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 developmental phase:	Approved by FDA in 1981
Development status:	Approved, off-patent (available in many different formulations, including topical and inhalation)

Chemical structure(s):
Canonical 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
Isomeric 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:	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
InChI Key:	LKCWBDHBTVXHDL-RMDFUYIESA-N
Structure link:	https://pubchem.ncbi.nlm.nih.gov/compound/37768

External links:
Guide to Pharmacology:	amikacin
Main Source:	https://pubmed.ncbi.nlm.nih.gov/62815/
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/