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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

Molecular Formula C21H43N5O7
Molecular Weight 477.5954
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 13 / 13
E/Z Centers 0
Optical Activity UNSPECIFIED

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
[Evaluation of ototoxicity of amikacin (BB-K8) by animal test (author's transl)].
1975 Jun
Acute renal failure associated with cephalosporin therapy.
1975 Jun
[The intratympanic treatment of Menière's disease with ototoxic antibiotics. A follow-up study of 55 cases (author's transl)].
1977 May
Reactive oxygen metabolites in toxic acute renal failure.
1992
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
Ototoxicity caused by aminoglycosides is ameliorated by melatonin without interfering with the antibiotic capacity of the drugs.
2000 Jan
Factors that affect absorption behavior of cyclosporin a in gentamicin-induced acute renal failure in rats.
2000 Mar
Protective effect of oral L-arginine administration on gentamicin-induced renal failure in rats.
2000 Mar 3
Expression of osteopontin in gentamicin-induced acute tubular necrosis and its recovery process.
2001 Mar
Inappropriate medical management of spinal epidural abscess.
2001 Mar
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
Endocarditis caused by methicillin-resistant Staphylococcus aureus: treatment failure with linezolid.
2002 Oct 15
Protective effect of Pongamia pinnata flowers against cisplatin and gentamicin induced nephrotoxicity in rats.
2003 Jan
Hearing loss after intratympanic gentamicin therapy for unilateral Ménière's Disease.
2003 Sep
alpha-L-iduronidase premature stop codons and potential read-through in mucopolysaccharidosis type I patients.
2004 Apr 30
Hematopoietic and nonhematopoietic potentials of Hoechst(low)/side population cells isolated from adult rat kidney.
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
Role of the renin-angiotensin system on the parathyroid hormone-related protein overexpression induced by nephrotoxic acute renal failure in the rat.
2005 Apr
[Expression of heat shock protein 70 mRNA in guinea pig cochlea with ototoxicity of gentamicin].
2005 Jun 25
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).
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:33:00 GMT 2023
Edited
by admin
on Fri Dec 15 15:33:00 GMT 2023
Record UNII
I904Y9FPPV
Record Status Validated (UNII)
Record Version
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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 GMT 2023 , Edited by admin on Fri Dec 15 15:33:00 GMT 2023
Code System Code Type Description
CHEBI
27412
Created by admin on Fri Dec 15 15:33:00 GMT 2023 , Edited by admin on Fri Dec 15 15:33:00 GMT 2023
PRIMARY
CAS
25876-10-2
Created by admin on Fri Dec 15 15:33:00 GMT 2023 , Edited by admin on Fri Dec 15 15:33:00 GMT 2023
PRIMARY
MESH
C100093
Created by admin on Fri Dec 15 15:33:00 GMT 2023 , Edited by admin on Fri Dec 15 15:33:00 GMT 2023
PRIMARY
EPA CompTox
DTXSID9023091
Created by admin on Fri Dec 15 15:33:00 GMT 2023 , Edited by admin on Fri Dec 15 15:33:00 GMT 2023
PRIMARY
FDA UNII
I904Y9FPPV
Created by admin on Fri Dec 15 15:33:00 GMT 2023 , Edited by admin on Fri Dec 15 15:33:00 GMT 2023
PRIMARY
PUBCHEM
72395
Created by admin on Fri Dec 15 15:33:00 GMT 2023 , Edited by admin on Fri Dec 15 15:33:00 GMT 2023
PRIMARY
NCI_THESAURUS
C76148
Created by admin on Fri Dec 15 15:33:00 GMT 2023 , Edited by admin on Fri Dec 15 15:33:00 GMT 2023
PRIMARY
MERCK INDEX
m5697
Created by admin on Fri Dec 15 15:33:00 GMT 2023 , Edited by admin on Fri Dec 15 15:33:00 GMT 2023
PRIMARY Merck Index
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