GENTAMICIN C1A

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C19H39N5O7
Molecular Weight	449.5423
Optical Activity	UNSPECIFIED
Defined Stereocenters	12 / 12
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[H][C@]3(O[C@@H]1[C@@H](N)C[C@@H](N)[C@H](O[C@@]2([H])OC[C@](C)(O)[C@H](NC)[C@H]2O)[C@H]1O)O[C@H](CN)CC[C@H]3N

InChI

InChIKey=VEGXETMJINRLTH-BOZYPMBZSA-N

InChI=1S/C19H39N5O7/c1-19(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/h8-18,24-27H,3-7,20-23H2,1-2H3/t8-,9+,10-,11+,12-,13+,14+,15-,16+,17+,18+,19-/m0/s1

HIDE SMILES / InChI

Description
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/062366s033lbl.pdf | https://www.ncbi.nlm.nih.gov/pubmed/9822590

Gentamicin is an antibiotic of the aminoglycoside group, is derived from the growth of Micromonospora purpurea, an actinomycete. Gentamicin is a complex of three different closely related aminoglycoside sulfates, Gentamicins C1, C2, and C1a that have different patterns of methylation at the 69 position of the ring. Gentamicin C1a is a broad-spectrum antibiotic against Gram-positive and Gram-negative bacteria but may cause ear and kidney damage. Gentamicin C1a binds to the A-site RNA of the 30S bacterial ribosomal subunit. Adverse reactions include adverse renal effects, neurotoxicity (dizziness, vertigo, tinnitus, roaring in the ears, hearing loss, peripheral neuropathy or encephalopathy), respiratory depression, lethargy, confusion, depression, visual disturbances, etc.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Ribosomal RNA A-site 6 Target ID: CHEMBL614640 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9822590	Inhibitor 8297		0.01 µM [Kd]

Conditions

Condition	Modality	Highest Phase	Product
Infection caused by Citrobacter species 6 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2014/062366s033lbl.pdf	Curative	Approved 8429	GENTAMICIN SULFATE 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 1982
Infection caused by Klebsiella-Enterobacter-Serratia species 6 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/062366s033lbl.pdf	Curative	Approved 8429	GENTAMICIN SULFATE 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 1982
Escherichia coli infections 15 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/062366s033lbl.pdf	Curative	Approved 8429	GENTAMICIN SULFATE 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 1982
Infection caused by Staphylococcus species 6 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/062366s033lbl.pdf	Curative	Approved 8429	GENTAMICIN SULFATE 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 1982

PubMed

Title	Date	PubMed
In vitro susceptibility of Mycobacterium avium complex to antibacterial agents.	1987 Nov	3440370
Broth microdilution testing of susceptibilities to 30 antimicrobial agents of Mycobacterium avium strains from patients with acquired immune deficiency syndrome.	1987 Oct	3501698
Treatment of experimental pneumocystosis: review of 7 years of experience and development of a new system for classifying antimicrobial drugs.	1992 Sep	1416885
Efficacy of 101 antimicrobials and other agents on the development of Cryptosporidium parvum in vitro.	1996 Dec	9039272
In-vitro activities of aminoglycoside-aminocyclitols against mycobacteria.	1997 Jul	9249201
Substituted xanthones as antimycobacterial agents, Part 2: Antimycobacterial activity.	1998 May	9691249
Antimycobacterial agents differ with respect to their bacteriostatic versus bactericidal activities in relation to time of exposure, mycobacterial growth phase, and their use in combination.	2005 Jun	15917538
N- and S-alpha-l-arabinopyranosyl[1,2,4]triazolo[3,4-b][1,3,4]thiadiazoles. First synthesis and biological evaluation.	2007 Sep	17408811
In vivo efficacy and pharmacokinetics of tomopenem (CS-023), a novel carbapenem, against Pseudomonas aeruginosa in a murine chronic respiratory tract infection model.	2008 Dec	18835805

Patents

Sample Use Guides

In Vivo Use Guide

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

Unknown

Name

Type

Language

GENTAMICIN C1A

Common Name

English

GENTAMICIN C1A [MI]

Common Name

English

D-STREPTAMINE, O-3-DEOXY-4-C-METHYL-3-(METHYLAMINO)-.BETA.-L-ARABINOPYRANOSYL-(1->6)-O-(2,6-DIAMINO-2,3,4,6-TETRADEOXY-.ALPHA.-D-ERYTHRO-HEXOPYRANOSYL-(1->4))-2-DEOXY-

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C2363