CHEBI:8774 - ramipril

ChEBI IDCHEBI:8774
ChEBI Nameramipril
Stars
DefinitionA dipeptide that is the prodrug for ramiprilat, the active metabolite obtained by hydrolysis of the ethyl ester group. An angiotensin-converting enzyme (ACE) inhibitor, used to treat high blood pressure and congestive heart failure.
Last Modified1 August 2024
DownloadsMolfile
FormulaC23H32N2O5
Net Charge0
Average Mass416.518
Monoisotopic Mass416.23112
SMILES[H][C@@]12CCC[C@]1([H])N(C(=O)[C@H](C)N[C@@H](CCc1ccccc1)C(=O)OCC)[C@H](C(=O)O)C2
InChIInChI=1S/C23H32N2O5/c1-3-30-23(29)18(13-12-16-8-5-4-6-9-16)24-15(2)21(26)25-19-11-7-10-17(19)14-20(25)22(27)28/h4-6,8-9,15,17-20,24H,3,7,10-14H2,1-2H3,(H,27,28)/t15-,17-,18-,19-,20-/m0/s1
InChIKeyHDACQVRGBOVJII-JBDAPHQKSA-N
Wikipedia
Roles Classification
Chemical Roles:
Bronsted acid  A molecular entity capable of donating a hydron to an acceptor (Brønsted base).
Bronsted base  A molecular entity capable of accepting a hydron from a donor (Brønsted acid).
Biological Roles:
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).
bradykinin receptor B2 agonist  A bradykinin agonist that binds to and activates bradykinin B2 receptors.
antiviral agent  A substance that destroys or inhibits replication of viruses.
Applications:
hypoglycemic agent  A drug which lowers the blood glucose level.
renoprotective agent  Any compound that is able to prevent damage to the kidneys.
cardioprotective agent  Any protective agent that is able to prevent damage to the heart.
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).
antihypertensive agent  Any drug used in the treatment of acute or chronic vascular hypertension regardless of pharmacological mechanism.
antiatherosclerotic agent  A cardiovascular drug that prevents atherosclerosis (a disease in which the inside of an artery narrows due to the build up of plaque). Compare with antiatherogenic agent.
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.
cardiovascular drug  A drug that affects the rate or intensity of cardiac contraction, blood vessel diameter or blood volume.
antirheumatic drug  A drug used to treat rheumatoid arthritis.
anti-arrhythmia drug  A drug used for the treatment or prevention of cardiac arrhythmias. Anti-arrhythmia drugs may affect the polarisation-repolarisation phase of the action potential, its excitability or refractoriness, or impulse conduction or membrane responsiveness within cardiac fibres.
ChEBI Ontology
Outgoing Relation(s)
ramipril (CHEBI:8774) has role anti-arrhythmia drug (CHEBI:38070)
ramipril (CHEBI:8774) has role antiatherosclerotic agent (CHEBI:145947)
ramipril (CHEBI:8774) has role antihypertensive agent (CHEBI:35674)
ramipril (CHEBI:8774) has role antirheumatic drug (CHEBI:35842)
ramipril (CHEBI:8774) has role antiviral agent (CHEBI:22587)
ramipril (CHEBI:8774) has role bradykinin receptor B2 agonist (CHEBI:77496)
ramipril (CHEBI:8774) has role cardioprotective agent (CHEBI:77307)
ramipril (CHEBI:8774) has role cardiovascular drug (CHEBI:35554)
ramipril (CHEBI:8774) has role EC 3.4.15.1 (peptidyl-dipeptidase A) inhibitor (CHEBI:35457)
ramipril (CHEBI:8774) has role hypoglycemic agent (CHEBI:35526)
ramipril (CHEBI:8774) has role matrix metalloproteinase inhibitor (CHEBI:50664)
ramipril (CHEBI:8774) has role prodrug (CHEBI:50266)
ramipril (CHEBI:8774) has role renoprotective agent (CHEBI:231911)
ramipril (CHEBI:8774) is a azabicycloalkane (CHEBI:38295)
ramipril (CHEBI:8774) is a cyclopentapyrrole (CHEBI:38296)
ramipril (CHEBI:8774) is a dicarboxylic acid monoester (CHEBI:36244)
ramipril (CHEBI:8774) is a dipeptide (CHEBI:46761)
ramipril (CHEBI:8774) is a ethyl ester (CHEBI:23990)
ramipril (CHEBI:8774) is conjugate acid of ramipril(1−) (CHEBI:231704)
Incoming Relation(s)
ramipril(1−) (CHEBI:231704) is conjugate base of ramipril (CHEBI:8774)
IUPAC Name 
(2S,3aS,6aS)-1-[(2S)-2-{[(1S)-1-ethoxycarbonyl-3-phenylpropyl]amino}propanoyl]octahydrocyclopenta[b]pyrrole-2-carboxylic acid
INN  Source
ramiprilChemIDplus
Synonyms  Source
(2S-(1(R*(R*)),2alpha,3abeta,6abeta))-1-(2-((1-(Ethoxycarbonyl)-3-phenylpropyl)amino)-1-oxopropyl)octahydrocyclopenta(b)pyrrole-2-carboxylic acidChemIDplus
Altace (TN)KEGG DRUG
C09AA05ChEMBL
CardaceChEMBL
CorprilChEMBL
DelixChEMBL
Brand Names  Source
AltaceChEMBL
LopaceChEMBL
Ramipril component of polycapChEMBL
RanaceChEMBL
Manual XrefsDatabases
1888VSDB
2356DrugCentral
D00421KEGG DRUG
DB00178DrugBank
HMDB0014324HMDB
LSM-5950LINCS
RamiprilWikipedia
Registry NumbersSources
Reaxys:4214464Reaxys
CAS:87333-19-5KEGG DRUG
CAS:87333-19-5ChemIDplus
Citations