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CHEBI:3380 - captopril

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ChEBI Name captopril
ChEBI ID CHEBI:3380
Definition A L-proline derivative in which L-proline is substituted on nitrogen with a (2S)-2-methyl-3-sulfanylpropanoyl group. It is used as an anti-hypertensive ACE inhibitor drug.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C9H15NO3S
Net Charge 0
Average Mass 217.28500
Monoisotopic Mass 217.077
InChI InChI=1S/C9H15NO3S/c1-6(5-14)8(11)10-4-2-3-7(10)9(12)13/h6-7,14H,2-5H2,1H3,(H,12,13)/t6-,7+/m1/s1
InChIKey FAKRSMQSSFJEIM-RQJHMYQMSA-N
SMILES C[C@H](CS)C(=O)N1CCC[C@H]1C(O)=O
Roles Classification
Chemical Role(s): Bronsted acid
A molecular entity capable of donating a hydron to an acceptor (Bronsted base).
(via oxoacid )
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): 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.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing captopril (CHEBI:3380) has role antihypertensive agent (CHEBI:35674)
captopril (CHEBI:3380) has role EC 3.4.15.1 (peptidyl-dipeptidase A) inhibitor (CHEBI:35457)
captopril (CHEBI:3380) is a N-acylpyrrolidine (CHEBI:46766)
captopril (CHEBI:3380) is a L-proline derivative (CHEBI:84186)
captopril (CHEBI:3380) is a alkanethiol (CHEBI:47908)
captopril (CHEBI:3380) is a pyrrolidinemonocarboxylic acid (CHEBI:46701)
Incoming captopril disulfide (CHEBI:53236) has functional parent captopril (CHEBI:3380)
IUPAC Name
1-[(2S)-2-methyl-3-sulfanylpropanoyl]-L-proline
INNs Sources
captopril ChemIDplus
captoprilum ChemIDplus
Synonyms Sources
(2S)-1-[(2S)-2-methyl-3-sulfanylpropanoyl]pyrrolidine-2-carboxylic acid ChEBI
Captopryl DrugBank
CP ChEBI
D-2-methyl-3-mercaptopropanoyl-L-proline ChemIDplus
D-3-mercapto-2-methylpropanoyl-L-proline ChemIDplus
L-Captopril DrugBank
Brand Names Sources
Acepress DrugBank
Apopril DrugBank
Capoten DrugBank
Captolane DrugBank
Captoril DrugBank
Cesplon DrugBank
Dilabar DrugBank
Garranil DrugBank
Hypertil DrugBank
Lopirin DrugBank
Tenosbon DrugBank
Tensobon DrugBank
Tensoprel DrugBank
Database Links Databases
Captopril Wikipedia
D00251 KEGG DRUG
DB01197 DrugBank
LSM-5648 LINCS
US4046889 Patent
US4105776 Patent
View more database links
Registry Numbers Types Sources
477887 Beilstein Registry Number Beilstein
62571-86-2 CAS Registry Number KEGG DRUG
62571-86-2 CAS Registry Number NIST Chemistry WebBook
62571-86-2 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
23137627 PubMed citation Europe PMC
23161035 PubMed citation Europe PMC
23278692 PubMed citation Europe PMC
23299024 PubMed citation Europe PMC
23328620 PubMed citation Europe PMC
23397376 PubMed citation Europe PMC
23410042 PubMed citation Europe PMC
23422724 PubMed citation Europe PMC
23429803 PubMed citation Europe PMC
23435971 PubMed citation Europe PMC
2420897 PubMed citation Europe PMC
Last Modified
25 February 2016