Gentamicin
Identification
- Name
- Gentamicin
- Accession Number
- DB00798
- 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).
- Type
- Small Molecule
- Groups
- Approved, Vet approved
- Structure
Structure for Gentamicin (DB00798)
- Weight
- Average: 477.5954
Monoisotopic: 477.316248755 - Chemical Formula
- C21H43N5O7
- Synonyms
- Gentamicin
- Gentamicina
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
- Bacterial Conjunctivitis
- Bacterial Infections
- Bacterial dacryocystitis
- Blepharoconjunctivitis
- Central Nervous System Infections
- Conjunctivitis allergic
- Corneal infection
- Dermatitis infected
- Ecthyma
- Eczematous dermatitis infected
- Eye inflammation
- Folliculitis
- Furunculosis
- Gram-negative enteric bacilli neonatal sepsis
- Impetigo contagious
- Keratitis bacterial
- Keratoconjunctivitis
- Meibomianitis
- Meningitis, Bacterial
- Peritonitis bacterial
- Pustular Psoriasis (PP)
- Pustular acne
- Pyoderma Gangrenosum
- Seborrheic Dermatitis
- Septicemia gram-negative
- Skin Infections
- Skin and Subcutaneous Tissue Bacterial Infections
- Skin bacterial infection
- Sycosis barbae
- Bacterial blepharitis
- Bacterial corneal ulcers
- Complicated Bacterial Urinary Tract Infections
- Complicated Respiratory tract infection bacterial
- Ocular bacterial infections
- Severe Endocarditis enterococcal
- Severe Infection Pseudomonas aeruginosa
- Severe Staphylococcal infection
- Contraindications & Blackbox Warnings
Learn about our commercial Contraindications & Blackbox Warnings data.
Learn More- 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.
Target Actions Organism A30S ribosomal protein S12 adductEscherichia coli (strain K12) A16S ribosomal RNA adductEnteric bacteria and other eubacteria NLow-density lipoprotein receptor-related protein 2 other/unknownHumans UNH(3)-dependent NAD(+) synthetase Not Available Bacillus subtilis (strain 168) UDihydrofolate reductase Not Available Humans - 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
- Adverse Effects
Learn about our commercial Adverse Effects data.
Learn More- 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
Pathway Category Gentamicin Action Pathway Drug action - Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- 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.
Drug Interaction Unlock Additional DataAbacavir Gentamicin may decrease the excretion rate of Abacavir which could result in a higher serum level. Acarbose Gentamicin may decrease the excretion rate of Acarbose which could result in a higher serum level. Aceclofenac Aceclofenac may decrease the excretion rate of Gentamicin which could result in a higher serum level. Acemetacin Acemetacin may decrease the excretion rate of Gentamicin which could result in a higher serum level. Acenocoumarol The risk or severity of bleeding can be increased when Gentamicin is combined with Acenocoumarol. Acetaminophen Gentamicin may decrease the excretion rate of Acetaminophen which could result in a higher serum level. Acetylcholine The therapeutic efficacy of Acetylcholine can be decreased when used in combination with Gentamicin. Acetyldigitoxin The risk or severity of adverse effects can be increased when Gentamicin is combined with Acetyldigitoxin. Acetylsalicylic acid Acetylsalicylic acid may decrease the excretion rate of Gentamicin which could result in a higher serum level. Aclidinium Gentamicin may decrease the excretion rate of Aclidinium which could result in a higher serum level. Additional Data Available- Extended DescriptionExtended DescriptionAvailable for Purchase
Extended description of the mechanism of action and particular properties of each drug interaction.
Learn more - SeveritySeverityAvailable for Purchase
A severity rating for each drug interaction, from minor to major.
Learn more - Evidence LevelEvidence LevelAvailable for Purchase
A rating for the strength of the evidence supporting each drug interaction.
Learn more - ActionActionAvailable for Purchase
An effect category for each drug interaction. Know how this interaction affects the subject drug.
Learn more
- Food Interactions
- No interactions found.
Products
Purchasing individual compounds or compound libraries for your research?
Learn More- Product Ingredients
Ingredient UNII CAS InChI Key Gentamicin sulfate 8X7386QRLV 1405-41-0 Not applicable - International/Other Brands
- Alcomicin / Bristagen / G-Mycin / Genoptic (Allergan) / Gentacidin / Gentafair / Gentamar / Jenamicin / Ocu-Mycin / Spectro-Genta / U-gencin (U-Liang)
- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Unlock Additional DataAlcomicin Oph Sol 3mg/ml Liquid Ophthalmic Alcon, Inc. 1983-12-31 2009-04-24 Canada 
Cidomycin Inj 10mg/ml Liquid Intramuscular; Intravenous Hoechst Roussel Canada Inc. 1995-12-31 2000-07-28 Canada Cidomycin Inj 40mg/ml Liquid Intramuscular; Intravenous Roussel Canada Inc. 1979-12-31 1997-08-05 Canada Cidomycin Inj 40mg/ml Liquid Intramuscular; Intravenous Hoechst Roussel Canada Inc. 1995-12-31 1999-08-20 Canada Cidomycin Inj Pediatric 10mg Liquid Intramuscular; Intravenous Roussel Canada Inc. 1972-12-31 1997-08-05 Canada Garamycin Cream 0.1% Cream Topical Schering Plough 1966-12-31 2007-08-03 Canada Garamycin Inj 10mg/ml Pediatric Solution Intramuscular; Intravenous Schering Plough 1970-12-31 2004-07-21 Canada Garamycin Inj 40mg/ml Solution Intramuscular; Intravenous Schering Plough 1966-12-31 2004-07-21 Canada Garamycin Ont 0.1% Ointment Topical Schering Plough 1966-12-31 2007-08-03 Canada Garamycin Ophthalmic Drops 0.3% Solution / drops Ophthalmic Merck Ltd. 1981-12-31 2014-09-02 Canada Additional Data Available- Application NumberApplication NumberAvailable for Purchase
A unique ID assigned by the FDA when a product is submitted for approval by the labeller.
Learn more - Product CodeProduct CodeAvailable for Purchase
A governmentally-recognized ID which uniquely identifies the product within its regulatory market.
Learn more
- Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Unlock Additional DataGaramycin Ointment 3 mg/1g Ophthalmic Fera Pharmaceuticals 2010-10-08 2013-06-14 US 
Garamycin Solution / drops 3 mg/1mL Ophthalmic Fera Pharmaceuticals 2011-05-15 2013-06-14 US Garamycin Gentamicin Sulfate Solution 3 mg/1mL Ophthalmic Paddock Laboratories, Inc. 2014-06-05 2016-04-01 US Gentak Ointment 3 mg/1g Ophthalmic A-S Medication Solutions 2006-05-08 Not applicable US Gentak Ointment 3 mg/1g Ophthalmic Preferred Pharmaceuticals, Inc. 2012-10-23 Not applicable US Gentak Ointment 3 mg/1g Ophthalmic Proficient Rx LP 2006-05-08 Not applicable US Gentak Ointment 3 mg/1g Ophthalmic Remedy Repack 2012-11-21 2017-02-15 US Gentak Ointment 3 mg/1g Ophthalmic Lake Erie Medical & Surgical Supply DBA Quality Care Products LLC 2012-03-27 2019-10-11 US Gentak Ointment 3 mg/1g Ophthalmic Akorn, Inc. 2006-05-08 Not applicable US Gentak Ointment 3 mg/1g Ophthalmic A S Medication Solutions 2006-05-08 Not applicable US Additional Data Available- Application NumberApplication NumberAvailable for Purchase
A unique ID assigned by the FDA when a product is submitted for approval by the labeller.
Learn more - Product CodeProduct CodeAvailable for Purchase
A governmentally-recognized ID which uniquely identifies the product within its regulatory market.
Learn more
- Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image Amolg A Gentamicin sulfate (1 mg/1g) + Betamethasone valerate (0.61 mg/1g) Cream Topical OASIS TRADING 2018-11-15 Not applicable US Betamycin Ophthalmic/otic Solution Gentamicin (3 mg) + Betamethasone (1 mg) Solution Auricular (otic); Ophthalmic Sterimax Inc Not applicable Not applicable Canada Celestone-G Gentamicin sulfate (1 mg/1g) + Betamethasone valerate (0.61 mg/1g) Ointment Topical OASIS TRADING 2018-11-15 Not applicable US Celestone-G Gentamicin sulfate (1 mg/1g) + Betamethasone valerate (0.61 mg/1g) Ointment Topical OASIS TRADING 2018-11-15 Not applicable US Diprogen Cream Gentamicin sulfate (0.1 %) + Betamethasone (0.05 %) Cream Topical Merck Ltd. 1980-12-31 2017-03-13 Canada Diprogen Ointment Gentamicin (0.1 %) + Betamethasone (0.05 %) Ointment Topical Merck Ltd. 1980-12-31 2017-03-13 Canada Dom-gentamicin-betamethasone Gentamicin (3 mg) + Betamethasone (1 mg) Liquid Auricular (otic); Ophthalmic Dominion Pharmacal Not applicable Not applicable Canada Garasone Ophthalmic and Otic Solution Gentamicin (3 mg) + Betamethasone (1 mg) Solution Auricular (otic); Ophthalmic Merck Ltd. 1987-12-31 2014-04-01 Canada Garasone Ophthalmic Ointment Gentamicin (3 mg) + Betamethasone (1 mg) Ointment Ophthalmic Merck Ltd. 1983-12-31 2013-07-15 Canada Gentamicin Sulfate In 0.9% Sodium Chloride Injection Gentamicin (0.8 mg) + Sodium chloride (9 mg) Solution Intravenous Hospira Healthcare Ulc 1991-12-31 2018-11-22 Canada - Unapproved/Other Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image Amolg A Gentamicin sulfate (1 mg/1g) + Betamethasone valerate (0.61 mg/1g) Cream Topical OASIS TRADING 2018-11-15 Not applicable US Celestone-G Gentamicin sulfate (1 mg/1g) + Betamethasone valerate (0.61 mg/1g) Ointment Topical OASIS TRADING 2018-11-15 Not applicable US Celestone-G Gentamicin sulfate (1 mg/1g) + Betamethasone valerate (0.61 mg/1g) Ointment Topical OASIS TRADING 2018-11-15 Not applicable US
Categories
- ATC Codes
- S01AA11 — GentamicinS02AA14 — GentamicinD06AX07 — Gentamicin
- D06AX — Other antibiotics for topical use
- D06A — ANTIBIOTICS FOR TOPICAL USE
- D06 — ANTIBIOTICS AND CHEMOTHERAPEUTICS FOR DERMATOLOGICAL USE
- D — DERMATOLOGICALS
- S03AA — Antiinfectives
- S03A — ANTIINFECTIVES
- S03 — OPHTHALMOLOGICAL AND OTOLOGICAL PREPARATIONS
- S — SENSORY ORGANS
- Drug Categories
- Agents that produce neuromuscular block (indirect)
- alpha-Galactosidase, antagonists & inhibitors
- Aminoglycoside Antibacterials
- Anti-Bacterial Agents
- Anti-Infective Agents
- Antibacterials for Systemic Use
- Antibiotics for Topical Use
- Antiinfectives for Systemic Use
- Carbohydrates
- Dermatologicals
- Drugs that are Mainly Renally Excreted
- Drugs that are Mainly Renally Excreted with a Narrow Therapeutic Index
- Enzyme Inhibitors
- Gentamicins
- Glycosides
- Narrow Therapeutic Index Drugs
- Nephrotoxic agents
- OAT1/SLC22A6 inhibitors
- Ophthalmological and Otological Preparations
- Ophthalmologicals
- Otologicals
- Protein Synthesis Inhibitors
- Sensory Organs
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as aminocyclitol glycosides. These are organic compounds containing an amicocyclitol moiety glycosidically linked to a carbohydrate moiety. There are two major classes of aminoglycosides containing a 2-streptamine core. They are called 4,5- and 4,6-disubstituted 2-deoxystreptamines.
- Kingdom
- Organic compounds
- Super Class
- Organic oxygen compounds
- Class
- Organooxygen compounds
- Sub Class
- Carbohydrates and carbohydrate conjugates
- Direct Parent
- Aminocyclitol glycosides
- Alternative Parents
- 2-deoxystreptamine aminoglycosides / O-glycosyl compounds / Aminocyclitols and derivatives / Cyclohexylamines / Cyclohexanols / Oxanes / Monosaccharides / Tertiary alcohols / 1,2-aminoalcohols / Oxacyclic compounds show 5 more
- Substituents
- 1,2-aminoalcohol / 2-deoxystreptamine aminoglycoside / Acetal / Alcohol / Aliphatic heteromonocyclic compound / Amine / Amino cyclitol glycoside / Aminocyclitol or derivatives / Cyclic alcohol / Cyclitol or derivatives show 18 more
- Molecular Framework
- Aliphatic heteromonocyclic compounds
- External Descriptors
- Not Available
Chemical Identifiers
- UNII
- T6Z9V48IKG
- CAS number
- 1403-66-3
- 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
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
- 1596450
- ChEBI
- 17833
- ChEMBL
- CHEMBL329592
- Therapeutic Targets Database
- DAP000116
- PharmGKB
- PA449753
- Guide to Pharmacology
- GtP Drug Page
- RxList
- RxList Drug Page
- Drugs.com
- Drugs.com Drug Page
- PDRhealth
- PDRhealth Drug Page
- Wikipedia
- Gentamicin
- AHFS Codes
- 08:12.02 — Aminoglycosides
- 52:04.04 — Antibacterials
- 84:04.04 — Antibiotics
- MSDS
- Download (59.2 KB)
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count 4 Active Not Recruiting Treatment Exacerbation of Ulcerative Colitis / Granulomatous Colitis / Ulcerative Colitis, Active Severe 1 4 Completed Not Available Staphylococcus Aureus 1 4 Completed Prevention Benign Prostatic Hyperplasia (BPH) 1 4 Completed Prevention Calcium Nephrolithiasis / Urinary Tract Infection 1 4 Completed Prevention Inguinal Hernias 1 4 Completed Treatment Bacteremia 1 4 Completed Treatment Bronchiectasis 1 4 Completed Treatment Complicated Appendicitis 1 4 Completed Treatment Diabetic Foot Ulcers (DFU) 1 4 Completed Treatment Gonorrhoea 1
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
Form Route Strength Cream Topical Solution / drops Auricular (otic); Ophthalmic 1 mg/ml Solution / drops Ophthalmic 0.3 %W/V Solution / drops Auricular (otic); Ophthalmic 0.3 %W/V Cream Topical 0.05 % Ointment Topical 0.05 % Cream Topical 64 mg/100g Cream Topical 0.064 % w/w Ointment Cutaneous 0.17 % w/w Solution / drops Auricular (otic); Ophthalmic 0.3 % w/v Cream Topical 100 mg/100g Cream Topical 3 MG/G Solution Intramuscular 160 mg Ointment Topical Liquid Intramuscular; Intravenous Ointment 0.3 % Cream Topical 0.05 g Cream Topical 0.04 g Solution / drops Ophthalmic 1 mg/ml Suspension Auricular (otic) 90 mg Cream Topical 0.5 mg/g Ointment Topical 0.5 mg/g Cream Topical 0.5 mg Liquid Auricular (otic); Ophthalmic Ointment 100 mg/100g Implant Topical 130 mg Solution Parenteral 160 mg Solution Parenteral 80 mg Cream Topical Solution Ophthalmic 3 mg/1mL Ointment Topical Injection, solution 280 mg/2ml Solution Auricular (otic); Ophthalmic Solution / drops Auricular (otic) Solution / drops Ophthalmic Cream Topical 1.67 MG Injection, solution Intramuscular; Intravenous 160 mg/2ml Injection, solution Intramuscular; Intravenous 40 mg Injection, solution Intramuscular; Intravenous 80 mg Injection Intramuscular; Intravenous 20 mg/2ml Injection Intramuscular; Intravenous 40 mg/1ml Injection Intramuscular; Intravenous 40 mg/2ml Injection Intramuscular; Intravenous 80 mg/2ml Solution / drops; suspension / drops Ophthalmic 5 mg Ointment Ophthalmic 5 mg Solution 100 mg/ml Injection Intramuscular; Intravenous 120 mg Injection Intramuscular; Intravenous 160 mg Injection Intramuscular; Intravenous 20 mg Injection Intramuscular; Intravenous 40 mg Injection Intramuscular; Intravenous 80 mg Solution / drops Ophthalmic 0.3 % w/v Solution / drops Ophthalmic 1.5 g/100mL Solution / drops Auricular (otic) 5 ml Solution / drops Ophthalmic 0.1 % Solution / drops Ophthalmic 3 mg Cream Topical 0.1 % w/w Solution / drops Auricular (otic); Ophthalmic 0.3 % Cream Topical 15 g Cream Topical 30 g Ointment Topical 15 g Ointment Topical 30 g Ointment Ophthalmic 5 g Solution / drops Ophthalmic 300 mg/100mL Cream 25 mg/100g Solution / drops Auricular (otic); Ophthalmic 5 ml Injection, solution Intramuscular 80 MG/2ML Injection, solution Intramuscular; Intravenous 10 mg/1mL Injection, solution Intramuscular; Intravenous 40 mg/1mL Ointment Ophthalmic 0.3 % Solution Ophthalmic .3 % Solution Ophthalmic 0.3 % Cream Cutaneous 0.1 % Solution Parenteral 1 MG/ML Solution Parenteral 3 MG/ML Solution / drops Ophthalmic 1.4 g/100mL Solution Intramuscular; Intravenous Kit 5 mg Injection, solution Parenteral 40 MG/ML Injection, solution Parenteral 160 MG Injection, solution Parenteral 80 MG Solution Intramuscular; Intravenous 80 mg/2ml Cream Topical 1 mg/1g Cream Topical 1.6639 MG Injection, solution Intravenous 120 mg/50mL Injection, solution Intravenous 40 mg/100mL Injection, solution Intravenous 60 mg/100mL Injection, solution, concentrate Intramuscular; Intravenous 40 mg/1mL Injection, solution, concentrate Intravenous 10 mg/1mL Ointment Ointment Ophthalmic Ointment Ophthalmic 3 mg/1g Ointment Topical 1 mg/1g Powder Not applicable 1 g/1g Powder Not applicable 1 kg/1kg Solution Ophthalmic 3.0 mg/1mL Solution / drops Ophthalmic 3 mg/1mL Solution Intravenous Injection, solution Intravenous 0.6 mg/1mL Injection, solution Intravenous 0.8 mg/1mL Injection, solution Intravenous 0.9 mg/1mL Injection, solution Intravenous 1 mg/1mL Injection, solution Intravenous 1.2 mg/1mL Injection, solution Intravenous 1.4 mg/1mL Injection, solution Intravenous 1.6 mg/1mL Injection, solution Intravenous 100 mg/50mL Injection, solution Intravenous 100 mg/100mL Injection, solution Intravenous 60 mg/50mL Injection, solution Intravenous 80 mg/100mL Injection, solution Intravenous 80 mg/50mL Solution / drops Ophthalmic 0.3 % Solution Intravenous Cream Topical 0.1 g Solution Conjunctival; Ophthalmic 3 mg Solution Intramuscular; Intravenous 120 mg Solution Intramuscular; Intravenous 160 mg Solution Intramuscular; Intravenous 0.16 g Solution Intramuscular; Intravenous; Parenteral 20 mg Solution Intramuscular; Intravenous 20 mg Solution Intramuscular; Intravenous 40 mg Solution Intramuscular; Intravenous; Parenteral 40 mg Solution Intramuscular; Intravenous 80 mg Injection, solution Parenteral 40 MG/2ML Injection, solution Parenteral 80 MG/2ML Solution / drops Auricular (otic); Ophthalmic 1.4 g/100mL Solution / drops Ophthalmic 500 mg/100mL Solution / drops Ophthalmic 5 ml Cream Topical 0.065 % w/w Ointment Ophthalmic 5 mg/g Solution / drops Ophthalmic 3 mg/ml Injection Intramuscular; Intravenous 40 mg/ml Solution / drops Ophthalmic 3 % Solution Conjunctival; Ophthalmic 0.003 g Injection, solution Intramuscular; Intravenous 120 mg/2ml Injection, solution Intramuscular; Intravenous 20 mg/2ml Injection, solution Intramuscular; Intravenous 80 mg/2ml Injection Intramuscular; Intravenous 120 mg/2ml Solution / drops Auricular (otic); Ophthalmic 15 mg/5ml Injection Intramuscular; Intravenous 160 mg/2ml Ointment Topical 5 gr Injection, solution 80 mg/2mL Injection, solution 20 mg/2mL Cream Cutaneous 0.17 % W/W Solution / drops Ophthalmic 5 mg Ointment Ophthalmic 3 mg Solution / drops; suspension / drops Ophthalmic 3 mg Cream Topical 1 mg Ointment 1 mg Cream Topical 1.6 MG Solution / drops Ophthalmic; Topical Ointment Conjunctival; Ophthalmic 0.3 g Cream Topical 300 mg/100g Injection Intramuscular; Intravenous 28 0MG/2ML Cream Topical 0.3 % w/w Liquid Ophthalmic; Topical Ointment Ophthalmic; Topical Solution Ophthalmic Solution Ophthalmic 3 mg Solution / drops Auricular (otic) 5 mg Cream Cutaneous 0.1 %/g Solution / drops Auricular (otic); Ophthalmic 300 mg/100mL Ointment Ophthalmic Suspension / drops Ophthalmic Liquid Ophthalmic Cream Topical 0.1 % Injection, solution Parenteral 10 mg Solution Intramuscular; Intravenous; Subconjunctival 10 mg/2ml Injection, solution Parenteral 120 mg Solution Intramuscular; Intravenous; Subconjunctival 120 mg/2ml Cream Topical 1 mg/g Injection, solution Parenteral 40 mg Solution Intramuscular; Intravenous; Subconjunctival 40 mg/ml Solution Intramuscular; Intravenous; Subconjunctival 80 mg/2ml Solution / drops Auricular (otic); Ophthalmic Solution Auricular (otic) Bead Intracavitary 4.5 mg/1bead Implant Parenteral Cream Topical 50 mg/100g Cream Topical 0.05 mg Injection, solution Intramuscular; Intravenous 40 mg/ml Solution / drops Ophthalmic 1.6 g/100mL Solution / drops Ophthalmic 100 mg/100mL - Prices
Unit description Cost Unit Gentak 0.3% Ointment 3.5 gm Tube 19.99USD tube Gentamicin Sulfate 0.1% Cream 15 gm Tube 12.99USD tube Gentamicin Sulfate 0.1% Ointment 15 gm Tube 11.99USD tube Gentamicin Sulfate 0.3% Solution 5ml Bottle 11.99USD bottle Gentamicin sulfate powder 5.05USD g Gentamicin Sulfate 10 mg/ml Solution 2ml Vial 5.0USD vial Gentamicin 40 mg/ml 2.82USD ml Gentamicin ped 10 mg/ml vial 2.4USD ml Gentak 3 mg/ml eye drops 1.91USD ml Gentamicin 3 mg/ml eye drops 1.89USD ml Gentamicin 10 mg/ml vial 1.29USD ml Garamycin 0.3 % Ointment 1.2USD g Sandoz Gentamicin Sulfate 0.3 % Ointment 1.2USD g Garamycin 0.3 % Solution 0.75USD ml Sandoz Gentamicin Sulfate 0.3 % Solution 0.75USD ml Gentamicin 40 mg/ml vial 0.45USD ml Ratio-Gentamicin Sulfate 0.1 % Cream 0.43USD g Ratio-Gentamicin Sulfate 0.1 % Ointment 0.37USD g Gentamicin 0.1% cream 0.16USD g Iso gentamicin 120 mg/100 ml 0.09USD ml Gentamicin 90 mg/ns 100 ml pb 0.05USD ml Isoton gentamicin 40 mg/100 ml 0.05USD ml Gentamicin 60 mg/ns 100 ml pb 0.04USD ml Gentamicin 100 mg/ns 100 ml 0.03USD ml Gentamicin 80 mg/ns 100 ml pb 0.03USD ml DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 105 °C PhysProp water solubility 100 mg/mL Not Available logP -3.1 Not Available - Predicted Properties
Property Value Source Water Solubility 12.6 mg/mL ALOGPS logP -1.6 ALOGPS logP -3.1 ChemAxon logS -1.6 ALOGPS pKa (Strongest Acidic) 12.55 ChemAxon pKa (Strongest Basic) 10.18 ChemAxon Physiological Charge 5 ChemAxon Hydrogen Acceptor Count 12 ChemAxon Hydrogen Donor Count 8 ChemAxon Polar Surface Area 199.73 Å2 ChemAxon Rotatable Bond Count 7 ChemAxon Refractivity 118.02 m3·mol-1 ChemAxon Polarizability 51.92 Å3 ChemAxon Number of Rings 3 ChemAxon Bioavailability 0 ChemAxon Rule of Five No ChemAxon Ghose Filter No ChemAxon Veber's Rule No ChemAxon MDDR-like Rule Yes ChemAxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption - 0.944 Blood Brain Barrier - 0.9826 Caco-2 permeable - 0.6987 P-glycoprotein substrate Substrate 0.6882 P-glycoprotein inhibitor I Non-inhibitor 0.6808 P-glycoprotein inhibitor II Non-inhibitor 0.9586 Renal organic cation transporter Non-inhibitor 0.8738 CYP450 2C9 substrate Non-substrate 0.8001 CYP450 2D6 substrate Non-substrate 0.8314 CYP450 3A4 substrate Substrate 0.5917 CYP450 1A2 substrate Non-inhibitor 0.9034 CYP450 2C9 inhibitor Non-inhibitor 0.891 CYP450 2D6 inhibitor Non-inhibitor 0.9331 CYP450 2C19 inhibitor Non-inhibitor 0.9043 CYP450 3A4 inhibitor Non-inhibitor 0.9517 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9294 Ames test Non AMES toxic 0.7338 Carcinogenicity Non-carcinogens 0.9696 Biodegradation Not ready biodegradable 0.9588 Rat acute toxicity 2.0383 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9954 hERG inhibition (predictor II) Non-inhibitor 0.8784
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS Not Available Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-0i29-1319700000-e55d2931137c5abc8493 Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-03di-0904000000-de986ac47725d8f3a72a Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-0592-9602000000-c7fd77457525743faeba Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-014i-2911100000-93e47b752e7992b12263 Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-014i-2958400000-7303bf3ebe16dd1c1d60 Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-0udi-2692000000-a8234ed8e0131019f62b
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
- 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]
- 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]
- 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]
- Schroeder R, Waldsich C, Wank H: Modulation of RNA function by aminoglycoside antibiotics. EMBO J. 2000 Jan 4;19(1):1-9. [PubMed:10619838]
Yes
Adduct
References
- 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]
- 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]
- 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]
- 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
- Humans
- 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
- 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]
- 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]
- 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
- 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
- Humans
- 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
- 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
- Humans
- 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
- 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 November 25, 2020 08:52
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