CHEBI:9139 - sildenafil

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ChEBI Name sildenafil
ChEBI ID CHEBI:9139
Definition A pyrazolo[4,3-d]pyrimidin-7-one having a methyl substituent at the 1-position, a propyl substituent at the 3-position and a 2-ethoxy-5-[(4-methylpiperazin-1-yl)sulfonyl]phenyl group at the 5-position.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:46436, CHEBI:600437
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Formula C22H30N6O4S
Net Charge 0
Average Mass 474.57600
InChI InChI=1S/C22H30N6O4S/c1-5-7-17-19-20(27(4)25-17)22(29)24-21(23-19)16-14-15(8-9-18(16)32-6-2)33(30,31)28-12-10-26(3)11-13-28/h8-9,14H,5-7,10-13H2,1-4H3,(H,23,24,29)
InChIKey BNRNXUUZRGQAQC-UHFFFAOYSA-N
SMILES CCCc1nn(C)c2c1nc([nH]c2=O)-c1cc(ccc1OCC)S(=O)(=O)N1CCN(C)CC1
Roles Classification
Biological Role(s): EC 3.1.4.35 (3',5'-cyclic-GMP phosphodiesterase) inhibitor
An EC 3.1.4.* (phosphoric diester hydrolase) inhibitor that blocks the action of 3',5'-cyclic-GMP phosphodiesterase (EC 3.1.4.35).
Application(s): vasodilator agent
A drug used to cause dilation of the blood vessels.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing sildenafil (CHEBI:9139) has role EC 3.1.4.35 (3',5'-cyclic-GMP phosphodiesterase) inhibitor (CHEBI:71942)
sildenafil (CHEBI:9139) has role vasodilator agent (CHEBI:35620)
sildenafil (CHEBI:9139) is a piperazines (CHEBI:26144)
sildenafil (CHEBI:9139) is a pyrazolopyrimidine (CHEBI:38669)
sildenafil (CHEBI:9139) is a sulfonamide (CHEBI:35358)
Incoming sildenafil citrate (CHEBI:58987) has part sildenafil (CHEBI:9139)
IUPAC Name
5-{2-ethoxy-5-[(4-methylpiperazin-1-yl)sulfonyl]phenyl}-1-methyl-3-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one
INN Source
sildenafil KEGG DRUG
Synonym Source
1-((3-(4,7-Dihydro-1-methyl-7-oxo-3-propyl-1H-pyrazolo(4,3-d)pyrimidin-5-yl)-4-ethoxyphenyl)sulfonyl)-4-methylpiperazine ChemIDplus
Database Links Databases
C07259 KEGG COMPOUND
D08514 KEGG DRUG
DB00203 DrugBank
EP463756 Patent
Sildenafil Wikipedia
US5250534 Patent
VIA PDBeChem
View more database links
Registry Numbers Types Sources
139755-83-2 CAS Registry Number ChemIDplus
7673458 Beilstein Registry Number Beilstein
Last Modified
28 January 2013