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

General Information of Drug (ID: DR1825)
Drug Name
UK-453,061
Synonyms
Lersivirine; Lersivirine [USAN:INN]; R3ZGC15A9A; UK 453,061; UK-453,061; UK-453061; 2won; 3-CYANO-5-[[3,5-DIETHYL-1-(2-HYDROXYETHYL)-1H-PYRAZOL-4-YL]OXY]BENZONITRILE; 473921-12-9; 5-((3,5-Diethyl-1-(2-hydroxyethyl)-1H-pyrazol-4-yl)oxy)benzene-1,3-dicarbonitrile; 5-((3,5-diethyl-1-(2-hydroxyethyl)-1H-pyrazol-4-yl)oxy)isophthalonitrile; 5-[3,5-diethyl-1-(2-hydroxyethyl)pyrazol-4-yl]oxybenzene-1,3-dicarbonitrile; 5-{[3,5-Diethyl-1-(2-Hydroxyethyl)-1h-Pyrazol-4-Yl]oxy}benzene-1,3-Dicarbonitrile; UNII-R3ZGC15A9A; ZZE
Indication Human immunodeficiency virus infection [ICD11: 1C60] Phase 2 [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 310.35 Topological Polar Surface Area 94.9
Heavy Atom Count 23 Rotatable Bond Count 6
Hydrogen Bond Donor Count 1 Hydrogen Bond Acceptor Count 5
Cross-matching ID
PubChem CID
16739244
CAS Number
473921-12-9
TTD Drug ID
D08SSP
Formula
C17H18N4O2
Canonical SMILES
CCC1=C(C(=NN1CCO)CC)OC2=CC(=CC(=C2)C#N)C#N
InChI
1S/C17H18N4O2/c1-3-15-17(16(4-2)21(20-15)5-6-22)23-14-8-12(10-18)7-13(9-14)11-19/h7-9,22H,3-6H2,1-2H3
InChIKey
MCPUZZJBAHRIPO-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
UK-453,061 Metabolite M1 DM003638 N. A. Unclear 1 [2]
UK-453,061 Metabolite M10 DM003639 N. A. Unclear 1 [2]
UK-453,061 Metabolite M12 DM003640 N. A. Unclear 1 [2]
UK-453,061 Metabolite M13 DM003632 N. A. Unclear 1 [2]
UK-453,061 Metabolite M15 DM003645 N. A. Unclear 1 [2]
UK-453,061 Metabolite M17 DM003630 N. A. Oxidation - Mono-oxidation 1 [2]
UK-453,061 Metabolite M18 DM003646 N. A. Unclear 1 [2]
UK-453,061 Metabolite M19 DM003637 N. A. Unclear 1 [2]
UK-453,061 Metabolite M21 DM003634 N. A. Unclear 1 [2]
UK-453,061 Metabolite M3 DM003643 N. A. Multi-steps Reaction - Glucuronidation; monohydroxylation 1 [2]
UK-453,061 Metabolite M4 DM003641 N. A. Multi-steps Reaction - Oxidationn; glucuronidation; hydrolysis 1 [2]
UK-453,061 Metabolite M5 DM003642 N. A. Unclear 1 [2]
UK-453,061 Metabolite M6 DM003644 N. A. Multi-steps Reaction - Glucuronidation; monohydroxylation 1 [2]
UK-453,061 Metabolite M16 DM003633 N. A. Unclear 2 [2]
UK-453,061 Metabolite M2 DM003636 N. A. Multi-steps Reaction - Glucuronidation; N-dealkylation; mono-oxidation 2 [2]
UK-453,061 Metabolite M22 DM003635 N. A. Unclear 2 [2]
UK-453,061 Metabolite M8 DM003631 N. A. Multi-steps Reaction - Glucuronidation; monohydroxylation 2 [2]
UK-453,061 Metabolite M9 DM020002 N. A. Multi-steps Reaction - N-dealkylation; glucuronidation 2 [2]
⏷ Show the Full List of 18  DM(s)
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR012792 UK-453,061 UK-453,061 Metabolite M17 Oxidation - Mono-oxidation CYP3A4 [2]
MR012794 UK-453,061 UK-453,061 Metabolite M13 Unclear Unclear [2]
MR012796 UK-453,061 UK-453,061 Metabolite M21 Unclear Unclear [2]
MR012801 UK-453,061 UK-453,061 Metabolite M1 Unclear Unclear [2]
MR012802 UK-453,061 UK-453,061 Metabolite M10 Unclear Unclear [2]
MR012803 UK-453,061 UK-453,061 Metabolite M12 Unclear Unclear [2]
MR012804 UK-453,061 UK-453,061 Metabolite M4 Multi-steps Reaction - Oxidationn; glucuronidation; hydrolysis Unclear [2]
MR012805 UK-453,061 UK-453,061 Metabolite M5 Unclear Unclear [2]
MR012806 UK-453,061 UK-453,061 Metabolite M3 Multi-steps Reaction - Glucuronidation; monohydroxylation Unclear [2]
MR012807 UK-453,061 UK-453,061 Metabolite M6 Multi-steps Reaction - Glucuronidation; monohydroxylation Unclear [2]
MR012808 UK-453,061 UK-453,061 Metabolite M19 Unclear Unclear [2]
MR012809 UK-453,061 UK-453,061 Metabolite M15 Unclear Unclear [2]
MR012810 UK-453,061 UK-453,061 Metabolite M18 Unclear Unclear [2]
MR012795 UK-453,061 Metabolite M13 UK-453,061 Metabolite M16 Unclear Unclear [2]
MR012793 UK-453,061 Metabolite M17 UK-453,061 Metabolite M8 Multi-steps Reaction - Glucuronidation; monohydroxylation Unclear [2]
MR012797 UK-453,061 Metabolite M21 UK-453,061 Metabolite M16 Unclear Unclear [2]
MR012798 UK-453,061 Metabolite M21 UK-453,061 Metabolite M22 Unclear Unclear [2]
MR012799 UK-453,061 Metabolite M21 UK-453,061 Metabolite M2 Multi-steps Reaction - Glucuronidation; N-dealkylation; mono-oxidation Unclear [2]
MR012800 UK-453,061 Metabolite M21 UK-453,061 Metabolite M9 Multi-steps Reaction - N-dealkylation; glucuronidation Unclear [2]
⏷ Show the Full List of 19 MR(s)
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]
UDP-glucuronosyltransferase 2B7 (UGT2B7) DME0040 Homo sapiens
UD2B7_HUMAN
2.4.1.17
[2]
References
1 ClinicalTrials.gov (NCT01254656) A Long Term Safety Study Of Lersivirine For The Treatment Of HIV-1 Infection In Subjects Who Have Completed Treatment With Lersivirine In Studies A5271015 And A5271022.
2 Excretion and metabolism of lersivirine (5-{[3,5-diethyl-1-(2-hydroxyethyl)(3,5-14C2)-1H-pyrazol-4-yl]oxy}benzene-1,3-dicarbonitrile), a next-generation non-nucleoside reverse transcriptase inhibitor, after administration of [14C]Lersivirine to healthy volunteers. Drug Metab Dispos. 2010 May;38(5):789-800.

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