Compound ID | 1839

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Gentamicin

Class: Aminoglycoside

Spectrum of activity: Gram-positive  &  Gram-negative
Details of activity: Inhibits protein synthesis by binding to the 30S subunit of the bacterial ribosome. Active against Gram-positive and Gram-negative bacteria, mainly used against severe infections caused by Pseudomonas aeruginosa in combination
Description: Micromonospora natural product. Available in parenteral, enteral (selective decontamination) and topical formulations; veterinary and human use
Year first mentioned: 1962
Highest developmental phase: Approved by FDA in 1970
Development status: Approved, off-patent
Reason Dropped: Several formulations discontinued due to safety or effectiveness reasons
Chemical structure(s):
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Molecular weight: 477.6
Iso. SMILES: CC(C1CCC(C(O1)OC2C(CC(C(C2O)OC3C(C(C(CO3)(C)O)NC)O)N)N)N)NC
InChI Key: CEAZRRDELHUEMR-UHFFFAOYSA-N
Can. SMILES: CC(C1CCC(C(O1)OC2C(CC(C(C2O)OC3C(C(C(C)(CO3)O)NC)O)N)N)N)NC
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
External links:
PubChem link: https://pubchem.ncbi.nlm.nih.gov/compound/3467
Guide to Pharmacology: gentamicin
Citations:
  • https://go.drugbank.com/drugs/DB00798
  • https://pubmed.ncbi.nlm.nih.gov/34711521/
  • https://pubmed.ncbi.nlm.nih.gov/35303195/
  • https://go.drugbank.com/drugs/DB00798

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