Compound ID | 1841

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Amikacin

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 (incl. Mycobacterium tuberculosis) and Gram-negative bacteria, especially Pseudomonas aeruginosa
Description: Semisynthetic, derived from kanamycin. Veterinary use, human use as parenterial and inhaled formulation (for Mycobacterium avium complex lung disease)
Year first mentioned: 1976
Highest development stage: Approved by FDA in 1981
Development status: Approved, off-patent (available in many different formulations, including topical and inhalation)
Chemical structure(s):
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Molecular weight: 585.6
Iso. SMILES: C1[C@@H]([C@H]([C@@H]([C@H]([C@@H]1NC(=O)[C@H](CCN)O)O[C@@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CO)O)N)O)O)O[C@@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CN)O)O)O)N
InChI Key: LKCWBDHBTVXHDL-RMDFUYIESA-N
Can. SMILES: C(CN)[C@@H](C(=O)N[C@@H]1C[C@@H]([C@H]([C@@H]([C@H]1O[C@@H]2[C@@H]([C@H]([C@@H]([C@@H](CO)O2)O)N)O)O)O[C@@H]3[C@@H]([C@H]([C@@H]([C@@H](CN)O3)O)O)O)N)O
InChI: InChI=1S/C22H43N5O13/c23-2-1-8(29)20(36)27-7-3-6(25)18(39-22-16(34)15(33)13(31)9(4-24)37-22)17(35)19(7)40-21-14(32)11(26)12(30)10(5-28)38-21/h6-19,21-22,28-35H,1-5,23-26H2,(H,27,36)/t6-,7+,8-,9+,10+,11-,12+,13+,14+,15-,16+,17-,18+,19-,21+,22+/m0/s1
External links:
PubChem link: https://pubchem.ncbi.nlm.nih.gov/compound/37768
Guide to Pharmacology: amikacin
Citations:
  • https://mdpi-res.com/d_attachment/molecules/molecules-22-02267/article_deploy/molecules-22-02267.pdf?version=1513693659
  • https://pubmed.ncbi.nlm.nih.gov/34390724/
  • https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8053653/
  • https://pubmed.ncbi.nlm.nih.gov/62815/

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