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

General Information of Drug (ID: DR5976)
Drug Name
Fexinidazole
Synonyms
Fexinidazole (human African trypanosomiasis); Fexinidazole (African sleeping sickness), Drugs for Neglected Diseases initiative; Fexinidazole (HAT), Drugs for Neglected Diseases initiative; Fexinidazole (human African trypanosomiasis), Drugs for Neglected Diseases initiative
Indication Trypanosomiasis [ICD11: 1D51-1F53] 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
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 [2] , [3]
Fexinidazole sulfone metabolite (M2) DM005050
21429076
Oxidation - Oxidationn 2 [2] , [3]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR005476 Fexinidazole Fexinidazole sulfoxide metabolite (M1) Oxidation - Oxidationn CYP1A2 ... [2], [3]
MR005477 Fexinidazole sulfoxide metabolite (M1) Fexinidazole sulfone metabolite (M2) Oxidation - Oxidationn CYP1A2 ... [2], [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] , [3]
Cytochrome P450 1A2 (CYP1A2) DME0003 Homo sapiens
CP1A2_HUMAN
1.14.14.1
[3]
Cytochrome P450 2B6 (CYP2B6) DME0020 Homo sapiens
CP2B6_HUMAN
1.14.14.1
[2] , [3]
Cytochrome P450 2B6 (CYP2B6) DME0020 Homo sapiens
CP2B6_HUMAN
1.14.14.1
[3]
Cytochrome P450 2D6 (CYP2D6) DME0009 Homo sapiens
CP2D6_HUMAN
1.14.14.1
[2] , [3]
Cytochrome P450 2D6 (CYP2D6) DME0009 Homo sapiens
CP2D6_HUMAN
1.14.14.1
[3]
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[2] , [3]
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[3]
Cytochrome P450 3A5 (CYP3A5) DME0012 Homo sapiens
CP3A5_HUMAN
1.14.14.1
[2] , [3]
Cytochrome P450 3A5 (CYP3A5) DME0012 Homo sapiens
CP3A5_HUMAN
1.14.14.1
[3]
Dimethylaniline oxidase 3 (FMO3) DME0039 Homo sapiens
FMO3_HUMAN
1.14.13.8
[2] , [3]
Dimethylaniline oxidase 3 (FMO3) DME0039 Homo sapiens
FMO3_HUMAN
1.14.13.8
[3]
Mephenytoin 4-hydroxylase (CYP2C19) DME0021 Homo sapiens
CP2CJ_HUMAN
1.14.14.1
[2] , [3]
Mephenytoin 4-hydroxylase (CYP2C19) DME0021 Homo sapiens
CP2CJ_HUMAN
1.14.14.1
[3]
Nitroreductase (NTR) DME1064 Giardia intestinalis
A0A482G3K9_GIAIN
1.5.1.39
[4]
⏷ Show the Full List of 15  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. U.S. National Institutes of Health.
2 Determination of an optimal dosing regimen for fexinidazole, a novel oral drug for the treatment of human African trypanosomiasis: first-in-human studies
3 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.
4 Assessing the essentiality of Leishmania donovani nitroreductase and its role in nitro drug activation

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