Gentamicin

Identification

Summary

Gentamicin is an aminoglycoside used to treat a wide variety of aerobic infections in the body.

Brand Names
Gentak, Pred-G, Valisone-G
Generic Name
Gentamicin
DrugBank Accession Number
DB00798
Background

Gentamicin is a bactericidal aminoglycoside that was discovered and isolated from Micromonospora purpurea in 1963.7 It is one of the most frequently prescribed aminoglycosides due to its spectrum of activity, low cost, and availability.5,8 Gentamicin is effective against both gram-positive and gram-negative organisms but is particularly useful for the treatment of severe gram-negative infections including those caused by Pseudomonas aeruginosa.6,10,11 There is the added benefit of synergy when gentamicin is co-administered with other antibacterials such as beta-lactams.11 This synergistic activity is not only important for the treatment of complex infections, but can also contribute to dose optimization and reduced adverse effects.10,11

Although gentamicin is well-established and may be used in a variety of clinical applications, it is also associated with severe adverse effects including nephrotoxicity and ototoxicity which may limit its use.12

Type
Small Molecule
Groups
Approved, Vet approved
Structure
Weight
Average: 1390.728
Monoisotopic: 1389.901796041
Chemical Formula
C60H123N15O21
Synonyms
  • Gentamicin
  • Gentamicina

Pharmacology

Indication

Not Available

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Associated Conditions
Indication TypeIndicationCombined Product DetailsApproval LevelAge GroupPatient CharacteristicsDose Form
Used in combination to treatBacterial conjunctivitisCombination Product in combination with: Dexamethasone (DB01234)•••••••••••••••••••• • •••••
Treatment ofBacterial infections••••••••••••
Treatment ofBacterial meningitis•••••••••••••••••••••• ••••••••• •••••••••• ••••••••• •••••••••••
Treatment ofBacterial corneal ulcer••••••••••••••••••••••
Treatment ofBacterial dacryocystitis••••••••••••••••••••••
Contraindications & Blackbox Warnings
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Pharmacodynamics

Not Available

Mechanism of action

There are 3 key phases of aminoglycoside entry into cells.9 The first “ionic binding phase” occurs when polycationic aminoglycosides bind electrostatically to negatively charged components of bacterial cell membranes including with lipopolysaccharides and phospholipids within the outer membrane of Gram-negative bacteria and to teichoic acids and phospholipids within the cell membrane of Gram-positive bacteria. This binding results in displacement of divalent cations and increased membrane permeability, allowing for aminoglycoside entry.9,13,14,15 The second “energy-dependent phase I” of aminoglycoside entry into the cytoplasm relies on the proton-motive force and allows a limited amount of aminoglycoside access to its primary intracellular target - the bacterial 30S ribosome.9,15 This ultimately results in the mistranslation of proteins and disruption of the cytoplasmic membrane.16 Finally, in the “energy-dependent phase II” stage, concentration-dependent bacterial killing is observed. Aminoglycoside rapidly accumulates in the cell due to the damaged cytoplasmic membrane, and protein mistranslation and synthesis inhibition is amplified.9,15 The necessity of oxygen-dependent active transport explains why aminoglycosides are ineffective against anaerobic bacteria.1 Hence, aminoglycosides have both immediate bactericidal effects through membrane disruption and delayed bactericidal effects through impaired protein synthesis; observed experimental data and mathematical modeling support this two-mechanism model.9 Inhibition of protein synthesis is a key component of aminoglycoside efficacy. Structural and cell biological studies suggest that aminoglycosides bind to the 16S rRNA in helix 44 (h44), near the A site of the 30S ribosomal subunit, altering interactions between h44 and h45. This binding also displaces two important residues, A1492 and A1493, from h44, mimicking normal conformational changes that occur with successful codon-anticodon pairing in the A site.17 Overall, aminoglycoside binding has several negative effects including inhibition of translation, initiation, elongation, and ribosome recycling.9,18,19 Recent evidence suggests that the latter effect is due to a cryptic second binding site situated in h69 of the 23S rRNA of the 50S ribosomal subunit.17,19 Also, by stabilizing a conformation that mimics correct codon-anticodon pairing, aminoglycosides promote error-prone translation.20 Mistranslated proteins can incorporate into the cell membrane, inducing the damage discussed above.9

TargetActionsOrganism
A30S ribosomal protein S12
binder
Escherichia coli (strain K12)
A16S ribosomal RNA
binder
Enteric bacteria and other eubacteria
A23S ribosomal RNA
inhibitor
Enteric bacteria and other eubacteria
ABacterial outer membrane
incorporation into and destabilization
Bacteria
ACytoplasmic membrane
incorporation into and destabilization
Bacteria
UNH(3)-dependent NAD(+) synthetase
inhibitor
Bacillus subtilis (strain 168)
UDihydrofolate reductaseNot AvailableHumans
Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Studies have determined that plasma protein binding of gentamicin is between 0-30% depending on the method of testing.21

Metabolism

Gentamicin undergoes little to no metabolism.24

Route of elimination

Gentamicin is excreted primarily by the kidneys. In patients with normal renal function, 70% or more of an initial gentamicin dose can be recovered in the urine within 24 hours. Excretion of gentamicin is significantly reduced in patients with renal impairment.24

Half-life

One study assessing the pharmacokinetics of gentamicin in children and adults reported a mean half-life of 75 minutes after intravenous administration.2 The mean half-life associated with intramuscular administration was about 29 minutes longer.2 Fever and anemia may result in a shorter half-life although dose adjustments are not usually necessary.2,24 Severe burns are also associated with a shorter half-life and may result in lower gentamicin serum concentrations.24

Clearance

The renal clearance of gentamicin is comparable to individual creatinine clearance.3,24

Adverse Effects
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Toxicity

As with other aminoglycosides, nephrotoxicity and ototoxicity are associated with gentamicin.9 Signs of nephrotoxicity include an increase in plasma creatinine and urea, while signs of ototoxicity include issues with balance, nausea, tinnitus, and hearing loss.5 It is important to note that aminoglycoside-induced nephrotoxicity is typically reversible, while ototoxicity is more likely to be permanent.9 The risk of both toxicities increases with long-term gentamicin therapy.1 Gentamicin is considered to be more vestibulotoxic than cochleotoxic compared to other aminoglycosides.9,4 Unfortunately, gentamicin-related ototoxicity does not correlate with cumulative dosing, peak and trough levels, or dosing schedule.5 The unpredictability of ototoxicity supports close monitoring of the patient throughout treatment.5 In cases of toxicity or overdose, the medication should be discontinued immediately; hemodialysis may be initiated to lower gentamicin serum concentrations.24

Pathways
PathwayCategory
Gentamicin Action PathwayDrug 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.
DrugInteraction
AbacavirAbacavir may decrease the excretion rate of Gentamicin 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.
AcetaminophenAcetaminophen may decrease the excretion rate of Gentamicin which could result in a higher serum level.
Food Interactions
No interactions found.

Products

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dosage, form, labeller, route of administration, and marketing period.
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Product Ingredients
IngredientUNIICASInChI Key
Gentamicin sulfate8X7386QRLV1405-41-0RDEIXVOBVLKYNT-VQBXQJRRSA-N
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
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Alcomicin Oph Sol 3mg/mlLiquid3 mg / mLOphthalmicAlcon, Inc.1983-12-312009-04-24Canada flag
Cidomycin Inj 10mg/mlLiquid10 mg / mLIntramuscular; IntravenousHoechst Roussel Canada Inc.1995-12-312000-07-28Canada flag
Cidomycin Inj 40mg/mlLiquid40 mg / mLIntramuscular; IntravenousRoussel Canada Inc.1979-12-311997-08-05Canada flag
Cidomycin Inj 40mg/mlLiquid40 mg / mLIntramuscular; IntravenousHoechst Roussel Canada Inc.1995-12-311999-08-20Canada flag
Cidomycin Inj Pediatric 10mgLiquid10 mg / mLIntramuscular; IntravenousRoussel Canada Inc.1972-12-311997-08-05Canada flag
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
GaramycinSolution / drops3 mg/1mLOphthalmicFera Pharmaceuticals2011-05-152013-06-14US flag
GaramycinOintment3 mg/1gOphthalmicFera Pharmaceuticals2010-10-082013-06-14US flag
Garamycin Gentamicin SulfateSolution3 mg/1mLOphthalmicPaddock Laboratories, Inc.2014-06-052016-04-01US flag
GentakOintment3 mg/1gOphthalmicA-S Medication Solutions2006-05-08Not applicableUS flag
GentakOintment3 mg/1gOphthalmicREMEDYREPACK INC.2017-07-242020-04-07US flag
Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
ELTACIN 0.1%Ointment0.1 %w/wTopicalบริษัท โอลิค (ประเทศไทย) จำกัด2008-04-01Not applicableThailand flag
GENTAL EYE DROPSLiquid3 mg/1mlOphthalmicบริษัท เยนเนอร์ราลดรั๊กส์เฮ้าส์ จำกัด1985-07-18Not applicableThailand flag
MIRAMYCIN EYE/EAR DROPLiquid3 mg/1mlOphthalmicบริษัท โรงงานเภสัชกรรมแอตแลนติค จำกัด1986-06-062020-06-11Thailand flag
ยาหยอดตา มาโนเจนต้าSolution40 mg/1mlบริษัท โรงงานเภสัชกรรมแหลมทองการแพทย์ จำกัด จำกัด2009-12-18Not applicableThailand flag
สกินเฟ็กต์ ครีมCream0.1 %w/wTopicalบริษัท บางกอกแล็ป แอนด์ คอสเมติค จำกัด จำกัด2000-07-12Not applicableThailand flag
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
Amolg AGentamicin sulfate (1 mg/1g) + Betamethasone valerate (0.61 mg/1g)CreamTopicalOASIS TRADING2018-11-15Not applicableUS flag
ANTASONE CREAMGentamicin (1 mg) + Betamethasone (1 mg/g)CreamTopicalZYFAS PHARMA PTE LTD1988-06-25Not applicableSingapore flag
B-MYCIN CREAMGentamicin (1 mg/g) + Betamethasone (0.5 mg/g)CreamTopicalYUNG SHIN PHARMACEUTICAL (SINGAPORE) PTE LTD2013-07-25Not applicableSingapore flag
B-TASONE-G CREAMGentamicin (0.3 % w/w) + Betamethasone (0.1 % w/w)CreamTopicalBEACONS PHARMACEUTICALS PTE. LTD.1990-02-26Not applicableSingapore flag
BELOGENT %0,05+%0,1 KREM, 15 GGentamicin sulfate (0.1 %) + Betamethasone dipropionate (0.05 %)CreamTopicalFARMA-TEK İLAÇ SAN. VE TİC. A.Ş.2015-09-29Not applicableTurkey flag
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
Amolg AGentamicin sulfate (1 mg/1g) + Betamethasone valerate (0.61 mg/1g)CreamTopicalOASIS TRADING2018-11-15Not applicableUS flag
Celestone-GGentamicin sulfate (1 mg/1g) + Betamethasone valerate (0.61 mg/1g)OintmentTopicalOASIS TRADING2018-11-15Not applicableUS flag
Celestone-GGentamicin sulfate (1 mg/1g) + Betamethasone valerate (0.61 mg/1g)OintmentTopicalOASIS TRADING2018-11-15Not applicableUS flag
GENSIF 20 MG/2 ML AMPULGentamicin (20 mg/2ml)InjectionIntramuscular; IntravenousAVİCENNA FARMA DIŞ TİC. VE PAZ. A.Ş.2019-04-30Not applicableTurkey flag
GENSIF 40 MG/2 ML AMPULGentamicin (40 mg/2ml)InjectionIntramuscular; IntravenousAVİCENNA FARMA DIŞ TİC. VE PAZ. A.Ş.2019-04-30Not applicableTurkey flag

Categories

ATC Codes
S01AA11 — GentamicinS02AA14 — GentamicinD06AX07 — GentamicinS03AA06 — GentamicinJ01GB03 — Gentamicin
Drug Categories
Classification
Not classified
Affected organisms
  • Enteric bacteria and other eubacteria
  • Pseudomonas aeruginosa
  • Yersinia pestis
  • Francisella tularensis
  • Serratia marcescens
  • Proteus vulgaris

Chemical Identifiers

UNII
T6Z9V48IKG
CAS number
1403-66-3
InChI Key
NPEFREDMMVQEPL-RWPARATISA-N
InChI
InChI=1S/C21H43N5O7.C20H41N5O7.C19H39N5O7/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;1-8(21)12-5-4-9(22)18(30-12)31-15-10(23)6-11(24)16(13(15)26)32-19-14(27)17(25-3)20(2,28)7-29-19;1-19(27)7-28-18(13(26)16(19)24-2)31-15-11(23)5-10(22)14(12(15)25)30-17-9(21)4-3-8(6-20)29-17/h9-20,25-29H,5-8,22-24H2,1-4H3;8-19,25-28H,4-7,21-24H2,1-3H3;8-18,24-27H,3-7,20-23H2,1-2H3/t9?,10-,11+,12-,13+,14+,15-,16-,17+,18-,19-,20-,21+;8?,9-,10+,11-,12+,13+,14-,15-,16+,17-,18-,19-,20+;8-,9+,10-,11+,12-,13+,14+,15-,16+,17+,18+,19-/m110/s1
IUPAC Name
(2R,3R,4R,5R)-2-{[(1S,2S,3R,4S,6R)-4,6-diamino-3-{[(2R,3R,6S)-3-amino-6-(1-aminoethyl)oxan-2-yl]oxy}-2-hydroxycyclohexyl]oxy}-5-methyl-4-(methylamino)oxane-3,5-diol; (2R,3R,4R,5R)-2-{[(1S,2S,3R,4S,6R)-4,6-diamino-3-{[(2R,3R,6S)-3-amino-6-(aminomethyl)oxan-2-yl]oxy}-2-hydroxycyclohexyl]oxy}-5-methyl-4-(methylamino)oxane-3,5-diol; (2R,3R,4R,5R)-2-{[(1S,2S,3R,4S,6R)-4,6-diamino-3-{[(2R,3R,6S)-3-amino-6-[1-(methylamino)ethyl]oxan-2-yl]oxy}-2-hydroxycyclohexyl]oxy}-5-methyl-4-(methylamino)oxane-3,5-diol
SMILES
[H][C@@]1(CN)CC[C@@H](N)[C@@H](O[C@]2([H])[C@@H](N)C[C@@H](N)[C@H](O[C@@]3([H])OC[C@](C)(O)[C@H](NC)[C@H]3O)[C@H]2O)O1.[H][C@]1(CC[C@@H](N)[C@@H](O[C@]2([H])[C@@H](N)C[C@@H](N)[C@H](O[C@@]3([H])OC[C@](C)(O)[C@H](NC)[C@H]3O)[C@H]2O)O1)C(C)N.[H][C@]1(CC[C@@H](N)[C@@H](O[C@]2([H])[C@@H](N)C[C@@H](N)[C@H](O[C@@]3([H])OC[C@](C)(O)[C@H](NC)[C@H]3O)[C@H]2O)O1)C(C)NC

References

Synthesis Reference

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

US4100268
General References
  1. Chaves BJ, Tadi P: Gentamicin . [Article]
  2. Siber GR, Echeverria P, Smith AL, Paisley JW, Smith DH: Pharmacokinetics of gentamicin in children and adults. J Infect Dis. 1975 Dec;132(6):637-51. doi: 10.1093/infdis/132.6.637. [Article]
  3. Jones TE, Peter JV, Field J: Aminoglycoside clearance is a good estimate of creatinine clearance in intensive care unit patients. Anaesth Intensive Care. 2009 Nov;37(6):944-52. doi: 10.1177/0310057X0903700611. [Article]
  4. Ahmed RM, Hannigan IP, MacDougall HG, Chan RC, Halmagyi GM: Gentamicin ototoxicity: a 23-year selected case series of 103 patients. Med J Aust. 2012 Jun 18;196(11):701-4. doi: 10.5694/mja11.10850. [Article]
  5. Black FO, Pesznecker S, Stallings V: Permanent gentamicin vestibulotoxicity. Otol Neurotol. 2004 Jul;25(4):559-69. doi: 10.1097/00129492-200407000-00025. [Article]
  6. Authors unspecified: Aminoglycosides . [Article]
  7. Authors unspecified: Gentamicin. Br Med J. 1967 Jan 21;1(5533):158-9. [Article]
  8. Kushner B, Allen PD, Crane BT: Frequency and Demographics of Gentamicin Use. Otol Neurotol. 2016 Feb;37(2):190-5. doi: 10.1097/MAO.0000000000000937. [Article]
  9. Serio AW, Keepers T, Andrews L, Krause KM: Aminoglycoside Revival: Review of a Historically Important Class of Antimicrobials Undergoing Rejuvenation. EcoSal Plus. 2018 Nov;8(1). doi: 10.1128/ecosalplus.ESP-0002-2018. [Article]
  10. Chen C, Chen Y, Wu P, Chen B: Update on new medicinal applications of gentamicin: evidence-based review. J Formos Med Assoc. 2014 Feb;113(2):72-82. doi: 10.1016/j.jfma.2013.10.002. Epub 2013 Nov 9. [Article]
  11. Krause KM, Serio AW, Kane TR, Connolly LE: Aminoglycosides: An Overview. Cold Spring Harb Perspect Med. 2016 Jun 1;6(6). pii: 6/6/a027029. doi: 10.1101/cshperspect.a027029. [Article]
  12. Hayward RS, Harding J, Molloy R, Land L, Longcroft-Neal K, Moore D, Ross JDC: Adverse effects of a single dose of gentamicin in adults: a systematic review. Br J Clin Pharmacol. 2018 Feb;84(2):223-238. doi: 10.1111/bcp.13439. Epub 2017 Nov 3. [Article]
  13. Moore RA, Bates NC, Hancock RE: Interaction of polycationic antibiotics with Pseudomonas aeruginosa lipopolysaccharide and lipid A studied by using dansyl-polymyxin. Antimicrob Agents Chemother. 1986 Mar;29(3):496-500. doi: 10.1128/aac.29.3.496. [Article]
  14. Hancock RE, Raffle VJ, Nicas TI: Involvement of the outer membrane in gentamicin and streptomycin uptake and killing in Pseudomonas aeruginosa. Antimicrob Agents Chemother. 1981 May;19(5):777-85. doi: 10.1128/aac.19.5.777. [Article]
  15. Taber HW, Mueller JP, Miller PF, Arrow AS: Bacterial uptake of aminoglycoside antibiotics. Microbiol Rev. 1987 Dec;51(4):439-57. [Article]
  16. Waters M, Tadi P: Streptomycin . [Article]
  17. Ying L, Zhu H, Shoji S, Fredrick K: Roles of specific aminoglycoside-ribosome interactions in the inhibition of translation. RNA. 2019 Feb;25(2):247-254. doi: 10.1261/rna.068460.118. Epub 2018 Nov 9. [Article]
  18. Wallace BJ, Tai PC, Herzog EL, Davis BD: Partial inhibition of polysomal ribosomes of Escherichia coli by streptomycin. Proc Natl Acad Sci U S A. 1973 Apr;70(4):1234-7. doi: 10.1073/pnas.70.4.1234. [Article]
  19. Borovinskaya MA, Pai RD, Zhang W, Schuwirth BS, Holton JM, Hirokawa G, Kaji H, Kaji A, Cate JH: Structural basis for aminoglycoside inhibition of bacterial ribosome recycling. Nat Struct Mol Biol. 2007 Aug;14(8):727-32. doi: 10.1038/nsmb1271. Epub 2007 Jul 29. [Article]
  20. Tai PC, Wallace BJ, Davis BD: Streptomycin causes misreading of natural messenger by interacting with ribosomes after initiation. Proc Natl Acad Sci U S A. 1978 Jan;75(1):275-9. doi: 10.1073/pnas.75.1.275. [Article]
  21. FDA Approved Drug Products: Gentamicin solution for injection [Link]
  22. FDA Approved Drug Products: PRED-G (gentamicin and prednisolone acetate) ophthalmic suspension [Link]
  23. FDA Approved Drug Products: PRED-G (gentamicin and prednisolone acetate) ophthalmic ointment [Link]
  24. DailyMed Drug Label Information: Gentamicin sulfate injection [Link]
  25. DailyMed Drug Label Information: Gentamicin ophthalmic solution [Link]
  26. DailyMed Drug Label Information: Gentamicin topical cream [Link]
  27. DPD Approved Drug Products: Gentamicin solution for injection [Link]
Human Metabolome Database
HMDB0014936
KEGG Compound
C00505
PubChem Compound
3467
PubChem Substance
46506523
ChemSpider
8074297
BindingDB
50476074
RxNav
1596450
ChEBI
17833
ChEMBL
CHEMBL3039597
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
MSDS
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Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4Active Not RecruitingTreatmentAppendicitis1
4CompletedNot AvailableStaphylococcus Aureus1
4CompletedPreventionBenign Prostatic Hyperplasia (BPH)1
4CompletedPreventionInguinal Hernias1
4CompletedPreventionKidney Stones / Urinary Tract Infection1

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
CreamTopical
CreamTopical0.1 %
Solution / dropsAuricular (otic); Ophthalmic
CreamTopical0.1 % w/w
Solution / dropsOphthalmic0.3 %W/V
Solution / dropsAuricular (otic); Ophthalmic0.3 %W/V
CreamTopical0.05 % w/w
OintmentCutaneous
Solution / dropsOphthalmic
SolutionIntramuscular160 mg
SolutionParenteral40 mg
SolutionParenteral120 mg
OintmentTopical
SolutionIntramuscular80 mg
SolutionIntravenous20 mg
LiquidIntramuscular; Intravenous40 mg / mL
LiquidIntramuscular; Intravenous10 mg / mL
Gel
OintmentTopical
OintmentOphthalmic0.3 g
Cream
CreamTopical0.1 % w/w
SolutionOphthalmic1 mg/ml
OintmentOphthalmic0.3 mg/g
SuspensionAuricular (otic)
OintmentTopical0.1 %w/w
Cream
InjectionIntramuscular; Intravenous
ImplantTopical130 mg
OintmentConjunctival; Ophthalmic300 mg
SolutionParenteral160 mg
SolutionParenteral80 mg
SolutionParenteral20.00 mg
CreamTopical.1 %
SolutionOphthalmic3 mg/1mL
SolutionIntramuscular; Intravenous10 mg / mL
SolutionIntramuscular; Intravenous40 mg / mL
OintmentTopical1 mg / g
OintmentOphthalmic0.3 %
Solution / dropsAuricular (otic)3 mg / mL
InjectionIntramuscular; Intravenous80 mg/2ml
SolutionAuricular (otic); Ophthalmic
Solution / dropsOphthalmic5 mg / mL
Solution / dropsAuricular (otic)5 mg / mL
Solution / dropsOphthalmic
CreamTopical
SolutionParenteral80.0 mg
GelTopical
Injection, solutionIntramuscular; Intravenous160 mg/2ml
Injection, solutionIntramuscular; Intravenous40 mg
Injection, solutionIntramuscular; Intravenous80 mg
Ointment
OintmentOphthalmic
SolutionParenteral160.000 mg
SolutionParenteral40.000 mg
SolutionParenteral20.000 mg
InjectionIntramuscular; Intravenous40 mg/1ml
InjectionIntramuscular; Intravenous40 mg/2ml
Solution / drops; suspension / dropsOphthalmic5 mg
OintmentOphthalmic5 mg
SolutionIntramuscular; Intravenous160 g
InjectionIntramuscular; Intravenous120 mg
InjectionIntramuscular; Intravenous160 mg
InjectionIntramuscular; Intravenous20 mg
InjectionIntramuscular; Intravenous40 mg
InjectionIntramuscular; Intravenous80 mg
Solution / dropsAuricular (otic)5 ml
Solution / dropsOphthalmic3 mg / mL
SolutionParenteral8 g
Solution / dropsAuricular (otic); Ophthalmic0.3 %
CreamTopical15 g
CreamTopical30 g
OintmentTopical15 g
OintmentTopical30 g
OintmentOphthalmic5 g
LiquidOphthalmic3 mg/1ml
Injection, solution10 MG/1ML
Injection, solution120 MG/1.5ML
Injection, solution160 MG/2ML
Injection, solution20 MG/2ML
OintmentTopical0.1 %
SolutionParenteral280 mg
Solution / dropsAuricular (otic); Ophthalmic5 ml
Injection, solutionIntramuscular
Injection, solution
Injection, solutionIntramuscular; Intravenous10 mg/1mL
Injection, solutionIntramuscular; Intravenous40 mg/1mL
SolutionOphthalmic.3 %
SolutionOphthalmic0.3 %
SolutionParenteral1 MG/ML
SolutionParenteral3 MG/ML
CreamTopical0.3 % w/w
Injection, solution40 mg/1ml
Kit
Injection, solutionParenteral40 MG/ML
Injection, solutionParenteral160 MG
Injection, solutionParenteral80 MG
SolutionIntramuscular; Intravenous80 mg/2ml
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 kg/1kg
PowderNot applicable1 g/1g
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/100mL
Injection, solutionIntravenous100 mg/50mL
Injection, solutionIntravenous60 mg/50mL
Injection, solutionIntravenous80 mg/50mL
Injection, solutionIntravenous80 mg/100mL
SolutionOphthalmic3 mg/ml
SolutionIntravenous1 mg / mL
SolutionIntravenous1.6 mg / mL
SolutionIntravenous1.2 mg / mL
CreamTopical0.1 g
SolutionConjunctival; Ophthalmic300000 mg
SolutionConjunctival; Ophthalmic0.003 g
SolutionConjunctival; Ophthalmic3 mg
SolutionParenteral126 mg
SolutionIntramuscular; Intravenous120 mg
SolutionIntramuscular120 mg
SolutionIntramuscular; Intravenous0.16 g
SolutionIntramuscular; Intravenous160 mg
SolutionIntramuscular; Intravenous; Parenteral20 mg
SolutionIntramuscular; Intravenous20 mg
SolutionIntramuscular; Intravenous40 mg
SolutionIntramuscular; Intravenous; Parenteral40 mg
SolutionIntramuscular; Intravenous80 mg
InjectionParenteral80 mg
SolutionIntramuscular; Intravenous; Parenteral80 mg
SolutionParenteral20 mg
SolutionIntramuscular; Intravenous16000000 mg
SolutionParenteral60 mg
Injection, solution80 MG/2ML
Injection, solutionParenteral40 MG/2ML
Injection, solutionParenteral80 MG/2ML
SolutionIntravenous3 mg
SolutionIntravenous80 mg
SolutionOphthalmic3.000 mg
Solution / dropsOphthalmic5 ml
Solution / dropsOphthalmic3 mg/ml
OintmentOphthalmic5 mg/g
InjectionIntramuscular; Intravenous160 mg/2ml
InjectionIntramuscular; Intravenous40 mg/ml
Solution / dropsOphthalmic3 %
SolutionParenteral80.000 mg
Injection, solutionIntramuscular; Intravenous
OintmentOphthalmic3 mg / g
Injection, solutionIntramuscular; Intravenous120 mg/2ml
Injection, solutionIntramuscular; Intravenous80 mg/2ml
Solution20 mg/2ml
InjectionIntramuscular; Intravenous120 mg/2ml
Solution / dropsAuricular (otic); Ophthalmic15 mg/5ml
InjectionIntramuscular; Intravenous20 mg/2ml
OintmentTopical5 gr
SolutionConjunctival; Ophthalmic214.8 mg
OintmentConjunctival; Ophthalmic0.537 g
CreamCutaneous
CreamTopical1 mg/g
CreamCutaneous0.1 %
SuspensionConjunctival; Ophthalmic
Solution / drops; suspension / dropsOphthalmic3 mg
CreamTopical1 mg
Ointment1 mg
SolutionParenteral1.6 mg
Ointment20 g
Ointment70 g
Solution / dropsOphthalmic; Topical0.3 % w/v
OintmentConjunctival; Ophthalmic0.3 g
Solution140 mg/1ml
CreamTopical0.3 %w/w
InjectionIntramuscular280 mg/2ml
InjectionParenteral
CreamTopical0.5 mg/g
LiquidOphthalmic; Topical3 mg / mL
OintmentOphthalmic; Topical3 mg / g
OintmentOphthalmic5 mg / g
SolutionOphthalmic5 mg / mL
SolutionOphthalmic3 mg
OintmentOphthalmic3 mg
SolutionOphthalmic0.3 % w/v
Solution / dropsOphthalmic0.3 % W/V
Solution / dropsAuricular (otic)5 mg
CreamCutaneous
CreamTopical1 mg / g
OintmentOphthalmic
Suspension / dropsOphthalmic
LiquidOphthalmic3 mg / mL
OintmentTopical.1 %
Injection, solutionParenteral10 mg
SolutionIntramuscular; Intravenous; Subconjunctival10 mg/2ml
Injection, solutionParenteral120 mg
SolutionIntramuscular; Intravenous; Subconjunctival120 mg/2ml
Injection, solutionParenteral40 mg
SolutionIntramuscular; Intravenous; Subconjunctival40 mg/ml
SolutionIntramuscular; Intravenous; Subconjunctival80 mg/2ml
Injection, powder, for solutionParenteral1.25 g
CreamTopical0.64 mg/g
Solution / dropsAuricular (otic); Ophthalmic
SolutionAuricular (otic)3 mg / mL
Bead
ImplantParenteral4.5 mg
Drug delivery systemTopical1.7 mg
Implant; spongeIntralesional
SolutionIntramuscular160.000 mg
Solution / dropsOphthalmic3 mg/5mL
Injection, solutionIntramuscular; Intravenous20 mg/2ml
Injection, solutionIntramuscular; Intravenous40 mg/ml
OintmentOphthalmic; Topical0.3 g
Solution10 mg/1ml
LiquidAuricular (otic); Ophthalmic
CreamTopical0.1 %w/w
Solution40 mg/1ml
Ointment
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
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)10.12Chemaxon
Physiological Charge5Chemaxon
Hydrogen Acceptor Count12Chemaxon
Hydrogen Donor Count8Chemaxon
Polar Surface Area199.73 Å2Chemaxon
Rotatable Bond Count19Chemaxon
Refractivity118.02 m3·mol-1Chemaxon
Polarizability51.52 Å3Chemaxon
Number of Rings9Chemaxon
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
Not Available
Chromatographic Properties
Collision Cross Sections (CCS)
Not Available

Targets

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Kind
Protein
Organism
Escherichia coli (strain K12)
Pharmacological action
Yes
Actions
Binder
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. [Article]
  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. [Article]
  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. [Article]
  4. Schroeder R, Waldsich C, Wank H: Modulation of RNA function by aminoglycoside antibiotics. EMBO J. 2000 Jan 4;19(1):1-9. [Article]
Kind
Nucleotide
Organism
Enteric bacteria and other eubacteria
Pharmacological action
Yes
Actions
Binder
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.
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. [Article]
  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. [Article]
  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. [Article]
  4. Schroeder R, Waldsich C, Wank H: Modulation of RNA function by aminoglycoside antibiotics. EMBO J. 2000 Jan 4;19(1):1-9. [Article]
Kind
Nucleotide
Organism
Enteric bacteria and other eubacteria
Pharmacological action
Yes
Actions
Inhibitor
In prokaryotes, the 23S rRNA is part of the large subunit (the 50S) that joins with the 30S small subunit to create the functional 70S ribosome. The ribosome is comprised of 3 RNAs: the 23S, the 16S and the 5S ribosomal RNAs. The 23S and the 5S associate with their respective proteins to make up the large subunit of the ribosome, while the 16S RNA associates with its proteins to make up the small subunit.
References
  1. Ying L, Zhu H, Shoji S, Fredrick K: Roles of specific aminoglycoside-ribosome interactions in the inhibition of translation. RNA. 2019 Feb;25(2):247-254. doi: 10.1261/rna.068460.118. Epub 2018 Nov 9. [Article]
  2. Borovinskaya MA, Pai RD, Zhang W, Schuwirth BS, Holton JM, Hirokawa G, Kaji H, Kaji A, Cate JH: Structural basis for aminoglycoside inhibition of bacterial ribosome recycling. Nat Struct Mol Biol. 2007 Aug;14(8):727-32. doi: 10.1038/nsmb1271. Epub 2007 Jul 29. [Article]
4. Bacterial outer membrane
Kind
Group
Organism
Bacteria
Pharmacological action
Yes
Actions
Incorporation into and destabilization
References
  1. Serio AW, Keepers T, Andrews L, Krause KM: Aminoglycoside Revival: Review of a Historically Important Class of Antimicrobials Undergoing Rejuvenation. EcoSal Plus. 2018 Nov;8(1). doi: 10.1128/ecosalplus.ESP-0002-2018. [Article]
  2. Moore RA, Bates NC, Hancock RE: Interaction of polycationic antibiotics with Pseudomonas aeruginosa lipopolysaccharide and lipid A studied by using dansyl-polymyxin. Antimicrob Agents Chemother. 1986 Mar;29(3):496-500. doi: 10.1128/aac.29.3.496. [Article]
  3. Hancock RE, Raffle VJ, Nicas TI: Involvement of the outer membrane in gentamicin and streptomycin uptake and killing in Pseudomonas aeruginosa. Antimicrob Agents Chemother. 1981 May;19(5):777-85. doi: 10.1128/aac.19.5.777. [Article]
  4. Taber HW, Mueller JP, Miller PF, Arrow AS: Bacterial uptake of aminoglycoside antibiotics. Microbiol Rev. 1987 Dec;51(4):439-57. [Article]
5. Cytoplasmic membrane
Kind
Group
Organism
Bacteria
Pharmacological action
Yes
Actions
Incorporation into and destabilization
References
  1. Serio AW, Keepers T, Andrews L, Krause KM: Aminoglycoside Revival: Review of a Historically Important Class of Antimicrobials Undergoing Rejuvenation. EcoSal Plus. 2018 Nov;8(1). doi: 10.1128/ecosalplus.ESP-0002-2018. [Article]
  2. Taber HW, Mueller JP, Miller PF, Arrow AS: Bacterial uptake of aminoglycoside antibiotics. Microbiol Rev. 1987 Dec;51(4):439-57. [Article]
  3. Davis BD, Chen LL, Tai PC: Misread protein creates membrane channels: an essential step in the bactericidal action of aminoglycosides. Proc Natl Acad Sci U S A. 1986 Aug;83(16):6164-8. doi: 10.1073/pnas.83.16.6164. [Article]
Kind
Protein
Organism
Bacillus subtilis (strain 168)
Pharmacological action
Unknown
Actions
Inhibitor
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. [Article]
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
  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. [Article]

Transporters

Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Substrate
General Function
Quaternary ammonium group transmembrane transporter activity
Specific Function
Mediates tubular uptake of organic compounds from circulation. Mediates the influx of agmatine, dopamine, noradrenaline (norepinephrine), serotonin, choline, famotidine, ranitidine, histamin, creat...
Gene Name
SLC22A2
Uniprot ID
O15244
Uniprot Name
Solute carrier family 22 member 2
Molecular Weight
62579.99 Da
References
  1. Gai Z, Visentin M, Hiller C, Krajnc E, Li T, Zhen J, Kullak-Ublick GA: Organic Cation Transporter 2 Overexpression May Confer an Increased Risk of Gentamicin-Induced Nephrotoxicity. Antimicrob Agents Chemother. 2016 Aug 22;60(9):5573-80. doi: 10.1128/AAC.00907-16. Print 2016 Sep. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Substrate
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. [Article]
  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. [Article]
  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. [Article]
  4. Elsakka EGE, Elsisi AM, Mansour OAA, Elsadek BEM, Abd Elaziz AI, Salama SA, Allam S: Androgen/androgen receptor affects gentamicin-induced nephrotoxicity through regulation of megalin expression. Life Sci. 2020 Jun 15;251:117628. doi: 10.1016/j.lfs.2020.117628. Epub 2020 Apr 2. [Article]
  5. Dagil R, O'Shea C, Nykjaer A, Bonvin AM, Kragelund BB: Gentamicin binds to the megalin receptor as a competitive inhibitor using the common ligand binding motif of complement type repeats: insight from the nmr structure of the 10th complement type repeat domain alone and in complex with gentamicin. J Biol Chem. 2013 Feb 8;288(6):4424-35. doi: 10.1074/jbc.M112.434159. Epub 2012 Dec 27. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Substrate
General Function
Organic anion transmembrane transporter activity
Specific Function
Mediates hepatobiliary excretion of numerous organic anions. May function as a cellular cisplatin transporter.
Gene Name
ABCC2
Uniprot ID
Q92887
Uniprot Name
Canalicular multispecific organic anion transporter 1
Molecular Weight
174205.64 Da
References
  1. Notenboom S, Wouterse AC, Peters B, Kuik LH, Heemskerk S, Russel FG, Masereeuw R: Increased apical insertion of the multidrug resistance protein 2 (MRP2/ABCC2) in renal proximal tubules following gentamicin exposure. J Pharmacol Exp Ther. 2006 Sep;318(3):1194-202. doi: 10.1124/jpet.106.104547. Epub 2006 Jun 6. [Article]

Drug created at June 13, 2005 13:24 / Updated at March 18, 2024 16:48