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

General Information of Drug (ID: DR1873)
Drug Name
HOE-239
Synonyms
Fexinidazol; Fexinidazol [INN-Spanish]; Fexinidazole; Fexinidazole (HOE-239); Fexinidazole (INN); Fexinidazole [INN]; Fexinidazolum; Fexinidazolum [INN-Latin]; SCHEMBL1163575; ZINC1448; fexinidazole[inn]; 1-Methyl-2-((4-(methylthio)phenoxy)-methyl)-5-nitro-1H-imidazole; 1-Methyl-2-((4-(methylthio)phenoxy)methyl)-5-nitro-1H-imidazole; 1-methyl-2-[(4-methylsulfanylphenoxy)methyl]-5-nitroimidazole; 306ERL82IR; 59729-37-2; AC1L2AGG; AK116408; CHEMBL1631694; DTXSID00208448; HOE 239; Hoe-239; MLS006010234; UNII-306ERL82IR
Indication Trypanosomiasis [ICD11: 1F51] Phase 2/3 [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 279.32 Topological Polar Surface Area 98.2
Heavy Atom Count 19 Rotatable Bond Count 4
Hydrogen Bond Donor Count 0 Hydrogen Bond Acceptor Count 5
Cross-matching ID
PubChem CID
68792
CAS Number
59729-37-2
TTD Drug ID
D00RWW
Formula
C12H13N3O3S
Canonical SMILES
CN1C(=CN=C1COC2=CC=C(C=C2)SC)[N+](=O)[O-]
InChI
1S/C12H13N3O3S/c1-14-11(13-7-12(14)15(16)17)8-18-9-3-5-10(19-2)6-4-9/h3-7H,8H2,1-2H3
InChIKey
MIWWSGDADVMLTG-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
Fexinidazole sulfoxide metabolite (M1) DM005049
21418407
Oxidation - Oxidationn 1 [3]
Fexinidazole Sulfone M2 DM005675
68792
Oxidation - Oxidationn 2 [3]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR006055 HOE-239 Fexinidazole Sulfone M1 Oxidation - Oxidationn CYP1A2 ... [3]
MR006056 Fexinidazole Sulfone M1 Fexinidazole Sulfone M2 Oxidation - Oxidationn CYP1A2 ... [3]
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Cytochrome P450 1A2 (CYP1A2) DME0003 Homo sapiens
CP1A2_HUMAN
1.14.14.1
[2]
Cytochrome P450 2B6 (CYP2B6) DME0020 Homo sapiens
CP2B6_HUMAN
1.14.14.1
[2]
Cytochrome P450 2D6 (CYP2D6) DME0009 Homo sapiens
CP2D6_HUMAN
1.14.14.1
[2]
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]
Mephenytoin 4-hydroxylase (CYP2C19) DME0021 Homo sapiens
CP2CJ_HUMAN
1.14.14.1
[2]
⏷ Show the Full List of 6  DME(s)
References
1 ClinicalTrials.gov (NCT02169557) Efficacy and Safety of Fexinidazole in Patients With Stage 1 or Early Stage 2 Human African Trypanosomiasis (HAT) Due to T.b. Gambiense: a Prospective, Multicentre, Open-label Cohort Study, plug-in to the Pivotal Study.
2 Fexinidazole--a new oral nitroimidazole drug candidate entering clinical development for the treatment of sleeping sickness. PLoS Negl Trop Dis. 2010 Dec 21;4(12):e923.
3 Determination of an optimal dosing regimen for fexinidazole, a novel oral drug for the treatment of human African trypanosomiasis: first-in-human studies

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