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

Similar Structures

Weight: Average: 1390.728
Monoisotopic: 1389.901796041
Chemical Formula: C₆₀H₁₂₃N₁₅O₂₁

Synonyms

Gentamicin
Gentamicina

Pharmacology

Indication

Not Available

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Associated Conditions

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

Target	Actions	Organism
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 reductase	Not Available	Humans

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

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
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Abacavir	Abacavir may decrease the excretion rate of Gentamicin 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	Acetaminophen may decrease the excretion rate of Gentamicin 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	Aclidinium may decrease the excretion rate of Gentamicin which could result in a higher serum level.
Acrivastine	Acrivastine may decrease the excretion rate of Gentamicin which could result in a higher serum level.

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Food Interactions

No interactions found.

Products

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Product Ingredients

Ingredient	UNII	CAS	InChI Key
Gentamicin sulfate	8X7386QRLV	1405-41-0	RDEIXVOBVLKYNT-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

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End
Alcomicin Oph Sol 3mg/ml	Liquid	3 mg / mL	Ophthalmic	Alcon, Inc.	1983-12-31	2009-04-24
Cidomycin Inj 10mg/ml	Liquid	10 mg / mL	Intramuscular; Intravenous	Hoechst Roussel Canada Inc.	1995-12-31	2000-07-28
Cidomycin Inj 40mg/ml	Liquid	40 mg / mL	Intramuscular; Intravenous	Roussel Canada Inc.	1979-12-31	1997-08-05
Cidomycin Inj 40mg/ml	Liquid	40 mg / mL	Intramuscular; Intravenous	Hoechst Roussel Canada Inc.	1995-12-31	1999-08-20
Cidomycin Inj Pediatric 10mg	Liquid	10 mg / mL	Intramuscular; Intravenous	Roussel Canada Inc.	1972-12-31	1997-08-05
Garamycin Cream 0.1%	Cream	.1 %	Topical	Schering Plough	1966-12-31	2007-08-03
Garamycin Inj 10mg/ml Pediatric	Solution	10 mg / mL	Intramuscular; Intravenous	Schering Plough	1970-12-31	2004-07-21
Garamycin Inj 40mg/ml	Solution	40 mg / mL	Intramuscular; Intravenous	Schering Plough	1966-12-31	2004-07-21
Garamycin Ont 0.1%	Ointment	1 mg / g	Topical	Schering Plough	1966-12-31	2007-08-03
Garamycin Ophthalmic Drops 0.3%	Solution / drops	3 mg / mL	Ophthalmic	Merck Ltd.	1981-12-31	2014-09-02

Generic Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End
Garamycin	Ointment	3 mg/1g	Ophthalmic	Fera Pharmaceuticals	2010-10-08	2013-06-14
Garamycin	Solution / drops	3 mg/1mL	Ophthalmic	Fera Pharmaceuticals	2011-05-15	2013-06-14
Garamycin Gentamicin Sulfate	Solution	3 mg/1mL	Ophthalmic	Paddock Laboratories, Inc.	2014-06-05	2016-04-01
Gentak	Ointment	3 mg/1g	Ophthalmic	A-S Medication Solutions	2006-05-08	Not applicable
Gentak	Ointment	3 mg/1g	Ophthalmic	Lake Erie Medical & Surgical Supply DBA Quality Care Products LLC	2012-03-27	2019-10-11
Gentak	Ointment	3 mg/1g	Ophthalmic	Nucare Pharmaceuticals,inc.	2006-05-08	Not applicable
Gentak	Ointment	3 mg/1g	Ophthalmic	Proficient Rx LP	2006-05-08	Not applicable
Gentak	Ointment	3 mg/1g	Ophthalmic	Remedy Repack	2012-11-21	2017-02-15
Gentak	Ointment	3 mg/1g	Ophthalmic	REMEDYREPACK INC.	2017-07-24	2020-04-07
Gentak	Ointment	3 mg/1g	Ophthalmic	Akorn	2013-03-11	Not applicable

Over the Counter Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End
ELTACIN 0.1%	Ointment	0.1 %w/w	Topical	บริษัท โอลิค (ประเทศไทย) จำกัด	2008-04-01	Not applicable
GENTAL EYE DROPS	Liquid	3 mg/1ml	Ophthalmic	บริษัท เยนเนอร์ราลดรั๊กส์เฮ้าส์ จำกัด	1985-07-18	Not applicable
MIRAMYCIN EYE/EAR DROP	Liquid	3 mg/1ml	Ophthalmic	บริษัท โรงงานเภสัชกรรมแอตแลนติค จำกัด	1986-06-06	2020-06-11
ยาหยอดตา มาโนเจนต้า	Solution	40 mg/1ml		บริษัท โรงงานเภสัชกรรมแหลมทองการแพทย์ จำกัด จำกัด	2009-12-18	Not applicable
สกินเฟ็กต์ ครีม	Cream	0.1 %w/w	Topical	บริษัท บางกอกแล็ป แอนด์ คอสเมติค จำกัด จำกัด	2000-07-12	Not applicable
เจนซิดาล ครีม	Cream	0.1 %w/w	Topical	บริษัท ไทยนครพัฒนา จำกัด	1998-11-05	Not applicable
เย็นตั้ล ครีม	Cream	0.1 %w/w	Topical	บริษัท เยนเนอร์ราลดรั๊กส์เฮ้าส์ จำกัด	1984-04-25	Not applicable
เยนต้า ครีม	Cream	0.1 %w/w	Topical	บริษัท เอเชี่ยนยูเนี่ยนแล็บบอราตอรี่ จำกัด จำกัด	1987-03-27	Not applicable
เย็นต้า-อ๊อฟ ยาหยอดตา	Liquid	3 mg/1ml	Ophthalmic	บริษัท แสงไทยกำปะนี จำกัด	1986-07-07	Not applicable
เยนตาเดอร์ม ครีม	Cream	0.1 %w/w	Topical	บริษัท ที.โอ.เคมีคอลส์ (1979) จำกัด	1990-06-26	Not applicable

Mixture Products

Name	Ingredients	Dosage	Route	Labeller	Marketing Start	Marketing End
Amolg A	Gentamicin sulfate (1 mg/1g) + Betamethasone valerate (0.61 mg/1g)	Cream	Topical	OASIS TRADING	2018-11-15	Not applicable
ANTASONE CREAM	Gentamicin (1 mg) + Betamethasone (1 mg/g)	Cream	Topical	ZYFAS PHARMA PTE LTD	1988-06-25	Not applicable
B-MYCIN CREAM	Gentamicin (1 mg/g) + Betamethasone (0.5 mg/g)	Cream	Topical	YUNG SHIN PHARMACEUTICAL (SINGAPORE) PTE LTD	2013-07-25	Not applicable
B-TASONE-G CREAM	Gentamicin (0.3 % w/w) + Betamethasone (0.1 % w/w)	Cream	Topical	BEACONS PHARMACEUTICALS PTE. LTD.	1990-02-26	Not applicable
BELOGENT %0,05+%0,1 KREM, 15 G	Gentamicin sulfate (0.1 %) + Betamethasone dipropionate (0.05 %)	Cream	Topical	FARMA-TEK İLAÇ SAN. VE TİC. A.Ş.	2020-08-14	Not applicable
BELOGENT %0,05+%0,1 KREM, 30 G	Gentamicin sulfate (0.1 %) + Betamethasone dipropionate (0.05 %)	Cream	Topical	FARMA-TEK İLAÇ SAN. VE TİC. A.Ş.	2020-08-14	Not applicable
BELOGENT %0,05+%0,1 MERHEM, 15 G	Gentamicin sulfate (0.1 %) + Betamethasone dipropionate (0.05 %)	Ointment	Topical	FARMA-TEK İLAÇ SAN. VE TİC. A.Ş.	2020-08-14	Not applicable
BELOGENT %0,05+%0,1 MERHEM, 30 G	Gentamicin sulfate (0.1 %) + Betamethasone dipropionate (0.05 %)	Ointment	Topical	FARMA-TEK İLAÇ SAN. VE TİC. A.Ş.	2020-08-14	Not applicable
BEPROGENT CREAM	Gentamicin sulfate (0.1 % w/w) + Betamethasone dipropionate (0.05 % w/w)	Cream	Topical	ZUELLIG PHARMA PTE. LTD.	1996-11-28	Not applicable
BEPROGENT OINTMENT	Gentamicin sulfate (0.17 % w/w) + Betamethasone dipropionate (0.064 % w/w)	Ointment	Cutaneous	HOE PHARMACEUTICALS SDN. BHD.	2020-09-08	Not applicable

Unapproved/Other Products

Name	Ingredients	Dosage	Route	Labeller	Marketing Start	Marketing End
Amolg A	Gentamicin sulfate (1 mg/1g) + Betamethasone valerate (0.61 mg/1g)	Cream	Topical	OASIS TRADING	2018-11-15	Not applicable
Celestone-G	Gentamicin sulfate (1 mg/1g) + Betamethasone valerate (0.61 mg/1g)	Ointment	Topical	OASIS TRADING	2018-11-15	Not applicable
Celestone-G	Gentamicin sulfate (1 mg/1g) + Betamethasone valerate (0.61 mg/1g)	Ointment	Topical	OASIS TRADING	2018-11-15	Not applicable
GENSIF 20 MG/2 ML AMPUL	Gentamicin (20 mg/2ml)	Injection	Intramuscular; Intravenous	AVİCENNA FARMA DIŞ TİC. VE PAZ. A.Ş.	2020-08-14	Not applicable
GENSIF 40 MG/2 ML AMPUL	Gentamicin (40 mg/2ml)	Injection	Intramuscular; Intravenous	AVİCENNA FARMA DIŞ TİC. VE PAZ. A.Ş.	2020-08-14	Not applicable
GENSIF 80 MG/2 ML AMPUL	Gentamicin (80 mg/2ml)	Injection	Intramuscular; Intravenous	AVİCENNA FARMA DIŞ TİC. VE PAZ. A.Ş.	2020-08-14	Not applicable

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

Chaves BJ, Tadi P: Gentamicin . [Article]
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]
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]
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]
Black FO, Pesznecker S, Stallings V: Permanent gentamicin vestibulotoxicity. Otol Neurotol. 2004 Jul;25(4):559-69. doi: 10.1097/00129492-200407000-00025. [Article]
Authors unspecified: Aminoglycosides . [Article]
Authors unspecified: Gentamicin. Br Med J. 1967 Jan 21;1(5533):158-9. [Article]
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]
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]
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]
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]
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]
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]
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]
Taber HW, Mueller JP, Miller PF, Arrow AS: Bacterial uptake of aminoglycoside antibiotics. Microbiol Rev. 1987 Dec;51(4):439-57. [Article]
Waters M, Tadi P: Streptomycin . [Article]
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]
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]
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]
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]
FDA Approved Drug Products: Gentamicin solution for injection [Link]
FDA Approved Drug Products: PRED-G (gentamicin and prednisolone acetate) ophthalmic suspension [Link]
FDA Approved Drug Products: PRED-G (gentamicin and prednisolone acetate) ophthalmic ointment [Link]
DailyMed Drug Label Information: Gentamicin sulfate injection [Link]
DailyMed Drug Label Information: Gentamicin ophthalmic solution [Link]
DailyMed Drug Label Information: Gentamicin topical cream [Link]
DPD Approved Drug Products: Gentamicin solution for injection [Link]

External Links

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

Phase	Status	Purpose	Conditions	Count
4	Active Not Recruiting	Treatment	Appendicitis	1
4	Completed	Not Available	Staphylococcus Aureus	1
4	Completed	Prevention	Benign Prostatic Hyperplasia (BPH)	1
4	Completed	Prevention	Inguinal Hernias	1
4	Completed	Prevention	Kidney Stones / Urinary Tract Infection	1
4	Completed	Treatment	Bacteremia	1
4	Completed	Treatment	Bronchiectasis	1
4	Completed	Treatment	Complicated Appendicitis	1
4	Completed	Treatment	Diabetic Foot Ulcers (DFUs)	1
4	Completed	Treatment	Infant Bacterial Meningitis	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
Cream	Topical	0.1 %
Solution / drops	Auricular (otic); Ophthalmic
Cream	Topical	0.1 % w/w
Solution / drops	Ophthalmic	0.3 %W/V
Solution / drops	Auricular (otic); Ophthalmic	0.3 %W/V
Cream	Topical	0.05 % w/w
Ointment	Cutaneous
Solution / drops	Ophthalmic
Solution	Parenteral	40 mg
Ointment	Topical
Solution	Intramuscular	160 mg
Solution	Intravenous	20 mg
Liquid	Intramuscular; Intravenous	40 mg / mL
Liquid	Intramuscular; Intravenous	10 mg / mL
Gel
Ointment	Ophthalmic	0.3 g
Cream	Topical	0.05 g
Cream
Cream	Topical	0.1 % w/w
Solution	Ophthalmic	1 mg/ml
Ointment	Ophthalmic	0.3 mg/g
Suspension	Auricular (otic)
Ointment	Topical	0.1 %w/w
Cream
Injection	Intramuscular; Intravenous
Implant	Topical	130 mg
Ointment	Conjunctival; Ophthalmic	300 mg
Solution	Parenteral	20.00 mg
Cream	Topical	.1 %
Solution	Ophthalmic	3 mg/1mL
Solution	Intramuscular; Intravenous	10 mg / mL
Solution	Intramuscular; Intravenous	40 mg / mL
Ointment	Topical	1 mg / g
Ointment	Ophthalmic	0.3 %
Solution / drops	Auricular (otic)	3 mg / mL
Injection	Intramuscular; Intravenous	80 mg/2ml
Solution	Auricular (otic); Ophthalmic
Solution / drops	Ophthalmic	5 mg / mL
Solution / drops	Auricular (otic)	5 mg / mL
Solution / drops	Ophthalmic
Injection	Intramuscular; Intravenous	80 mg
Solution	Parenteral	80.0 mg
Gel	Topical
Injection, solution	Intramuscular; Intravenous	160 mg/2ml
Injection, solution	Intramuscular; Intravenous	40 mg
Injection, solution	Intramuscular; Intravenous	80 mg
Ointment
Ointment	Ophthalmic
Solution	Parenteral	160.000 mg
Solution	Parenteral	40.000 mg
Solution	Parenteral	20.000 mg
Injection	Intramuscular; Intravenous	20 mg/2ml
Injection	Intramuscular; Intravenous	40 mg/1ml
Injection	Intramuscular; Intravenous	40 mg/2ml
Solution / drops; suspension / drops	Ophthalmic	5 mg
Ointment	Ophthalmic	5 mg
Solution	Intramuscular; Intravenous	160 g
Injection	Intramuscular; Intravenous	120 mg
Injection	Intramuscular; Intravenous	160 mg
Injection	Intramuscular; Intravenous	20 mg
Injection	Intramuscular; Intravenous	40 mg
Solution / drops	Auricular (otic)	5 ml
Solution / drops	Ophthalmic	3 mg / mL
Solution	Parenteral	8 g
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
Liquid	Ophthalmic	3 mg/1ml
Injection, solution
Ointment	Topical
Solution	Parenteral	280 mg
Solution / drops	Auricular (otic); Ophthalmic	5 ml
Injection, solution	Intramuscular
Injection, solution	Intramuscular; Intravenous	10 mg/1mL
Injection, solution	Intramuscular; Intravenous	40 mg/1mL
Solution	Ophthalmic	.3 %
Solution	Ophthalmic	0.3 %
Solution	Parenteral
Solution	Parenteral	1 MG/ML
Solution	Parenteral	3 MG/ML
Cream	Topical	0.3 % w/w
Injection, solution		40 mg/1ml
Kit
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
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	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/100mL
Injection, solution	Intravenous	100 mg/50mL
Injection, solution	Intravenous	60 mg/50mL
Injection, solution	Intravenous	80 mg/100mL
Injection, solution	Intravenous	80 mg/50mL
Solution	Ophthalmic	3 mg/ml
Solution	Intravenous	1 mg / mL
Solution	Intravenous	1.6 mg / mL
Solution	Intravenous	1.2 mg / mL
Cream	Topical	0.1 g
Solution	Conjunctival; Ophthalmic	3 mg
Solution	Parenteral	120 mg
Solution	Parenteral	126 mg
Solution	Intramuscular; Intravenous	120 mg
Solution	Intramuscular	120 mg
Solution	Intramuscular; Intravenous	0.16 g
Solution	Intramuscular; Intravenous	160 mg
Solution	Parenteral	160 mg
Solution	Intramuscular; Intravenous; Parenteral	20 mg
Solution	Intramuscular; Intravenous	20 mg
Solution	Intramuscular; Intravenous	40 mg
Solution	Intramuscular; Intravenous; Parenteral	40 mg
Solution	Intramuscular	80 mg
Injection	Parenteral	80 mg
Solution	Intramuscular; Intravenous; Parenteral	80 mg
Solution	Parenteral	20 mg
Solution	Parenteral	60 mg
Injection, solution		80 MG/2ML
Injection, solution	Parenteral	40 MG/2ML
Injection, solution	Parenteral	80 MG/2ML
Solution	Ophthalmic	3 mg
Solution	Intravenous	3 mg
Solution	Intramuscular; Intravenous	80 mg
Solution	Parenteral	80 mg
Solution	Intravenous	80 mg
Solution	Ophthalmic	3.000 mg
Solution / drops	Ophthalmic	5 ml
Ointment	Ophthalmic	5 mg/g
Solution / drops	Ophthalmic	3 mg/ml
Injection	Intramuscular; Intravenous	160 mg/2ml
Injection	Intramuscular; Intravenous	40 mg/ml
Solution / drops	Ophthalmic	3 %
Solution	Parenteral	80.000 mg
Injection, solution	Intramuscular; Intravenous
Solution	Conjunctival; Ophthalmic	0.003 g
Ointment	Ophthalmic	3 mg / g
Injection, solution	Intramuscular; Intravenous	120 mg/2ml
Injection, solution	Intramuscular; Intravenous	80 mg/2ml
Solution		20 mg/2ml
Injection	Intramuscular; Intravenous	120 mg/2ml
Solution / drops	Auricular (otic); Ophthalmic	15 mg/5ml
Ointment	Topical	5 gr
Solution	Conjunctival; Ophthalmic	214.8 mg
Ointment	Conjunctival; Ophthalmic	0.537 g
Cream	Cutaneous
Cream	Topical	1 mg/g
Cream	Cutaneous	0.1 %
Suspension	Conjunctival; Ophthalmic
Solution / drops; suspension / drops	Ophthalmic	3 mg
Cream	Topical	1 mg
Ointment		1 mg
Solution	Parenteral	1.6 mg
Ointment		20 g
Ointment		70 g
Solution / drops	Ophthalmic; Topical	0.3 % w/v
Ointment	Conjunctival; Ophthalmic	0.3 g
Solution		140 mg/1ml
Cream	Topical	0.3 %w/w
Injection	Intramuscular	280 mg/2ml
Injection	Parenteral
Cream	Topical	0.5 mg/g
Liquid	Ophthalmic; Topical	3 mg / mL
Ointment	Ophthalmic; Topical	3 mg / g
Ointment	Ophthalmic	5 mg / g
Solution	Ophthalmic	5 mg / mL
Ointment	Ophthalmic	3 mg
Solution	Ophthalmic	0.3 % w/v
Solution / drops	Ophthalmic	0.3 % W/V
Solution / drops	Auricular (otic)	5 mg
Cream	Cutaneous
Cream	Topical	1 mg / g
Ointment	Ophthalmic
Suspension / drops	Ophthalmic
Liquid	Ophthalmic	3 mg / mL
Ointment	Topical	.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
Injection, solution	Parenteral	40 mg
Solution	Intramuscular; Intravenous; Subconjunctival	40 mg/ml
Solution	Intramuscular; Intravenous; Subconjunctival	80 mg/2ml
Injection, powder, for solution	Parenteral	1.25 g
Cream	Topical	0.64 mg/g
Solution / drops	Auricular (otic); Ophthalmic
Solution	Auricular (otic)	3 mg / mL
Bead
Implant	Parenteral	4.5 mg
Drug delivery system	Topical	1.7 mg
Implant; sponge	Intralesional
Solution	Intramuscular	160.000 mg
Solution / drops	Ophthalmic	3 mg/5mL
Injection, solution	Intramuscular; Intravenous	20 mg/2ml
Injection, solution	Intramuscular; Intravenous	40 mg/ml
Ointment	Ophthalmic; Topical	0.3 g
Solution		10 mg/1ml
Liquid	Auricular (otic); Ophthalmic
Cream	Topical	0.1 %w/w
Solution		40 mg/1ml
Ointment

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
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)	10.12	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	19	Chemaxon
Refractivity	118.02 m³·mol^-1	Chemaxon
Polarizability	51.52 Å³	Chemaxon
Number of Rings	9	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

ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST): Not Available
Spectra: Not Available

Targets

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Details1. 30S ribosomal protein S12

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

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

Details2. 16S ribosomal RNA

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

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

Details3. 23S ribosomal RNA

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

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]
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

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]
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]
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]
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

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]
Taber HW, Mueller JP, Miller PF, Arrow AS: Bacterial uptake of aminoglycoside antibiotics. Microbiol Rev. 1987 Dec;51(4):439-57. [Article]
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]

Details6. NH(3)-dependent NAD(+) synthetase

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

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]

Details7. Dihydrofolate reductase

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. [Article]

Transporters

Details1. Solute carrier family 22 member 2

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

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]

Details2. Low-density lipoprotein receptor-related protein 2

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

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]
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]
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]
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]
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]

Details3. Canalicular multispecific organic anion transporter 1

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

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 December 01, 2023 08:05

Gentamicin

Identification

Structure for Gentamicin (DB00798)

Pharmacology

Interactions

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Clinical Trials

Pharmacoeconomics

Properties

Spectra

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Transporters

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