CHEBI:71940 - tadalafil

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ChEBI Name tadalafil
ChEBI ID CHEBI:71940
Definition A pyrazinopyridoindole that is 2,3,6,7,12,12a-hexahydropyrazino[1',2':1,6]pyrido[3,4-b]indole-1,4-dione substituted at position 2 by a methyl group and at position 6 by a 1,3-benzodioxol-5-yl group (the 6R,12aR-diastereomer). A phosphodiesterase V inhibitor inhibitor, currently marketed in pill form for treating erectile dysfunction under the name Cialis; and under the name Adcirca for the treatment of pulmonary arterial hypertension.
Stars This entity has been manually annotated by the ChEBI Team.
Submitter Anonymous
Secondary ChEBI IDs CHEBI:41488, CHEBI:32177
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Formula C22H19N3O4
Net Charge 0
Average Mass 389.40400
Monoisotopic Mass 389.138
InChI InChI=1S/C22H19N3O4/c1-24-10-19(26)25-16(22(24)27)9-14-13-4-2-3-5-15(13)23-20(14)21(25)12-6-7-17-18(8-12)29-11-28-17/h2-8,16,21,23H,9-11H2,1H3/t16-,21-/m1/s1
InChIKey WOXKDUGGOYFFRN-IIBYNOLFSA-N
SMILES [H][C@]12Cc3c([nH]c4ccccc34)[C@H](N1C(=O)CN(C)C2=O)c1ccc2OCOc2c1
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 tadalafil (CHEBI:71940) has role EC 3.1.4.35 (3',5'-cyclic-GMP phosphodiesterase) inhibitor (CHEBI:71942)
tadalafil (CHEBI:71940) has role vasodilator agent (CHEBI:35620)
tadalafil (CHEBI:71940) is a benzodioxoles (CHEBI:38298)
tadalafil (CHEBI:71940) is a pyrazinopyridoindole (CHEBI:48346)
IUPAC Name
(6R,12aR)-6-(1,3-benzodioxol-5-yl)-2-methyl-2,3,6,7,12,12a-hexahydropyrazino[1',2':1,6]pyrido[3,4-b]indole-1,4-dione
INN Source
tadalafil KEGG DRUG
Synonyms Sources
(6R,12aR)-2,3,6,7,12,12a-Hexahydro-2-methyl-6-(3,4-(methylenedioxy)phenyl) pyrazino(1',2':1,6)pyrido(3,4-b)indole-1,4-dione ChemIDplus
(6R-trans)-6-(1,3-Benzodioxol-5-yl)-2,3,6,7,12,12a-hexahydro-2-methyl-pyrazino(1',2':1,6)pyrido(3,4-b)indole-1,4-dione ChemIDplus
6-BENZO[1,3]DIOXOL-5-YL-2-METHYL-2,3,6,7,12,12A-HEXAHYDRO-PYRAZINO[1',2':1,6]PYRIDO[3,4-B]INDOLE-1,4-DIONE PDBeChem
Brand Names Sources
Adcirca KEGG DRUG
Cialis KEGG DRUG
Manual Xrefs Databases
2553 DrugCentral
CIA PDBeChem
D02008 KEGG DRUG
DB00820 DrugBank
EP2107059 Patent
EP2238979 Patent
HMDB0014958 HMDB
LSM-4109 LINCS
Tadalafil Wikipedia
US2003229080 Patent
US2004157847 Patent
WO2005068464 Patent
WO2007113243 Patent
WO2009144734 Patent
WO2010049500 Patent
WO2012107549 Patent
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Registry Numbers Types Sources
171596-29-5 CAS Registry Number ChemIDplus
171596-29-5 CAS Registry Number KEGG DRUG
9589181 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
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Last Modified
22 February 2017