNA. Specifically gentamicin binds to four nucleotides of 16S rRNA and a single amino acid of protein S12. This interferes with decoding site in the vicinity of nucleotide 1400 in 16S rRNA of 30S subunit. This region interacts with the wobble base in the anticodon of tRNA. This leads to interference with the initiation complex, misreading of mRNA so incorrect amino acids are inserted into the polypeptide leading to nonfunctional or toxic peptides and the breakup of polysomes into nonfunctional monosomes.

TargetActionsOrganism
A30S ribosomal protein S12
adduct
Escherichia coli (strain K12)
A16S rRNA
adduct
Enteric bacteria and other eubacteria
NLow-density lipoprotein receptor-related protein 2
other/unknown
Human
UNH(3)-dependent NAD(+) synthetaseNot AvailableBacillus subtilis (strain 168)
UDihydrofolate reductaseNot AvailableHuman
Absorption

Injections lead to peak serum concentrations in 30-60 minutes. Topical gentamicin is readily absorbed from large burned, denuded, or granulating areas but not through intact skin. Absorption of gentamicin is faster and greater with the cream compared to the ointment. Gentamicin is absorbed in small quantities following topical application to the eye. Gentamicin is also absorbed in small amounts following topical application to the ear (especially if the eardrum is perforated or if tissue damage is present). Gentamicin is very poorly absorbed orally.

Volume of distribution
Not Available
Protein binding

Low (between 0 and 30%)

Metabolism
Not Available
Route of elimination
Not Available
Half life

3-3½ hours in infants one week to six months of age; this increases to 5½ hours in full-term and large premature infants less than one week old.

Clearance
Not Available
Toxicity

Mild and reversible nephrotoxicity may be observed in 5 - 25% of patients. Gentamicin accumulates in proximal renal tubular cells and causes cell damage. Tubular cell regeneration occurs despite continued drug exposure. Toxicity usually occurs several days following initiation of therapy. May cause irreversible ototoxicity. Otoxocity appears to be correlated to cumulative lifetime exposure. Drug accumulation in the endolymph and perilymph of the inner ear causes irreversible damage to hair cells of the cochlea or summit of ampullar cristae in the vestibular complex. High frequency hearing is lost first with progression leading to loss of low frequency hearing. Further toxicity may lead to retrograde degeneration of the 8th cranial (vestibulocochlear) nerve. Vestibular toxicity may cause vertigo, nausea, vomiting, dizziness and loss of balance. Mouse, intravenous LD50: 52 mg/kg; rat, intravenous LD50: 96 mg/kg.

Affected organisms
  • Enteric bacteria and other eubacteria
  • Pseudomonas aeruginosa
  • Yersinia pestis
  • Francisella tularensis
  • Serratia marcescens
  • Proteus vulgaris
Pathways
PathwayCategory
Gentamicin Action PathwayDrug action
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteractionDrug group
AceclofenacAceclofenac may decrease the excretion rate of Gentamicin which could result in a higher serum level.Approved, Investigational
AcemetacinAcemetacin may decrease the excretion rate of Gentamicin which could result in a higher serum level.Approved, Experimental, Investigational
AcetyldigitoxinThe serum concentration of Acetyldigitoxin can be decreased when it is combined with Gentamicin.Approved
AcetyldigoxinThe serum concentration of Acetyldigoxin can be decreased when it is combined with Gentamicin.Experimental
Acetylsalicylic acidAcetylsalicylic acid may decrease the excretion rate of Gentamicin which could result in a higher serum level.Approved, Vet Approved
AdapaleneAdapalene may decrease the excretion rate of Gentamicin which could result in a higher serum level.Approved
Agalsidase betaThe therapeutic efficacy of Agalsidase beta can be decreased when used in combination with Gentamicin.Approved, Investigational
AlclofenacAlclofenac may decrease the excretion rate of Gentamicin which could result in a higher serum level.Approved, Withdrawn
AlcuroniumGentamicin may increase the respiratory depressant activities of Alcuronium.Experimental
Alendronic acidGentamicin may increase the hypocalcemic activities of Alendronic acid.Approved
AlminoprofenAlminoprofen may decrease the excretion rate of Gentamicin which could result in a higher serum level.Experimental
AmdinocillinThe serum concentration of Gentamicin can be decreased when it is combined with Amdinocillin.Investigational, Withdrawn
AmoxicillinThe serum concentration of Gentamicin can be decreased when it is combined with Amoxicillin.Approved, Vet Approved
Amphotericin BAmphotericin B may increase the nephrotoxic activities of Gentamicin.Approved, Investigational
AmpicillinThe serum concentration of Gentamicin can be decreased when it is combined with Ampicillin.Approved, Vet Approved
AndrographolideAndrographolide may decrease the excretion rate of Gentamicin which could result in a higher serum level.Investigational
AnisodamineAnisodamine may decrease the excretion rate of Gentamicin which could result in a higher serum level.Investigational
AntipyrineAntipyrine may decrease the excretion rate of Gentamicin which could result in a higher serum level.Approved
ApocyninApocynin may decrease the excretion rate of Gentamicin which could result in a higher serum level.Investigational
ApremilastApremilast may decrease the excretion rate of Gentamicin which could result in a higher serum level.Approved, Investigational
AspoxicillinThe serum concentration of Gentamicin can be decreased when it is combined with Aspoxicillin.Experimental
AtracuriumGentamicin may increase the respiratory depressant activities of Atracurium.Experimental, Investigational
Atracurium besylateGentamicin may increase the respiratory depressant activities of Atracurium besylate.Approved
AzapropazoneAzapropazone may decrease the excretion rate of Gentamicin which could result in a higher serum level.Withdrawn
AzelastineAzelastine may decrease the excretion rate of Gentamicin which could result in a higher serum level.Approved
AzidocillinThe serum concentration of Gentamicin can be decreased when it is combined with Azidocillin.Approved
AzlocillinThe serum concentration of Gentamicin can be decreased when it is combined with Azlocillin.Approved
BacampicillinThe serum concentration of Gentamicin can be decreased when it is combined with Bacampicillin.Approved, Investigational
BalsalazideBalsalazide may decrease the excretion rate of Gentamicin 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 Gentamicin.Investigational
BendazacBendazac may decrease the excretion rate of Gentamicin which could result in a higher serum level.Experimental
BenorilateBenorilate may decrease the excretion rate of Gentamicin which could result in a higher serum level.Experimental
BenoxaprofenBenoxaprofen may decrease the excretion rate of Gentamicin which could result in a higher serum level.Withdrawn
Benzathine benzylpenicillinThe serum concentration of Gentamicin can be decreased when it is combined with Benzathine benzylpenicillin.Approved, Vet Approved
BenzydamineBenzydamine may decrease the excretion rate of Gentamicin which could result in a higher serum level.Approved
BenzylpenicillinThe serum concentration of Gentamicin can be decreased when it is combined with Benzylpenicillin.Approved, Vet Approved
Benzylpenicilloyl PolylysineThe serum concentration of Gentamicin can be decreased when it is combined with Benzylpenicilloyl Polylysine.Approved
BevoniumBevonium may decrease the excretion rate of Gentamicin which could result in a higher serum level.Experimental
Botulinum Toxin Type AGentamicin may increase the neuromuscular blocking activities of Botulinum Toxin Type A.Approved, Investigational
Botulinum Toxin Type BGentamicin may increase the neuromuscular blocking activities of Botulinum Toxin Type B.Approved
BromfenacBromfenac may decrease the excretion rate of Gentamicin which could result in a higher serum level.Approved
BucillamineBucillamine may decrease the excretion rate of Gentamicin which could result in a higher serum level.Investigational
BufexamacBufexamac may decrease the excretion rate of Gentamicin which could result in a higher serum level.Experimental
BumadizoneBumadizone may decrease the excretion rate of Gentamicin which could result in a higher serum level.Experimental
BumetanideThe risk or severity of adverse effects can be increased when Bumetanide is combined with Gentamicin.Approved
CapreomycinCapreomycin may increase the neuromuscular blocking activities of Gentamicin.Approved
CarbenicillinThe serum concentration of Gentamicin can be decreased when it is combined with Carbenicillin.Approved, Investigational
Carbenicillin indanylThe serum concentration of Gentamicin can be decreased when it is combined with Carbenicillin indanyl.Approved, Investigational
CarboplatinGentamicin may increase the ototoxic activities of Carboplatin.Approved
CarfecillinThe serum concentration of Gentamicin can be decreased when it is combined with Carfecillin.Experimental
CarprofenCarprofen may decrease the excretion rate of Gentamicin which could result in a higher serum level.Approved, Vet Approved, Withdrawn
CastanospermineCastanospermine may decrease the excretion rate of Gentamicin which could result in a higher serum level.Experimental
CelecoxibCelecoxib may decrease the excretion rate of Gentamicin which could result in a higher serum level.Approved, Investigational
ChloroquineChloroquine may decrease the excretion rate of Gentamicin which could result in a higher serum level.Approved, Vet Approved
Choline magnesium trisalicylateCholine magnesium trisalicylate may decrease the excretion rate of Gentamicin which could result in a higher serum level.Approved
CisatracuriumGentamicin may increase the respiratory depressant activities of Cisatracurium.Approved, Experimental
Cisatracurium besylateGentamicin may increase the respiratory depressant activities of Cisatracurium besylate.Approved
CisplatinCisplatin may increase the nephrotoxic activities of Gentamicin.Approved
Clodronic AcidGentamicin may increase the hypocalcemic activities of Clodronic Acid.Approved, Investigational, Vet Approved
ClonixinClonixin may decrease the excretion rate of Gentamicin which could result in a higher serum level.Approved
CloxacillinThe serum concentration of Gentamicin can be decreased when it is combined with Cloxacillin.Approved, Vet Approved
ColistimethateGentamicin may increase the nephrotoxic activities of Colistimethate.Approved, Vet Approved
CurcuminCurcumin may decrease the excretion rate of Gentamicin which could result in a higher serum level.Investigational
CyclacillinThe serum concentration of Gentamicin can be decreased when it is combined with Cyclacillin.Approved
CyclosporineGentamicin may increase the nephrotoxic activities of Cyclosporine.Approved, Investigational, Vet Approved
CymarinThe serum concentration of Cymarin can be decreased when it is combined with Gentamicin.Experimental
D-LimoneneD-Limonene may decrease the excretion rate of Gentamicin which could result in a higher serum level.Investigational
DecamethoniumGentamicin may increase the respiratory depressant activities of Decamethonium.Approved
DeslanosideThe serum concentration of Deslanoside can be decreased when it is combined with Gentamicin.Approved
DiclofenacDiclofenac may decrease the excretion rate of Gentamicin which could result in a higher serum level.Approved, Vet Approved
DicloxacillinThe serum concentration of Gentamicin can be decreased when it is combined with Dicloxacillin.Approved, Vet Approved
DifenpiramideDifenpiramide may decrease the excretion rate of Gentamicin which could result in a higher serum level.Experimental
DiflunisalDiflunisal may decrease the excretion rate of Gentamicin which could result in a higher serum level.Approved
DigitoxinThe serum concentration of Digitoxin can be decreased when it is combined with Gentamicin.Approved, Investigational
DigoxinThe serum concentration of Digoxin can be decreased when it is combined with Gentamicin.Approved
Digoxin Immune Fab (Ovine)The serum concentration of Digoxin Immune Fab (Ovine) can be decreased when it is combined with Gentamicin.Approved
Domoic AcidGentamicin may increase the respiratory depressant activities of Domoic Acid.Experimental
Doxacurium chlorideGentamicin may increase the respiratory depressant activities of Doxacurium chloride.Approved
DroxicamDroxicam may decrease the excretion rate of Gentamicin which could result in a higher serum level.Approved
DuvelisibDuvelisib may decrease the excretion rate of Gentamicin which could result in a higher serum level.Investigational
E-6201E-6201 may decrease the excretion rate of Gentamicin which could result in a higher serum level.Investigational
EpicillinThe serum concentration of Gentamicin can be decreased when it is combined with Epicillin.Experimental
EpirizoleEpirizole may decrease the excretion rate of Gentamicin 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 Gentamicin.Approved
EtanerceptEtanercept may decrease the excretion rate of Gentamicin which could result in a higher serum level.Approved, Investigational
EthenzamideEthenzamide may decrease the excretion rate of Gentamicin which could result in a higher serum level.Experimental
Etidronic acidGentamicin may increase the hypocalcemic activities of Etidronic acid.Approved
EtodolacEtodolac may decrease the excretion rate of Gentamicin which could result in a higher serum level.Approved, Investigational, Vet Approved
EtofenamateEtofenamate may decrease the excretion rate of Gentamicin which could result in a higher serum level.Approved, Investigational
EtoricoxibEtoricoxib may decrease the excretion rate of Gentamicin which could result in a higher serum level.Approved, Investigational
Evening primrose oilEvening primrose oil may decrease the excretion rate of Gentamicin which could result in a higher serum level.Approved, Investigational
exisulindexisulind may decrease the excretion rate of Gentamicin which could result in a higher serum level.Investigational
FelbinacFelbinac may decrease the excretion rate of Gentamicin which could result in a higher serum level.Experimental
FenbufenFenbufen may decrease the excretion rate of Gentamicin which could result in a higher serum level.Approved
FenoprofenFenoprofen may decrease the excretion rate of Gentamicin which could result in a higher serum level.Approved
FentiazacFentiazac may decrease the excretion rate of Gentamicin which could result in a higher serum level.Experimental
FeprazoneFeprazone may decrease the excretion rate of Gentamicin which could result in a higher serum level.Experimental
Ferulic acidFerulic acid may decrease the excretion rate of Gentamicin which could result in a higher serum level.Experimental
FloctafenineFloctafenine may decrease the excretion rate of Gentamicin which could result in a higher serum level.Approved, Withdrawn
FlucloxacillinThe serum concentration of Gentamicin can be decreased when it is combined with Flucloxacillin.Approved, Investigational
FlunixinFlunixin may decrease the excretion rate of Gentamicin which could result in a higher serum level.Vet Approved
FlunoxaprofenFlunoxaprofen may decrease the excretion rate of Gentamicin which could result in a higher serum level.Experimental
FlurbiprofenFlurbiprofen may decrease the excretion rate of Gentamicin which could result in a higher serum level.Approved, Investigational
FoscarnetFoscarnet may increase the nephrotoxic activities of Gentamicin.Approved
FurosemideThe risk or severity of adverse effects can be increased when Furosemide is combined with Gentamicin.Approved, Vet Approved
GallamineGentamicin may increase the respiratory depressant activities of Gallamine.Experimental
Gallamine TriethiodideGentamicin may increase the respiratory depressant activities of Gallamine Triethiodide.Approved
GitoformateThe serum concentration of Gitoformate can be decreased when it is combined with Gentamicin.Experimental
GuacetisalGuacetisal may decrease the excretion rate of Gentamicin which could result in a higher serum level.Experimental
HigenamineHigenamine may decrease the excretion rate of Gentamicin which could result in a higher serum level.Investigational
IbandronateGentamicin may increase the hypocalcemic activities of Ibandronate.Approved, Investigational
IbuprofenIbuprofen may decrease the excretion rate of Gentamicin which could result in a higher serum level.Approved
IbuproxamIbuproxam may decrease the excretion rate of Gentamicin which could result in a higher serum level.Withdrawn
IcatibantIcatibant may decrease the excretion rate of Gentamicin which could result in a higher serum level.Approved
Imidazole salicylateImidazole salicylate may decrease the excretion rate of Gentamicin which could result in a higher serum level.Experimental
IndobufenIndobufen may decrease the excretion rate of Gentamicin which could result in a higher serum level.Investigational
IndomethacinIndomethacin may decrease the excretion rate of Gentamicin which could result in a higher serum level.Approved, Investigational
IndoprofenIndoprofen may decrease the excretion rate of Gentamicin which could result in a higher serum level.Withdrawn
IsoxicamIsoxicam may decrease the excretion rate of Gentamicin which could result in a higher serum level.Withdrawn
KebuzoneKebuzone may decrease the excretion rate of Gentamicin which could result in a higher serum level.Experimental
KetoprofenKetoprofen may decrease the excretion rate of Gentamicin which could result in a higher serum level.Approved, Vet Approved
KetorolacKetorolac may decrease the excretion rate of Gentamicin which could result in a higher serum level.Approved
Lanatoside CThe serum concentration of Lanatoside C can be decreased when it is combined with Gentamicin.Experimental
LeflunomideLeflunomide may decrease the excretion rate of Gentamicin which could result in a higher serum level.Approved, Investigational
LisofyllineLisofylline may decrease the excretion rate of Gentamicin which could result in a higher serum level.Investigational
LonazolacLonazolac may decrease the excretion rate of Gentamicin which could result in a higher serum level.Experimental
LornoxicamLornoxicam may decrease the excretion rate of Gentamicin which could result in a higher serum level.Approved, Investigational
LoxoprofenLoxoprofen may decrease the excretion rate of Gentamicin which could result in a higher serum level.Approved, Investigational
LumiracoxibLumiracoxib may decrease the excretion rate of Gentamicin which could result in a higher serum level.Approved, Investigational
Magnesium salicylateMagnesium salicylate may decrease the excretion rate of Gentamicin which could result in a higher serum level.Approved
MannitolMannitol may increase the nephrotoxic activities of Gentamicin.Approved, Investigational
MasoprocolMasoprocol may decrease the excretion rate of Gentamicin which could result in a higher serum level.Approved, Investigational
MecamylamineGentamicin may increase the neuromuscular blocking activities of Mecamylamine.Approved
Meclofenamic acidMeclofenamic acid may decrease the excretion rate of Gentamicin which could result in a higher serum level.Approved, Vet Approved
Mefenamic acidMefenamic acid may decrease the excretion rate of Gentamicin which could result in a higher serum level.Approved
MeloxicamMeloxicam may decrease the excretion rate of Gentamicin which could result in a higher serum level.Approved, Vet Approved
MesalazineMesalazine may decrease the excretion rate of Gentamicin which could result in a higher serum level.Approved
MetamizoleMetamizole may decrease the excretion rate of Gentamicin which could result in a higher serum level.Investigational, Withdrawn
MetampicillinThe serum concentration of Gentamicin can be decreased when it is combined with Metampicillin.Experimental
MeticillinThe serum concentration of Gentamicin can be decreased when it is combined with Meticillin.Approved, Investigational
MetildigoxinThe serum concentration of Metildigoxin can be decreased when it is combined with Gentamicin.Experimental
MetocurineGentamicin may increase the respiratory depressant activities of Metocurine.Approved
Metocurine IodideGentamicin may increase the respiratory depressant activities of Metocurine Iodide.Withdrawn
MezlocillinThe serum concentration of Gentamicin can be decreased when it is combined with Mezlocillin.Approved, Investigational
MivacuriumGentamicin may increase the respiratory depressant activities of Mivacurium.Approved
MizoribineMizoribine may decrease the excretion rate of Gentamicin which could result in a higher serum level.Investigational
MofebutazoneMofebutazone may decrease the excretion rate of Gentamicin which could result in a higher serum level.Experimental
Mycophenolate mofetilMycophenolate mofetil may decrease the excretion rate of Gentamicin which could result in a higher serum level.Approved, Investigational
Mycophenolic acidMycophenolic acid may decrease the excretion rate of Gentamicin which could result in a higher serum level.Approved
NabumetoneNabumetone may decrease the excretion rate of Gentamicin which could result in a higher serum level.Approved
NafamostatNafamostat may decrease the excretion rate of Gentamicin which could result in a higher serum level.Approved, Investigational
NafcillinThe serum concentration of Gentamicin can be decreased when it is combined with Nafcillin.Approved
NaftifineNaftifine may decrease the excretion rate of Gentamicin which could result in a higher serum level.Approved
NaproxenNaproxen may decrease the excretion rate of Gentamicin which could result in a higher serum level.Approved, Vet Approved
NeosaxitoxinGentamicin may increase the respiratory depressant activities of Neosaxitoxin.Investigational
NepafenacNepafenac may decrease the excretion rate of Gentamicin which could result in a higher serum level.Approved
NifenazoneNifenazone may decrease the excretion rate of Gentamicin which could result in a higher serum level.Experimental
Niflumic AcidNiflumic Acid may decrease the excretion rate of Gentamicin which could result in a higher serum level.Approved
NimesulideNimesulide may decrease the excretion rate of Gentamicin which could result in a higher serum level.Approved, Investigational, Withdrawn
NitroaspirinNitroaspirin may decrease the excretion rate of Gentamicin which could result in a higher serum level.Investigational
OleandrinThe serum concentration of Oleandrin can be decreased when it is combined with Gentamicin.Experimental, Investigational
OlopatadineOlopatadine may decrease the excretion rate of Gentamicin which could result in a higher serum level.Approved
OlsalazineOlsalazine may decrease the excretion rate of Gentamicin which could result in a higher serum level.Approved
OrgoteinOrgotein may decrease the excretion rate of Gentamicin which could result in a higher serum level.Vet Approved
OuabainThe serum concentration of Ouabain can be decreased when it is combined with Gentamicin.Approved
OxacillinThe serum concentration of Gentamicin can be decreased when it is combined with Oxacillin.Approved
OxaprozinOxaprozin may decrease the excretion rate of Gentamicin which could result in a higher serum level.Approved
OxyphenbutazoneOxyphenbutazone may decrease the excretion rate of Gentamicin which could result in a higher serum level.Approved, Withdrawn
PamidronateGentamicin may increase the hypocalcemic activities of Pamidronate.Approved
PancuroniumGentamicin may increase the respiratory depressant activities of Pancuronium.Approved
ParecoxibParecoxib may decrease the excretion rate of Gentamicin which could result in a higher serum level.Approved
ParthenolideParthenolide may decrease the excretion rate of Gentamicin which could result in a higher serum level.Investigational
PenamecillinThe serum concentration of Gentamicin can be decreased when it is combined with Penamecillin.Experimental
PenimepicyclineThe serum concentration of Gentamicin can be decreased when it is combined with Penimepicycline.Experimental
PeruvosideThe serum concentration of Peruvoside can be decreased when it is combined with Gentamicin.Experimental
PhenoxymethylpenicillinThe serum concentration of Gentamicin can be decreased when it is combined with Phenoxymethylpenicillin.Approved, Vet Approved
PhenylbutazonePhenylbutazone may decrease the excretion rate of Gentamicin 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 Gentamicin.Approved
PimecrolimusPimecrolimus may decrease the excretion rate of Gentamicin which could result in a higher serum level.Approved, Investigational
PipecuroniumGentamicin may increase the respiratory depressant activities of Pipecuronium.Approved
PiperacillinThe serum concentration of Gentamicin 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 Gentamicin.Experimental
PirfenidonePirfenidone may decrease the excretion rate of Gentamicin which could result in a higher serum level.Approved, Investigational
PiroxicamPiroxicam may decrease the excretion rate of Gentamicin which could result in a higher serum level.Approved, Investigational
PirprofenPirprofen may decrease the excretion rate of Gentamicin which could result in a higher serum level.Experimental
PivampicillinThe serum concentration of Gentamicin can be decreased when it is combined with Pivampicillin.Approved
PivmecillinamThe serum concentration of Gentamicin can be decreased when it is combined with Pivmecillinam.Approved
PranoprofenPranoprofen may decrease the excretion rate of Gentamicin which could result in a higher serum level.Experimental, Investigational
Procaine benzylpenicillinThe serum concentration of Gentamicin can be decreased when it is combined with Procaine benzylpenicillin.Approved, Vet Approved
ProglumetacinProglumetacin may decrease the excretion rate of Gentamicin which could result in a higher serum level.Experimental
PropacetamolPropacetamol may decrease the excretion rate of Gentamicin which could result in a higher serum level.Approved, Investigational
PropicillinThe serum concentration of Gentamicin can be decreased when it is combined with Propicillin.Experimental
PropyphenazonePropyphenazone may decrease the excretion rate of Gentamicin which could result in a higher serum level.Experimental
ProquazoneProquazone may decrease the excretion rate of Gentamicin which could result in a higher serum level.Experimental
ProscillaridinThe serum concentration of Proscillaridin can be decreased when it is combined with Gentamicin.Experimental
PTC299PTC299 may decrease the excretion rate of Gentamicin which could result in a higher serum level.Investigational
PyrantelGentamicin may increase the respiratory depressant activities of Pyrantel.Approved, Vet Approved
RapacuroniumGentamicin may increase the respiratory depressant activities of Rapacuronium.Withdrawn
ResveratrolResveratrol may decrease the excretion rate of Gentamicin which could result in a higher serum level.Approved, Experimental, Investigational
RisedronateGentamicin may increase the hypocalcemic activities of Risedronate.Approved, Investigational
RocuroniumGentamicin may increase the respiratory depressant activities of Rocuronium.Approved
RofecoxibRofecoxib may decrease the excretion rate of Gentamicin which could result in a higher serum level.Investigational, Withdrawn
SalicylamideSalicylamide may decrease the excretion rate of Gentamicin which could result in a higher serum level.Approved
Salicylic acidSalicylic acid may decrease the excretion rate of Gentamicin which could result in a higher serum level.Approved, Vet Approved
SalsalateSalsalate may decrease the excretion rate of Gentamicin which could result in a higher serum level.Approved
SemapimodSemapimod may decrease the excretion rate of Gentamicin which could result in a higher serum level.Investigational
SeratrodastSeratrodast may decrease the excretion rate of Gentamicin which could result in a higher serum level.Approved
SerrapeptaseSerrapeptase may decrease the excretion rate of Gentamicin which could result in a higher serum level.Investigational
SRT501SRT501 may decrease the excretion rate of Gentamicin which could result in a higher serum level.Investigational
SuccinylcholineGentamicin may increase the respiratory depressant activities of Succinylcholine.Approved
SulbactamThe serum concentration of Gentamicin can be decreased when it is combined with Sulbactam.Approved
SulbenicillinThe serum concentration of Gentamicin can be decreased when it is combined with Sulbenicillin.Experimental
SulfasalazineSulfasalazine may decrease the excretion rate of Gentamicin which could result in a higher serum level.Approved
SulindacSulindac may decrease the excretion rate of Gentamicin which could result in a higher serum level.Approved
SultamicillinThe serum concentration of Gentamicin can be decreased when it is combined with Sultamicillin.Investigational
SuprofenSuprofen may decrease the excretion rate of Gentamicin which could result in a higher serum level.Approved, Withdrawn
SuxibuzoneSuxibuzone may decrease the excretion rate of Gentamicin which could result in a higher serum level.Experimental
TalampicillinThe serum concentration of Gentamicin can be decreased when it is combined with Talampicillin.Experimental
TarenflurbilTarenflurbil may decrease the excretion rate of Gentamicin which could result in a higher serum level.Investigational
TazobactamThe serum concentration of Gentamicin can be decreased when it is combined with Tazobactam.Approved
Technetium Tc-99m etidronateGentamicin may increase the hypocalcemic activities of Technetium Tc-99m etidronate.Approved
Technetium Tc-99m medronateGentamicin may increase the hypocalcemic activities of Technetium Tc-99m medronate.Approved
TenidapTenidap may decrease the excretion rate of Gentamicin which could result in a higher serum level.Experimental
Tenofovir disoproxilThe serum concentration of Gentamicin can be increased when it is combined with Tenofovir disoproxil.Approved, Investigational
TenoxicamTenoxicam may decrease the excretion rate of Gentamicin which could result in a higher serum level.Approved
TepoxalinTepoxalin may decrease the excretion rate of Gentamicin which could result in a higher serum level.Vet Approved
TeriflunomideTeriflunomide may decrease the excretion rate of Gentamicin which could result in a higher serum level.Approved
Tiaprofenic acidTiaprofenic acid may decrease the excretion rate of Gentamicin which could result in a higher serum level.Approved
TicarcillinThe serum concentration of Gentamicin can be decreased when it is combined with Ticarcillin.Approved, Investigational, Vet Approved
Tiludronic acidGentamicin may increase the hypocalcemic activities of Tiludronic acid.Approved, Investigational, Vet Approved
TinoridineTinoridine may decrease the excretion rate of Gentamicin which could result in a higher serum level.Investigational
Tolfenamic AcidTolfenamic Acid may decrease the excretion rate of Gentamicin which could result in a higher serum level.Approved
TolmetinTolmetin may decrease the excretion rate of Gentamicin which could result in a higher serum level.Approved
TorasemideThe risk or severity of adverse effects can be increased when Torasemide is combined with Gentamicin.Approved
TranilastTranilast may decrease the excretion rate of Gentamicin which could result in a higher serum level.Approved, Investigational
TribenosideTribenoside may decrease the excretion rate of Gentamicin which could result in a higher serum level.Experimental
TriptolideTriptolide may decrease the excretion rate of Gentamicin which could result in a higher serum level.Investigational
TubocurarineGentamicin may increase the respiratory depressant activities of Tubocurarine.Approved
ValdecoxibValdecoxib may decrease the excretion rate of Gentamicin which could result in a higher serum level.Investigational, Withdrawn
VancomycinVancomycin may increase the nephrotoxic activities of Gentamicin.Approved
VecuroniumGentamicin may increase the respiratory depressant activities of Vecuronium.Approved
ZaltoprofenZaltoprofen may decrease the excretion rate of Gentamicin which could result in a higher serum level.Approved, Investigational
ZileutonZileuton may decrease the excretion rate of Gentamicin which could result in a higher serum level.Approved, Investigational, Withdrawn
Zoledronic acidGentamicin may increase the hypocalcemic activities of Zoledronic acid.Approved
ZomepiracZomepirac may decrease the excretion rate of Gentamicin which could result in a higher serum level.Withdrawn
Food Interactions
Not Available

References

Synthesis Reference

George H. Scherr, "Preparation of gentamicin sensitized particles for agglutination tests." U.S. Patent US4100268, issued August, 1975.

US4100268
General References
Not Available
External Links
Human Metabolome Database
HMDB14936
KEGG Compound
C00505
PubChem Compound
3467
PubChem Substance
46506523
ChemSpider
3348
ChEBI
17833
ChEMBL
CHEMBL329592
Therapeutic Targets Database
DAP000116
PharmGKB
PA449753
IUPHAR
2427
Guide to Pharmacology
GtP Drug Page
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
PDRhealth
PDRhealth Drug Page
Wikipedia
Gentamicin
ATC Codes
S02AA14 — GentamicinS03AA06 — GentamicinD06AX07 — GentamicinS01AA11 — GentamicinJ01GB03 — Gentamicin
AHFS Codes
  • 08:12.02 — Aminoglycosides
  • 52:04.04 — Antibacterials
  • 84:04.04 — Antibiotics
MSDS
Download (59.2 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
0CompletedBasic ScienceBMI >30 kg/m2 / Bone destruction / Diabetes Mellitus (DM) / Inflammatory Reaction1
0CompletedTreatmentBacterial Resistance / Respiratory Failure / Respiratory Tract Infections (RTI)1
0RecruitingTreatmentOsteomyelitis1
1CompletedTreatmentBecker's Muscular Dystrophy (BMD) / Duchenne's Muscular Dystrophy (DMD)1
1CompletedTreatmentVentilator-Associated Pneumonia (VAP)1
1RecruitingHealth Services ResearchBreast Implant Infection / Breast Reconstruction1
1, 2RecruitingTreatmentRecessive Dystrophic Epidermolysis Bullosa1
1, 2TerminatedTreatmentDiabetic Foot Ulcers (DFU)1
2CompletedTreatmentLeishmaniasis, Cutaneous1
2TerminatedTreatmentCystic Fibrosis (CF)1
2TerminatedTreatmentLeishmaniasis, Cutaneous2
2, 3Active Not RecruitingTreatmentChorioamnionitis1
2, 3CompletedPreventionChorioamnionitis / Neonatal Early Onset Sepsis / Neonatal Meningitis / Neonatal Pneumonia / Puerperal Endometritis1
2, 3CompletedTreatmentComplicated Intra Abdominal Infections1
2, 3CompletedTreatmentMenière's Disease1
2, 3CompletedTreatmentPlague1
2, 3SuspendedTreatmentFolliculitis1
3CompletedTreatmentDermatitis, Eczematous1
3CompletedTreatmentInfection NOS / Neonatal Sepsis / Sepsis1
3CompletedTreatmentLeishmaniasis, Cutaneous1
3CompletedTreatmentSepsis1
3Not Yet RecruitingTreatmentChronic Rhinosinusitis (Diagnosis)1
3RecruitingTreatmentCat scratch disease1
3Unknown StatusTreatmentBacterial Infections / Newborn Infants / Sepsis1
4Active Not RecruitingPreventionCalcium Nephrolithiasis / Urinary Tract Infections (UTIs)1
4Active Not RecruitingTreatmentInfection NOS1
4CompletedNot AvailablePerforated Appendicitis1
4CompletedNot AvailablePregnancy1
4CompletedPreventionInguinal Hernias1
4CompletedTreatmentBronchiectasis1
4CompletedTreatmentGonorrhoea1
4CompletedTreatmentInfant Bacterial Meningitis1
4RecruitingPreventionUrinary Tract Infections (UTIs)1
4RecruitingPreventionVestibular Schwannomas1
4RecruitingTreatmentAcute maxillary sinusitis caused by M. catarrhalis1
4RecruitingTreatmentAppendicitis1
4RecruitingTreatmentUrinary Tract Infections (UTIs)1
4TerminatedNot AvailableRenal Failure Chronic Requiring Hemodialysis1
4TerminatedTreatmentAtopic Dermatitis (AD) / Skin Diseases, Eczematous1
4TerminatedTreatmentInfective Endocarditis1
4Unknown StatusPreventionInfection NOS1
4Unknown StatusPreventionRate of Atypical Mycobacterial Infection / Rate of Exit Site Infection / Rate of Peritoneal Dialysis1
Not AvailableCompletedNot AvailableDrug Metabolism During Pregnancy1
Not AvailableCompletedNot AvailableEnd Stage Renal Disease (ESRD) / Infection NOS1
Not AvailableCompletedPreventionCholangitis1
Not AvailableCompletedSupportive CareVestibular Schwannomas1
Not AvailableCompletedTreatmentChorioamnionitis1
Not AvailableCompletedTreatmentSepsis1
Not AvailableEnrolling by InvitationTreatmentRecessive Dystrophic Epidermolysis Bullosa1
Not AvailableRecruitingNot AvailablePneumonia1
Not AvailableRecruitingOtherColic / Gastrointestinal Diseases1
Not AvailableRecruitingPreventionCalcium Nephrolithiasis / Sepsis / Urinary Tract Infections (UTIs)1
Not AvailableRecruitingTreatmentCancer, Breast1
Not AvailableUnknown StatusTreatmentPeritonitis1

Pharmacoeconomics

Manufacturers
  • Schering corp sub schering plough corp
  • Pharmafair inc
  • Alpharma us pharmaceuticals division
  • Bausch and lomb pharmaceuticals inc
  • E fougera div altana inc
  • Perrigo new york inc
  • Pharmaderm div altana inc
  • Taro pharmaceuticals usa inc
  • King pharmaceuticals inc
  • Bristol laboratories inc div bristol myers co
  • International medication systems ltd
  • Abbott laboratories pharmaceutical products div
  • App pharmaceuticals llc
  • Baxter healthcare corp anesthesia and critical care
  • Hospira inc
  • Kalapharm inc
  • Pharmaceutical specialist assoc
  • Solopak laboratories inc
  • Teva parenteral medicines inc
  • Watson laboratories inc
  • Wyeth ayerst laboratories
  • B braun medical inc
  • Baxter healthcare corp
  • Pharmacia and upjohn co
  • Novartis pharmaceuticals corp
  • Akorn inc
  • Altana inc
  • Allergan
  • Alcon universal ltd
  • Falcon pharmaceuticals ltd
  • Paco research corp
Packagers
Dosage forms
FormRouteStrength
LiquidIntramuscular; Intravenous40 mg
LiquidIntramuscular; Intravenous10 mg
OintmentTopical
LiquidAuricular (otic); Ophthalmic
OintmentOphthalmic3 mg/g
CreamTopical.1 %
SolutionOphthalmic3 mg/mL
OintmentTopical1 mg
Solution / dropsAuricular (otic)3 mg
SolutionAuricular (otic); Ophthalmic
OintmentOphthalmic
Solution / dropsOphthalmic5 mg
Solution / dropsAuricular (otic)5 mg
Solution / dropsOphthalmic3 mg
Injection, solutionIntramuscular; Intravenous10 mg/mL
Injection, solutionIntramuscular; Intravenous40 mg/mL
SolutionOphthalmic.3 %
SolutionOphthalmic0.3 %
SolutionIntramuscular; Intravenous10 mg
SolutionIntramuscular; Intravenous40 mg
CreamTopical1 mg/g
Injection, solution, concentrateIntramuscular; Intravenous40 mg/mL
Injection, solution, concentrateIntravenous10 mg/mL
OintmentTopical1 mg/g
Solution / dropsOphthalmic3 mg/mL
SolutionIntravenous
Injection, solutionIntravenous.8 mg/mL
Injection, solutionIntravenous.9 mg/mL
Injection, solutionIntravenous1 mg/mL
Injection, solutionIntravenous1.2 mg/mL
Injection, solutionIntravenous1.4 mg/mL
Injection, solutionIntravenous1.6 mg/mL
Injection, solutionIntravenous100 mg/50mL
Injection, solutionIntravenous100 mg/100mL
Injection, solutionIntravenous60 mg/50mL
Injection, solutionIntravenous80 mg/100mL
Injection, solutionIntravenous80 mg/50mL
SolutionIntravenous1 mg
SolutionIntravenous1.2 mg
SolutionIntravenous1.6 mg
OintmentOphthalmic3 mg
Solution / dropsOphthalmic; Topical0.3 %
LiquidOphthalmic; Topical3 mg
OintmentOphthalmic; Topical3 mg
OintmentOphthalmic5 mg
SolutionOphthalmic5 mg
CreamTopical1 mg
OintmentOphthalmic0.3 %
Suspension / dropsOphthalmic
LiquidOphthalmic3 mg
CreamTopical0.1 %
OintmentTopical.1 %
SolutionAuricular (otic)3 mg
ImplantParenteral4.5 mg
CreamTopical
Prices
Unit descriptionCostUnit
Gentak 0.3% Ointment 3.5 gm Tube19.99USD tube
Gentamicin Sulfate 0.1% Cream 15 gm Tube12.99USD tube
Gentamicin Sulfate 0.1% Ointment 15 gm Tube11.99USD tube
Gentamicin Sulfate 0.3% Solution 5ml Bottle11.99USD bottle
Gentamicin sulfate powder5.05USD g
Gentamicin Sulfate 10 mg/ml Solution 2ml Vial5.0USD vial
Gentamicin 40 mg/ml2.82USD ml
Gentamicin ped 10 mg/ml vial2.4USD ml
Gentak 3 mg/ml eye drops1.91USD ml
Gentamicin 3 mg/ml eye drops1.89USD ml
Gentamicin 10 mg/ml vial1.29USD ml
Garamycin 0.3 % Ointment1.2USD g
Sandoz Gentamicin Sulfate 0.3 % Ointment1.2USD g
Garamycin 0.3 % Solution0.75USD ml
Sandoz Gentamicin Sulfate 0.3 % Solution0.75USD ml
Gentamicin 40 mg/ml vial0.45USD ml
Ratio-Gentamicin Sulfate 0.1 % Cream0.43USD g
Ratio-Gentamicin Sulfate 0.1 % Ointment0.37USD g
Gentamicin 0.1% cream0.16USD g
Iso gentamicin 120 mg/100 ml0.09USD ml
Gentamicin 90 mg/ns 100 ml pb0.05USD ml
Isoton gentamicin 40 mg/100 ml0.05USD ml
Gentamicin 60 mg/ns 100 ml pb0.04USD ml
Gentamicin 100 mg/ns 100 ml0.03USD ml
Gentamicin 80 mg/ns 100 ml pb0.03USD ml
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)105 °CPhysProp
water solubility100 mg/mLNot Available
logP-3.1Not Available
Predicted Properties
PropertyValueSource
Water Solubility12.6 mg/mLALOGPS
logP-1.6ALOGPS
logP-3.1ChemAxon
logS-1.6ALOGPS
pKa (Strongest Acidic)12.55ChemAxon
pKa (Strongest Basic)10.18ChemAxon
Physiological Charge5ChemAxon
Hydrogen Acceptor Count12ChemAxon
Hydrogen Donor Count8ChemAxon
Polar Surface Area199.73 Å2ChemAxon
Rotatable Bond Count7ChemAxon
Refractivity118.02 m3·mol-1ChemAxon
Polarizability51.92 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption-0.944
Blood Brain Barrier-0.9826
Caco-2 permeable-0.6987
P-glycoprotein substrateSubstrate0.6882
P-glycoprotein inhibitor INon-inhibitor0.6808
P-glycoprotein inhibitor IINon-inhibitor0.9586
Renal organic cation transporterNon-inhibitor0.8738
CYP450 2C9 substrateNon-substrate0.8001
CYP450 2D6 substrateNon-substrate0.8314
CYP450 3A4 substrateSubstrate0.5917
CYP450 1A2 substrateNon-inhibitor0.9034
CYP450 2C9 inhibitorNon-inhibitor0.891
CYP450 2D6 inhibitorNon-inhibitor0.9331
CYP450 2C19 inhibitorNon-inhibitor0.9043
CYP450 3A4 inhibitorNon-inhibitor0.9517
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9294
Ames testNon AMES toxic0.7338
CarcinogenicityNon-carcinogens0.9696
BiodegradationNot ready biodegradable0.9588
Rat acute toxicity2.0383 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9954
hERG inhibition (predictor II)Non-inhibitor0.8784
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/MSsplash10-0i29-1319700000-e55d2931137c5abc8493
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-03di-0904000000-de986ac47725d8f3a72a
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0592-9602000000-c7fd77457525743faeba
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-014i-2911100000-93e47b752e7992b12263
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-014i-2958400000-7303bf3ebe16dd1c1d60
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0udi-2692000000-a8234ed8e0131019f62b

Taxonomy

Description
This compound belongs to the class of organic compounds known as aminocyclitol glycosides. These are organic compounds containing an amicocyclitol moiety glycosidically linked to a carbohydrate moiety. There are two major classes of aminoglycosides containing a 2-streptamine core. They are called 4,5- and 4,6-disubstituted 2-deoxystreptamines.
Kingdom
Organic compounds
Super Class
Organic oxygen compounds
Class
Organooxygen compounds
Sub Class
Carbohydrates and carbohydrate conjugates
Direct Parent
Aminocyclitol glycosides
Alternative Parents
2-deoxystreptamine aminoglycosides / O-glycosyl compounds / Aminocyclitols and derivatives / Cyclohexylamines / Cyclohexanols / Oxanes / Monosaccharides / Tertiary alcohols / 1,2-aminoalcohols / Oxacyclic compounds
show 5 more
Substituents
Amino cyclitol glycoside / 2-deoxystreptamine aminoglycoside / Glycosyl compound / O-glycosyl compound / Aminocyclitol or derivatives / Cyclohexanol / Cyclohexylamine / Cyclitol or derivatives / Monosaccharide / Oxane
show 18 more
Molecular Framework
Aliphatic heteromonocyclic compounds
External Descriptors
Not Available

Targets

Kind
Protein
Organism
Escherichia coli (strain K12)
Pharmacological action
Yes
Actions
Adduct
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. 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]
  2. Tamehiro N, Hosaka T, Xu J, Hu H, Otake N, Ochi K: Innovative approach for improvement of an antibiotic-overproducing industrial strain of Streptomyces albus. Appl Environ Microbiol. 2003 Nov;69(11):6412-7. [PubMed:14602594]
  3. Hu H, Ochi K: Novel approach for improving the productivity of antibiotic-producing strains by inducing combined resistant mutations. Appl Environ Microbiol. 2001 Apr;67(4):1885-92. [PubMed:11282646]
  4. Schroeder R, Waldsich C, Wank H: Modulation of RNA function by aminoglycoside antibiotics. EMBO J. 2000 Jan 4;19(1):1-9. [PubMed:10619838]
2. 16S rRNA
Kind
Nucleotide
Organism
Enteric bacteria and other eubacteria
Pharmacological action
Yes
Actions
Adduct
References
  1. 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]
  2. 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]
  3. Aslangul E, Massias L, Meulemans A, Chau F, Andremont A, Courvalin P, Fantin B, Ruimy R: Acquired gentamicin resistance by permeability impairment in Enterococcus faecalis. Antimicrob Agents Chemother. 2006 Nov;50(11):3615-21. [PubMed:17065620]
  4. Schroeder R, Waldsich C, Wank H: Modulation of RNA function by aminoglycoside antibiotics. EMBO J. 2000 Jan 4;19(1):1-9. [PubMed:10619838]
Kind
Protein
Organism
Human
Pharmacological action
No
Actions
Other/unknown
General Function
Calcium ion binding
Specific Function
Acts together with cubilin to mediate HDL endocytosis (By similarity). May participate in regulation of parathyroid-hormone and para-thyroid-hormone-related protein release.
Gene Name
LRP2
Uniprot ID
P98164
Uniprot Name
Low-density lipoprotein receptor-related protein 2
Molecular Weight
521952.77 Da
References
  1. Watanabe A, Nagai J, Adachi Y, Katsube T, Kitahara Y, Murakami T, Takano M: Targeted prevention of renal accumulation and toxicity of gentamicin by aminoglycoside binding receptor antagonists. J Control Release. 2004 Mar 24;95(3):423-33. [PubMed:15023454]
  2. Takamoto K, Kawada M, Ikeda D, Yoshida M: Apolipoprotein E3 (apoE3) safeguards pig proximal tubular LLC-PK1 cells against reduction in SGLT1 activity induced by gentamicin C. Biochim Biophys Acta. 2005 Apr 15;1722(3):247-53. [PubMed:15777622]
  3. Nagai J, Saito M, Adachi Y, Yumoto R, Takano M: Inhibition of gentamicin binding to rat renal brush-border membrane by megalin ligands and basic peptides. J Control Release. 2006 May 1;112(1):43-50. Epub 2006 Feb 20. [PubMed:16488503]
Kind
Protein
Organism
Bacillus subtilis (strain 168)
Pharmacological action
Unknown
General Function
Nad+ synthase activity
Specific Function
Catalyzes a key step in NAD biosynthesis, transforming deamido-NAD into NAD by a two-step reaction.
Gene Name
nadE
Uniprot ID
P08164
Uniprot Name
NH(3)-dependent NAD(+) synthetase
Molecular Weight
30394.995 Da
References
  1. Velu SE, Cristofoli WA, Garcia GJ, Brouillette CG, Pierson MC, Luan CH, DeLucas LJ, Brouillette WJ: Tethered dimers as NAD synthetase inhibitors with antibacterial activity. J Med Chem. 2003 Jul 17;46(15):3371-81. [PubMed:12852767]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Nadph binding
Specific Function
Key enzyme in folate metabolism. Contributes to the de novo mitochondrial thymidylate biosynthesis pathway. Catalyzes an essential reaction for de novo glycine and purine synthesis, and for DNA pre...
Gene Name
DHFR
Uniprot ID
P00374
Uniprot Name
Dihydrofolate reductase
Molecular Weight
21452.61 Da
References
  1. Al-Omary FA, Abou-Zeid LA, Nagi MN, Habib el-SE, Abdel-Aziz AA, El-Azab AS, Abdel-Hamide SG, Al-Omar MA, Al-Obaid AM, El-Subbagh HI: Non-classical antifolates. Part 2: synthesis, biological evaluation, and molecular modeling study of some new 2,6-substituted-quinazolin-4-ones. Bioorg Med Chem. 2010 Apr 15;18(8):2849-63. doi: 10.1016/j.bmc.2010.03.019. Epub 2010 Mar 12. [PubMed:20350811]

Transporters

Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Sodium-independent organic anion transmembrane transporter activity
Specific Function
Involved in the renal elimination of endogenous and exogenous organic anions. Functions as organic anion exchanger when the uptake of one molecule of organic anion is coupled with an efflux of one ...
Gene Name
SLC22A6
Uniprot ID
Q4U2R8
Uniprot Name
Solute carrier family 22 member 6
Molecular Weight
61815.78 Da
References
  1. Jariyawat S, Sekine T, Takeda M, Apiwattanakul N, Kanai Y, Sophasan S, Endou H: The interaction and transport of beta-lactam antibiotics with the cloned rat renal organic anion transporter 1. J Pharmacol Exp Ther. 1999 Aug;290(2):672-7. [PubMed:10411577]

Drug created on June 13, 2005 07:24 / Updated on December 10, 2017 17:18