General Information
Drug ID
DR01260
Drug Name
Tadalafil
Synonyms
(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,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; (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; ADCIRCA; Acdirca; Cialis; Cialis (TN); Cialis, GF 196960, IC 351, ICOS 351, Tadalafil; GF 196960; GF-196960; IC 351; IC-351; ICOS 351; Ic351; KS-1117; Lilly brand of tadalafil; Tadalafil (JAN/USAN/INN); Tadalafil [USAN]; Tadanafil
Drug Type
Small molecular drug
Indication Benign prostatic hyperplasia [ICD11:GA90] Approved [1]
Erectile dysfunction [ICD11:HA01] Approved [1]
Pulmonary arterial hypertension [ICD11:BB01.0] Approved [1]
Therapeutic Class
Antiimpotence Agents
Structure
3D MOL 2D MOL
Formula
C22H19N3O4
Canonical SMILES
CN1CC(=O)N2C(C1=O)CC3=C(C2C4=CC5=C(C=C4)OCO5)NC6=CC=CC=C36
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
CAS Number
CAS 171596-29-5
Pharmaceutical Properties Molecular Weight 389.4 Topological Polar Surface Area 74.9
Heavy Atom Count 29 Rotatable Bond Count 1
Hydrogen Bond Donor Count 1 Hydrogen Bond Acceptor Count 4
XLogP
2.3
PubChem CID
110635
PubChem SID
585746 ,833257 ,7849070 ,7980303 ,10235225 ,12015128 ,14756405 ,14805118 ,26719828 ,44439099 ,46386604 ,46393582 ,46507646 ,46515102 ,48631155 ,49665805 ,49666420 ,49681754 ,50070180 ,50070554 ,50071306 ,50930588 ,53789230 ,57338564 ,71826083 ,92308507 ,103205141 ,104253184 ,104386552 ,118046114 ,124658965 ,124757304 ,124801305 ,124976968 ,125164108 ,126670668 ,126730649 ,129612837 ,131407413 ,134337906 ,134358339 ,135067956 ,137002812 ,142183965 ,144075910 ,144206195 ,152031978 ,152344458 ,160709391 ,160821591
ChEBI ID
CHEBI:71940
TTD Drug ID
D05MQK
DT(s) Transporting This Drug P-GP Transporter Info P-glycoprotein 1 Substrate [2]
References
1 Tadalafil was approved by FDA. The official website of the U.S. Food and Drug Administration. (2019)
2 In Vitro P-Glycoprotein-Mediated Transport of Tadalafil: A Comparison with Sildenafil. Biol Pharm Bull. 2017;40(8):1314-1319.

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