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

General Information of Drug (ID: DR1526)
Drug Name
Tafenoquine
Prodrug Info Tafenoquine is the prodrug of 5,6-ortho-quinone
Synonyms
Tafenoquine; Tafenoquine [INN:BAN]; Arakoda; Etaquine; Krintafel; SB-252263; WR 238605; WR-238605; WR238605; (R)-N3-(2,6-Dimethoxy-4-methyl-5-(3-trifluoromethyl)phenoxy)quinolin-8-yl)pentane-1,4-diamine; (RS)-N(sup 3)-(2,6-Dimethoxy-4-methyl-5-(3-trifluoro-methylphenoxy)quinolin-8-yl)pentane-1,4-diamine; 1,4-Pentanediamine, N4-(2,6-dimethoxy-4-methyl-5-(3-(trifluoromethyl)phenoxy)-8-quinolinyl)-; 106635-80-7; N(4)-(2,6-Dimethoxy-4-methyl-5-((3-trifluoromethyl)phenoxy)-8-quinolinyl)-1,4-pentanediamine
Indication Malaria [ICD11: 1F40] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 463.5 Topological Polar Surface Area 78.6
Heavy Atom Count 33 Rotatable Bond Count 9
Hydrogen Bond Donor Count 2 Hydrogen Bond Acceptor Count 9
Cross-matching ID
PubChem CID
115358
PubChem SID
602533 ; 10236751 ; 14784788 ; 29296849 ; 50064119 ; 50683558 ; 57339134 ; 103230320 ; 104398192 ; 112378993 ; 128464465 ; 135072665 ; 137249474 ; 139445279 ; 172232583 ; 179148060 ; 224112192 ; 226682048
ChEBI ID
CHEBI:141487
CAS Number
106635-80-7
TTD Drug ID
D07TWN
Formula
C24H28F3N3O3
Canonical SMILES
CC1=CC(=NC2=C1C(=C(C=C2NC(C)CCCN)OC)OC3=CC=CC(=C3)C(F)(F)F)OC
InChI
1S/C24H28F3N3O3/c1-14-11-20(32-4)30-22-18(29-15(2)7-6-10-28)13-19(31-3)23(21(14)22)33-17-9-5-8-16(12-17)24(25,26)27/h5,8-9,11-13,15,29H,6-7,10,28H2,1-4H3
InChIKey
LBHLFPGPEGDCJG-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
5,6-ortho-quinone DM000434 N. A. Hydrolysis - Hydrolysis 1 [3] , [2]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR002330 Tafenoquine 5,6-ortho-quinone Hydrolysis - Hydrolysis CYP2D6 [3], [2]
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Cytochrome P450 2D6 (CYP2D6) DME0009 Homo sapiens
CP2D6_HUMAN
1.14.14.1
[2]
References
1 Tafenoquine was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Tafenoquine and its potential in the treatment and relapse prevention of Plasmodium vivax malaria: the evidence to date. Drug Des Devel Ther. 2016 Jul 26;10:2387-99.
3 Tafenoquine treatment of Plasmodium vivax malaria: suggestive evidence that CYP2D6 reduced metabolism is not associated with relapse in the Phase 2b DETECTIVE trial Malar J. 2016 Feb 18;15:97. doi: 10.1186/s12936-016-1145-5.

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