gentamicin   Click here for help

GtoPdb Ligand ID: 2427

Synonyms: Garamycin® | gentamicin sulfate
Approved drug
gentamicin is an approved drug (FDA (1970))
Compound class: Synthetic organic
Comment: The approved drug gentamicin is a complex of three closely-related aminoglycoside sulfates: C1, C1a and C2. The structure shown here is representative of the general structure of the compounds. For more information on the structure of the individual components of gentamicin, please see the relevant entries on ChEBI: (CHEBI:27412, CHEBI:27784, CHEBI:28292).
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 12
Hydrogen bond donors 8
Rotatable bonds 7
Topological polar surface area 199.73
Molecular weight 477.32
XLogP -2.88
No. Lipinski's rules broken 2
SMILES / InChI / InChIKey
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Canonical SMILES CNC(C1CCC(C(O1)OC1C(N)CC(C(C1O)OC1OCC(C(C1O)NC)(C)O)N)N)C
Isomeric SMILES CNC(C1CCC(C(O1)OC1C(N)CC(C(C1O)OC1OCC(C(C1O)NC)(C)O)N)N)C
InChI 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
InChI Key CEAZRRDELHUEMR-UHFFFAOYSA-N
No information available.
Summary of Clinical Use Click here for help
Antibiotic used in the treatment of infections caused by 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).
Mechanism Of Action and Pharmacodynamic Effects Click here for help
Gentamycin binds to 30S-subunit proteins and 16S rRNA which interferes with the decoding site in the region that interacts with the wobble base in the anticodon on tRNA, leading to interference with the initiation complex and misreading of mRNA. As a result incorrect amino acids are inserted into the polypeptide leading to nonfunctional or toxic peptides.