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

General Information of Drug (ID: DR1673)
Drug Name
Vardenafil hydrochloride
Synonyms
Vardenafil (hydrochloride); Vardenafil HCL; Vardenafil Hydrochloride Salt; Vardenafil hydrochloride; Vardenafil hydrochloride (USAN); Vardenafil hydrochloride [USAN]; Vardenafil; 224785-90-4; Levitra; Vivanza; UNII-UCE6F4125H; HSDB 7304; Levitra (TN); BAY 38-9456; CHEMBL1520; UCE6F4125H; 2-{2-ETHOXY-5-[(4-ETHYLPIPERAZIN-1-YL)SULFONYL]PHENYL}-5-METHYL-7-PROPYLIMIDAZO[5,1-F][1,2,4]TRIAZIN-4(1H)-ONE; VDN; CHEBI:46295; SECKRCOLJRRGGV-UHFFFAOYSA-N; 2-(2-Ethoxy-5-(4-ethylpiperazin-1-yl-1-sulfonyl)phenyl)-5-methyl-7-propyl-3H-imidazo(5,1-f)(1,2,4)triazin-4-one; BAY38-9456; XCMULUAPJXCOHI-UHFFFAOYSA-N; 224785-90-4 (base); 224785-91-5; 224789-15-5; 224789-15-5 (di-hcl); AKOS025312515; AKOS032400217; BCP21908; C23H32N6O4S.HCl; C23H33ClN6O4S; CCG-213406; CHEMBL1339; CS-2765; DTXSID30945152; HY-B0442A; IF61NL91H3; MCULE-5671555647; MFCD07369690; MLS006011996; NSC-759103; NSC759103; Pharmakon1600-01505374; SCHEMBL973820; UNII-IF61NL91H3
Indication Erectile dysfunction [ICD11: HA01] Approved [1]
Structure
3D MOL is unavailable 2D MOL
Pharmaceutical Properties Molecular Weight 525.1 Topological Polar Surface Area 118
Heavy Atom Count 35 Rotatable Bond Count 8
Hydrogen Bond Donor Count 2 Hydrogen Bond Acceptor Count 8
Cross-matching ID
PubChem CID
135438569
CAS Number
224789-15-5
TTD Drug ID
D0C9SY
Formula
C23H33ClN6O4S
Canonical SMILES
CCCC1=NC(=C2N1N=C(NC2=O)C3=C(C=CC(=C3)S(=O)(=O)N4CCN(CC4)CC)OCC)C.Cl
InChI
1S/C23H32N6O4S.ClH/c1-5-8-20-24-16(4)21-23(30)25-22(26-29(20)21)18-15-17(9-10-19(18)33-7-3)34(31,32)28-13-11-27(6-2)12-14-28;/h9-10,15H,5-8,11-14H2,1-4H3,(H,25,26,30);1H
InChIKey
XCMULUAPJXCOHI-UHFFFAOYSA-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
N-desethyl vardenafil DM003039
135565210
Oxidation - N-Deethylation 1 [4] , [5] , [3]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR002504 Vardenafil hydrochloride N-desethyl vardenafil Oxidation - N-Deethylation CYP3A4 ... [4], [5], [3]
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
[3]
References
1 Vardenafil Hydrochloride was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Erectile dysfunction drugs changed the protein expressions and activities of drug-metabolising enzymes in the liver of male rats. Oxid Med Cell Longev. 2016;2016:4970906.
3 The contributions of cytochromes P450 3A4 and 3A5 to the metabolism of the phosphodiesterase type 5 inhibitors sildenafil, udenafil, and vardenafil. Drug Metab Dispos. 2008 Jun;36(6):986-90.
4 Vardenafil preclinical trial data: potency, pharmacodynamics, pharmacokinetics, and adverse events Int J Impot Res. 2004 Jun;16 Suppl 1:S34-7. doi: 10.1038/sj.ijir.3901213.
5 High-performance liquid chromatographic method with amperometric detection employing boron-doped diamond electrode for the determination of sildenafil, vardenafil and their main metabolites in plasma J Chromatogr A. 2011 Nov 4;1218(44):7996-8001. doi: 10.1016/j.chroma.2011.09.001.

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