Accession Number
DB00798  (APRD00214)
Small Molecule
Approved, Vet approved

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).

  • Gentamicin
  • Gentamicina
Product Ingredients
IngredientUNIICASInChI Key
Gentamicin sulfate8X7386QRLV1405-41-0Not applicable
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Alcomicin Oph Sol 3mg/mlLiquidOphthalmicAlcon, Inc.1983-12-312009-04-24Canada
Cidomycin Inj 10mg/mlLiquidIntramuscular; IntravenousHoechst Roussel Canada Inc.1995-12-312000-07-28Canada
Cidomycin Inj 40mg/mlLiquidIntramuscular; IntravenousHoechst Roussel Canada Inc.1995-12-311999-08-20Canada
Cidomycin Inj 40mg/mlLiquidIntramuscular; IntravenousRoussel Canada Inc.1979-12-311997-08-05Canada
Cidomycin Inj Pediatric 10mgLiquidIntramuscular; IntravenousRoussel Canada Inc.1972-12-311997-08-05Canada
Garamycin Cream 0.1%CreamTopicalSchering Plough1966-12-312007-08-03Canada
Garamycin Inj 10mg/ml PediatricSolutionIntramuscular; IntravenousSchering Plough1970-12-312004-07-21Canada
Garamycin Inj 40mg/mlSolutionIntramuscular; IntravenousSchering Plough1966-12-312004-07-21Canada
Garamycin Ont 0.1%OintmentTopicalSchering Plough1966-12-312007-08-03Canada
Garamycin Ophthalmic Drops 0.3%Solution / dropsOphthalmicMerck Ltd.1981-12-312014-09-02Canada
Additional Data Available
  • Application Number
    Application Number

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

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  • Product Code
    Product Code

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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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/1gOphthalmicLake Erie Medical &Surgical Supply Dba Quality Care Products Llc2012-03-27Not applicableUs
GentakOintment3 mg/1gOphthalmicREMEDYREPACK INC.2017-07-24Not applicableUs
GentakOintment3 mg/1gOphthalmicRemedy Repack2012-11-212017-02-15Us
GentakOintment3 mg/1gOphthalmicProficient Rx LP2006-05-08Not applicableUs
GentakOintment3 mg/1gOphthalmicAkorn2006-05-08Not applicableUs
GentakOintment3 mg/1gOphthalmicAkorn2013-03-11Not applicableUs
Additional Data Available
  • Application Number
    Application Number

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

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  • Product Code
    Product Code

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
Amolg AGentamicin sulfate (1 mg/1g) + Betamethasone valerate (0.61 mg/1g)CreamTopicalOASIS TRADING2018-11-15Not applicableUs
Betamycin Ophthalmic/otic SolutionGentamicin (3 mg) + Betamethasone (1 mg)SolutionAuricular (otic); OphthalmicSterimax IncNot applicableNot applicableCanada
Celestone-GGentamicin sulfate (1 mg/1g) + Betamethasone valerate (0.61 mg/1g)OintmentTopicalOASIS TRADING2018-11-15Not applicableUs
Celestone-GGentamicin sulfate (1 mg/1g) + Betamethasone valerate (0.61 mg/1g)OintmentTopicalOASIS TRADING2018-11-15Not applicableUs
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 Healthcare Ulc1991-12-312018-11-22Canada
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
Amolg AGentamicin sulfate (1 mg/1g) + Betamethasone valerate (0.61 mg/1g)CreamTopicalOASIS TRADING2018-11-15Not applicableUs
Celestone-GGentamicin sulfate (1 mg/1g) + Betamethasone valerate (0.61 mg/1g)OintmentTopicalOASIS TRADING2018-11-15Not applicableUs
Celestone-GGentamicin sulfate (1 mg/1g) + Betamethasone valerate (0.61 mg/1g)OintmentTopicalOASIS TRADING2018-11-15Not applicableUs
International/Other Brands
Alcomicin / Bristagen / G-Mycin / Genoptic (Allergan) / Gentacidin / Gentafair / Gentamar / Jenamicin / Ocu-Mycin / Spectro-Genta / U-gencin (U-Liang)
CAS number
Average: 477.5954
Monoisotopic: 477.316248755
Chemical Formula
InChI Key



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

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.

A30S ribosomal protein S12
Escherichia coli (strain K12)
A16S ribosomal RNA
Enteric bacteria and other eubacteria
NLow-density lipoprotein receptor-related protein 2
UNH(3)-dependent NAD(+) synthetaseNot AvailableBacillus subtilis (strain 168)
UDihydrofolate reductaseNot AvailableHumans
Additional Data Available
Adverse Effects

Comprehensive structured data on known drug adverse effects with statistical prevalence. MedDRA and ICD10 ids are provided for adverse effect conditions and symptoms.

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Additional Data Available

Structured data covering drug contraindications. Each contraindication describes a scenario in which the drug is not to be used. Includes restrictions on co-administration, contraindicated populations, and more.

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Additional Data Available
Blackbox Warnings

Structured data representing warnings from the black box section of drug labels. These warnings cover important and dangerous risks, contraindications, or adverse effects.

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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%)

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.

Not Available

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
Gentamicin Action PathwayDrug action
Pharmacogenomic Effects/ADRs
Not Available


Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
(R)-warfarinThe risk or severity of bleeding can be increased when Gentamicin is combined with (R)-warfarin.
(S)-WarfarinThe risk or severity of bleeding can be increased when Gentamicin is combined with (S)-Warfarin.
4-hydroxycoumarinThe risk or severity of bleeding can be increased when Gentamicin is combined with 4-hydroxycoumarin.
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.
AceclofenacAceclofenac may decrease the excretion rate of Gentamicin which could result in a higher serum level.
AcemetacinAcemetacin may decrease the excretion rate of Gentamicin which could result in a higher serum level.
AcenocoumarolThe risk or severity of bleeding can be increased when Gentamicin is combined with Acenocoumarol.
AcetaminophenGentamicin may decrease the excretion rate of Acetaminophen which could result in a higher serum level.
AcetylcholineThe therapeutic efficacy of Acetylcholine can be decreased when used in combination with Gentamicin.
Additional Data Available
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  • Severity

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Food Interactions
No interactions found.


Synthesis Reference

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

General References
Not Available
External Links
Human Metabolome Database
KEGG Compound
PubChem Compound
PubChem Substance
Therapeutic Targets Database
Guide to Pharmacology
GtP Drug Page
RxList Drug Page Drug Page
PDRhealth Drug Page
ATC Codes
S01AA11 — GentamicinS02AA14 — GentamicinD06AX07 — GentamicinS03AA06 — GentamicinJ01GB03 — Gentamicin
AHFS Codes
  • 08:12.02 — Aminoglycosides
  • 52:04.04 — Antibacterials
  • 84:04.04 — Antibiotics
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Clinical Trials

Clinical Trials
0CompletedBasic ScienceBMI >30 kg/m2 / Diabetes / Inflammatory Reaction / Osteoporosis1
0CompletedTreatmentAntibiotic Resistance, Bacterial / Respiratory Failure / Respiratory Tract Infections (RTI)1
1CompletedHealth Services ResearchBreast Implant Infection / Breast Reconstruction1
1CompletedTreatmentBecker's Muscular Dystrophy (BMD) / Duchenne's Muscular Dystrophy (DMD)1
1CompletedTreatmentDuchenne's Muscular Dystrophy (DMD)1
1CompletedTreatmentVentilator-associated Bacterial Pneumonia / Ventilator-Associated Pneumonia (VAP)1
1, 2CompletedTreatmentRecessive Dystrophic Epidermolysis Bullosa2
1, 2RecruitingTreatmentJunctional Epidermolysis Bullosa2
1, 2RecruitingTreatmentRecessive Dystrophic Epidermolysis Bullosa1
1, 2TerminatedTreatmentDiabetic Foot Ulcers (DFU)1
2CompletedTreatmentBacteremia / Chronic Lung Disease of Prematurity / Chronic Lung Diseases / Ileal perforation / Intraventricular Hemorrhage / Necrotizing Enterocolitis / Periventricular Leukomalacia1
2CompletedTreatmentDiabetic Foot Ulcers (DFU)2
2CompletedTreatmentLeishmaniasis, Cutaneous2
2CompletedTreatmentRespiratory Tract Infections (RTI) / Tracheobronchitis / Ventilator-associated Bacterial Pneumonia1
2Not Yet RecruitingTreatmentHereditary Hypotrichosis Simplex1
2Not Yet RecruitingTreatmentNasopharyngeal Neoplasms / Stomatitis1
2Not Yet RecruitingTreatmentStomatitis1
2RecruitingPreventionNeurogenic Bladder Dysfunction / Spinal Cord Injuries (SCI)1
2RecruitingPreventionPelvic Organ Prolapse (POP) / Postoperative Urinary Tract Infection / Stress Urinary Incontinence (SUI)1
2RecruitingTreatmentAbdominal Abscess1
2TerminatedPreventionDiabetic Foot Ulcers (DFU)1
2TerminatedTreatmentCystic Fibrosis (CF)1
2TerminatedTreatmentLeishmaniasis, Cutaneous3
2TerminatedTreatmentPneumonia, Bacterial1
2, 3Active Not RecruitingPreventionNeurogenic Bladder Dysfunction / Spinal Cord Diseases / Spinal Cord Injuries (SCI) / Urinary Tract Infection1
2, 3CompletedPreventionChorioamnionitis / Neonatal Early Onset Sepsis / Neonatal Meningitis / Neonatal Pneumonia / Puerperal Endometritis1
2, 3CompletedTreatmentChorioamnionitis1
2, 3CompletedTreatmentComplicated Intra Abdominal Infections / Complicated Intra-Abdominal Infections1
2, 3CompletedTreatmentMenière's Disease1
2, 3CompletedTreatmentPlague1
2, 3CompletedTreatmentVentilator-associated Bacterial Pneumonia1
2, 3Not Yet RecruitingPreventionBypass Complication / Peripheral Vascular Disease Patient / Surgical Site Infections / Vascular Diseases1
2, 3RecruitingTreatmentMalignancies1
2, 3SuspendedTreatmentFolliculitis1
2, 3TerminatedTreatmentPharyngeal Gonococcal Infection1
3Active Not RecruitingTreatmentAntibiotic Resistance, Bacterial / Antibiotic Toxicity / Severe Malnutrition1
3Active Not RecruitingTreatmentDiabetic Foot Ulcers (DFU) / Infection2
3CompletedPreventionAxillary Drainage Volume After Lymph Node Dissection1
3CompletedPreventionBreast Cancer1
3CompletedPreventionPostoperative Wound Infection / Surgery, Colorectal1
3CompletedPreventionSternal Wound Infection / Surgery, Cardiac1
3CompletedTreatmentDermatitis, Eczematous1
3CompletedTreatmentInfection / Neonatal Sepsis / Sepsis1
3CompletedTreatmentLeishmaniasis, Cutaneous1
3Not Yet RecruitingTreatmentChronic Rhinosinusitis (Diagnosis)1
3Not Yet RecruitingTreatmentPneumonia1
3RecruitingTreatmentCat scratch disease1
3RecruitingTreatmentKeratitis; Infectious Disease (Manifestation)1
3Unknown StatusTreatmentBacterial Infections / Newborn Infants / Sepsis1
4Active Not RecruitingTreatmentExacerbation of Ulcerative Colitis / Granulomatous Colitis / Ulcerative Colitis, Active Severe1
4CompletedNot AvailablePerforated Appendicitis1
4CompletedNot AvailablePregnancy1
4CompletedNot AvailableStaphylococcus Aureus1
4CompletedPreventionBenign Prostatic Hyperplasia (BPH)1
4CompletedPreventionCalcium Nephrolithiasis / Urinary Tract Infection1
4CompletedPreventionInguinal Hernias1
4CompletedTreatmentComplicated Appendicitis1
4CompletedTreatmentDiabetic Foot Ulcers (DFU)1
4CompletedTreatmentInfant Bacterial Meningitis1
4CompletedTreatmentPeritonitis / Renal Failure1
4Enrolling by InvitationPreventionKidney Stones1
4RecruitingPreventionFractures, Open / Post-Op Wound Infection1
4RecruitingPreventionUrinary Tract Infection1
4RecruitingTreatmentBacterial Sinusitis1
4SuspendedPreventionVestibular Schwannomas2
4TerminatedOtherRenal Failure Chronic Requiring Hemodialysis1
4TerminatedTreatmentAtopic Dermatitis (AD) / Skin Diseases, Eczematous1
4TerminatedTreatmentInfective Endocarditis1
4Unknown StatusPreventionInfection1
4Unknown StatusPreventionRate of Atypical Mycobacterial Infection / Rate of Exit Site Infection / Rate of Peritoneal Dialysis1
4WithdrawnTreatmentChronic Rhinosinusitis1
4WithdrawnTreatmentUrinary Tract Infection1
Not AvailableActive Not RecruitingOtherColic / Gastrointestinal Diseases1
Not AvailableCompletedNot AvailableDrug Metabolism During Pregnancy1
Not AvailableCompletedNot AvailableEnd Stage Renal Disease (ESRD) / Infection1
Not AvailableCompletedNot AvailablePneumonia1
Not AvailableCompletedPreventionAntibiotic Resistance, Bacterial / Postoperative Wound Infection1
Not AvailableCompletedPreventionCholangitis1
Not AvailableCompletedSupportive CareVestibular Schwannomas1
Not AvailableCompletedTreatmentChorioamnionitis1
Not AvailableCompletedTreatmentKlebsiella Pneumoniae Carbapenemase Resistant Associated Bacteremia or Pneumonia / Patients Diagnosed With Concomitant KPC Associated Disease ,Bacteremia, Pneumonia1
Not AvailableCompletedTreatmentSepsis1
Not AvailableNot Yet RecruitingTreatmentOpen tíbia Fracture1
Not AvailableRecruitingPreventionCalcium Nephrolithiasis / Sepsis / Urinary Tract Infection1
Not AvailableRecruitingTreatmentBreast Cancer1
Not AvailableUnknown StatusNot AvailableAsymptomatic Infections / Bacteriuria / Transplantation Infection / Urinary Tract Infection1
Not AvailableUnknown StatusPreventionInfection1
Not AvailableUnknown StatusTreatmentChorioamnionitis1
Not AvailableUnknown StatusTreatmentPeritonitis1


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Dosage forms
LiquidIntramuscular; Intravenous
LiquidAuricular (otic); Ophthalmic
SolutionOphthalmic3 mg/1mL
SolutionAuricular (otic); Ophthalmic
Solution / dropsAuricular (otic)
Solution / dropsOphthalmic
Injection, solutionIntramuscular; Intravenous10 mg/1mL
Injection, solutionIntramuscular; Intravenous40 mg/1mL
OintmentOphthalmic0.3 %
SolutionOphthalmic.3 %
SolutionOphthalmic0.3 %
SolutionIntramuscular; Intravenous
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
PowderNot applicable1 g/1g
PowderNot applicable1 kg/1kg
SolutionOphthalmic3.0 mg/1mL
Solution / dropsOphthalmic3 mg/1mL
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/100mL
Injection, solutionIntravenous100 mg/50mL
Injection, solutionIntravenous60 mg/50mL
Injection, solutionIntravenous80 mg/100mL
Injection, solutionIntravenous80 mg/50mL
Solution / dropsOphthalmic; Topical
LiquidOphthalmic; Topical
OintmentOphthalmic; Topical
Suspension / dropsOphthalmic
SolutionAuricular (otic)
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.
Not Available


Experimental Properties
melting point (°C)105 °CPhysProp
water solubility100 mg/mLNot Available
logP-3.1Not Available
Predicted Properties
Water Solubility12.6 mg/mLALOGPS
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
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET features
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
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)


Mass Spec (NIST)
Not Available
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


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.
Organic compounds
Super Class
Organic oxygen compounds
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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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


Escherichia coli (strain K12)
Pharmacological action
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
Uniprot ID
Uniprot Name
30S ribosomal protein S12
Molecular Weight
13736.995 Da
  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]
Enteric bacteria and other eubacteria
Pharmacological action
In prokaryotes, the 16S rRNA is essential for recognizing the 5' end of mRNA and hence positioning it correctly on the ribosome. The 16S rRNA has a characteristic secondary structure in which half of the nucleotides are base-paired. The 16S rRNA sequence has been highly conserved and is often used for evolutionary and species comparative analysis.
  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]
Pharmacological action
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
Uniprot ID
Uniprot Name
Low-density lipoprotein receptor-related protein 2
Molecular Weight
521952.77 Da
  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]
Bacillus subtilis (strain 168)
Pharmacological action
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
Uniprot ID
Uniprot Name
NH(3)-dependent NAD(+) synthetase
Molecular Weight
30394.995 Da
  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]
Pharmacological action
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
Uniprot ID
Uniprot Name
Dihydrofolate reductase
Molecular Weight
21452.61 Da
  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]


Pharmacological action
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
Uniprot ID
Uniprot Name
Solute carrier family 22 member 6
Molecular Weight
61815.78 Da
  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 May 30, 2020 00:21

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