CHEBI:2637 - amikacin

ChEBI IDCHEBI:2637
ChEBI Nameamikacin
Stars
DefinitionAn amino cyclitol glycoside that is kanamycin A acylated at the N-1 position by a 4-amino-2-hydroxybutyryl group.
Last Modified12 September 2024
DownloadsMolfile
FormulaC22H43N5O13
Net Charge0
Average Mass585.608
Monoisotopic Mass585.28574
SMILESNCC[C@H](O)C(=O)N[C@@H]1C[C@H](N)[C@@H](O[C@H]2O[C@H](CN)[C@@H](O)[C@H](O)[C@H]2O)[C@H](O)[C@H]1O[C@H]1O[C@H](CO)[C@@H](O)[C@H](N)[C@H]1O
InChIInChI=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
InChIKeyLKCWBDHBTVXHDL-RMDFUYIESA-N
Wikipedia
Roles Classification
Biological Roles:
antibacterial agent  A substance (or active part thereof) that kills or slows the growth of bacteria.
nephrotoxic agent  A role played by any chemical compound (natural or synthetic) exhibiting itself through the ability to induce damage to the kidneys.
antitubercular agent  A substance that kills or slows the growth of Mycobacterium tuberculosis and is used in the treatment of tuberculosis.
antibacterial drug  A drug used to treat or prevent bacterial infections.
antimicrobial agent  A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.
Applications:
antiinfective agent  A substance used in the prophylaxis or therapy of infectious diseases.
antitubercular agent  A substance that kills or slows the growth of Mycobacterium tuberculosis and is used in the treatment of tuberculosis.
ophthalmology drug  Any compound used for the treatment of eye conditions or eye diseases.
antibacterial drug  A drug used to treat or prevent bacterial infections.
ChEBI Ontology
Outgoing Relation(s)
amikacin (CHEBI:2637) has functional parent kanamycin A (CHEBI:17630)
amikacin (CHEBI:2637) has role antibacterial agent (CHEBI:33282)
amikacin (CHEBI:2637) has role antibacterial drug (CHEBI:36047)
amikacin (CHEBI:2637) has role antiinfective agent (CHEBI:35441)
amikacin (CHEBI:2637) has role antimicrobial agent (CHEBI:33281)
amikacin (CHEBI:2637) has role antimicrobial agent (CHEBI:33281)
amikacin (CHEBI:2637) has role antitubercular agent (CHEBI:33231)
amikacin (CHEBI:2637) has role nephrotoxic agent (CHEBI:50909)
amikacin (CHEBI:2637) has role ophthalmology drug (CHEBI:66981)
amikacin (CHEBI:2637) is a amino cyclitol glycoside (CHEBI:22479)
amikacin (CHEBI:2637) is a aminoglycoside (CHEBI:47779)
amikacin (CHEBI:2637) is a carboxamide (CHEBI:37622)
amikacin (CHEBI:2637) is a α-D-glucoside (CHEBI:22390)
amikacin (CHEBI:2637) is conjugate base of amikacin(4+) (CHEBI:84739)
Incoming Relation(s)
amikacin(4+) (CHEBI:84739) is conjugate acid of amikacin (CHEBI:2637)
IUPAC Name 
(2S)-4-amino-N-[(1R,2S,3S,4R,5S)-5-amino-2-(3-amino-3-deoxy-α-D-glucopyranosyloxy)-4-(6-amino-6-deoxy-α-D-glucopyranosyloxy)-3-hydroxycyclohexyl]-2-hydroxybutanamide
INNs  Source
amikacinChemIDplus
amikacinaChemIDplus
amikacineChemIDplus
amikacinumChemIDplus
Synonyms  Source
1-N-(L(−)-γ-amino-α-hydroxybutyryl)kanamycin AChemIDplus
AmikacinKEGG COMPOUND
BAY 41-6551ChEMBL
O-3-amino-3-deoxy-α-D-glucopyranosyl-(1→4)-O-(6-amino-6-deoxy-α-D-glucopyranosyl-(1→6))-N3-(4-amino-L-2-hydroxybutyryl)-2-deoxy-L-streptamineChemIDplus
NSC-177001ChEMBL
PotentoxChEMBL
Brand Names  Source
AmicacinDrugBank
Amiglyde-VDrugBank
AmikavetDrugBank
BriclinDrugBank
Manual XrefsDatabases
157DrugCentral
AmikacinWikipedia
C06820KEGG COMPOUND
CPD-14197MetaCyc
D02543KEGG DRUG
DB00479DrugBank
DE2234315Patent
HMDB0014622HMDB
LSM-5935LINCS
US3781268Patent
Registry NumbersSources
Reaxys:5915117Reaxys
CAS:37517-28-5ChemIDplus
CAS:37517-28-5KEGG COMPOUND
Citations