CHEBI:2668 - amlodipine

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ChEBI Name amlodipine
ChEBI ID CHEBI:2668
Definition A fully substituted dialkyl 1,4-dihydropyridine-3,5-dicarboxylate derivative, which is used for the treatment of hypertension, chronic stable angina and confirmed or suspected vasospastic angina.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C20H25ClN2O5
Net Charge 0
Average Mass 408.87600
Monoisotopic Mass 408.145
InChI InChI=1S/C20H25ClN2O5/c1-4-28-20(25)18-15(11-27-10-9-22)23-12(2)16(19(24)26-3)17(18)13-7-5-6-8-14(13)21/h5-8,17,23H,4,9-11,22H2,1-3H3
InChIKey HTIQEAQVCYTUBX-UHFFFAOYSA-N
SMILES CCOC(=O)C1=C(COCCN)NC(C)=C(C1c1ccccc1Cl)C(=O)OC
Roles Classification
Chemical Role(s): Bronsted base
A molecular entity capable of accepting a hydron from a donor (Bronsted acid).
(via organic amino compound )
Biological Role(s): calcium channel blocker
One of a class of drugs that acts by selective inhibition of calcium influx through cell membranes or on the release and binding of calcium in intracellular pools.
Application(s): antihypertensive agent
Any drug used in the treatment of acute or chronic vascular hypertension regardless of pharmacological mechanism.
vasodilator agent
A drug used to cause dilation of the blood vessels.
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ChEBI Ontology
Outgoing amlodipine (CHEBI:2668) has role antihypertensive agent (CHEBI:35674)
amlodipine (CHEBI:2668) has role calcium channel blocker (CHEBI:38215)
amlodipine (CHEBI:2668) has role vasodilator agent (CHEBI:35620)
amlodipine (CHEBI:2668) is a dihydropyridine (CHEBI:50075)
amlodipine (CHEBI:2668) is a ethyl ester (CHEBI:23990)
amlodipine (CHEBI:2668) is a methyl ester (CHEBI:25248)
amlodipine (CHEBI:2668) is a monochlorobenzenes (CHEBI:83403)
amlodipine (CHEBI:2668) is a primary amino compound (CHEBI:50994)
Incoming amlodipine benzenesulfonate (CHEBI:2669) has part amlodipine (CHEBI:2668)
(R)-amlodipine (CHEBI:53795) is a amlodipine (CHEBI:2668)
(S)-amlodipine (CHEBI:53796) is a amlodipine (CHEBI:2668)
IUPAC Name
3-ethyl 5-methyl 2-[(2-aminoethoxy)methyl]-4-(2-chlorophenyl)-6-methyl-1,4-dihydropyridine-3,5-dicarboxylate
INNs Sources
amlodipine ChEBI
amlodipine KEGG DRUG
amlodipino DrugBank
amlodipinum DrugBank
Synonyms Sources
3-Ethyl-5-methyl (±)-2-(2-aminoethoxymethyl)-4-(o-chlorophenyl)-1,4-dihydro-6-methyl-3,5-pyridinedicarboxylate ChemIDplus
Amlodipine Free Base DrugBank
Manual Xrefs Databases
183 DrugCentral
2963 VSDB
Amlodipine Wikipedia
C06825 KEGG COMPOUND
D07450 KEGG DRUG
DB00381 DrugBank
EP89167 Patent
LSM-1388 LINCS
US4572909 Patent
View more database links
Registry Numbers Types Sources
3570229 Beilstein Registry Number Beilstein
3570229 Reaxys Registry Number Reaxys
88150-42-9 CAS Registry Number DrugBank
88150-42-9 CAS Registry Number KEGG DRUG
88150-42-9 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
1532771 PubMed citation Europe PMC
16422032 PubMed citation Europe PMC
1834846 PubMed citation Europe PMC
19450066 PubMed citation Europe PMC
21591999 PubMed citation Europe PMC
7522286 PubMed citation Europe PMC
8310972 PubMed citation Europe PMC
8310973 PubMed citation Europe PMC
9156957 PubMed citation Europe PMC
Last Modified
22 February 2017