CHEBI:9649 - trandolapril

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ChEBI Name trandolapril
ChEBI ID CHEBI:9649
Definition A heterobicylic compound that is (2S,3aR,7aS)-1-[(2S)-2-aminopropanoyl]octahydro-1H-indole-2-carboxylic acid in which the hydrogen of the amino group is substituted by a (2R)-1-ethoxy-1-oxo-4-phenylbutan-2-yl group. It is a angiotensin-converting enzyme inhibitor and a prodrug used for the treatment of hypertension.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information No supplier information found for this compound.
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Formula C24H34N2O5
Net Charge 0
Average Mass 430.545
Monoisotopic Mass 430.24677
InChI InChI=1S/C24H34N2O5/c1-3-31-24(30)19(14-13-17-9-5-4-6-10-17)25-16(2)22(27)26-20-12-8-7-11-18(20)15-21(26)23(28)29/h4-6,9-10,16,18-21,25H,3,7-8,11-15H2,1-2H3,(H,28,29)/t16-,18+,19-,20-,21-/m0/s1
InChIKey VXFJYXUZANRPDJ-WTNASJBWSA-N
SMILES [H][C@@]12C[C@H](N(C(=O)[C@H](C)N[C@@H](CCC3=CC=CC=C3)C(=O)OCC)[C@@]1([H])CCCC2)C(O)=O
Roles Classification
Chemical Role(s): Bronsted acid
A molecular entity capable of donating a hydron to an acceptor (Bronsted base).
(via oxoacid )
Bronsted base
A molecular entity capable of accepting a hydron from a donor (Bronsted acid).
(via organic amino compound )
Biological Role(s): EC 3.4.15.1 (peptidyl-dipeptidase A) inhibitor
An EC 3.4.15.* (peptidyl-dipeptidase) inhibitor that interferes with the action of peptidyl-dipeptidase A (EC 3.4.15.1).
Application(s): prodrug
A compound that, on administration, must undergo chemical conversion by metabolic processes before becoming the pharmacologically active drug for which it is a prodrug.
antihypertensive agent
Any drug used in the treatment of acute or chronic vascular hypertension regardless of pharmacological mechanism.
EC 3.4.15.1 (peptidyl-dipeptidase A) inhibitor
An EC 3.4.15.* (peptidyl-dipeptidase) inhibitor that interferes with the action of peptidyl-dipeptidase A (EC 3.4.15.1).
View more via ChEBI Ontology
ChEBI Ontology
Outgoing trandolapril (CHEBI:9649) has functional parent trandolaprilat (CHEBI:141521)
trandolapril (CHEBI:9649) has role antihypertensive agent (CHEBI:35674)
trandolapril (CHEBI:9649) has role EC 3.4.15.1 (peptidyl-dipeptidase A) inhibitor (CHEBI:35457)
trandolapril (CHEBI:9649) has role prodrug (CHEBI:50266)
trandolapril (CHEBI:9649) is a dicarboxylic acid monoester (CHEBI:36244)
trandolapril (CHEBI:9649) is a dipeptide (CHEBI:46761)
trandolapril (CHEBI:9649) is a ethyl ester (CHEBI:23990)
trandolapril (CHEBI:9649) is a organic heterobicyclic compound (CHEBI:27171)
trandolapril (CHEBI:9649) is a secondary amino compound (CHEBI:50995)
trandolapril (CHEBI:9649) is a tertiary carboxamide (CHEBI:140326)
IUPAC Name
(2S,3aR,7aS)-1-[(2S)-2-{[(2S)-1-ethoxy-1-oxo-4-phenylbutan-2-yl]amino}propanoyl]octahydro-1H-indole-2-carboxylic acid
INNs Sources
trandolapril WHO MedNet
trandolapril WHO MedNet
trandolapril WHO MedNet
trandolaprilum WHO MedNet
Synonyms Sources
(2S,3aR,7aS)-1-((S)-N-((S)-1-carboxy-3-phenylpropyl)alanyl)hexahydro-2-indolinecarboxylic acid, 1-ethyl ester ChemIDplus
RU 44570 ChemIDplus
RU-44570 ChEBI
RU44570 ChEBI
Brand Names Sources
Gopten ChemIDplus
Mavik ChemIDplus
Odrik ChemIDplus
Manual Xrefs Databases
2712 DrugCentral
4588590 ChemSpider
D00383 KEGG DRUG
DB00519 DrugBank
HMDB0014660 HMDB
KR20080046630 Patent
Trandolapril Wikipedia
WO2006014916 Patent
View more database links
Registry Numbers Types Sources
8655766 Reaxys Registry Number Reaxys
87679-37-6 CAS Registry Number KEGG COMPOUND
87679-37-6 CAS Registry Number ChemIDplus
Citations Types Sources
1648489 PubMed citation Europe PMC
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Last Modified
05 July 2021