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
GaramycinSolution / drops3 mg/1mLOphthalmicFera Pharmaceuticals2011-05-152013-06-14Us
GaramycinOintment3 mg/1gOphthalmicFera Pharmaceuticals2010-10-082013-06-14Us
Garamycin Gentamicin SulfateSolution3 mg/1mLOphthalmicPaddock Laboratories, Inc.2014-06-052016-04-01Us
GentakOintment3 mg/1gOphthalmicA-S Medication Solutions2006-05-08Not applicableUs
GentakOintment3 mg/1gOphthalmicA S Medication Solutions2006-05-08Not applicableUs
GentakOintment3 mg/1gOphthalmicAkorn2006-05-08Not applicableUs
GentakOintment3 mg/1gOphthalmicLake Erie Medical &Surgical Supply Dba Quality Care Products Llc2012-03-27Not applicableUs
GentakOintment3 mg/1gOphthalmicAkorn2013-03-11Not applicableUs
GentakOintment3 mg/1gOphthalmicRemedy Repack2017-07-24Not applicableUs
GentakOintment3 mg/1gOphthalmicPreferreed Pharmaceuticals Inc.2012-10-23Not applicableUs
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
Betamycin Ophthalmic/otic SolutionGentamicin (3 mg) + Betamethasone (1 mg)SolutionAuricular (otic); OphthalmicSterimax IncNot applicableNot applicableCanada
Diprogen CreamGentamicin sulfate (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 mg) + Sodium Chloride (9 mg)SolutionIntravenousHospira, Inc.1994-12-312011-08-05Canada
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 O.9% InjGentamicin (0.8 mg) + Sodium Chloride (9 mg)SolutionIntravenousHospira, Inc.1991-12-312014-08-01Canada
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
Gentamicin SulfateGentamicin sulfate (40 mg/100mL)Injection, solutionIntravenousBaxter Healthcare Corporation2007-03-312007-03-31Us
Gentamicin SulfateGentamicin sulfate (120 mg/50mL)Injection, solutionIntravenousBaxter Healthcare Corporation2007-03-312007-03-31Us
Gentamicin SulfateGentamicin sulfate (60 mg/100mL)Injection, solutionIntravenousBaxter Healthcare Corporation2007-03-312007-03-31Us
International/Other Brands
Alcomicin / Bristagen / G-Mycin / Genoptic (Allergan) / Gentacidin / Gentafair / Gentamar / Jenamicin / Ocu-Mycin / Spectro-Genta / U-gencin (U-Liang)
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).

Associated Conditions
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
DrugInteraction
1,10-PhenanthrolineThe therapeutic efficacy of 1,10-Phenanthroline can be decreased when used in combination with Gentamicin.
2,5-Dimethoxy-4-ethylthioamphetamineThe risk or severity of adverse effects can be increased when Gentamicin is combined with 2,5-Dimethoxy-4-ethylthioamphetamine.
3,4-MethylenedioxyamphetamineThe risk or severity of adverse effects can be increased when 3,4-Methylenedioxyamphetamine is combined with Gentamicin.
4-Bromo-2,5-dimethoxyamphetamineThe risk or severity of adverse effects can be increased when 4-Bromo-2,5-dimethoxyamphetamine is combined with Gentamicin.
4-MethoxyamphetamineThe risk or severity of adverse effects can be increased when 4-Methoxyamphetamine is combined with Gentamicin.
5-methoxy-N,N-dimethyltryptamineThe risk or severity of adverse effects can be increased when Gentamicin is combined with 5-methoxy-N,N-dimethyltryptamine.
7-NitroindazoleThe risk or severity of adverse effects can be increased when 7-Nitroindazole is combined with Gentamicin.
7,8-Dichloro-1,2,3,4-tetrahydroisoquinolineThe risk or severity of adverse effects can be increased when 7,8-Dichloro-1,2,3,4-tetrahydroisoquinoline is combined with Gentamicin.
AbacavirGentamicin may decrease the excretion rate of Abacavir which could result in a higher serum level.
AcarboseGentamicin may decrease the excretion rate of Acarbose which could result in a higher serum level.
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
HMDB0014936
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 — GentamicinD06AX07 — GentamicinS01AA11 — GentamicinS03AA06 — 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, 2Not Yet RecruitingTreatmentJunctional Epidermolysis Bullosa1
1, 2Not Yet RecruitingTreatmentRecessive Dystrophic Epidermolysis Bullosa1
1, 2RecruitingTreatmentRecessive Dystrophic Epidermolysis Bullosa1
1, 2TerminatedTreatmentDiabetic Foot Ulcers (DFU)1
2CompletedTreatmentLeishmaniasis, Cutaneous1
2Not Yet RecruitingTreatmentHereditary Hypotrichosis Simplex1
2TerminatedTreatmentCystic Fibrosis (CF)1
2TerminatedTreatmentLeishmaniasis, Cutaneous2
2, 3CompletedPreventionChorioamnionitis / Neonatal Early Onset Sepsis / Neonatal Meningitis / Neonatal Pneumonia / Puerperal Endometritis1
2, 3CompletedTreatmentChorioamnionitis1
2, 3CompletedTreatmentComplicated Intra Abdominal Infections1
2, 3CompletedTreatmentMenière's Disease1
2, 3CompletedTreatmentPlague1
2, 3Not Yet RecruitingTreatmentPharyngeal Gonococcal Infection1
2, 3RecruitingPreventionNeurogenic Bladder Dysfunction / Spinal Cord Diseases / Spinal Cord Injuries (SCI) / Urinary Tract Infections (UTIs)1
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
4RecruitingPreventionFractures, Open / Post-Op Wound Infection1
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 AvailableActive Not RecruitingNot AvailablePneumonia1
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 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
  • Accutome Inc.
  • Advanced Pharmaceutical Services Inc.
  • Akorn Inc.
  • Alcon Laboratories
  • APP Pharmaceuticals
  • A-S Medication Solutions LLC
  • B. Braun Melsungen AG
  • Bausch & Lomb Inc.
  • Baxter International Inc.
  • Cardinal Health
  • Carlisle Laboratories Inc.
  • Darby Dental Supply Co. Inc.
  • Dispensing Solutions
  • Diversified Healthcare Services Inc.
  • E. Fougera and Co.
  • Falcon Pharmaceuticals Ltd.
  • General Injectables and Vaccines Inc.
  • H.J. Harkins Co. Inc.
  • Hospira Inc.
  • Innoviant Pharmacy Inc.
  • Keltman Pharmaceuticals Inc.
  • Major Pharmaceuticals
  • Martin Surgical Supply
  • Medisca Inc.
  • MWI Veterinary Supply Co.
  • Novartis AG
  • Nycomed Inc.
  • Ocusoft
  • OMJ Pharmaceuticals
  • Pacific Pharma Lp
  • Palmetto Pharmaceuticals Inc.
  • PD-Rx Pharmaceuticals Inc.
  • Perrigo Co.
  • Pharmedix
  • Physicians Total Care Inc.
  • Preferred Pharmaceuticals Inc.
  • Qualitest
  • Rebel Distributors Corp.
  • Redpharm Drug
  • Rx Veterinary Products
  • Stat Rx Usa
  • Stat Scripts LLC
  • Taro Pharmaceuticals USA
  • Taylor Pharmaceuticals
  • Vedco Inc.
  • Wa Butler Co.
Dosage forms
FormRouteStrength
LiquidIntramuscular; Intravenous40 mg
LiquidIntramuscular; Intravenous10 mg
OintmentTopical
LiquidAuricular (otic); Ophthalmic
CreamTopical.1 %
OintmentTopical1 mg
OintmentOphthalmic0.3 %
Solution / dropsAuricular (otic)3 mg
SolutionAuricular (otic); Ophthalmic
OintmentOphthalmic
Solution / dropsOphthalmic5 mg
Solution / dropsAuricular (otic)5 mg
Solution / dropsOphthalmic3 mg
Injection, solutionIntramuscular; Intravenous10 mg/1mL
Injection, solutionIntramuscular; Intravenous40 mg/1mL
SolutionOphthalmic.3 %
SolutionOphthalmic0.3 %
SolutionIntramuscular; Intravenous10 mg
SolutionIntramuscular; Intravenous40 mg
CreamTopical1 mg/1g
Injection, solutionIntravenous120 mg/50mL
Injection, solutionIntravenous40 mg/100mL
Injection, solutionIntravenous60 mg/100mL
Injection, solution, concentrateIntramuscular; Intravenous40 mg/1mL
Injection, solution, concentrateIntravenous10 mg/1mL
OintmentOphthalmic3 mg/1g
OintmentTopical1 mg/1g
SolutionOphthalmic3 mg/1mL
SolutionOphthalmic3.0 mg/1mL
Solution / dropsOphthalmic3 mg/1mL
SolutionIntravenous
Injection, solutionIntravenous0.6 mg/1mL
Injection, solutionIntravenous0.8 mg/1mL
Injection, solutionIntravenous0.9 mg/1mL
Injection, solutionIntravenous1 mg/1mL
Injection, solutionIntravenous1.2 mg/1mL
Injection, solutionIntravenous1.4 mg/1mL
Injection, solutionIntravenous1.6 mg/1mL
Injection, solutionIntravenous100 mg/50mL
Injection, solutionIntravenous100 mg/100mL
Injection, solutionIntravenous60 mg/50mL
Injection, solutionIntravenous80 mg/50mL
Injection, solutionIntravenous80 mg/100mL
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
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
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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 September 25, 2018 03:08