Preferred Name |
tadalafil |
|
Synonyms |
tadalafil (2R,8R)-2-(2H-1,3-benzodioxol-5-yl)-6-methyl-3,6,17-triazatetracyclo[8.7.0.0^{3,8}.0^{11,16}]heptadeca-1(10),11,13,15-tetraene-4,7-dione Cialis (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 Adcirca 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 (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 C22H19N3O4 (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 |
|
ID |
http://purl.obolibrary.org/obo/CHEBI_71940 |
|
AHFScode |
24:12.12 |
|
altId |
CHEBI:32177 CHEBI:41488 |
|
ATCCode |
G04BE08 |
|
CASRN |
171596-29-5 |
|
DBBrand |
cialis |
|
DBname |
tadalafil |
|
DBSynonym |
icos 351 tadanafil |
|
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. |
|
has effect |
http://purl.obolibrary.org/obo/OAE_0000388 http://purl.obolibrary.org/obo/OAE_0000496 http://purl.obolibrary.org/obo/OAE_0000453 http://purl.obolibrary.org/obo/OAE_0001373 http://purl.obolibrary.org/obo/OAE_0000597 http://purl.obolibrary.org/obo/OAE_0000081 http://purl.obolibrary.org/obo/OAE_0000236 http://purl.obolibrary.org/obo/OAE_0000557 http://purl.obolibrary.org/obo/OAE_0000377 http://purl.obolibrary.org/obo/OAE_0001045 http://purl.obolibrary.org/obo/OAE_0000391 http://purl.obolibrary.org/obo/OAE_0000376 http://purl.obolibrary.org/obo/OAE_0000335 http://purl.obolibrary.org/obo/OAE_0000479 http://purl.obolibrary.org/obo/OAE_0000406 http://purl.obolibrary.org/obo/OAE_0000561 http://purl.obolibrary.org/obo/OAE_0001509 http://purl.obolibrary.org/obo/OAE_0000493 http://purl.obolibrary.org/obo/OAE_0001360 http://purl.obolibrary.org/obo/OAE_0000373 http://purl.obolibrary.org/obo/OAE_0000577 http://purl.obolibrary.org/obo/OAE_0000418 http://purl.obolibrary.org/obo/OAE_0000319 http://purl.obolibrary.org/obo/OAE_0000021 http://purl.obolibrary.org/obo/OAE_0000412 http://purl.obolibrary.org/obo/OAE_0000317 http://purl.obolibrary.org/obo/OAE_0000660 http://purl.obolibrary.org/obo/OAE_0000482 http://purl.obolibrary.org/obo/OAE_0000382 http://purl.obolibrary.org/obo/OAE_0000281 http://purl.obolibrary.org/obo/OAE_0000600 http://purl.obolibrary.org/obo/OAE_0000310 http://purl.obolibrary.org/obo/OAE_0000632 http://purl.obolibrary.org/obo/OAE_0000601 http://purl.obolibrary.org/obo/OAE_0001463 http://purl.obolibrary.org/obo/OAE_0000375 http://purl.obolibrary.org/obo/OAE_0000353 http://purl.obolibrary.org/obo/OAE_0000551 http://purl.obolibrary.org/obo/OAE_0001234 http://purl.obolibrary.org/obo/OAE_0000498 http://purl.obolibrary.org/obo/OAE_0000400 http://purl.obolibrary.org/obo/OAE_0000086 http://purl.obolibrary.org/obo/OAE_0000584 http://purl.obolibrary.org/obo/OAE_0002206 http://purl.obolibrary.org/obo/OAE_0000414 http://purl.obolibrary.org/obo/OAE_0000607 http://purl.obolibrary.org/obo/OAE_0000355 http://purl.obolibrary.org/obo/OAE_0000038 http://purl.obolibrary.org/obo/OAE_0000968 http://purl.obolibrary.org/obo/OAE_0000034 http://purl.obolibrary.org/obo/OAE_0002122 http://purl.obolibrary.org/obo/OAE_0000460 http://purl.obolibrary.org/obo/OAE_0000866 http://purl.obolibrary.org/obo/OAE_0000508 http://purl.obolibrary.org/obo/OAE_0000401 http://purl.obolibrary.org/obo/OAE_0000343 http://purl.obolibrary.org/obo/OAE_0000505 http://purl.obolibrary.org/obo/OAE_0000022 http://purl.obolibrary.org/obo/OAE_0000385 http://purl.obolibrary.org/obo/OAE_0000336 http://purl.obolibrary.org/obo/OAE_0000362 http://purl.obolibrary.org/obo/OAE_0000470 http://purl.obolibrary.org/obo/OAE_0000296 http://purl.obolibrary.org/obo/OAE_0000501 http://purl.obolibrary.org/obo/OAE_0000374 http://purl.obolibrary.org/obo/OAE_0000462 http://purl.obolibrary.org/obo/OAE_0000358 http://purl.obolibrary.org/obo/OAE_0001366 |
|
has pharmacological target | ||
has role | ||
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 |
InChIKey=WOXKDUGGOYFFRN-IIBYNOLFSA-N |
|
inhibits |
http://purl.obolibrary.org/obo/dinto_0411 |
|
is metabolised by | ||
label |
tadalafil |
|
prefixIRI |
obo2:CHEBI_71940 |
|
prefLabel |
tadalafil |
|
SMILES |
[H][C@]12CC3=C(NC4=CC=CC=C34)[C@H](N1C(=O)CN(C)C2=O)C1=CC2=C(OCO2)C=C1 [H][C@]12Cc3c([nH]c4ccccc34)[C@H](N1C(=O)CN(C)C2=O)c1ccc2OCOc2c1 |
|
Synonym |
tadalafil (2R,8R)-2-(2H-1,3-benzodioxol-5-yl)-6-methyl-3,6,17-triazatetracyclo[8.7.0.0^{3,8}.0^{11,16}]heptadeca-1(10),11,13,15-tetraene-4,7-dione Cialis (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 Adcirca 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 (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 C22H19N3O4 (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 |
|
xref |
National Drug Code Directory:0002-4465-34 Drugs.com:http://www.drugs.com/tadalafil.html CiteXplore:23234619 CiteXplore:21680058 Reaxys:9589181 CiteXplore:23118430 Patent:EP2238979 DrugBank:DB00820 CiteXplore:23347176 PubChem Compound:110635 PharmGKB:PA10333 CiteXplore:23190275 CiteXplore:22776546 HMDB:HMDB14958 PDB:CIA CiteXplore:23033484 PDRhealth:http://www.pdrhealth.com/drug_info/rxdrugprofiles/drugs/cia1687.shtml Wikipedia:http://en.wikipedia.org/wiki/Tadalafil Patent:WO2005068464 CiteXplore:21056623 BindingDB:14777 Drugs Product Database (DPD):2248088 CiteXplore:22328305 Patent:WO2007113243 CiteXplore:22996758 PubChem Substance:46507646 PDBeChem:CIA CiteXplore:22971615 CiteXplore:22494518 CiteXplore:23216015 CiteXplore:23219525 RxList:http://www.rxlist.com/cgi/generic3/cialis.htm Patent:EP2107059 ChemSpider:99301 ChEMBL:144920 KEGG DRUG:D02008 Patent:US2004157847 Patent:WO2010049500 CiteXplore:23312193 CiteXplore:23346990 Patent:US2003229080 CiteXplore:22014651 CiteXplore:23140258 CiteXplore:23072271 Patent:WO2009144734 Patent:WO2012107549 CiteXplore:22816778 CASRN:171596-29-5 CiteXplore:22982422 Wikipedia:Tadalafil |
|
subClassOf |