CHEBI:66876 - avanafil

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ChEBI Name avanafil
Definition A monocarboxylic acid amide obtained by formal condensation of the carboxy group of 4-[(3-chloro-4-methoxybenzyl)amino]-2-[(2S)-2-(hydroxymethyl)pyrrolidin-1-yl]pyrimidine-5-carboxylic acid with the amino group of pyrimidin-2-ylmethylamine. Used for treatment of erectile dysfunction.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C23H26ClN7O3
Net Charge 0
Average Mass 483.95100
Monoisotopic Mass 483.17857
InChI InChI=1S/C23H26ClN7O3/c1-34-19-6-5-15(10-18(19)24)11-27-21-17(22(33)28-13-20-25-7-3-8-26-20)12-29-23(30-21)31-9-2-4-16(31)14-32/h3,5-8,10,12,16,32H,2,4,9,11,13-14H2,1H3,(H,28,33)(H,27,29,30)/t16-/m0/s1
SMILES COc1ccc(CNc2nc(ncc2C(=O)NCc2ncccn2)N2CCC[C@H]2CO)cc1Cl
Roles Classification
Chemical Role(s): Bronsted base
A molecular entity capable of accepting a hydron from a donor (Bronsted acid).
(via organic amino compound )
Biological Role(s): EC 3.1.4.* (phosphoric diester hydrolase) inhibitor
An EC 3.1.* (ester hydrolase) inhibitor that interferes with the action of a phosphoric diester hydrolase (EC 3.1.4.*).
Application(s): vasodilator agent
A drug used to cause dilation of the blood vessels.
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ChEBI Ontology
Outgoing avanafil (CHEBI:66876) has role EC 3.1.4.* (phosphoric diester hydrolase) inhibitor (CHEBI:50218)
avanafil (CHEBI:66876) has role vasodilator agent (CHEBI:35620)
avanafil (CHEBI:66876) is a aromatic amide (CHEBI:62733)
avanafil (CHEBI:66876) is a monocarboxylic acid amide (CHEBI:29347)
avanafil (CHEBI:66876) is a organochlorine compound (CHEBI:36683)
avanafil (CHEBI:66876) is a prolinols (CHEBI:59654)
avanafil (CHEBI:66876) is a pyrimidines (CHEBI:39447)
INN Source
avanafil KEGG DRUG
Synonym Source
(S)-4-(3-Chloro-4-methoxybenzylamino)-2-(2-hydroxymethylpyrrolidin-1-yl)-N-pyrimidin-2-ylmethyl-5-pyrimidinecarboxamide ChemIDplus
Brand Name Source
Manual Xrefs Databases
4305 DrugCentral
Avanafil Wikipedia
EP1366760 Patent
US6403597 Patent
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Registry Numbers Types Sources
11746013 Reaxys Registry Number Reaxys
330784-47-9 CAS Registry Number KEGG DRUG
330784-47-9 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
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Last Modified
22 February 2017