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 antibacterial 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
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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
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes (FDA (1981), EMA (2020))
WHO Essential Medicine WHO Essential Medicines List (EML) (23rd List, 2023). Access PDF version.
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IUPAC Name Click here for help
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
Specialist databases
Antibiotic DB Antibiotic DB Database logo Amikacin
Other databases
BindingDB Ligand 50237603
CAS Registry No. 37517-28-5 (source: WHO INN record)
DrugBank Ligand DB00479
DrugCentral Ligand 157
GtoPdb PubChem SID 405560335
PubChem CID 37768
Search Google for chemical match using the InChIKey LKCWBDHBTVXHDL-RMDFUYIESA-N
Search Google for chemicals with the same backbone LKCWBDHBTVXHDL
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UniChem Compound Search for chemical match using the InChIKey LKCWBDHBTVXHDL-RMDFUYIESA-N
UniChem Connectivity Search for chemical match using the InChIKey LKCWBDHBTVXHDL-RMDFUYIESA-N