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CHEBI:9649 - trandolapril

ChEBI IDCHEBI:9649
ChEBI Nametrandolapril
Stars
DefinitionA 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.
Last Modified5 July 2021
DownloadsMolfile
FormulaC24H34N2O5
Net Charge0
Average Mass430.545
Monoisotopic Mass430.24677
SMILES[H][C@]12CCCC[C@]1([H])N(C(=O)[C@H](C)N[C@@H](CCc1ccccc1)C(=O)OCC)[C@H](C(=O)O)C2
InChIInChI=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
InChIKeyVXFJYXUZANRPDJ-WTNASJBWSA-N
Wikipedia
Roles Classification
Chemical Roles:
Bronsted base  A molecular entity capable of accepting a hydron from a donor (Brønsted acid).
Bronsted acid  A molecular entity capable of donating a hydron to an acceptor (Brønsted base).
Biological Role:
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).
Applications:
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).
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.
ChEBI Ontology
Outgoing Relation(s)
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  Source
trandolaprilWHO MedNet
trandolaprilWHO MedNet
trandolaprilWHO MedNet
trandolaprilumWHO MedNet
Synonyms  Source
RU 44570ChemIDplus
RU44570ChEBI
RU-44570ChEBI
(2S,3aR,7aS)-1-((S)-N-((S)-1-carboxy-3-phenylpropyl)alanyl)hexahydro-2-indolinecarboxylic acid, 1-ethyl esterChemIDplus
Brand Names  Source
MavikChemIDplus
GoptenChemIDplus
OdrikChemIDplus
Manual XrefsDatabases
D00383KEGG DRUG
2712DrugCentral
DB00519DrugBank
HMDB0014660HMDB
TrandolaprilWikipedia
4588590ChemSpider
KR20080046630Patent
WO2006014916Patent
Registry NumbersSources
Reaxys:8655766Reaxys
CAS:87679-37-6KEGG COMPOUND
CAS:87679-37-6ChemIDplus
Citations