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Identification
NameGentamicin
Accession NumberDB00798  (APRD00214)
TypeSmall Molecule
GroupsApproved
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
SynonymLanguageCode
GentamicinNot AvailableNot Available
Prescription ProductsNot Available
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Gentamicin Sulfatecream1 mg/gtopicalE. Fougera & CO., A division of Fougera Pharmaceuticals Inc.1984-07-05Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Gentamicin Sulfateointment1 mg/gtopicalE. Fougera & Co. a division of Fougera Pharmaceuticals Inc.2010-03-17Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Gentamicin Sulfateinjection, solution40 mg/mLintramuscular; intravenousHospira, Inc.1983-08-08Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Gentamicin Sulfateinjection, solution40 mg/mLintramuscular; intravenousHospira, Inc.2014-07-01Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Gentamicin Sulfateinjection, solution, concentrate10 mg/mLintravenousHospira, Inc.2011-11-30Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Gentamicin Sulfateinjection, solution, concentrate10 mg/mLintravenousHospira, Inc.2011-11-30Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Gentamicin Sulfateinjection, solution, concentrate10 mg/mLintravenousHospira, Inc.2011-11-30Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Gentamicin Sulfateointment3 mg/gophthalmicPaddock Laboratories, LLC2013-12-12Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Gentamicin Sulfatecream1 mg/gtopicalSTAT Rx USA LLC2009-08-11Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Gentamicin Sulfatesolution/ drops3 mg/mLophthalmicAkorn, Inc.2006-12-13Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Gentakointment3 mg/gophthalmicAkorn, Inc.2006-05-08Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Gentamicin Sulfatesolution/ drops3 mg/mLophthalmicAkorn, Inc.2013-03-11Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Gentakointment3 mg/gophthalmicAkorn, Inc.2013-03-11Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Gentamicin Sulfatesolution3 mg/mLophthalmicRebel Distributors Corp1984-10-10Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Gentamicin Sulfatesolution/ drops3 mg/mLophthalmicBausch & Lomb Incorporated1994-05-11Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Gentamicin Sulfatesolution/ drops3 mg/mLophthalmicAidarex Pharmaceuticals LLC1998-01-05Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Gentamicin Sulfatesolution/ drops3 mg/mLophthalmicLake Erie Medical & Surgical Suppy DBA Quality Care Products LLC1998-01-05Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Gentamicin Sulfateointment1 mg/gtopicalPerrigo New York Inc2006-07-10Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Gentamicin Sulfatecream1 mg/gtopicalPerrigo New York Inc2006-08-23Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Garamycinointment3 mg/gophthalmicFera Pharmaceuticals, LLC2010-10-08Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Garamycinsolution/ drops3 mg/mLophthalmicFera Pharmaceuticals, LLC2011-05-15Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Gentamicin Sulfateointment3 mg/gophthalmicFera Pharmaceuticals, LLC2011-01-03Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Gentamicin Sulfatesolution/ drops3 mg/mLophthalmicLake Erie Medical & Surgical Supply DBA Quality Care Products LLC2012-03-12Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Gentakointment3 mg/gophthalmicLake Erie Medical & Surgical Supply DBA Quality Care Products LLC2012-03-27Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Gentamicin Sulfatesolution/ drops3 mg/mLophthalmicUnit Dose Services1994-05-11Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Gentakointment3 mg/gophthalmicREMEDYREPACK INC.2013-06-24Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Gentamicin Sulfatesolution/ drops3 mg/mLophthalmicREMEDYREPACK INC.2013-12-05Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Gentamicin Sulfatesolution/ drops3 mg/mLophthalmicREMEDYREPACK INC.2013-07-05Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Gentamicininjection, solution40 mg/mLintramuscular; intravenousGeneral Injectables & Vaccines, Inc2010-09-01Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Gentamicin Sulfateinjection, solution, concentrate40 mg/mLintramuscular; intravenousGeneral Injectables & Vaccines, Inc2010-08-01Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Gentamicin Sulfateointment1 mg/gtopicalA S Medication Solutions Llc2010-03-17Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Gentamicin Sulfatesolution/ drops3 mg/mLophthalmicA S Medication Solutions Llc1994-05-11Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Gentakointment3 mg/gophthalmicA S Medication Solutions Llc2006-05-08Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Gentamicin Sulfateointment3 mg/gophthalmicPhysicians Total Care, Inc.1994-09-21Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Gentamicin Sulfatecream1 mg/gtopicalPhysicians Total Care, Inc.1995-05-12Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Gentamicin Sulfateointment1 mg/gtopicalPhysicians Total Care, Inc.2010-06-02Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Gentamicin Sulfatesolution/ drops3 mg/mLophthalmicPhysicians Total Care, Inc.1993-09-17Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Gentamicin Sulfatecream1 mg/gtopicalDispensing Solutions, Inc.1984-07-05Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Gentamicin Sulfateinjection, solution, concentrate40 mg/mLintramuscular; intravenousCardinal Health1983-08-15Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Gentamicininjection, solution40 mg/mLintramuscular; intravenousCardinal Health2000-08-10Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Gentamicininjection, solution10 mg/mLintramuscular; intravenousCardinal Health2004-11-29Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Gentamicininjection, solution10 mg/mLintramuscular; intravenousCardinal Health1982-03-04Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Gentamicin Sulfatesolution/ drops3 mg/mLophthalmicClinical Solutions Wholesale1994-05-11Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Gentamicin Sulfatesolution/ drops3 mg/mLophthalmicPacific Pharma, Inc.1998-01-05Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Gentamicin Sulfatesolution3 mg/mLophthalmicSandoz Inc1996-04-05Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Gentamicin Sulfatesolution/ drops3 mg/mLophthalmicDIRECT RX2014-01-01Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Gentamicin Sulfatesolution/ drops3 mg/mLophthalmicProficient Rx LP1998-01-05Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Gentamicininjection, solution40 mg/mLintramuscular; intravenousFresenius Kabi USA, LLC2000-08-10Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Gentamicininjection, solution40 mg/mLintramuscular; intravenousFresenius Kabi USA, LLC2000-08-10Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Gentamicininjection, solution40 mg/mLintramuscular; intravenousFresenius Kabi USA, LLC2000-08-10Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Gentamicininjection, solution10 mg/mLintramuscular; intravenousAPP Pharmaceuticals, LLC2004-11-29Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Gentamicininjection, solution10 mg/mLintramuscular; intravenousFresenius Kabi USA, LLC2004-11-29Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Gentamicininjection, solution10 mg/mLintramuscular; intravenousFresenius Kabi USA, LLC2004-11-29Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Gentamicininjection, solution10 mg/mLintramuscular; intravenousAPP Pharmaceuticals, LLC1982-03-04Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Gentamicin Sulfatesolution/ drops3 mg/mLophthalmicPreferred Pharmaceuticals, Inc.2013-03-14Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Gentakointment3 mg/gophthalmicPreferred Pharmaceuticals, Inc.2012-10-23Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Gentamicin Sulfatesolution/ drops3 mg/mLophthalmicPreferred Pharmaceuticals, Inc.2014-03-25Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Gentamicinsolution.3 %ophthalmicIvax Pharmaceuticals IncorporatedNot AvailableNot AvailableCanada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Over the Counter ProductsNot 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
Brand NameIngredients
Diprogen CreamBetamethasone Dipropionate + Gentamicin Sulfate
Diprogen OntBetamethasone Dipropionate + Gentamicin Sulfate
Garasone Oph/Ot SolBetamethasone + Gentamicin Sulfate
Garasone Ophthalmic OintmentBetamethasone + Gentamicin Sulfate
Gentamicin Sulfate in Nacl 0.9% InjGentamicin Sulfate + Sodium Chloride
Gentocin DurafilmBetamethasone 21-Acetate + Gentamicin Sulfate
Gentocin Otic SolutionBetamethasone + Gentamicin Sulfate
Otomax OintmentBetamethasone + Clotrimazole + Gentamicin Sulfate
PRED-GGentamicin + Prednisolone
Sandoz PentasoneBetamethasone + Gentamicin Sulfate
Topagen OntBetamethasone + Gentamicin Sulfate
Topagen SprayBetamethasone + Gentamicin Sulfate
Valisone G CreamBetamethasone + Gentamicin Sulfate
Valisone G OintmentBetamethasone + Gentamicin Sulfate
Salts
Name/CASStructureProperties
Gentamicin Sulfate
Thumb
  • InChI Key: CEAZRRDELHUEMR-UHFFFAOYNA-N
  • Monoisotopic Mass: 477.316248755
  • Average Mass: 477.5954
DBSALT000690
Categories
CAS number1403-66-3
WeightAverage: 477.5954
Monoisotopic: 477.316248755
Chemical FormulaC21H43N5O7
InChI KeyCEAZRRDELHUEMR-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.
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
PathwaysNot Available
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 substrateNon-inhibitor0.891
CYP450 2D6 substrateNon-inhibitor0.9331
CYP450 2C19 substrateNon-inhibitor0.9043
CYP450 3A4 substrateNon-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
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
Creamtopical1 mg/g
Injection, solutionintramuscular; intravenous10 mg/mL
Injection, solutionintramuscular; intravenous40 mg/mL
Injection, solution, concentrateintramuscular; intravenous40 mg/mL
Injection, solution, concentrateintravenous10 mg/mL
Ointmentophthalmic3 mg/g
Ointmenttopical1 mg/g
Solutionophthalmic.3 %
Solutionophthalmic3 mg/mL
Solution/ dropsophthalmic3 mg/mL
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
SpectraMS/MS
References
Synthesis Reference

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

US4100268
General ReferenceNot 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
Amphotericin BAmphotericin B may enhance the nephrotoxic effect of Aminoglycosides.
AtracuriumMay enhance the respiratory depressant effect of Neuromuscular-Blocking Agents.
Botulinum Toxin Type AMay enhance the neuromuscular-blocking effect of AbobotulinumtoxinA.
Botulinum Toxin Type BMay enhance the neuromuscular-blocking effect of RimabotulinumtoxinB.
BumetanideLoop Diuretics may enhance the adverse/toxic effect of Aminoglycosides. Specifically, nephrotoxicity and ototoxicity.
CapreomycinCapreomycin may enhance the neuromuscular-blocking effect of Aminoglycosides.
CarboplatinMay enhance the ototoxic effect of CARBOplatin. Especially with higher doses of carboplatin.
CefaclorCephalosporins (2nd Generation) may enhance the nephrotoxic effect of Aminoglycosides.
CefdinirCephalosporins (3rd Generation) may enhance the nephrotoxic effect of Aminoglycosides.
CefepimeCephalosporins (4th Generation) may enhance the nephrotoxic effect of Aminoglycosides.
CefiximeCephalosporins (3rd Generation) may enhance the nephrotoxic effect of Aminoglycosides.
CefotaximeCephalosporins (3rd Generation) may enhance the nephrotoxic effect of Aminoglycosides.
CefotetanCephalosporins (2nd Generation) may enhance the nephrotoxic effect of Aminoglycosides.
CefoxitinCephalosporins (2nd Generation) may enhance the nephrotoxic effect of Aminoglycosides.
CefpodoximeCephalosporins (3rd Generation) may enhance the nephrotoxic effect of Aminoglycosides.
CefprozilCephalosporins (2nd Generation) may enhance the nephrotoxic effect of Aminoglycosides.
CeftazidimeCephalosporins (3rd Generation) may enhance the nephrotoxic effect of Aminoglycosides.
CeftibutenCephalosporins (3rd Generation) may enhance the nephrotoxic effect of Aminoglycosides.
CeftriaxoneCephalosporins (3rd Generation) may enhance the nephrotoxic effect of Aminoglycosides.
CefuroximeCephalosporins (2nd Generation) may enhance the nephrotoxic effect of Aminoglycosides.
CelecoxibNonsteroidal Anti-Inflammatory Agents may decrease the excretion of Aminoglycosides. Data only in premature infants.
Cisatracurium BesylateMay enhance the respiratory depressant effect of Neuromuscular-Blocking Agents.
CisplatinCISplatin may enhance the nephrotoxic effect of Aminoglycosides.
ClodronateMay enhance the hypocalcemic effect of Bisphosphonate Derivatives.
ColistimethateMay enhance the nephrotoxic effect of Colistimethate. Aminoglycosides may enhance the neuromuscular-blocking effect of Colistimethate.
ColistinMay enhance the nephrotoxic effect of Colistimethate. Aminoglycosides may enhance the neuromuscular-blocking effect of Colistimethate.
DiflunisalNonsteroidal Anti-Inflammatory Agents may decrease the excretion of Aminoglycosides. Data only in premature infants.
DigoxinMay decrease the serum concentration of Cardiac Glycosides. This effect has only been demonstrated with oral aminoglycoside administration. Exceptions: Amikacin; Gentamicin (Systemic); Streptomycin; Tobramycin (Systemic, Oral Inhalation).
Ethacrynic acidLoop Diuretics may enhance the adverse/toxic effect of Aminoglycosides. Specifically, nephrotoxicity and ototoxicity.
EtodolacNonsteroidal Anti-Inflammatory Agents may decrease the excretion of Aminoglycosides. Data only in premature infants.
FenoprofenNonsteroidal Anti-Inflammatory Agents may decrease the excretion of Aminoglycosides. Data only in premature infants.
FloctafenineNonsteroidal Anti-Inflammatory Agents may decrease the excretion of Aminoglycosides. Data only in premature infants.
FoscarnetFoscarnet may enhance the nephrotoxic effect of Aminoglycosides.
FurosemideLoop Diuretics may enhance the adverse/toxic effect of Aminoglycosides. Specifically, nephrotoxicity and ototoxicity.
IbandronateMay enhance the hypocalcemic effect of Bisphosphonate Derivatives.
IbuprofenNonsteroidal Anti-Inflammatory Agents may decrease the excretion of Aminoglycosides. Data only in premature infants.
IndomethacinNonsteroidal Anti-Inflammatory Agents may decrease the excretion of Aminoglycosides. Data only in premature infants.
KetoprofenNonsteroidal Anti-Inflammatory Agents may decrease the excretion of Aminoglycosides. Data only in premature infants.
KetorolacNonsteroidal Anti-Inflammatory Agents may decrease the excretion of Aminoglycosides. Data only in premature infants.
MannitolMannitol may enhance the nephrotoxic effect of Aminoglycosides.
Mefenamic acidNonsteroidal Anti-Inflammatory Agents may decrease the excretion of Aminoglycosides. Data only in premature infants.
MeloxicamNonsteroidal Anti-Inflammatory Agents may decrease the excretion of Aminoglycosides. Data only in premature infants.
NabumetoneNonsteroidal Anti-Inflammatory Agents may decrease the excretion of Aminoglycosides. Data only in premature infants.
NaproxenNonsteroidal Anti-Inflammatory Agents may decrease the excretion of Aminoglycosides. Data only in premature infants.
OxaprozinNonsteroidal Anti-Inflammatory Agents may decrease the excretion of Aminoglycosides. Data only in premature infants.
PamidronateMay enhance the hypocalcemic effect of Bisphosphonate Derivatives.
PancuroniumMay enhance the respiratory depressant effect of Neuromuscular-Blocking Agents.
PiperacillinPenicillins may decrease the serum concentration of Aminoglycosides. Primarily associated with extended spectrum penicillins, and patients with renal dysfunction.
PiroxicamNonsteroidal Anti-Inflammatory Agents may decrease the excretion of Aminoglycosides. Data only in premature infants.
RisedronateMay enhance the hypocalcemic effect of Bisphosphonate Derivatives.
RocuroniumMay enhance the respiratory depressant effect of Neuromuscular-Blocking Agents.
SuccinylcholineMay enhance the respiratory depressant effect of Neuromuscular-Blocking Agents.
SulindacNonsteroidal Anti-Inflammatory Agents may decrease the excretion of Aminoglycosides. Data only in premature infants.
TenofovirTenofovir may increase the serum concentration of Aminoglycosides. Aminoglycosides may increase the serum concentration of Tenofovir.
Tiaprofenic acidNonsteroidal Anti-Inflammatory Agents may decrease the excretion of Aminoglycosides. Data only in premature infants.
TicarcillinPenicillins may decrease the serum concentration of Aminoglycosides. Primarily associated with extended spectrum penicillins, and patients with renal dysfunction.
TiludronateMay enhance the hypocalcemic effect of Bisphosphonate Derivatives.
TolmetinNonsteroidal Anti-Inflammatory Agents may decrease the excretion of Aminoglycosides. Data only in premature infants.
TorasemideLoop Diuretics may enhance the adverse/toxic effect of Aminoglycosides. Specifically, nephrotoxicity and ototoxicity.
VancomycinVancomycin may enhance the nephrotoxic effect of Aminoglycosides.
VecuroniumMay enhance the respiratory depressant effect of Neuromuscular-Blocking Agents.
ZoledronateMay enhance the hypocalcemic effect of Bisphosphonate Derivatives.
Food InteractionsNot Available

Targets

1. 30S ribosomal protein S12

Kind: protein

Organism: Escherichia coli (strain K12)

Pharmacological action: yes

Actions: adduct

Components

Name UniProt ID Details
30S ribosomal protein S12 P0A7S3 Details

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
  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
  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
  4. Schroeder R, Waldsich C, Wank H: Modulation of RNA function by aminoglycoside antibiotics. EMBO J. 2000 Jan 4;19(1):1-9. Pubmed

2. 16S rRNA

Kind: nucleotide

Organism: Enteric bacteria and other eubacteria

Pharmacological action: yes

Actions: adduct

Components

Name UniProt ID Details

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
  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
  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
  4. Schroeder R, Waldsich C, Wank H: Modulation of RNA function by aminoglycoside antibiotics. EMBO J. 2000 Jan 4;19(1):1-9. Pubmed

3. Low-density lipoprotein receptor-related protein 2

Kind: protein

Organism: Human

Pharmacological action: no

Actions: other/unknown

Components

Name UniProt ID Details
Low-density lipoprotein receptor-related protein 2 P98164 Details

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
  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
  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

4. NH(3)-dependent NAD(+) synthetase

Kind: protein

Organism: Bacillus subtilis (strain 168)

Pharmacological action: unknown

Components

Name UniProt ID Details
NH(3)-dependent NAD(+) synthetase P08164 Details

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

5. Dihydrofolate reductase

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
Dihydrofolate reductase P00374 Details

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

Transporters

1. Solute carrier family 22 member 6

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Solute carrier family 22 member 6 Q4U2R8 Details

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

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Drug created on June 13, 2005 07:24 / Updated on May 22, 2014 10:21