Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C21H43N5O7.H2O4S |
Molecular Weight | 575.674 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 13 / 13 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
OS(O)(=O)=O.[H][C@]1(CC[C@@H](N)[C@@]([H])(O[C@@H]2[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@@H](C)NC
InChI
InChIKey=NWQISSNHRDDWRM-FDJABWOBSA-N
InChI=1S/C21H43N5O7.H2O4S/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;1-5(2,3)4/h9-20,25-29H,5-8,22-24H2,1-4H3;(H2,1,2,3,4)/t9-,10-,11+,12-,13+,14+,15-,16-,17+,18-,19-,20-,21+;/m1./s1
DescriptionSources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2014/062366s033lbl.pdfhttps://www.drugbank.ca/drugs/DB00798Curator's Comment: Description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/26083124
Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2014/062366s033lbl.pdfhttps://www.drugbank.ca/drugs/DB00798
Curator's Comment: Description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/26083124
Gentamicin C1 is a part of gentamicin C complex, containing gentamicin C1, gentamicin C1a, and gentamicin C2 which compose approximately 80% of gentamicin and have been found to have the highest antibacterial activity. Commercial gentamicin C is a mixture of gentamicin C1, C1a, and C2. Gentamicin C1 has a methyl group in the 6' position of the 2-amino-hexose ring and is N methylated at the same position. 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. 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. Gentamicin complex is used 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).
CNS Activity
Sources: https://books.google.ru/books?id=tMfQvYKNVz4C&pg=PA5&lpg=PA5&dq=gentamicin+not+readily+crosses+the+blood-brain+barrier&source=bl&ots=1t9bQV5WFT&sig=4pWiwGUCNf8NuKWscVRE6Ag9aHI&hl=ru&sa=X&ved=0ahUKEwivs63J9u_LAhWrCpoKHUZgA90Q6AEIQzAE#v=onepage&q=gentamicin%20not%20readily%20crosses%20the%20blood-brain%20barrier&f=falsehttps://www.ncbi.nlm.nih.gov/pubmed/6431059
Curator's Comment: In studies of 70 rats, the permeability of the normal blood-brain barrier to gentamicin was shown to be poor.
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
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Target ID: CHEMBL354 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20970332 |
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Target ID: CHEMBL352 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20970332 |
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Target ID: 30S subunit of the bacterial ribosome |
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Target ID: CHEMBL614640 Sources: http://www.ncbi.nlm.nih.gov/pubmed/9822590 |
2.0 µM [Kd] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Curative | GARAMYCIN Approved UseGentamicin sulfate ophthalmic solution, USP is indicated in the topical treatment of ocular bacterial infections including conjunctivitis, keratitis, keratoconjunctivitis, corneal ulcers, blepharitis, blepharoconjunctivitis, acute meibomianitis, and dacryocystitis, caused by susceptible strains of the following microorganisms: Staphylococcus aureus, Staphylococcus epidermidis, Streptococcus pyogenes, Streptococcus pneumoniae, Enterobacter aerogenes, Escherichia coli, Haemophilus influenzae, Klebsiella pneumoniae, Neisseria gonorrhoeae, Pseudomonas aeruginosa, and Serratia marcescens. Launch Date1970 |
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Curative | GARAMYCIN Approved UseGentamicin sulfate ophthalmic solution, USP is indicated in the topical treatment of ocular bacterial infections including conjunctivitis, keratitis, keratoconjunctivitis, corneal ulcers, blepharitis, blepharoconjunctivitis, acute meibomianitis, and dacryocystitis, caused by susceptible strains of the following microorganisms: Staphylococcus aureus, Staphylococcus epidermidis, Streptococcus pyogenes, Streptococcus pneumoniae, Enterobacter aerogenes, Escherichia coli, Haemophilus influenzae, Klebsiella pneumoniae, Neisseria gonorrhoeae, Pseudomonas aeruginosa, and Serratia marcescens. Launch Date1970 |
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Curative | GARAMYCIN Approved UseGentamicin sulfate ophthalmic solution, USP is indicated in the topical treatment of ocular bacterial infections including conjunctivitis, keratitis, keratoconjunctivitis, corneal ulcers, blepharitis, blepharoconjunctivitis, acute meibomianitis, and dacryocystitis, caused by susceptible strains of the following microorganisms: Staphylococcus aureus, Staphylococcus epidermidis, Streptococcus pyogenes, Streptococcus pneumoniae, Enterobacter aerogenes, Escherichia coli, Haemophilus influenzae, Klebsiella pneumoniae, Neisseria gonorrhoeae, Pseudomonas aeruginosa, and Serratia marcescens. Launch Date1970 |
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Curative | GARAMYCIN Approved UseGentamicin sulfate ophthalmic solution, USP is indicated in the topical treatment of ocular bacterial infections including conjunctivitis, keratitis, keratoconjunctivitis, corneal ulcers, blepharitis, blepharoconjunctivitis, acute meibomianitis, and dacryocystitis, caused by susceptible strains of the following microorganisms: Staphylococcus aureus, Staphylococcus epidermidis, Streptococcus pyogenes, Streptococcus pneumoniae, Enterobacter aerogenes, Escherichia coli, Haemophilus influenzae, Klebsiella pneumoniae, Neisseria gonorrhoeae, Pseudomonas aeruginosa, and Serratia marcescens. Launch Date1970 |
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Curative | GARAMYCIN Approved UseGentamicin sulfate ophthalmic solution, USP is indicated in the topical treatment of ocular bacterial infections including conjunctivitis, keratitis, keratoconjunctivitis, corneal ulcers, blepharitis, blepharoconjunctivitis, acute meibomianitis, and dacryocystitis, caused by susceptible strains of the following microorganisms: Staphylococcus aureus, Staphylococcus epidermidis, Streptococcus pyogenes, Streptococcus pneumoniae, Enterobacter aerogenes, Escherichia coli, Haemophilus influenzae, Klebsiella pneumoniae, Neisseria gonorrhoeae, Pseudomonas aeruginosa, and Serratia marcescens. Launch Date1970 |
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Curative | GARAMYCIN Approved UseGentamicin sulfate ophthalmic solution, USP is indicated in the topical treatment of ocular bacterial infections including conjunctivitis, keratitis, keratoconjunctivitis, corneal ulcers, blepharitis, blepharoconjunctivitis, acute meibomianitis, and dacryocystitis, caused by susceptible strains of the following microorganisms: Staphylococcus aureus, Staphylococcus epidermidis, Streptococcus pyogenes, Streptococcus pneumoniae, Enterobacter aerogenes, Escherichia coli, Haemophilus influenzae, Klebsiella pneumoniae, Neisseria gonorrhoeae, Pseudomonas aeruginosa, and Serratia marcescens. Launch Date1970 |
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Curative | GARAMYCIN Approved UseGentamicin sulfate ophthalmic solution, USP is indicated in the topical treatment of ocular bacterial infections including conjunctivitis, keratitis, keratoconjunctivitis, corneal ulcers, blepharitis, blepharoconjunctivitis, acute meibomianitis, and dacryocystitis, caused by susceptible strains of the following microorganisms: Staphylococcus aureus, Staphylococcus epidermidis, Streptococcus pyogenes, Streptococcus pneumoniae, Enterobacter aerogenes, Escherichia coli, Haemophilus influenzae, Klebsiella pneumoniae, Neisseria gonorrhoeae, Pseudomonas aeruginosa, and Serratia marcescens. Launch Date1970 |
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Curative | GARAMYCIN Approved UseGentamicin sulfate ophthalmic solution, USP is indicated in the topical treatment of ocular bacterial infections including conjunctivitis, keratitis, keratoconjunctivitis, corneal ulcers, blepharitis, blepharoconjunctivitis, acute meibomianitis, and dacryocystitis, caused by susceptible strains of the following microorganisms: Staphylococcus aureus, Staphylococcus epidermidis, Streptococcus pyogenes, Streptococcus pneumoniae, Enterobacter aerogenes, Escherichia coli, Haemophilus influenzae, Klebsiella pneumoniae, Neisseria gonorrhoeae, Pseudomonas aeruginosa, and Serratia marcescens. Launch Date1970 |
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Curative | GARAMYCIN Approved UseGentamicin sulfate ophthalmic solution, USP is indicated in the topical treatment of ocular bacterial infections including conjunctivitis, keratitis, keratoconjunctivitis, corneal ulcers, blepharitis, blepharoconjunctivitis, acute meibomianitis, and dacryocystitis, caused by susceptible strains of the following microorganisms: Staphylococcus aureus, Staphylococcus epidermidis, Streptococcus pyogenes, Streptococcus pneumoniae, Enterobacter aerogenes, Escherichia coli, Haemophilus influenzae, Klebsiella pneumoniae, Neisseria gonorrhoeae, Pseudomonas aeruginosa, and Serratia marcescens. Launch Date1970 |
PubMed
Title | Date | PubMed |
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[Letter: Cauda equina syndrome due to intrathecal gentamicin]. | 1975 Jan 18 |
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Nephrotoxicity of combined cephalothin-gentamicin regimen. | 1975 Jun |
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Reactive oxygen metabolites in toxic acute renal failure. | 1992 |
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An investigation of the acute effect of gentamicin on the renal handling of electrolytes in the rat. | 1992 Apr |
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Chrononephrotoxicity in rat of a vancomycin and gentamicin combination. | 1992 Jul |
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Gentamicin-induced hypercalciuria in the rat: assessment of nephron site involved. | 1992 Oct |
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Small molecules that selectively block RNA binding of HIV-1 Rev protein inhibit Rev function and viral production. | 1993 Sep 24 |
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Salicylate attenuates gentamicin-induced ototoxicity. | 1999 Jul |
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Nephrotoxicity by dicloxacillin and gentamicin in 163 patients with intertrochanteric hip fractures. | 2000 |
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Renoprotective role of nifedipine during gentamicin therapy: randomized controlled trial. | 2000 Dec |
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Antibacterials for the prophylaxis and treatment of bacterial endocarditis in children. | 2001 |
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Aminoglycoside-mediated suppression of nonsense mutations in late infantile neuronal ceroid lipofuscinosis. | 2001 |
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Renal osteopontin protein and mRNA upregulation during acute nephrotoxicity in the rat. | 2001 Apr |
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Gentamicin-mediated suppression of Hurler syndrome stop mutations restores a low level of alpha-L-iduronidase activity and reduces lysosomal glycosaminoglycan accumulation. | 2001 Feb 1 |
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Inappropriate medical management of spinal epidural abscess. | 2001 Mar |
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Familial isolated parathyroid adenoma in a consanguineous family. | 2001 May |
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Aortic root replacement in a patient with vancomycin-resistant Enterococcus faecium endocarditis and leukemia. | 2001 Nov |
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The effect of calcium load and the calcium channel blocker verapamil on gentamicin nephrotoxicity in rats. | 2002 Dec |
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Correction of CFTR malfunction and stimulation of Ca-activated Cl channels restore HCO3- secretion in cystic fibrosis bile ductular cells. | 2002 Jan |
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The effect of treatment with gum Arabic on gentamicin nephrotoxicity in rats: a preliminary study. | 2003 Jan |
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Gentamicin administration in Duchenne patients with premature stop codon. Preliminary results. | 2003 May |
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Intratympanic gentamicin for intractable Meniere's disease: 5-year follow-up. | 2003 Oct |
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Gentamicin-induced correction of CFTR function in patients with cystic fibrosis and CFTR stop mutations. | 2003 Oct 9 |
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Protective effects of glycyrrhizin on gentamicin-induced acute renal failure in rats. | 2003 Sep |
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Classification and rescue of ROMK mutations underlying hyperprostaglandin E syndrome/antenatal Bartter syndrome. | 2003 Sep |
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Inhibition of nuclear factor-kappaB activation attenuates tubulointerstitial nephritis induced by gentamicin. | 2004 |
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Plasma protein extravasation and vascular endothelial growth factor expression with endothelial nitric oxide synthase induction in gentamicin-induced acute renal failure in rats. | 2004 Apr |
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Effect of tempol (4-hydroxy tempo) on gentamicin-induced nephrotoxicity in rats. | 2004 Feb |
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Gentamicin treatment induces simultaneous mesangial proliferation and apoptosis in rats. | 2004 Jun |
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Evaluation of factors to decrease bioavailability of cyclosporin A in rats with gentamicin-induced acute renal failure. | 2004 Mar |
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Deficiency of polycystin-2 reduces Ca2+ channel activity and cell proliferation in ADPKD lymphoblastoid cells. | 2004 May |
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Correction of ATM gene function by aminoglycoside-induced read-through of premature termination codons. | 2004 Nov 2 |
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Delayed diagnosis of penicillin-resistant Streptococcus mitis endocarditis following single-dose amoxicillin prophylaxis in a child. | 2004 Oct |
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Treatment of urinary tract infections among febrile young children with daily intravenous antibiotic therapy at a day treatment center. | 2004 Oct |
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In vivo efficacy of linezolid in combination with gentamicin for the treatment of experimental endocarditis due to methicillin-resistant Staphylococcus aureus. | 2004 Oct |
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Protective effect of L-arginine intake on the impaired renal vascular responses in the gentamicin-treated rats. | 2005 |
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Efficacy of a non-vancomycin-based peritoneal dialysis peritonitis protocol. | 2005 Apr |
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Nociceptor and hair cell transducer properties of TRPA1, a channel for pain and hearing. | 2005 Apr 20 |
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Pyomyositis caused by methicillin-resistant Staphylococcus aureus. | 2005 Apr 7 |
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[Expression of heat shock protein 70 mRNA in guinea pig cochlea with ototoxicity of gentamicin]. | 2005 Jun 25 |
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Aminoglycosides induce acute cell signaling and chronic cell death in renal cells that express the calcium-sensing receptor. | 2005 May |
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Aminoglycoside suppression of nonsense mutations in severe hemophilia. | 2005 Nov 1 |
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Gentamicin induces Jun-AP1 expression and JNK activation in renal glomeruli and cultured mesangial cells. | 2005 Sep 16 |
Patents
Sample Use Guides
In Vivo Use Guide
Curator's Comment: Gentamicin injection may be given IM or IV. Gentamicin is recommended to be administered in three equal doses every eight hours. For adult patients with life-threatening infections, dosages up to 5 mg/kg/day may be administered in three or four equal doses.
Adults: 3 mg/kg/day
Adult patients with life-threatening infections: 5 mg/kg/day
Children: 6 to 7.5 mg/kg/day
Infants and Neonates: 7.5 mg/kg/day
Premature or Full-Term Neonates One Week of Age or Less: 5 mg/kg/day
Route of Administration:
Other
In Vitro Use Guide
Sources: http://www.ncbi.nlm.nih.gov/pubmed/4790564/
Serratia marcescens was susceptible to gentamicin (mean MIC, 0.34±0.14 μg/ml).
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DTXSID00191866
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44563965
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38539-12-7
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PARENT (SALT/SOLVATE)
SUBSTANCE RECORD