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CHEBI:71940 - tadalafil

ChEBI IDCHEBI:71940
ChEBI Nametadalafil
Stars
DefinitionA 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.
Secondary ChEBI IDsCHEBI:32177, CHEBI:41488
Last Modified22 February 2017
DownloadsMolfile
FormulaC22H19N3O4
Net Charge0
Average Mass389.411
Monoisotopic Mass389.13756
SMILES[H][C@]12Cc3c(nc4ccccc34)[C@@H](c3ccc4c(c3)OCO4)N1C(=O)CN(C)C2=O
InChIInChI=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
InChIKeyWOXKDUGGOYFFRN-IIBYNOLFSA-N
Wikipedia
Roles Classification
Biological Role:
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:
vasodilator agent  A drug used to cause dilation of the blood vessels.
ChEBI Ontology
Outgoing Relation(s)
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
tadalafilKEGG DRUG
Synonyms  Source
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-DIONEPDBeChem
(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-dioneChemIDplus
(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-dioneChemIDplus
Brand Names  Source
CialisKEGG DRUG
AdcircaKEGG DRUG
Manual XrefsDatabases
D02008KEGG DRUG
CIAPDBeChem
DB00820DrugBank
WO2012107549Patent
WO2005068464Patent
WO2009144734Patent
WO2010049500Patent
EP2107059Patent
WO2007113243Patent
US2004157847Patent
EP2238979Patent
US2003229080Patent
HMDB0014958HMDB
TadalafilWikipedia
LSM-4109LINCS
2553DrugCentral
Registry NumbersSources
Reaxys:9589181Reaxys
CAS:171596-29-5KEGG DRUG
CAS:171596-29-5ChemIDplus
Citations