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Details

Stereochemistry ABSOLUTE
Molecular Formula C21H43N5O7
Molecular Weight 477.5954
Optical Activity UNSPECIFIED
Defined Stereocenters 13 / 13
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of GENTAMICIN C1

SMILES

[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=CEAZRRDELHUEMR-CAMVTXANSA-N
InChI=1S/C21H43N5O7/c1-9(25-3)13-6-5-10(22)19(31-13)32-16-11(23)7-12(24)17(14(16)27)33-20-15(28)18(26-4)21(2,29)8-30-20/h9-20,25-29H,5-8,22-24H2,1-4H3/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

1.46016E10
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

1.46016E10
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

1.46016E10
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

1.46016E10
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

1.46016E10
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

1.46016E10
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

1.45152E10
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

1.45152E10
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

1.45152E10
PubMed

PubMed

TitleDatePubMed
Renal damage caused by gentamicin: a study of the effects on renal morphology and urinary enzyme excretion.
1976 Mar
[The intratympanic treatment of Menière's disease with ototoxic antibiotics. A follow-up study of 55 cases (author's transl)].
1977 May
Effects of desoxycorticosterone acetate (DOCA) plus saline drinking on gentamicin-mediated nephropathy in rats.
1992
Comparison of methods for prediction of nephrotoxicity during development.
1992
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
Sense of smell after gentamicin nose-drops.
1992 Feb 1
Chrononephrotoxicity in rat of a vancomycin and gentamicin combination.
1992 Jul
Calcium supplementation and thyroid hormone protect against gentamicin-induced inhibition of proximal tubular Na+,K(+)-ATPase activity and other renal functional changes.
1992 Jun
Effects of aminoglycoside antibiotics on the auditory brainstem response and post rotatory nystagmus in rats.
1992 May
Detection of uremic peaks in dogs by anion exchange high performance liquid chromatography.
1992 Oct
Gentamicin-induced hypercalciuria in the rat: assessment of nephron site involved.
1992 Oct
Changes in concentration of essential metals in kidneys and urine as indices of gentamicin nephrotoxicity in female Wistar rats.
1992 Sep
Protective effect of Pongamia pinnata flowers against cisplatin and gentamicin induced nephrotoxicity in rats.
2003 Jan
Acute renal failure and cystic fibrosis.
2003 Jul
Diallyl disulfide ameliorates gentamicin-induced oxidative stress and nephropathy in rats.
2003 Jul 18
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
Hearing loss after intratympanic gentamicin therapy for unilateral Ménière's Disease.
2003 Sep
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
Absence of dystrophin in mice reduces NO-dependent vascular function and vascular density: total recovery after a treatment with the aminoglycoside gentamicin.
2004 Apr
alpha-L-iduronidase premature stop codons and potential read-through in mucopolysaccharidosis type I patients.
2004 Apr 30
Effects of some antibiotics on human erythrocyte 6-phosphogluconate dehydrogenase: an in vitro and in vivo study.
2004 Aug
Efficacy of the combination ampicillin plus ceftriaxone in the treatment of a case of enterococcal endocarditis due to Enterococcus faecalis highly resistant to gentamicin: efficacy of the "ex vivo" synergism method.
2004 Aug
Effect of tempol (4-hydroxy tempo) on gentamicin-induced nephrotoxicity in rats.
2004 Feb
Influence of spironolactone treatment on gentamicin-induced nephrotoxicity in rats.
2004 Jul
Altered NMDA receptor expression in renal toxicity: Protection with a receptor antagonist.
2004 Jul
Gentamicin treatment induces simultaneous mesangial proliferation and apoptosis in rats.
2004 Jun
Identification of putative gene based markers of renal toxicity.
2004 Mar
Evaluation of factors to decrease bioavailability of cyclosporin A in rats with gentamicin-induced acute renal failure.
2004 Mar
Hematopoietic and nonhematopoietic potentials of Hoechst(low)/side population cells isolated from adult rat kidney.
2004 May
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
Early gene expression in the organ of Corti exposed to gentamicin.
2004 Sep
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
Role of the renin-angiotensin system on the parathyroid hormone-related protein overexpression induced by nephrotoxic acute renal failure in the rat.
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
MI  
Common Name English
GENTAMICIN C1 [MI]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C2363
Created by admin on Fri Dec 15 15:33:00 UTC 2023 , Edited by admin on Fri Dec 15 15:33:00 UTC 2023
Code System Code Type Description
CHEBI
27412
Created by admin on Fri Dec 15 15:33:00 UTC 2023 , Edited by admin on Fri Dec 15 15:33:00 UTC 2023
PRIMARY
CAS
25876-10-2
Created by admin on Fri Dec 15 15:33:00 UTC 2023 , Edited by admin on Fri Dec 15 15:33:00 UTC 2023
PRIMARY
MESH
C100093
Created by admin on Fri Dec 15 15:33:00 UTC 2023 , Edited by admin on Fri Dec 15 15:33:00 UTC 2023
PRIMARY
EPA CompTox
DTXSID9023091
Created by admin on Fri Dec 15 15:33:00 UTC 2023 , Edited by admin on Fri Dec 15 15:33:00 UTC 2023
PRIMARY
FDA UNII
I904Y9FPPV
Created by admin on Fri Dec 15 15:33:00 UTC 2023 , Edited by admin on Fri Dec 15 15:33:00 UTC 2023
PRIMARY
PUBCHEM
72395
Created by admin on Fri Dec 15 15:33:00 UTC 2023 , Edited by admin on Fri Dec 15 15:33:00 UTC 2023
PRIMARY
NCI_THESAURUS
C76148
Created by admin on Fri Dec 15 15:33:00 UTC 2023 , Edited by admin on Fri Dec 15 15:33:00 UTC 2023
PRIMARY
MERCK INDEX
m5697
Created by admin on Fri Dec 15 15:33:00 UTC 2023 , Edited by admin on Fri Dec 15 15:33:00 UTC 2023
PRIMARY Merck Index