CHEBI:2637 - amikacin

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ChEBI Name amikacin
ChEBI ID CHEBI:2637
Definition An amino cyclitol glycoside that is kanamycin A acylated at the N-1 position by a 4-amino-2-hydroxybutyryl group.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C22H43N5O13
Net Charge 0
Average Mass 585.60272
Monoisotopic Mass 585.28574
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
InChIKey LKCWBDHBTVXHDL-RMDFUYIESA-N
SMILES NCC[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
Roles Classification
Biological Role(s): antimicrobial agent
A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.
antibacterial drug
A drug used to treat or prevent bacterial infections.
nephrotoxic agent
A role played by any chemical compound (natural or synthetic) exhibiting itself through the ability to induce damage to the kidneys.
Application(s): antibacterial drug
A drug used to treat or prevent bacterial infections.
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ChEBI Ontology
Outgoing amikacin (CHEBI:2637) has functional parent kanamycin A (CHEBI:17630)
amikacin (CHEBI:2637) has role antibacterial drug (CHEBI:36047)
amikacin (CHEBI:2637) has role antimicrobial agent (CHEBI:33281)
amikacin (CHEBI:2637) has role nephrotoxic agent (CHEBI:50909)
amikacin (CHEBI:2637) is a α-D-glucoside (CHEBI:22390)
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 conjugate base of amikacin(4+) (CHEBI:84739)
Incoming 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 Sources
amikacin ChemIDplus
amikacina ChemIDplus
amikacine ChemIDplus
amikacinum ChemIDplus
Synonyms Sources
1-N-(L(−)-γ-amino-α-hydroxybutyryl)kanamycin A ChemIDplus
Amikacin KEGG COMPOUND
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-streptamine ChemIDplus
Brand Names Sources
Amicacin Deprecated term DrugBank
Amiglyde-V Deprecated term DrugBank
Amikavet Deprecated term DrugBank
Briclin Deprecated term DrugBank
Manual Xrefs Databases
157 DrugCentral
Amikacin Wikipedia
C06820 KEGG COMPOUND
CPD-14197 MetaCyc
D02543 KEGG DRUG
DB00479 DrugBank
DE2234315 Patent
HMDB0014622 HMDB
LSM-5935 LINCS
US3781268 Patent
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Registry Numbers Types Sources
37517-28-5 CAS Registry Number ChemIDplus
5915117 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
11744283 PubMed citation Europe PMC
15305513 PubMed citation Europe PMC
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19495517 PubMed citation Europe PMC
19752274 PubMed citation Europe PMC
20195673 PubMed citation Europe PMC
25296102 PubMed citation Europe PMC
25327505 PubMed citation Europe PMC
25339395 PubMed citation Europe PMC
25630642 PubMed citation Europe PMC
8622103 PubMed citation Europe PMC
8622117 PubMed citation Europe PMC
9327246 PubMed citation Europe PMC
Last Modified
12 September 2024