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

General Information of Drug (ID: DR1340)
Drug Name
Primidone
Synonyms
Prilepsin; Primacione; Primaclone; Primacone; Primakton; Primidon; Primidona; Primidonum; Primoline; Prysoline; Pyrimidone Medi-pets; Desoxyphenobarbital; Desoxyphenobarbitone; Hexadiona; Lepimidin; Lepsiral; Liskantin; Majsolin; Medi-Pets; Midone; Milepsin; Misodine; Misolyne; Mizodin; Mizolin; Myidone; Mylepsin; Mylepsinum; Mysedon; Mysoline; Neurosyn; Resimatil; Roe 101; Sertan; primidone; 125-33-7; 2-Deoxyphenobarbital; 2-Desoxyphenobarbital; 5-Phenyl-5-ethyl-hexahydropyrimidine-4,6-dione; Cyral
Indication Epilepsy [ICD11: 8A60] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 218.25 Topological Polar Surface Area 58.2
Heavy Atom Count 16 Rotatable Bond Count 2
Hydrogen Bond Donor Count 2 Hydrogen Bond Acceptor Count 2
Cross-matching ID
PubChem CID
4909
PubChem SID
9575 ; 96478 ; 855864 ; 5227599 ; 7847540 ; 7980382 ; 8149495 ; 8153020 ; 10506074 ; 11111659 ; 11112270 ; 11113350 ; 11335499 ; 11360738 ; 11363726 ; 11366288 ; 11368850 ; 11371825 ; 11374108 ; 11377012 ; 11461710 ; 11466961 ; 11468081 ; 11485061 ; 11486771 ; 11489109 ; 11490369 ; 11492300 ; 11494646 ; 15121366 ; 17389534 ; 17405579 ; 24277732 ; 26611888 ; 26679596 ; 26747018 ; 26747019 ; 26751542 ; 29223987 ; 46507775 ; 47291047 ; 47365104 ; 47440159 ; 47440160 ; 47440161 ; 47440162 ; 47588907 ; 47810657 ; 48184911 ; 48184912
ChEBI ID
CHEBI:8412
CAS Number
125-33-7
TTD Drug ID
D0U5RT
Formula
C12H14N2O2
Canonical SMILES
CCC1(C(=O)NCNC1=O)C2=CC=CC=C2
InChI
1S/C12H14N2O2/c1-2-12(9-6-4-3-5-7-9)10(15)13-8-14-11(12)16/h3-7H,2,8H2,1H3,(H,13,15)(H,14,16)
InChIKey
DQMZLTXERSFNPB-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
Phenobarbital DM003076
4763
Unclear 1 [3] , [4] , [5] , [6]
Phenylethylmalonamide (PEMA) DM002967
23611
Unclear 1 [3] , [4]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR002149 Primidone Phenylethylmalonamide (PEMA) Unclear CYP2E1 ... [3], [4]
MR002150 Primidone Phenobarbital Unclear CYP2E1 ... [3], [4], [5], [6]
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Cytochrome P450 2C9 (CYP2C9) DME0019 Homo sapiens
CP2C9_HUMAN
1.14.14.1
[2]
Cytochrome P450 2E1 (CYP2E1) DME0013 Homo sapiens
CP2E1_HUMAN
1.14.14.1
[2]
Mephenytoin 4-hydroxylase (CYP2C19) DME0021 Homo sapiens
CP2CJ_HUMAN
1.14.14.1
[2]
References
1 Primidone was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Clinically significant pharmacokinetic drug interactions between antiepileptic drugs. J Clin Pharm Ther. 1999 Apr;24(2):87-92.
3 Physiologically based pharmacokinetics model of primidone and its metabolites phenobarbital and phenylethylmalonamide in humans, rats, and mice Drug Metab Dispos. 1998 Jun;26(6):585-94.
4 Blood and cerebrospinal fluid pharmacokinetics of primidone and its primary pharmacologically active metabolites, phenobarbital and phenylethylmalonamide in the rat Eur J Drug Metab Pharmacokinet. 1999 Jul-Sep;24(3):255-64. doi: 10.1007/BF03190029.
5 Managing the Drug-Drug Interaction With Apixaban and Primidone: A Case Report. Hosp Pharm. 2023 Aug;58(4):345-349. doi: 10.1177/00185787221150928.
6 Ticagrelor and primidone interaction masquerading as dual antiplatelet therapy noncompliance. Future Cardiol. 2023 Jun 14. doi: 10.2217/fca-2023-0011.

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