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

General Information of Drug (ID: DR1737)
Drug Name
Zonisamide
Synonyms
Zonegran; Zonisamida; Zonisamida [Spanish]; Zonisamidum; Zonisamidum [Latin]; Exceglan; Excegram; Excegran; PD 110843; PD-110843; zonisamide; 1,2-Benzisoxazole-3-methanesulfonamide; 1,2-benzoxazol-3-ylmethanesulfonamide; 1-(1,2-Benzoxazol-3-Yl)methanesulfonamide; 1-(1,2-benzisoxazol-3-yl)methanesulfonamide; 3-(Sulfamoylmethyl)-1,2-benzisoxazole; 68291-97-4; AD 810; AD-810; BRN 1077076; Benzo[d]isoxazol-3-yl-methanesulfonamide; C8H8N2O3S; CI 912; CI-912; HSDB 7293; SPR_2; UNII-459384H98V; benzo[d]isoxazol-3-ylmethanesulfonamide
Indication Epilepsy [ICD11: 8A60] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 212.23 Topological Polar Surface Area 94.6
Heavy Atom Count 14 Rotatable Bond Count 2
Hydrogen Bond Donor Count 1 Hydrogen Bond Acceptor Count 5
Cross-matching ID
PubChem CID
5734
PubChem SID
9707 ; 5375171 ; 7847604 ; 8153515 ; 11528623 ; 12012838 ; 12016186 ; 15220241 ; 29215225 ; 29224771 ; 46505278 ; 46511458 ; 49666067 ; 50086000 ; 50109845 ; 57322921 ; 74524371 ; 81093137 ; 85174242 ; 85788213 ; 87322638 ; 92308963 ; 92714085 ; 92729687 ; 93166866 ; 93167201 ; 99437155 ; 103147645 ; 103200464 ; 103911541 ; 104170135 ; 104310103 ; 105859475 ; 117532844 ; 117843348 ; 118048699 ; 121362594 ; 124757254 ; 124801297 ; 125164058 ; 125324718 ; 125356086 ; 126629668 ; 126655670 ; 126670159 ; 129345232 ; 130010354 ; 131323538 ; 131377323 ; 134337793
ChEBI ID
CHEBI:10127
CAS Number
68291-97-4
TTD Drug ID
D09ZIS
Formula
C8H8N2O3S
Canonical SMILES
C1=CC=C2C(=C1)C(=NO2)CS(=O)(=O)N
InChI
1S/C8H8N2O3S/c9-14(11,12)5-7-6-3-1-2-4-8(6)13-10-7/h1-4H,5H2,(H2,9,11,12)
InChIKey
UBQNRHZMVUUOMG-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
2-sulfamoylacetylphenol DM005374
194588
Reduction - Reduction 1 [8]
N-acetyl zonisamide DM005376
10467478
Conjugation - N-acetylation 1 [8]
2-Sulfamoylacetyl phenol-o-glucuronide metabolite DM005375
91667748
Conjugation - Glucuronidation 2 [8]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR005703 Zonisamide 2-sulfamoylacetylphenol Reduction - Reduction CYP3A4 [8]
MR005705 Zonisamide N-acetyl zonisamide Conjugation - N-acetylation Unclear [8]
MR005704 2-sulfamoylacetylphenol 2-Sulfamoylacetyl phenol-o-glucuronide metabolite Conjugation - Glucuronidation Unclear [8]
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Aldehyde oxidase (AOX) DME1092 Clostridium sporogenes
A0A1V9IQJ2_CLOSG
1.17.1.4
[2]
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
[4]
Cytochrome P450 3A7 (CYP3A7) DME0015 Homo sapiens
CP3A7_HUMAN
1.14.14.1
[5]
Mephenytoin 4-hydroxylase (CYP2C19) DME0021 Homo sapiens
CP2CJ_HUMAN
1.14.14.1
[6]
UDP-glucuronosyltransferase 1A1 (UGT1A1) DME0004 Homo sapiens
UD11_HUMAN
2.4.1.17
[7]
⏷ Show the Full List of 6  DME(s)
References
1 Zonisamide was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 The role of mammalian intestinal bacteria in the reductive metabolism of zonisamide. J Pharm Pharmacol. 1997 Mar;49(3):253-6.
3 Pharmacokinetics and drug interactions with zonisamide. Epilepsia. 2007 Mar;48(3):435-41.
4 Prediction of drug-drug interactions of zonisamide metabolism in humans from in vitro data. Eur J Clin Pharmacol. 1998 Apr;54(2):177-83.
5 Differential catalytic properties in metabolism of endogenous and exogenous substrates among CYP3A enzymes expressed in COS-7 cells. Biochim Biophys Acta. 1998 May 8;1380(3):297-304.
6 Carbamazepine pharmacokinetics are not affected by zonisamide: in vitro mechanistic study and in vivo clinical study in epileptic patients. Epilepsy Res. 2004 Nov;62(1):1-11.
7 Actual and Predicted Pharmacokinetic Interactions Between Anticonvulsants and Antiretrovirals.
8 Zonisamide: review of pharmacology, clinical efficacy, tolerability, and safety

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