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

General Information of Drug (ID: DR2274)
Drug Name
EPX-100
Synonyms
Clemizol; Clemizole; Clemizolum; Depocural; Histacur; Histakool; Lergopenin; T97CB3796L; 1-(4-Chlorobenzyl)-2-(pyrrolidin-1-ylmethyl)-1H-benzo[d]imidazole; 1-(4-chlorobenzyl)-2-(pyrrolidin-1-ylmethyl)-1H-benzimidazole; 1-(p-Chlorobenzyl)-2-pyrrolidylmethylenebenzimidazole; 1-[(4-chlorophenyl)methyl]-2-(pyrrolidin-1-ylmethyl)benzimidazole; 1H-Benzimidazole, 1-[(4-chlorophenyl)methyl]-2-(1-pyrrolidinylmethyl)-; 442-52-4; CHEBI:52140; CJXAEXPPLWQRFR-UHFFFAOYSA-N; NSC 46261; UNII-T97CB3796L
Indication Dravet syndrome [ICD11: 8A61] Preclinical [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 325.8 Topological Polar Surface Area 21.1
Heavy Atom Count 23 Rotatable Bond Count 4
Hydrogen Bond Donor Count 0 Hydrogen Bond Acceptor Count 2
Cross-matching ID
PubChem CID
2782
PubChem SID
99695 ; 615231 ; 4445364 ; 8151794 ; 10522977 ; 11110952 ; 11110953 ; 11466255 ; 11467375 ; 11485930 ; 15347485 ; 29221937 ; 47216959 ; 47216960 ; 47810952 ; 47959954 ; 48110645 ; 48334694 ; 49698395 ; 50100200 ; 50104284 ; 57304882 ; 57321456 ; 79754667 ; 85209562 ; 85788561 ; 87906851 ; 90341639 ; 103826182 ; 104301595 ; 106178634 ; 117463367 ; 124662137 ; 124879655 ; 124879656 ; 124879657 ; 125823529 ; 127635999 ; 134974845 ; 134986591 ; 136351847 ; 137005449 ; 142245913 ; 160671857 ; 162224660 ; 170497650 ; 172915197 ; 179225225 ; 184531234 ; 185985216
ChEBI ID
CHEBI:52140
CAS Number
442-52-4
TTD Drug ID
D06XDJ
Formula
C19H20ClN3
Canonical SMILES
C1CCN(C1)CC2=NC3=CC=CC=C3N2CC4=CC=C(C=C4)Cl
InChI
1S/C19H20ClN3/c20-16-9-7-15(8-10-16)13-23-18-6-2-1-5-17(18)21-19(23)14-22-11-3-4-12-22/h1-2,5-10H,3-4,11-14H2
InChIKey
CJXAEXPPLWQRFR-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
EPX-100 M1 DM006480 N. A. Oxidation - Oxidationn 1 [2]
EPX-100 M12 DM006485 N. A. Unclear 1 [2]
EPX-100 M14 DM006484 N. A. Multi-steps Reaction - Oxidationn; conjugation 1 [2]
EPX-100 M19 DM006483 N. A. Oxidation - Oxidationn 1 [2]
EPX-100 M2 DM006481 N. A. Oxidation - Oxidationn 1 [2]
EPX-100 M6 DM006482 N. A. Oxidation - Oxidationn 1 [2]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR006964 EPX-100 EPX-100 M1 Oxidation - Oxidationn CYP3A4 ... [2]
MR006965 EPX-100 EPX-100 M2 Oxidation - Oxidationn CYP1A2 ... [2]
MR006966 EPX-100 EPX-100 M6 Oxidation - Oxidationn CYP [2]
MR006967 EPX-100 EPX-100 M19 Oxidation - Oxidationn CYP2C9 [2]
MR006968 EPX-100 EPX-100 M14 Multi-steps Reaction - Oxidationn; conjugation CYP2C9 [2]
MR006969 EPX-100 EPX-100 M12 Unclear Unclear [2]
⏷ Show the Full List of 6 MR(s)
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 2C9 (CYP2C9) DME0019 Homo sapiens
CP2C9_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]
Mephenytoin 4-hydroxylase (CYP2C19) DME0021 Homo sapiens
CP2CJ_HUMAN
1.14.14.1
[2]
Unclear metabolic mechanism (DME-unclear) DME1362 Bacteroides caccae Not Available Not Available [3]
Unclear metabolic mechanism (DME-unclear) DME1393 Blautia hansenii Not Available Not Available [3]
⏷ Show the Full List of 7  DME(s)
References
1 Clemizole and modulators of serotonin signalling suppress seizures in Dravet syndrome. Brain. 2017 Mar 1;140(3):669-683.
2 Using chimeric mice with humanized livers to predict human drug metabolism and a drug-drug interaction. J Pharmacol Exp Ther. 2013 Feb;344(2):388-96.
3 Mapping human microbiome drug metabolism by gut bacteria and their genes. Nature. 2019 Jun;570(7762):462-467.

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