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

General Information of Drug (ID: DR1866)
Drug Name
WR-6026
Synonyms
Sitamaquine; Sitamaquine [INN:BAN]; WR 006026; WR 6026; WR-6026; WR6026; ZINC1535009; 5330-29-0; 57695-04-2; 5AIJ4TGC6B; 6-Methoxy-8-(6-diethylaminohexylamino)-4-methylquinoline; 8-((6-(Diethylamino)hexyl)amino)-6-methoxy-4-methylquinoline; AC1L2824; BCP07171; CHEMBL57004; DB04909; DRG-0140; DTXSID70206395; MMV000063; N',N'-diethyl-N-(6-methoxy-4-methyl-8-quinolyl)hexane-1,6-diamine; SCHEMBL1070741; N,N-Diethyl-N'-(6-methoxy-4-methyl-8-quinolyl)hexane-1,6-diamine; NCGC00386990-01; NSC2452; UNII-5AIJ4TGC6B
Indication Protozoan infection [ICD11: 1F5Z] Phase 2 [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 343.5 Topological Polar Surface Area 37.4
Heavy Atom Count 25 Rotatable Bond Count 11
Hydrogen Bond Donor Count 1 Hydrogen Bond Acceptor Count 4
Cross-matching ID
PubChem CID
42548
CAS Number
57695-04-2
TTD Drug ID
D0Q1LO
Formula
C21H33N3O
Canonical SMILES
CCN(CC)CCCCCCNC1=CC(=CC2=C(C=CN=C12)C)OC
InChI
1S/C21H33N3O/c1-5-24(6-2)14-10-8-7-9-12-22-20-16-18(25-4)15-19-17(3)11-13-23-21(19)20/h11,13,15-16,22H,5-10,12,14H2,1-4H3
InChIKey
RVAKDGYPIVSYEU-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
8-(6-diethylaminohexylamino)-6-methoxy-4-hydroxymethyl quinoline DM005688 N. A. Unclear 1 [3]
8-(6-ethylaminohexylamino)-6-methoxy-lepidine DM005687
53733056
Unclear 1 [3]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR006068 WR-6026 8-(6-ethylaminohexylamino)-6-methoxy-lepidine Unclear CYP2D6 [3]
MR006069 WR-6026 8-(6-diethylaminohexylamino)-6-methoxy-4-hydroxymethyl quinoline Unclear CYP2D6 [3]
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 ClinicalTrials.gov (NCT00381394) A Study Evaluating Sitamaquine Compared With Amphotericin B In The Treatment Of Visceral Leishmaniasis..
2 Differential cytochrome P450 2D metabolism alters tafenoquine pharmacokinetics. Antimicrob Agents Chemother. 2015 Jul;59(7):3864-9.
3 Metabolism of a potential 8-aminoquinoline antileishmanial drug in rat liver microsomes

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