Chemical Component Summary

Name6-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
SynonymsTADALAFIL; CIALIS
Identifiersn/a
FormulaC22 H19 N3 O4
Molecular Weight389.404
TypeNON-POLYMER
Isomeric SMILESCN1CC(=O)N2[C@@H](C1=O)Cc3c4ccccc4[nH]c3[C@H]2c5ccc6c(c5)OCO6
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

Chemical Details

Formal Charge0
Atom Count48
Chiral Atom Count2
Bond Count53
Aromatic Bond Count16

Drug Info: DrugBank

DrugBank IDDB00820 
NameTadalafil
Groups
  • investigational
  • approved
DescriptionTadalafil is a selective phosphodiesterase-5 inhibitor that is used in the treatment of erectile dysfunction (ED), pulmonary arterial hypertension (PAH), and benign prostatic hypertrophy.[L39100, L39105] It was first approved in 2003 by the FDA for use in ED and later in 2009 for PAH. In contrast to other PDE5 inhibitors like [sildenafil], tadalafil has greater selectivity for PDE5 and a longer half-life which has made it a more suitable option for chronic once-daily dosing in the treatment of PAH.[A242287]
Synonyms
  • Tadalafilo
  • Tadalafil
  • (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
  • (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
Brand Names
  • Ipg-tadalafil
  • Jamp-tadalafil
  • Tadalafil Mylan
  • Priva-tadalafil
  • Ran-tadalafil
IndicationTadalafil is indicated for the treatment of erectile dysfunction (ED) and either alone or in combination with [finasteride] for the treatment of benign prostatic hypertrophy (BPH).[L39095,L39439] It is also indicated for the treatment of pulmonary arterial hypertension (PAH) both alone and in combination with [macitentan] or other endothelin-1 antagonists.[L39100,L39105]
Categories
  • 5-alpha Reductase Inhibitors
  • Antihypertensive Agents
  • Antihypertensives for Pulmonary Arterial Hypertension
  • Carbolines
  • Cardiovascular Agents
ATC-Code
  • G04BE08
  • C02KX52
  • G04CB51
  • G04CA54
  • C02KX54
CAS number171596-29-5

Drug Targets

NameTarget SequencePharmacological ActionActions
cGMP-specific 3',5'-cyclic phosphodiesteraseMERAGPSFGQQRQQQQPQQQKQQQRDQDSVEAWLDDHWDFTFSYFVRKAT...unknowninhibitor
Dual 3',5'-cyclic-AMP and -GMP phosphodiesterase 11AMAASRLDFGEVETFLDRHPELFEDYLMRKGKQEMVEKWLQRHSQGQGALG...unknowninhibitor
Retinal rod rhodopsin-sensitive cGMP 3',5'-cyclic phosphodiesterase subunit gammaMNLEPPKAEFRSATRVAGGPVTPRKGPPKFKQRQTRQFKSKPPKKGVQGF...unknowninhibitor
Cytochrome P450 3A4MALIPDLAMETWLLLAVSLVLLYLYGTHSHGLFKKLGIPGPTPLPFLGNI...unknownsubstrate
Drug Info/Drug Targets: DrugBank 3.0: a comprehensive resource for 'omics' research on drugs. Knox C, Law V, Jewison T, Liu P, Ly S, Frolkis A, Pon A, Banco K, Mak C, Neveu V, Djoumbou Y, Eisner R, Guo AC, Wishart DS. Nucleic Acids Res. 2011 Jan; 39 (Database issue):D1035-41. | PMID:21059682

Related Resource References

Resource NameReference
Pharos CHEMBL779
PubChem 110635
ChEMBL CHEMBL779
ChEBI CHEBI:71940
CCDC/CSD IQUMAI, LASZUC, LATBAL, LATBEP, KAJKUE, KAJKOY, IQUMAI01, CIKPIY, VAGMID
COD 7207636