Molecular Identity
amikacin
(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
PubChem CID: 37768
Amikacin is an amino cyclitol glycoside that is kanamycin A acylated at the N-1 position by a 4-amino-2-hydroxybutyryl group. It has a role as an antimicrobial agent, an antibacterial drug and a nephrotoxic agent. It is an alpha-D-glucoside, an amino cyclitol glycoside, a carboxamide and an aminoglycoside. It is functionally related to a kanamycin A. It is a conjugate base of an amikacin(4+).
2D Structure
Properties
C22H43N5O13
Molecular Formula
585.60
Molecular Weight
g/mol
585.2857
Exact Mass
Da
-7.9
XLogP
Drug-like (Lipinski: < 5)
332
TPSA
May have limited oral absorption
13
H-Bond Donors
17
H-Bond Acceptors
819
Complexity
SMILES
Canonical SMILES
SMILES: Synonyms(20)
amikacin37517-28-5LukadinamikacineAmikacinaAmikacinumPotentox1-N-(L(-)-gamma-Amino-alpha-hydroxybutyryl)kanamycin ABAY 41-6551CHEBI:2637DTXSID302258684319SGC3CNSC-177001DTXCID002586(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
Data from PubChem (NCBI)
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Drug Network
Trials and conditions connected to amikacin
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