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

General Information of Drug (ID: DR1618)
Drug Name
Topiramate
Synonyms
Tipiramate; Tipiramate [French]; Tipiramato; Tipiramato [Spanish]; Topamax; Topamax Sprinkle; Topiramato; Topiramato [INN-Spanish]; Topiramatum; Topiramatum [INN-Latin]; Epitomax; McN 4853; McN-4853; RWJ 17021; RWJ-17021; RWJ-17021-000; topiramate; topiramatum [Latin]; 2,3:4,5-Bis-O-(1-methylethylidene)-beta-D-fructopyranose sulfamate; 2,3:4,5-Di-O-isopropylidene-beta-D-fructopyranose sulfamate; 97240-79-4; C12H21NO8S; MFCD00865320; UNII-0H73WJJ391
Indication Focal seizure [ICD11: 8A68] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 339.36 Topological Polar Surface Area 124
Heavy Atom Count 22 Rotatable Bond Count 3
Hydrogen Bond Donor Count 1 Hydrogen Bond Acceptor Count 9
Cross-matching ID
PubChem CID
5284627
PubChem SID
9705 ; 7847603 ; 7980814 ; 11039383 ; 11484731 ; 11488944 ; 11528651 ; 12013555 ; 14777895 ; 14924784 ; 24724627 ; 25819957 ; 26612934 ; 26719832 ; 39317930 ; 46386619 ; 46508334 ; 46511457 ; 47277061 ; 47425755 ; 48416647 ; 48764342 ; 49681704 ; 49835829 ; 50070928 ; 50123385 ; 53787612 ; 57359151 ; 77351910 ; 85248100 ; 92124710 ; 92307910 ; 92308459 ; 93167012 ; 93167145 ; 97857519 ; 99437151 ; 104109398 ; 104234233 ; 104971753 ; 124658936 ; 124757247 ; 124800161 ; 125164051 ; 125312450 ; 126525327 ; 126606833 ; 126670104 ; 128389335 ; 134337459
ChEBI ID
CHEBI:63631
CAS Number
97240-79-4
TTD Drug ID
D07VDZ
Formula
C12H21NO8S
Canonical SMILES
CC1(OC2COC3(C(C2O1)OC(O3)(C)C)COS(=O)(=O)N)C
InChI
1S/C12H21NO8S/c1-10(2)18-7-5-16-12(6-17-22(13,14)15)9(8(7)19-10)20-11(3,4)21-12/h7-9H,5-6H2,1-4H3,(H2,13,14,15)/t7-,8-,9+,12+/m1/s1
InChIKey
KJADKKWYZYXHBB-XBWDGYHZSA-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
10-hydroxy topiramate DM006327
29982171
Oxidation - Hydrolyzationn 1 [3]
2,3-Desisopropylidene Topiramate DM006326
29977351
Hydrolysis - Hydrolysis 1 [3]
9-hydroxy topiramate DM006328
29982168
Oxidation - Hydrolyzationn 1 [3]
Topiramate metabolite M1 DM006321 N. A. Oxidation - Oxidationn 1 [4]
Topiramate metabolite M2 DM006323 N. A. Oxidation - Oxidationn 1 [4]
Topiramate metabolite M4 DM007071 N. A. Oxidation - Oxidationn 1 [4]
Topiramate metabolite M5 DM006324
10626041
Unclear 1 [3]
Topiramate metabolite M5 DM006324
10626041
Oxidation - Oxidationn 1 [4]
Topiramate metabolite M3 DM006322 N. A. Unclear 2 [4]
Topiramate metabolite M6 DM006325
22213760
Unclear 2 [4]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR006790 Topiramate Topiramate metabolite M1 Oxidation - Oxidationn Unclear [4]
MR006792 Topiramate Topiramate metabolite M2 Oxidation - Oxidationn Unclear [4]
MR006794 Topiramate Topiramate metabolite M5 Oxidation - Oxidationn Unclear [4]
MR006796 Topiramate Topiramate metabolite M4 Oxidation - Oxidationn Unclear [4]
MR006797 Topiramate 2,3-Desisopropylidene Topiramate Hydrolysis - Hydrolysis Unclear [3]
MR006798 Topiramate 10-hydroxy topiramate Oxidation - Hydrolyzationn Unclear [3]
MR006799 Topiramate 9-hydroxy topiramate Oxidation - Hydrolyzationn Unclear [3]
MR006793 Topiramate metabolite M2 Topiramate metabolite M3 Unclear Unclear [4]
MR006791 Topiramate metabolite M4 Topiramate metabolite M3 Unclear Unclear [4]
MR006795 Topiramate metabolite M5 Topiramate metabolite M6 Unclear Unclear [4]
⏷ Show the Full List of 10 MR(s)
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[2]
References
1 Topiramate was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Dose-dependent induction of cytochrome P450 (CYP) 3A4 and activation of pregnane X receptor by topiramate. Epilepsia. 2003 Dec;44(12):1521-8.
3 Pharmacokinetic and metabolic investigation of topiramate disposition in healthy subjects in the absence and in the presence of enzyme induction by carbamazepine
4 Metabolism and excretion of the antiepileptic/antimigraine drug, Topiramate in animals and humans

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