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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
Structure of GENTAMICIN C1 SULFATE

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

HIDE SMILES / InChI

Description
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).

Originator

Curator's Comment: Gentamicin was first reported in 1963 by Weinstein et al.

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
GARAMYCIN

Approved Use

Gentamicin 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 Date

1970
Curative
GARAMYCIN

Approved Use

Gentamicin 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 Date

1970
Curative
GARAMYCIN

Approved Use

Gentamicin 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 Date

1970
Curative
GARAMYCIN

Approved Use

Gentamicin 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 Date

1970
Curative
GARAMYCIN

Approved Use

Gentamicin 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 Date

1970
Curative
GARAMYCIN

Approved Use

Gentamicin 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 Date

1970
Curative
GARAMYCIN

Approved Use

Gentamicin 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 Date

1970
Curative
GARAMYCIN

Approved Use

Gentamicin 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 Date

1970
Curative
GARAMYCIN

Approved Use

Gentamicin 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 Date

1970
PubMed

PubMed

TitleDatePubMed
[Letter: Cauda equina syndrome due to intrathecal gentamicin].
1975 Jan 18
Nephrotoxicity of combined cephalothin-gentamicin regimen.
1975 Jun
Reactive oxygen metabolites in toxic acute renal failure.
1992
An investigation of the acute effect of gentamicin on the renal handling of electrolytes in the rat.
1992 Apr
Chrononephrotoxicity in rat of a vancomycin and gentamicin combination.
1992 Jul
Gentamicin-induced hypercalciuria in the rat: assessment of nephron site involved.
1992 Oct
Small molecules that selectively block RNA binding of HIV-1 Rev protein inhibit Rev function and viral production.
1993 Sep 24
Salicylate attenuates gentamicin-induced ototoxicity.
1999 Jul
Nephrotoxicity by dicloxacillin and gentamicin in 163 patients with intertrochanteric hip fractures.
2000
Renoprotective role of nifedipine during gentamicin therapy: randomized controlled trial.
2000 Dec
Antibacterials for the prophylaxis and treatment of bacterial endocarditis in children.
2001
Aminoglycoside-mediated suppression of nonsense mutations in late infantile neuronal ceroid lipofuscinosis.
2001
Renal osteopontin protein and mRNA upregulation during acute nephrotoxicity in the rat.
2001 Apr
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
Inappropriate medical management of spinal epidural abscess.
2001 Mar
Familial isolated parathyroid adenoma in a consanguineous family.
2001 May
Aortic root replacement in a patient with vancomycin-resistant Enterococcus faecium endocarditis and leukemia.
2001 Nov
The effect of calcium load and the calcium channel blocker verapamil on gentamicin nephrotoxicity in rats.
2002 Dec
Correction of CFTR malfunction and stimulation of Ca-activated Cl channels restore HCO3- secretion in cystic fibrosis bile ductular cells.
2002 Jan
The effect of treatment with gum Arabic on gentamicin nephrotoxicity in rats: a preliminary study.
2003 Jan
Gentamicin administration in Duchenne patients with premature stop codon. Preliminary results.
2003 May
Intratympanic gentamicin for intractable Meniere's disease: 5-year follow-up.
2003 Oct
Gentamicin-induced correction of CFTR function in patients with cystic fibrosis and CFTR stop mutations.
2003 Oct 9
Protective effects of glycyrrhizin on gentamicin-induced acute renal failure in rats.
2003 Sep
Classification and rescue of ROMK mutations underlying hyperprostaglandin E syndrome/antenatal Bartter syndrome.
2003 Sep
Inhibition of nuclear factor-kappaB activation attenuates tubulointerstitial nephritis induced by gentamicin.
2004
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
Effect of tempol (4-hydroxy tempo) on gentamicin-induced nephrotoxicity in rats.
2004 Feb
Gentamicin treatment induces simultaneous mesangial proliferation and apoptosis in rats.
2004 Jun
Evaluation of factors to decrease bioavailability of cyclosporin A in rats with gentamicin-induced acute renal failure.
2004 Mar
Deficiency of polycystin-2 reduces Ca2+ channel activity and cell proliferation in ADPKD lymphoblastoid cells.
2004 May
Correction of ATM gene function by aminoglycoside-induced read-through of premature termination codons.
2004 Nov 2
Delayed diagnosis of penicillin-resistant Streptococcus mitis endocarditis following single-dose amoxicillin prophylaxis in a child.
2004 Oct
Treatment of urinary tract infections among febrile young children with daily intravenous antibiotic therapy at a day treatment center.
2004 Oct
In vivo efficacy of linezolid in combination with gentamicin for the treatment of experimental endocarditis due to methicillin-resistant Staphylococcus aureus.
2004 Oct
Protective effect of L-arginine intake on the impaired renal vascular responses in the gentamicin-treated rats.
2005
Efficacy of a non-vancomycin-based peritoneal dialysis peritonitis protocol.
2005 Apr
Nociceptor and hair cell transducer properties of TRPA1, a channel for pain and hearing.
2005 Apr 20
Pyomyositis caused by methicillin-resistant Staphylococcus aureus.
2005 Apr 7
[Expression of heat shock protein 70 mRNA in guinea pig cochlea with ototoxicity of gentamicin].
2005 Jun 25
Aminoglycosides induce acute cell signaling and chronic cell death in renal cells that express the calcium-sensing receptor.
2005 May
Aminoglycoside suppression of nonsense mutations in severe hemophilia.
2005 Nov 1
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
Serratia marcescens was susceptible to gentamicin (mean MIC, 0.34±0.14 μg/ml).
Name Type Language
GENTAMICIN C1 SULFATE
Common Name English
GENTAMICIN C1, SULFATE
Common Name English
Code System Code Type Description
FDA UNII
WLI0S741IL
Created by admin on Fri Dec 15 15:55:26 GMT 2023 , Edited by admin on Fri Dec 15 15:55:26 GMT 2023
PRIMARY
EPA CompTox
DTXSID00191866
Created by admin on Fri Dec 15 15:55:26 GMT 2023 , Edited by admin on Fri Dec 15 15:55:26 GMT 2023
PRIMARY
PUBCHEM
44563965
Created by admin on Fri Dec 15 15:55:26 GMT 2023 , Edited by admin on Fri Dec 15 15:55:26 GMT 2023
PRIMARY
CAS
38539-12-7
Created by admin on Fri Dec 15 15:55:26 GMT 2023 , Edited by admin on Fri Dec 15 15:55:26 GMT 2023
PRIMARY