Compound: Tadalafil
SMILES: O=C1N(CC(=O)N2[C@@H]1Cc3c4c(cccc4)[nH]c3[C@H]2c5cc6OCOc6cc5)C
InChIKey: WOXKDUGGOYFFRN-IIBYNOLFSA-N
Synonyms: Tadalafil, Cialis, 171596-29-5, Ic351, ADCIRCA, IC 351, IC-351, Tadalafilo, Tadalafil mylan, Trans-tadalafil, CHEWTADZY, 742SXX0ICT, NSC-750236, NSC-759172, DTXSID9046786, LY-450190, (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, (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, LY450190, (6R,12aR)-2,3,6,7,12,12a-Hexahydro-2-methyl-6-(3,4-methylenedioxyphenyl)pyrazino(1',2':1,6)pyrido(3,4-b)indole-1,4-dione, DTXCID7026786, CHEBI:71940, ENTADFI COMPONENT TADALAFIL, OPSYNVI COMPONENT TADALAFIL, Pyrazino(1',2':1,6)pyrido(3,4-b)indole-1,4-dione, 6-(1,3-benzodioxol-5-yl)-2,3,6,7,12,12a-hexahydro-2-methyl-, (6R,12aR)-, Pyrazino(1',2':1,6)pyrido(3,4-b)indole-1,4-dione, 6-(1,3-benzodioxol-5-yl)-2,3,6,7,12,12a-hexahydro-2-methyl-, (6R-trans)-, Pyrazino[1',2':1,6]pyrido[3,4-b]indole-1,4-dione, 6-(1,3-benzodioxol-5-yl)-2,3,6,7,12,12a-hexahydro-2-methyl-, (6R,12aR)-, tadalafilum, (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, (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, Pyrazino[1',2':1,6]pyrido[3,4-b]indole-1,4-dione, 6-(1,3-benzodioxol-5-yl)-2,3,6,7,12,12a-hexahydro-2-methyl-, (6R-trans)-, ALYQ, TADLIQ, RefChem:6280, G04BE08, (6R,12aR)-6-(Benzo[d][1,3]dioxol-5-yl)-2-methyl-2,3,12,12a-tetrahydropyrazino[1',2':1,6]pyrido[3,4-b]indole-1,4(6H,7H)-dione, ICOS 351, Tadanafil, GF 196960, Tadalafil(Cialis), MFCD07771966, CHEMBL779, GF-196960, (6R,12aR)-6-(benzo[d][1,3]dioxol-5-yl)-2-methyl-2,3,6,7,12,12a-hexahydropyrazino[1',2':1,6]pyrido[3,4-b]indole-1,4-dione, (6R,12aR)-6-(1,3-Benzodioxol-5-yl)-2,3,6,7,12,12a-hexahydro-2-methylpyrazino[1',2':1,6]pyrido[3,4-b]indole-1,4-dione, Tadalafil [USAN], C22H19N3O4, (2R,8R)-2-(1,3-benzodioxol-5-yl)-6-methyl-3,6,17-triazatetracyclo[8.7.0.03,8.011,16]heptadeca-1(10),11,13,15-tetraene-4,7-dione, 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, Tadalafil Lilly, (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, CIA, SMR000466321, Cialis (TN), CAS-171596-29-5, HSDB 7303, UNII-742SXX0ICT, Tadalafila, Tadalafil [USAN:INN:BAN], Tadalafil bulk, Tadalafil?, Tadalafil API, Tadalafil CRS, Tadalafil USP, 1xoz, Cialis, Tadalafil, Tadalafil anhydrous, NCGC00168781-01, Adcirca (TN), Tadalafil (Cialis), Zalutia (TN), Tadalafil raw powder, Tadalafil (Standard), KS-1117, TADALAFIL [INN], TADALAFIL [JAN], TADALAFIL [MI], TADALAFIL; CIALIS, TADALAFIL [HSDB], TADALAFIL [VANDF], (-)-Tadalafil (6R), TADALAFIL [MART.], TADALAFIL [USP-RS], TADALAFIL [WHO-DD], Tadalafil (JAN/USP/INN), SCHEMBL33333, TADALAFIL [EMA EPAR], MLS000759426, MLS001165782, MLS001195644, MLS001424132, MLS006010126, Tadalafil - Bio-X trade mark, GTPL7299, orb1308738, orb3140154, TADALAFIL [ORANGE BOOK], SCHEMBL29358190, SCHEMBL29427554, TADALAFIL [EP MONOGRAPH], BDBM14777, TADALAFIL [USP MONOGRAPH], GLXC-07318, HMS2051N17, HMS2235L21, HMS3884G19, HY-90009AR, Pharmakon1600-01505639, EX-A2644, MSK10246, Tox21_112642, EBC-09118, HY-90009A, NSC750236, NSC759172, s1512, Tadalafil 1.0 mg/ml in Acetonitrile, AKOS015892559, Tox21_112642_1, AB42193, CCG-100973, CS-1414, DB00820, FB02802, NC00223, NSC 750236, NSC 759172, 1,3-benzodioxol-5-yl(methyl)[?]dione, NCGC00263909-02, Tadalafil 100 microg/mL in Acetonitrile, BT164435, NS00006532, SW197603-2, D02008, AB00639969-08, AB00639969_09, AB00639969_10, AR-270/43507798, Q424156, SR-05000001940, SR-05000001940-1, BRD-K93645900-001-04-8, BRD-K93645900-001-11-3, BRD-K93645900-001-12-1, Z1501485354, (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(16),12,14-tetraene-4,7-dione, (6R,12 aR)-6-(1,3-benzodioxol-5-yl)-2,3,6,7,12,12a-hexahydro-2-methylpyrazino[1',2':1,6]pyrido[3,4-b]indole-1,4-dione, (6R,12?R)-6-(Benzo[d][1,3]dioxol-5-yl)-2-methyl-2,3,12,12?-tetrahydropyrazino[1',2':1,6]pyrido[3,4-?]indole-1,4(6H,7H)-dione, (6R,12aR) 6-(1,3-benzodioxol-5-yl)-2,3,6,7,12,12a-hexahydro-2-methylpyrazino [1',2':1,6] pyrido[3,4-b]indole-1,4-dione, (6R,12aR) 6-(1,3-benzodioxol-5-yl)-2,3,6,7,12,12a-hexahydro-2-methylpyrazino[1',2':1,6]pyrido[3,4-b]indole-1,4-dione, (6R,12aR)-6-(1,3-Benzodioxol-5-yl)-2,3,6,7,12,12a-hexahydro-2-methylpyrazino[1,2:1,6]pyrido[3,4-b]indole-1,4-dione, (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, (6R,12aR)-6-(2H-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, (6R,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, 1242099-07-5, 171488-03-2, 6-(1,3-benzodioxol-5-yl)-2-methyl-2,3,6,7,12,12a-hexahydropyrazino[2',1':6,1]pyrido[3,4-b]indole-1,4-dione, Pyrazino[1',6]pyrido[3,4-b]indole-1,4-dione, 6-(1,3-benzodioxol-5-yl)-2,3,6,7,12,12ahexahydro-2-methyl-, (6R,12aR)-, rel-(6R,12aR)-6-(Benzo[d][1,3]dioxol-5-yl)-2-methyl-2,3,12,12a-tetrahydropyrazino[1',2':1,6]pyrido[3,4-b]indole-1,4(6H,7H)-dione
Theoretical properties:
molecular_formula: C22H19N3O4
molecular_weight: 389.4 g/mol
exact_mass: 389.13755610 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 1
hydrogen_bond_acceptor_count: 4
rotatable_bond_count: 1
heavy_atom_count: 29
topological_polar_surface_area: 74.9 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
melting_point: 301-302 °C
solubility: Practically insoluble in water
vapor_pressure: 2.2X10-14 mm Hg at 25 °C /Estimated/
Descriptions:
{"pubchem": "Tadalafil is 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. It has a role as a vasodilator agent and an EC 3.1.4.35 (3',5'-cyclic-GMP phosphodiesterase) inhibitor. It is a member of benzodioxoles and a pyrazinopyridoindole.", "chebi": "A pyrazinopyridoindole that is 2,3,6,7,12,12a-hexahydropyrazino[1',2':1,6]pyrido[3,4-<em>b</em>]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 6<i>R</i>,12a<i>R</i>-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.", "chembl": "TADALAFIL is a small molecule listed in the ChEMBL database and has reached clinical trial phase 4.0.", "wikipedia": "Tadalafil, sold under the brand name Cialis among others, is a medication used to treat erectile dysfunction, benign prostatic hyperplasia, and pulmonary arterial hypertension. It is taken by mouth. Onset is typically within half an hour and the duration is up to 36 hours.\nCommon side effects include headache, muscle pain, flushing, and nausea. Caution is advised in those with cardiovascular disease. Rare but serious side effects include a prolonged erection that can lead to damage to the penis, vision problems, and hearing loss. Tadalafil is not recommended in people taking nitrovasodilators such as nitroglycerin, as this may result in a serious drop in blood pressure. Tadalafil is a PDE5 inhibitor which increases blood flow to the penis. It also dilates blood vessels in the lungs, which lowers the pulmonary artery pressure.\nTadalafil was approved for medical use in the United States in 2003. It is available as a generic medication. In 2022, it was the 172nd most commonly prescribed medication in the United States, with more than 3 million prescriptions."}