amikacin   Click here for help

GtoPdb Ligand ID: 10894

Synonyms: Amikin® | AMK | Arikayce liposomal® | BB-K8
Approved drug PDB Ligand
amikacin is an approved drug (FDA (1981), EMA (2020))
Compound class: Synthetic organic
Comment: Amikacin is a semi-synthetic aminoglycoside antibiotic that is active against a broad spectrum of Gram-negative organisms, including pseudomonas and some Gram-positive organisms (principally Staphylococcus aureus, including some methicillin-resistant strains). It is a kanamycin derivative. Functionally it binds to the bacterial 30S ribosomal subunit and disrupts protein synthesis, thereby creating its bactericidal effect.
2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 18
Hydrogen bond donors 13
Rotatable bonds 11
Topological polar surface area 331.94
Molecular weight 585.29
XLogP -6.56
No. Lipinski's rules broken 2
SMILES / InChI / InChIKey
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Canonical SMILES NCC[C@@H](C(=O)N[C@@H]1C[C@H](N)[C@H]([C@@H]([C@H]1O[C@H]1O[C@H](CO)[C@H]([C@@H]([C@H]1O)N)O)O)O[C@H]1O[C@H](CN)[C@H]([C@@H]([C@H]1O)O)O)O
Isomeric SMILES NCC[C@@H](C(=O)N[C@@H]1C[C@H](N)[C@H]([C@@H]([C@H]1O[C@H]1O[C@H](CO)[C@H]([C@@H]([C@H]1O)N)O)O)O[C@H]1O[C@H](CN)[C@H]([C@@H]([C@H]1O)O)O)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
InChI Key LKCWBDHBTVXHDL-RMDFUYIESA-N
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes (FDA (1981), EMA (2020))
WHO Essential Medicine WHO Model List of Essential Medicines (21st List, 2019). Access PDF version.
IUPAC Name Click here for help
(2S)-4-amino-N-[(1R,2S,3S,4R,5S)-5-amino-2-[(2S,3R,4S,5S,6R)-4-amino-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4-[(2R,3R,4S,5S,6R)-6-(aminomethyl)-3,4,5-trihydroxyoxan-2-yl]oxy-3-hydroxycyclohexyl]-2-hydroxybutanamide
International Nonproprietary Names Click here for help
INN number INN
3492 amikacin
Synonyms Click here for help
Amikin® | AMK | Arikayce liposomal® | BB-K8
Database Links Click here for help
BindingDB Ligand 50237603
CAS Registry No. 37517-28-5 (source: WHO INN record)
ChEMBL Ligand CHEMBL177
DrugBank Ligand DB00479
DrugCentral Ligand 157
GtoPdb PubChem SID 405560335
PubChem CID 37768
RCSB PDB Ligand AKN
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