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

General Information of Drug (ID: DR0659)
Drug Name
Ethosuximide
Synonyms
Suxin; Emeside; Epileo Petit MAL; Ethosuccimide; Ethosuccinimide; Ethosuxide; Ethosuximidum; Ethymal; Etomal; Etosuximid; Etosuximida; Mesentol; Pemalin; Pentinimid; Peptinimid; Petinimid; Petnidan; Piknolepsin; Pyknolepsinum; Ronton; Aethosuximide; Asamid; Atysmal; Capitus; Simatin; Simatin(E); Succimal; Succimitin; Suxilep; Suximal; Suxinutin; Thetamid; Thilopemal; Zaraondan; Zarodan; Zarondan; Zarondan-Saft; Zarontin; Zartalin; ethosuximide; 2-Ethyl-2-methylsuccinimide; 3-Ethyl-3-methylpyrrolidine-2,5-dione; 77-67-8; Pemal
Indication Epilepsy [ICD11: 8A60] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 141.17 Topological Polar Surface Area 46.2
Heavy Atom Count 10 Rotatable Bond Count 1
Hydrogen Bond Donor Count 1 Hydrogen Bond Acceptor Count 2
Cross-matching ID
PubChem CID
3291
PubChem SID
9708 ; 110249 ; 221102 ; 5235097 ; 7847605 ; 7979200 ; 8149853 ; 8152091 ; 10321579 ; 10535639 ; 11109647 ; 11335393 ; 11360632 ; 11364279 ; 11366841 ; 11369403 ; 11372107 ; 11374481 ; 11377565 ; 11447536 ; 11461604 ; 11466193 ; 11467313 ; 11485201 ; 11485686 ; 11489299 ; 11490759 ; 11492865 ; 11495199 ; 15219092 ; 17405095 ; 24278423 ; 26612325 ; 26679258 ; 26747515 ; 26747516 ; 29222429 ; 46507617 ; 47365063 ; 47365064 ; 47440135 ; 47885289 ; 48034988 ; 48110335 ; 48334365 ; 48415978 ; 49698794 ; 50048516 ; 50106318 ; 50106319
ChEBI ID
CHEBI:4887
CAS Number
77-67-8
TTD Drug ID
D0Q4XQ
Formula
C7H11NO2
Canonical SMILES
CCC1(CC(=O)NC1=O)C
InChI
1S/C7H11NO2/c1-3-7(2)4-5(9)8-6(7)10/h3-4H2,1-2H3,(H,8,9,10)
InChIKey
HAPOVYFOVVWLRS-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-(1-hydroxyethyl)-2-methylsuccinimide DM000929
54520268
Oxidation - Hydroxylation 1 [4] , [3] , [5]
2-(2-hydroxyethyl)-2-methylsuccinimide DM000927
71365921
Oxidation - Hydroxylation 1 [4] , [3] , [6]
2-ethyl-2-hydroxymethyl succinimide DM000931
86084039
Oxidation - Hydroxylation 1 [4]
2-ethyl-3-hydroxy-2-methylsuccinimide DM000930
54322773
Oxidation - Hydroxylation 1 [4] , [3] , [6]
2-carboxymethyl-2-methylsuccinimide DM000928
54406343
Unclear 2 [4]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR002730 Ethosuximide 2-(2-hydroxyethyl)-2-methylsuccinimide Oxidation - Hydroxylation CYP3A4 ... [4], [3], [6]
MR002731 Ethosuximide 2-(1-hydroxyethyl)-2-methylsuccinimide Oxidation - Hydroxylation CYP3A4 ... [4], [3], [5]
MR002732 Ethosuximide 2-ethyl-3-hydroxy-2-methylsuccinimide Oxidation - Hydroxylation CYP3A4 ... [4], [3], [6]
MR002733 Ethosuximide 2-ethyl-2-hydroxymethyl succinimide Oxidation - Hydroxylation CYP3A4 ... [4]
MR002729 2-(2-hydroxyethyl)-2-methylsuccinimide 2-carboxymethyl-2-methylsuccinimide Unclear Unclear [4]
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 2D6 (CYP2D6) DME0009 Homo sapiens
CP2D6_HUMAN
1.14.14.1
[2]
Cytochrome P450 2E1 (CYP2E1) DME0013 Homo sapiens
CP2E1_HUMAN
1.14.14.1
[3]
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[3]
References
1 Ethosuximide was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Characterization of the cytochrome P450 enzymes involved in the in vitro metabolism of ethosuximide by human hepatic microsomal enzymes Xenobiotica. 2003 Mar;33(3):265-76. doi: 10.1080/0049825021000061606.
3 Characterization of the cytochrome P450 enzymes involved in the in vitro metabolism of ethosuximide by human hepatic microsomal enzymes. Xenobiotica. 2003 Mar;33(3):265-76.
4 Chiral aspects of the human metabolism of ethosuximide Biopharm Drug Dispos. 2005 Sep;26(6):225-32. doi: 10.1002/bdd.454.
5 Reactive metabolites of the anticonvulsant drugs and approaches to minimize the adverse drug reaction. Eur J Med Chem. 2021 Dec 15;226:113890. doi: 10.1016/j.ejmech.2021.113890.
6 The metabolism of ethosuximide Eur J Drug Metab Pharmacokinet. 1993 Oct-Dec;18(4):349-53. doi: 10.1007/BF03190184.

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