Details of the Drug Metabolized by Drug-Metabolizing Enzyme (DME)

General Information of Drug (ID: DR1525)
Drug Name
Tadalafil
Synonyms
Tadalafil; Tadalafil(Cialis); Tadanafil; (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; ADCIRCA; Cialis; GF 196960; GF-196960; ICOS 351; (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; 171596-29-5; 742SXX0ICT; CHEBI:71940; CHEMBL779; HSDB 7303; IC 351; IC-351; Ic351; UNII-742SXX0ICT
Indication Erectile dysfunction [ICD11: HA01] Approved [1]
Structure
3D MOL 2D MOL
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
Cross-matching ID
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
CAS Number
171596-29-5
TTD Drug ID
D05MQK
Formula
C22H19N3O4
Canonical SMILES
CN1CC(=O)N2C(C1=O)CC3=C(C2C4=CC5=C(C=C4)OCO5)NC6=CC=CC=C36
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
The Metabolic Roadmap of This Drug
The Full List of Drug Metabolites (DM) of This Drug
DM Name DM ID PubChem ID Reaction DM Level REF
Tadalafil catechol DM000431
9864503
Oxidation - Oxidation 1 [4] , [2]
Methyl Tadalafil catechol DM000432 N. A. Conjugation - Methylation 2 [4]
Methyl Tadalafil catechol glucuronide DM000433 N. A. Conjugation - Glucuronidation 3 [4]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR002329 Tadalafil Tadalafil catechol Oxidation - Oxidation CYP3A4 ... [4], [2]
MR002327 Tadalafil catechol Methyl Tadalafil catechol Conjugation - Methylation Unclear [4]
MR002328 Methyl Tadalafil catechol Methyl Tadalafil catechol glucuronide Conjugation - Glucuronidation Unclear [4]
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[2]
Cytochrome P450 3A5 (CYP3A5) DME0012 Homo sapiens
CP3A5_HUMAN
1.14.14.1
[2]
Cytochrome P450 3A7 (CYP3A7) DME0015 Homo sapiens
CP3A7_HUMAN
1.14.14.1
[2]
Unclear metabolic mechanism (DME-unclear) DME1251 Bacteroides fragilis Not Available Not Available [3]
Unclear metabolic mechanism (DME-unclear) DME1254 Bacteroides thetaiotaomicron Not Available Not Available [3]
References
1 Tadalafil was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Contribution of CYP3A isoforms to dealkylation of PDE5 inhibitors: a comparison between sildenafil N-demethylation and tadalafil demethylenation. Biol Pharm Bull. 2015;38(1):58-65.
3 Mapping human microbiome drug metabolism by gut bacteria and their genes. Nature. 2019 Jun;570(7762):462-467.
4 Effect of Ticagrelor, a Cytochrome P450 3A4 Inhibitor, on the Pharmacokinetics of Tadalafil in Rats Pharmaceutics. 2019 Jul 20;11(7):354. doi: 10.3390/pharmaceutics11070354.

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