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Gentamicin

Gentamicin :

Antibiotic ID : UD0027

Full Name : Gentamicin

Synonyms : Garamycin, gentamicin, Gentacycol, GENTAMYCIN, Gentamycinum, Cidomycin, Gentavet, Refobacin, Uromycine

Class : Beta Lactum

Chemical Description :

Molecular Formula : C₂₁H₄₃N₅O₇

Molecular Weight : 477.59542

InChIKey : CEAZRRDELHUEMR-UHFFFAOYSA-N

IUPAC Name : 2-[4,6-diamino-3-[3-amino-6-[1-(methylamino)ethyl]oxan-2-yl]oxy-2-hydroxycyclohexyl]oxy-5-methyl-4-(methylamino)oxane-3,5-diol

Structural Description :

Canonical SMILES : CC(C1CCC(C(O1)OC2C(CC(C(C2O)OC3C(C(C(CO3)(C)O)NC)O)N)N)N)NC

Isomeric SMILES : NA

2D Structure : 2D

3D Structure : 3D

SDF : SDF file

Fuctional Description :

Gentamicin Target : A complex of three different closely related aminoglycoside sulfates, Gentamicins C1, C2, and C1(subA), obtained from Micromonospora purpurea and related species. They are broad-spectrum antibiotics, but may cause ear and kidney damage. They act to inhibit protein synthesis (GENETIC TRANSLATION)(MeSH).

KEGG : D08013

DRUG BANK : DB00798

Pub Chem CID : 3467

Antibiotics Resistance Reports :

Upregulators :

Enzyme : CTX-Mβ-lactamases

Gene : aac(3)-IV, CTX-M β-lactamases

Downregulators :

Internal Effect : Loss of plasmid correlated to loss of antibiotic resistance

Drug positive relation : Positive relation to administration to rifampicin

Note : NA* - Not Available

Bibliography :

Shiga Toxin-Producing Escherichia coli Isolated from Bovine Mastitic Milk: Serogroups, Virulence Factors, and Antibiotic Resistance Properties, Momtaz H., Dehkordi F. S., Taktaz T., Rezvani A., and Yarali S., The Scientific World Journal, 2012, 2012:618709. PMID: 23213293.

Extended-spectrum beta-lactamase-producing Enterobacteriaceae: an emerging public-health concern, Pitout JD, Laupland KB., The Lancet Infectious Diseases, 2008, 8(3):159-66. PMID: 18291338

Antimicrobial Resistance Genes in Enterotoxigenic Escherichia coli O149:K91 Isolates Obtained over a 23-Year Period from Pigs, Maynard C., Fairbrother J. M., Bekal S., Sanschagrin F., Levesque R. C., Brousseau R., Masson L., Larivière S., and Harel J., Antimicrobial Agents and Chemotherapy, 2003, 47(10):3214–3221. PMID: 14506033.

Antimicrobial resistance and virulence genes of Escherichia coli isolates from swine in Ontario, Boerlin P, Travis R, Gyles CL, Reid-Smith R, Janecko N, Lim H, Nicholson V, McEwen SA, Friendship R, Archambault M., Applied and Environmental Microbiology, 2005, 71(11) :6753-61. PMID: 16269706.

Decrease in Shiga toxin expression using a minimal inhibitory concentration of rifampicin followed by bactericidal gentamicin treatment enhances survival of Escherichia coli O157:H7-infected BALB/c mice, Rahal EA, Kazzi N, Sabra A, Abdelnoor AM, Matar GM., Annals of Clinical Microbiology and Antimicrobials, 2011, 10 :34. PMID: 21906403.