tadalafil (CHEBI:71940)

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CHEBI:71940 - tadalafil

ChEBI ID	CHEBI:71940
ChEBI Name	tadalafil
Stars
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.
Secondary ChEBI IDs	CHEBI:32177, CHEBI:41488
Last Modified	22 February 2017
Downloads	Molfile

Formula	C22H19N3O4
Net Charge	0
Average Mass	389.411
Monoisotopic Mass	389.13756
SMILES	[H][C@]12Cc3c(nc4ccccc34)[C@@H](c3ccc4c(c3)OCO4)N1C(=O)CN(C)C2=O
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

Wikipedia

Roles Classification

Biological Roles:

anti-obesity agent Any substance which is used to reduce or control weight.

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).

insulin-sensitizing drug An agent which overcomes insulin resistance by activation of the peroxisome proliferator activated receptor gamma (PPAR-gamma).

Applications:

vasodilator agent A drug used to cause dilation of the blood vessels.

antineoplastic agent A substance that inhibits or prevents the proliferation of neoplasms.

hypoglycemic agent A drug which lowers the blood glucose level.

gastrointestinal drug A drug used for its effects on the gastrointestinal system, e.g. controlling gastric acidity, regulating gastrointestinal motility and water flow, and improving digestion.

antidepressant Antidepressants are mood-stimulating drugs used primarily in the treatment of affective disorders and related conditions.

insulin-sensitizing drug An agent which overcomes insulin resistance by activation of the peroxisome proliferator activated receptor gamma (PPAR-gamma).

antihypertensive agent Any drug used in the treatment of acute or chronic vascular hypertension regardless of pharmacological mechanism.

cardiovascular drug A drug that affects the rate or intensity of cardiac contraction, blood vessel diameter or blood volume.

ChEBI Ontology

Outgoing Relation(s)
	tadalafil (CHEBI:71940) has role anti-obesity agent (CHEBI:74518)
	tadalafil (CHEBI:71940) has role antidepressant (CHEBI:35469)
	tadalafil (CHEBI:71940) has role antihypertensive agent (CHEBI:35674)
	tadalafil (CHEBI:71940) has role antineoplastic agent (CHEBI:35610)
	tadalafil (CHEBI:71940) has role cardiovascular drug (CHEBI:35554)
	tadalafil (CHEBI:71940) has role EC 3.1.4.35 (3',5'-cyclic-GMP phosphodiesterase) inhibitor (CHEBI:71942)
	tadalafil (CHEBI:71940) has role gastrointestinal drug (CHEBI:55324)
	tadalafil (CHEBI:71940) has role hypoglycemic agent (CHEBI:35526)
	tadalafil (CHEBI:71940) has role insulin-sensitizing drug (CHEBI:50864)
	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

INNs	Source
tadalafil	KEGG DRUG
tadalafilo	WHO MedNet

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-DIONE	PDBeChem
(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
Chewtadzy	ChEMBL
IC-351	ChEMBL
LY-450190	ChEMBL

Brand Names	Source
Adcirca	KEGG DRUG
Adcirca (previously tadalafil lilly)	ChEMBL
Cialis	KEGG DRUG
Tadalafil component of entadfi	ChEMBL
Tadalafil component of opsynvi	ChEMBL
Tadalafil lilly	ChEMBL

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

Registry Numbers	Sources
Reaxys:9589181	Reaxys
CAS:171596-29-5	KEGG DRUG
CAS:171596-29-5	ChemIDplus

Citations