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
Supplier Information No supplier information found for this compound.
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Pyrvinium (Viprynium) is an anthelmintic effective for pinworms. Several forms of pyrvinium have been prepared with variable counter anions, such as halides, tosylate, triflate and pamoate. Pyrvinium was identified as a potent Wnt inhibitor, acting through activation of Casein kinase CK1α. Pyrvinium salts can also inhibit the growth of cancer cells. More specifically, the pamoate salt has been shown to have preferential toxicity for various cancer cell lines during glucose starvation.
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Formula C22H30N6O4S
Net Charge 0
Average Mass 474.57600
Monoisotopic Mass 474.20492
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.
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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
Manual Xrefs Databases
2441 DrugCentral
C07259 KEGG COMPOUND
D08514 KEGG DRUG
DB00203 DrugBank
EP463756 Patent
FDB023606 FooDB
HMDB0005039 HMDB
LSM-3797 LINCS
Sildenafil Wikipedia
US5250534 Patent
VIA PDBeChem
View more database links
Registry Numbers Types Sources
139755-83-2 CAS Registry Number KEGG COMPOUND
139755-83-2 CAS Registry Number ChemIDplus
7673458 Beilstein Registry Number Beilstein
Last Modified
21 February 2019