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Identification
NameGentamicin
Accession NumberDB00798  (APRD00214)
TypeSmall Molecule
GroupsApproved, 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). [PubChem]

Structure
Thumb
Synonyms
Gentamicin
External Identifiers Not Available
Approved Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Alcomicin Oph Sol 3mg/mlliquid3 mgophthalmicAlcon Canada Inc1983-12-312009-04-24Canada
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
Diogent Ointment 0.3%ointment.3 %ophthalmicDioptic Pharmaceuticals Inc1994-12-31Not applicableCanada
Diogent Solution 0.3%liquid.3 %ophthalmicDioptic Pharmaceuticals Inc1994-12-31Not applicableCanada
Garamycin Cream 0.1%cream.1 %topicalSchering Plough Canada Inc1966-12-312007-08-03Canada
Garamycin Inj 10mg/ml Pediatricsolution10 mgintramuscular; intravenousSchering Plough Canada Inc1970-12-312004-07-21Canada
Garamycin Inj 40mg/mlsolution40 mgintramuscular; intravenousSchering Plough Canada Inc1966-12-312004-07-21Canada
Garamycin Ont 0.1%ointment1 mgtopicalSchering Plough Canada Inc1966-12-312007-08-03Canada
Garamycin Ophthalmic Drops 0.3%drops3 mgophthalmicMerck Canada Inc1981-12-312014-09-02Canada
Garamycin Ophthalmic Ointment 0.3%ointment0.3 %ophthalmicMerck Canada Inc1969-12-312013-07-15Canada
Garamycin Otic Drops 0.3%drops3 mgoticMerck Canada Inc1981-12-312014-03-03Canada
Garatec Ophthalmic Dps 5mg/mldrops5 mgophthalmicTechnilab Pharma Inc.1992-12-312004-08-03Canada
Garatec Otic Dps 5mg/mldrops5 mgoticTechnilab Pharma Inc.1992-12-312004-08-03Canada
Gentacidin Oph Soln 3mg/mldrops3 mgophthalmicIolab Pharmaceuticals1991-12-311996-09-09Canada
Gentacidin Ophthalmic Solution 3mg/mldrops3 mgophthalmicCiba Vision Canada Inc1996-12-312000-06-30Canada
Gentamicinsolution.3 %ophthalmicIvax Pharmaceuticals Incorporated1996-09-102015-10-26Canada
Gentamicin Injection USPsolution40 mgintramuscular; intravenousSandoz Canada Incorporated2000-12-20Not applicableCanada
Gentamicin Injection USPsolution10 mgintramuscular; intravenousSandoz Canada Incorporated2005-08-29Not applicableCanada
Gentamicin Sulphate 0.3% - Liq Ophliquid3 mgophthalmicRivex Ophthalmics Inc.1997-05-072003-07-28Canada
Gentamicin Sulphate Injection USP-10mg/mlsolution10 mgintramuscular; intravenousNovopharm Limited1995-12-312005-08-10Canada
Gentamicin Sulphate Injection USP-40mg/mlsolution40 mgintramuscular; intravenousNovopharm Limited1995-12-312005-08-10Canada
Gentamicin(e) 100mg Liq IV 1mg/mlsolution1 mgintravenousBaxter Corporation1995-12-31Not applicableCanada
Gentamicin(e) 120mg Liq IV 1.2mg/mlsolution1.2 mgintravenousBaxter Corporation1995-12-31Not applicableCanada
Gentamicin(e) 80mg Liq IV 1.6mg/mlsolution1.6 mgintravenousBaxter Corporation1995-12-31Not applicableCanada
Gentrasul Liq 3mg/mldrops3 mgophthalmicBausch & Lomb Canada Inc.1988-12-311996-09-09Canada
Gentrasul Oph Ointment 3mg/gmointment3 mgophthalmicBausch & Lomb Canada Inc.1988-12-311996-09-09Canada
Minims Gentamicin Sulfate 0.3%drops0.3 %ophthalmic; topicalChauvin Pharmaceuticals Limited1995-12-312009-02-04Canada
Ocugram Liq 3mg/mlliquid3 mgophthalmic; topicalHerdt Et Charton Inc.1994-12-311999-01-16Canada
Ocugram Ont 3mg/gmointment3 mgophthalmic; topicalHerdt Et Charton Inc.1994-12-311999-01-16Canada
Odan-gentamicinointment5 mgophthalmicOdan Laboratories Ltd1994-12-31Not applicableCanada
Odan-gentamicinsolution5 mgophthalmicOdan Laboratories Ltd1991-12-31Not applicableCanada
PMS-gentamicin Cream 1mg/gmcream1 mgtopicalPharmascience Inc1990-12-31Not applicableCanada
PMS-gentamicin Ointment 1mg/gmointment1 mgtopicalPharmascience Inc1990-12-31Not applicableCanada
PMS-gentamicin Ophthalmic Ointment 0.3%ointment0.3 %ophthalmicPharmascience IncNot applicableNot applicableCanada
PMS-gentamicin Otic Drops 0.3%drops3 mgoticPharmascience Inc1997-07-18Not applicableCanada
PMS-gentamicin Sulfate Oph Dps 0.3%liquid3 mgophthalmicPharmascience Inc1989-12-31Not applicableCanada
R.O.-gentycinliquid3 mgophthalmicRichmond Pharmaceuticals Inc.1992-12-311997-08-11Canada
Ratio-gentamicinointment.1 %topicalRatiopharm Inc Division Of Teva Canada Limited1990-12-31Not applicableCanada
Ratio-gentamicincream0.1 %topicalRatiopharm Inc Division Of Teva Canada Limited1990-12-31Not applicableCanada
Sandoz Gentamicinointment3 mgophthalmicSandoz Canada Incorporated1997-11-25Not applicableCanada
Sandoz Gentamicinsolution3 mgoticSandoz Canada Incorporated1996-11-26Not applicableCanada
Sandoz Gentamicinliquid3 mgophthalmicSandoz Canada Incorporated1997-05-06Not applicableCanada
Septopalimplant4.5 mgimplantBiomet Orthopedics, Inc.1987-10-192014-07-24Canada
Approved Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Garamycinsolution/ drops3 mg/mLophthalmicFera Pharmaceuticals, LLC2011-05-15Not applicableUs
Garamycinointment3 mg/gophthalmicFera Pharmaceuticals, LLC2010-10-08Not applicableUs
Garamycin Gentamicin Sulfatesolution3 mg/mLophthalmicPaddock Laboratories, LLC2014-06-05Not applicableUs
Gentakointment3 mg/gophthalmicA S Medication Solutions Llc2006-05-08Not applicableUs
Gentakointment3 mg/gophthalmicLake Erie Medical & Surgical Supply DBA Quality Care Products LLC2012-03-27Not applicableUs
Gentakointment3 mg/gophthalmicPreferred Pharmaceuticals, Inc.2012-10-23Not applicableUs
Gentakointment3 mg/gophthalmicAkorn, Inc.2013-03-11Not applicableUs
Gentakointment3 mg/gophthalmicAkorn, Inc.2006-05-08Not applicableUs
Gentakointment3 mg/gophthalmicREMEDYREPACK INC.2013-06-24Not applicableUs
Gentamicininjection, solution10 mg/mLintramuscular; intravenousFresenius Kabi USA, LLC2004-11-29Not applicableUs
Gentamicininjection, solution10 mg/mLintramuscular; intravenousCardinal Health2004-11-29Not applicableUs
Gentamicininjection, solution40 mg/mLintramuscular; intravenousCardinal Health2000-08-10Not applicableUs
Gentamicininjection, solution40 mg/mLintramuscular; intravenousGeneral Injectables & Vaccines, Inc2010-09-01Not applicableUs
Gentamicininjection, solution40 mg/mLintramuscular; intravenousFresenius Kabi USA, LLC2000-08-10Not applicableUs
Gentamicininjection, solution10 mg/mLintramuscular; intravenousFresenius Kabi USA, LLC1982-03-04Not applicableUs
Gentamicininjection, solution10 mg/mLintramuscular; intravenousCardinal Health1982-03-04Not applicableUs
Gentamicin Sulfatesolution/ drops3 mg/mLophthalmicProficient Rx LP1994-05-11Not applicableUs
Gentamicin Sulfatesolution/ drops3 mg/mLophthalmicLake Erie Medical & Surgical Suppy DBA Quality Care Products LLC1998-01-05Not applicableUs
Gentamicin Sulfatecream1 mg/gtopicalE. Fougera & CO., A division of Fougera Pharmaceuticals Inc.1984-07-05Not applicableUs
Gentamicin Sulfatesolution/ drops3 mg/mLophthalmicMedsource Pharmaceuticals1994-05-11Not applicableUs
Gentamicin Sulfatecream1 mg/gtopicalPhysicians Total Care, Inc.1995-05-12Not applicableUs
Gentamicin Sulfatesolution/ drops3 mg/mLophthalmicUnit Dose Services1994-05-11Not applicableUs
Gentamicin Sulfatesolution/ drops3 mg/mLophthalmicUnit Dose Services1994-05-11Not applicableUs
Gentamicin Sulfatesolution/ drops3 mg/mLophthalmicAkorn, Inc.2006-12-13Not applicableUs
Gentamicin Sulfatesolution/ drops3 mg/mLophthalmicA S Medication Solutions Llc1994-05-11Not applicableUs
Gentamicin Sulfatesolution/ drops3 mg/mLophthalmicProficient Rx LP1998-01-05Not applicableUs
Gentamicin Sulfatesolution/ drops3 mg/mLophthalmicAidarex Pharmaceuticals LLC1998-01-05Not applicableUs
Gentamicin Sulfatecream1 mg/gtopicalPerrigo New York Inc2006-08-23Not applicableUs
Gentamicin Sulfatecream1 mg/gtopicalSTAT Rx USA LLC2009-08-11Not applicableUs
Gentamicin Sulfatesolution/ drops3 mg/mLophthalmicBausch & Lomb Incorporated1994-05-11Not applicableUs
Gentamicin Sulfateointment1 mg/gtopicalA S Medication Solutions Llc2010-03-17Not applicableUs
Gentamicin Sulfatesolution/ drops3 mg/mLophthalmicDIRECT RX2014-01-01Not applicableUs
Gentamicin Sulfateointment3 mg/gophthalmicMwi2015-03-23Not applicableUs
Gentamicin Sulfatesolution/ drops3 mg/mLophthalmicLake Erie Medical & Surgical Supply DBA Quality Care Products LLC2012-03-12Not applicableUs
Gentamicin Sulfateinjection, solution, concentrate40 mg/mLintramuscular; intravenousCardinal Health1983-08-15Not applicableUs
Gentamicin Sulfatesolution/ drops3 mg/mLophthalmicPreferred Pharmaceuticals, Inc.2014-03-25Not applicableUs
Gentamicin Sulfatesolution3 mg/mLophthalmicRebel Distributors Corp1984-10-10Not applicableUs
Gentamicin Sulfateinjection, solution, concentrate10 mg/mLintravenousHospira, Inc.2011-11-30Not applicableUs
Gentamicin Sulfateinjection, solution, concentrate40 mg/mLintramuscular; intravenousGeneral Injectables & Vaccines, Inc2010-08-01Not applicableUs
Gentamicin Sulfatesolution3 mg/mLophthalmicSandoz Inc1996-04-05Not applicableUs
Gentamicin Sulfateointment3 mg/gophthalmicPaddock Laboratories, LLC2013-12-12Not applicableUs
Gentamicin Sulfateointment3 mg/gophthalmicFera Pharmaceuticals, LLC2011-01-03Not applicableUs
Gentamicin Sulfatecream1 mg/gtopicalDispensing Solutions, Inc.1984-07-05Not applicableUs
Gentamicin Sulfateinjection, solution, concentrate10 mg/mLintravenousHospira, Inc.2011-11-30Not applicableUs
Gentamicin Sulfatesolution/ drops3 mg/mLophthalmicPacific Pharma, Inc.1998-01-05Not applicableUs
Gentamicin Sulfatesolution/ drops3 mg/mLophthalmicPhysicians Total Care, Inc.1993-09-17Not applicableUs
Gentamicin Sulfatesolution/ drops3 mg/mLophthalmicPreferred Pharmaceuticals, Inc.2013-03-14Not applicableUs
Gentamicin Sulfatesolution/ drops3 mg/mLophthalmicAkorn, Inc.2013-03-11Not applicableUs
Gentamicin Sulfateinjection, solution, concentrate10 mg/mLintravenousHospira, Inc.2011-11-30Not applicableUs
Gentamicin Sulfatesolution/ drops3 mg/mLophthalmicREMEDYREPACK INC.2013-07-05Not applicableUs
Gentamicin Sulfatesolution/ drops3 mg/mLophthalmicClinical Solutions Wholesale1994-05-11Not applicableUs
Gentamicin Sulfateointment3 mg/gophthalmicPhysicians Total Care, Inc.1994-09-21Not applicableUs
Gentamicin Sulfateointment1 mg/gtopicalPerrigo New York Inc2006-07-10Not applicableUs
Gentamicin Sulfateointment1 mg/gtopicalE. Fougera & Co. a division of Fougera Pharmaceuticals Inc.2010-03-17Not applicableUs
Gentamicin Sulfateointment1 mg/gtopicalPhysicians Total Care, Inc.2010-06-02Not applicableUs
Gentamicin Sulfateinjection, solution40 mg/mLintramuscular; intravenousHospira, Inc.1983-08-08Not applicableUs
Gentamicin Sulfate In Sodium Chlorideinjection, solution1.6 mg/mLintravenousHospira, Inc.2009-12-04Not applicableUs
Gentamicin Sulfate In Sodium Chlorideinjection, solution.9 mg/mLintravenousHospira, Inc.2009-12-04Not applicableUs
Gentamicin Sulfate In Sodium Chlorideinjection, solution100 mg/50mLintravenousBaxter Healthcare Corporation1982-09-07Not applicableUs
Gentamicin Sulfate In Sodium Chlorideinjection, solution1.4 mg/mLintravenousHospira, Inc.2009-12-04Not applicableUs
Gentamicin Sulfate In Sodium Chlorideinjection, solution80 mg/50mLintravenousBaxter Healthcare Corporation1982-09-07Not applicableUs
Gentamicin Sulfate In Sodium Chlorideinjection, solution1.2 mg/mLintravenousHospira, Inc.2009-12-04Not applicableUs
Gentamicin Sulfate In Sodium Chlorideinjection, solution60 mg/50mLintravenousBaxter Healthcare Corporation1982-09-07Not applicableUs
Gentamicin Sulfate In Sodium Chlorideinjection, solution100 mg/100mLintravenousBaxter Healthcare Corporation1982-09-07Not applicableUs
Gentamicin Sulfate In Sodium Chlorideinjection, solution80 mg/100mLintravenousBaxter Healthcare Corporation1982-09-07Not applicableUs
Gentamicin Sulfate In Sodium Chlorideinjection, solution.8 mg/mLintravenousHospira, Inc.2009-12-04Not applicableUs
Gentamicin Sulfate In Sodium Chlorideinjection, solution1 mg/mLintravenousHospira, Inc.2009-12-04Not applicableUs
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
NameCompany
AlcomicinNot Available
BristagenNot Available
G-MycinNot Available
GenopticAllergan
GentacidinNot Available
GentafairNot Available
GentamarNot Available
JenamicinNot Available
Ocu-MycinNot Available
Spectro-GentaNot Available
U-gencinU-Liang
Brand mixtures
NameLabellerIngredients
Betamycin Ophthalmic/otic SolutionSterimax Inc
Diprogen OintmentMerck Canada Inc
Dom-gentamicin-betamethasoneDominion Pharmacal
Garasone Ophthalmic and Otic SolutionMerck Canada Inc
Garasone Ophthalmic OintmentMerck Canada Inc
Gentamicin Sulfate In 0.9% Sodium Chloride InjectionHospira Healthcare Corporation
Gentamicin Sulfate In Nacl 0.9% InjHospira Healthcare Corporation
Gentamicin Sulfate In Nacl O.9% InjHospira Healthcare Corporation
PMS-gentamicin-betamethasonePharmascience Inc
Pred-GAllergan, Inc.
Sandoz PentasoneSandoz Canada Incorporated
Valisone-G CreamValeant Canada Lp Valeant Canada S.E.C.
Valisone-G OintmentValeant Canada Lp Valeant Canada S.E.C.
Salts
Name/CASStructureProperties
Gentamicin Sulfate
Thumb
  • InChI Key: CEAZRRDELHUEMR-UHFFFAOYNA-N
  • Monoisotopic Mass: 477.316248755
  • Average Mass: 477.5954
DBSALT000690
Categories
UNIIT6Z9V48IKG
CAS number1403-66-3
WeightAverage: 477.5954
Monoisotopic: 477.316248755
Chemical FormulaC21H43N5O7
InChI KeyInChIKey=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
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as aminoglycosides. These are molecules or a portion of a molecule composed of amino-modified sugars.
KingdomOrganic compounds
Super ClassOrganooxygen compounds
ClassCarbohydrates and carbohydrate conjugates
Sub ClassAminosaccharides
Direct ParentAminoglycosides
Alternative Parents
Substituents
  • Aminoglycoside core
  • 2-deoxystreptamine aminoglycoside
  • Glucosamine
  • Amino sugar
  • O-glycosyl compound
  • Glycosyl compound
  • Cyclohexylamine
  • Cyclohexanol
  • Oxane
  • Monosaccharide
  • Tertiary alcohol
  • Cyclic alcohol
  • Secondary alcohol
  • 1,2-aminoalcohol
  • Oxacycle
  • Organoheterocyclic compound
  • Secondary amine
  • Secondary aliphatic amine
  • Acetal
  • Hydrocarbon derivative
  • Primary amine
  • Organonitrogen compound
  • Primary aliphatic amine
  • Amine
  • Alcohol
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
Pharmacology
IndicationFor 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).
PharmacodynamicsGentamicin 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 actionAminoglycosides 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.
Related Articles
AbsorptionInjections 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 distributionNot Available
Protein bindingLow (between 0 and 30%)
MetabolismNot Available
Route of eliminationNot Available
Half life3-3½ 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.
ClearanceNot Available
ToxicityMild 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
PathwayCategorySMPDB ID
Gentamicin Action PathwayDrug actionSMP00254
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
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 )
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
Ointmentophthalmic.3 %
Liquidophthalmic.3 %
Liquidophthalmic; otic
Creamtopical.1 %
Solutionophthalmic3 mg/mL
Dropsophthalmic5 mg
Dropsotic5 mg
Dropsophthalmic3 mg
Injection, solutionintramuscular; intravenous10 mg/mL
Solutionophthalmic.3 %
Solutionintramuscular; intravenous10 mg
Solutionintramuscular; intravenous40 mg
Creamtopical1 mg/g
Injection, solutionintramuscular; intravenous40 mg/mL
Injection, solution, concentrateintramuscular; intravenous40 mg/mL
Injection, solution, concentrateintravenous10 mg/mL
Ointmentophthalmic3 mg/g
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/100mL
Injection, solutionintravenous100 mg/50mL
Injection, solutionintravenous60 mg/50mL
Injection, solutionintravenous80 mg/50mL
Injection, solutionintravenous80 mg/100mL
Solutionintravenous1 mg
Solutionintravenous1.2 mg
Solutionintravenous1.6 mg
Dropsophthalmic; topical0.3 %
Liquidophthalmic; topical3 mg
Ointmentophthalmic; topical3 mg
Ointmentophthalmic5 mg
Solutionophthalmic5 mg
Creamtopical1 mg
Ointmenttopical1 mg
Ointmentophthalmic0.3 %
Dropsotic3 mg
Ointmentophthalmic
Suspension/ dropsophthalmic
Creamtopical0.1 %
Ointmenttopical.1 %
Liquidophthalmic3 mg
Ointmentophthalmic3 mg
Solutionotic3 mg
Solutionophthalmic; otic
Implantimplant4.5 mg
Creamtopical
Ointmenttopical
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.
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point105 °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 FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0i29-1319700000-e55d2931137c5abc8493View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-0904000000-de986ac47725d8f3a72aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0592-9602000000-c7fd77457525743faebaView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-2911100000-93e47b752e7992b12263View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-2958400000-7303bf3ebe16dd1c1d60View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0udi-2692000000-a8234ed8e0131019f62bView in MoNA
References
Synthesis Reference

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

US4100268
General ReferencesNot Available
External Links
ATC CodesD06AX07J01GB03S01AA11S02AA14S03AA06
AHFS Codes
  • 08:12.02
  • 52:04.04
  • 84:04.04
PDB Entries
FDA labelNot Available
MSDSDownload (59.2 KB)
Interactions
Drug Interactions
Drug
Agalsidase betaThe therapeutic efficacy of Agalsidase beta can be decreased when used in combination with Gentamicin.
Alendronic acidGentamicin may increase the activities of Alendronate.
AmdinocillinThe serum concentration of Gentamicin can be decreased when it is combined with Amdinocillin.
AmoxicillinThe serum concentration of Gentamicin can be decreased when it is combined with Amoxicillin.
Amphotericin BAmphotericin B may increase the nephrotoxic activities of Gentamicin.
AmpicillinThe serum concentration of Gentamicin can be decreased when it is combined with Ampicillin.
Atracurium besylateGentamicin may increase the activities of Atracurium besylate.
AvibactamAvibactam may increase the nephrotoxic activities of Gentamicin.
AzidocillinThe serum concentration of Gentamicin can be decreased when it is combined with Azidocillin.
AzlocillinThe serum concentration of Gentamicin can be decreased when it is combined with Azlocillin.
BacampicillinThe serum concentration of Gentamicin can be decreased when it is combined with Bacampicillin.
BenzylpenicillinThe serum concentration of Gentamicin can be decreased when it is combined with Benzylpenicillin.
Botulinum Toxin Type AGentamicin may increase the neuromuscular blocking activities of Botulinum Toxin Type A.
Botulinum Toxin Type BGentamicin may increase the neuromuscular blocking activities of Botulinum Toxin Type B.
BumetanideThe risk or severity of adverse effects can be increased when Bumetanide is combined with Gentamicin.
CapreomycinCapreomycin may increase the neuromuscular blocking activities of Gentamicin.
CarbenicillinThe serum concentration of Gentamicin can be decreased when it is combined with Carbenicillin.
CarboplatinGentamicin may increase the ototoxic activities of Carboplatin.
CefaclorCefaclor may increase the nephrotoxic activities of Gentamicin.
CefdinirCefdinir may increase the nephrotoxic activities of Gentamicin.
CefepimeCefepime may increase the nephrotoxic activities of Gentamicin.
CefiximeCefixime may increase the nephrotoxic activities of Gentamicin.
CefmenoximeCefmenoxime may increase the nephrotoxic activities of Gentamicin.
CefotaximeCefotaxime may increase the nephrotoxic activities of Gentamicin.
CefotetanCefotetan may increase the nephrotoxic activities of Gentamicin.
CefoxitinCefoxitin may increase the nephrotoxic activities of Gentamicin.
CefpodoximeCefpodoxime may increase the nephrotoxic activities of Gentamicin.
CefprozilCefprozil may increase the nephrotoxic activities of Gentamicin.
CeftazidimeCeftazidime may increase the nephrotoxic activities of Gentamicin.
CeftibutenCeftibuten may increase the nephrotoxic activities of Gentamicin.
CeftriaxoneCeftriaxone may increase the nephrotoxic activities of Gentamicin.
CefuroximeCefuroxime may increase the nephrotoxic activities of Gentamicin.
CelecoxibCelecoxib may decrease the excretion rate of Gentamicin which could result in a lower serum level and potentially a reduction in efficacy.
Cisatracurium besylateGentamicin may increase the activities of Cisatracurium besylate.
CisplatinCisplatin may increase the nephrotoxic activities of Gentamicin.
ClavulanateThe serum concentration of Gentamicin can be decreased when it is combined with Clavulanate.
ClodronateGentamicin may increase the activities of Clodronate.
CloxacillinThe serum concentration of Gentamicin can be decreased when it is combined with Cloxacillin.
ColistimethateGentamicin may increase the nephrotoxic activities of Colistimethate.
ColistinGentamicin may increase the nephrotoxic activities of Colistin.
CyclacillinThe serum concentration of Gentamicin can be decreased when it is combined with Cyclacillin.
CyclosporineGentamicin may increase the nephrotoxic activities of Cyclosporine.
DiclofenacDiclofenac may decrease the excretion rate of Gentamicin which could result in a lower serum level and potentially a reduction in efficacy.
DicloxacillinThe serum concentration of Gentamicin can be decreased when it is combined with Dicloxacillin.
DiflunisalDiflunisal may decrease the excretion rate of Gentamicin which could result in a lower serum level and potentially a reduction in efficacy.
DigoxinThe serum concentration of Digoxin can be decreased when it is combined with Gentamicin.
Etacrynic acidThe risk or severity of adverse effects can be increased when Ethacrynic acid is combined with Gentamicin.
EtodolacEtodolac may decrease the excretion rate of Gentamicin which could result in a lower serum level and potentially a reduction in efficacy.
FenoprofenFenoprofen may decrease the excretion rate of Gentamicin which could result in a lower serum level and potentially a reduction in efficacy.
FloctafenineFloctafenine may decrease the excretion rate of Gentamicin which could result in a lower serum level and potentially a reduction in efficacy.
FlucloxacillinThe serum concentration of Gentamicin can be decreased when it is combined with Flucloxacillin.
FlurbiprofenFlurbiprofen may decrease the excretion rate of Gentamicin which could result in a lower serum level and potentially a reduction in efficacy.
FoscarnetFoscarnet may increase the nephrotoxic activities of Gentamicin.
FurosemideThe risk or severity of adverse effects can be increased when Furosemide is combined with Gentamicin.
HetacillinThe serum concentration of Gentamicin can be decreased when it is combined with Hetacillin.
IbandronateGentamicin may increase the activities of Ibandronate.
IbuprofenIbuprofen may decrease the excretion rate of Gentamicin which could result in a lower serum level and potentially a reduction in efficacy.
IndomethacinIndomethacin may decrease the excretion rate of Gentamicin which could result in a lower serum level and potentially a reduction in efficacy.
InfliximabInfliximab may decrease the excretion rate of Gentamicin which could result in a lower serum level and potentially a reduction in efficacy.
KetoprofenKetoprofen may decrease the excretion rate of Gentamicin which could result in a lower serum level and potentially a reduction in efficacy.
KetorolacKetorolac may decrease the excretion rate of Gentamicin which could result in a lower serum level and potentially a reduction in efficacy.
MannitolMannitol may increase the nephrotoxic activities of Gentamicin.
MecamylamineGentamicin may increase the neuromuscular blocking activities of Mecamylamine.
Mefenamic acidMefenamic acid may decrease the excretion rate of Gentamicin which could result in a lower serum level and potentially a reduction in efficacy.
MeloxicamMeloxicam may decrease the excretion rate of Gentamicin which could result in a lower serum level and potentially a reduction in efficacy.
MeticillinThe serum concentration of Gentamicin can be decreased when it is combined with Meticillin.
MezlocillinThe serum concentration of Gentamicin can be decreased when it is combined with Mezlocillin.
NabumetoneNabumetone may decrease the excretion rate of Gentamicin which could result in a lower serum level and potentially a reduction in efficacy.
NafcillinThe serum concentration of Gentamicin can be decreased when it is combined with Nafcillin.
NaproxenNaproxen may decrease the excretion rate of Gentamicin which could result in a lower serum level and potentially a reduction in efficacy.
OxacillinThe serum concentration of Gentamicin can be decreased when it is combined with Oxacillin.
OxaprozinOxaprozin may decrease the excretion rate of Gentamicin which could result in a lower serum level and potentially a reduction in efficacy.
PamidronateGentamicin may increase the activities of Pamidronate.
PancuroniumGentamicin may increase the activities of Pancuronium.
PhenoxymethylpenicillinThe serum concentration of Gentamicin can be decreased when it is combined with Phenoxymethylpenicillin.
Picosulfuric acidThe therapeutic efficacy of Sodium picosulfate can be decreased when used in combination with Gentamicin.
PiperacillinThe serum concentration of Gentamicin can be decreased when it is combined with Piperacillin.
PiroxicamPiroxicam may decrease the excretion rate of Gentamicin which could result in a lower serum level and potentially a reduction in efficacy.
PivampicillinThe serum concentration of Gentamicin can be decreased when it is combined with Pivampicillin.
PivmecillinamThe serum concentration of Gentamicin can be decreased when it is combined with Pivmecillinam.
RisedronateGentamicin may increase the activities of Risedronate.
RocuroniumGentamicin may increase the activities of Rocuronium.
SuccinylcholineGentamicin may increase the activities of Succinylcholine.
SulindacSulindac may decrease the excretion rate of Gentamicin which could result in a lower serum level and potentially a reduction in efficacy.
TenofovirThe serum concentration of Gentamicin can be increased when it is combined with Tenofovir.
Tiaprofenic acidTiaprofenic acid may decrease the excretion rate of Gentamicin which could result in a lower serum level and potentially a reduction in efficacy.
TicarcillinThe serum concentration of Gentamicin can be decreased when it is combined with Ticarcillin.
TiludronateGentamicin may increase the activities of Tiludronate.
TolmetinTolmetin may decrease the excretion rate of Gentamicin which could result in a lower serum level and potentially a reduction in efficacy.
TorasemideThe risk or severity of adverse effects can be increased when Torasemide is combined with Gentamicin.
VancomycinVancomycin may increase the nephrotoxic activities of Gentamicin.
VecuroniumGentamicin may increase the activities of Vecuronium.
Zoledronic acidGentamicin may increase the activities of Zoledronate.
Food InteractionsNot 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. Located at the interface of the 30S and 50S subunits, it traverses the body of the 30S subunit contacting proteins on the other side and probably holding the rRNA structure together. The combined cluste...
Gene Name:
rpsL
Uniprot ID:
P0A7S3
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
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
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 precursor synthesis. Binds its own mRNA and that of DHFRL1.
Gene Name:
DHFR
Uniprot ID:
P00374
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 molecule of endogenous dicarboxylic acid (glutarate, ketoglutarate, etc). Mediates the sodium-independent uptake of 2,3-dimercapto-1-propanesulfonic acid (DMPS) (By similarity). Mediates the sodium-in...
Gene Name:
SLC22A6
Uniprot ID:
Q4U2R8
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 ]
Comments
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Drug created on June 13, 2005 07:24 / Updated on May 22, 2014 10:21