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Showing drug card for Primidone (DB00794)

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Version 2.5
Creation Date 2005-06-13 13:24:05
Update Date 2009-06-23 18:08:24
Primary Accession Number DB00794
Secondary Accession Number
  • APRD00549
Name Primidone
Drug Type
  • Approved
  • Small Molecule
Description An antiepileptic agent related to the barbiturates; it is partly metabolized to phenobarbital in the body and owes some of its actions to this metabolite. Adverse effects are reported to be more frequent than with phenobarbital. (From Martindale, The Extra Pharmacopoeia, 30th ed, p309)
Synonyms Not Available
Brand Names
  1. Apo-Primidone
  2. Cyral
  3. Desoxyphenobarbitone
  4. Hexadiona
  5. Hexamidine
  6. Lepimidin
  7. Lepsiral
  8. Liskantin
  9. Majsolin
  10. Medi-Pets
  11. Midone
  12. Milepsin
  13. Misodine
  14. Misolyne
  15. Mizodin
  16. Mizolin
  17. Myidone
  18. Mylepsin
  19. Mylepsinum
  20. Mysedon
  21. Mysoline
  22. Neurosyn
  23. Pms Primidone
  24. Prilepsin
  25. Primacione
  26. Primaclone
  27. Primacone
  28. Primakton
  29. Primidon
  30. Primidone Methanol Solution
  31. Primoline
  32. Prysoline
  33. Pyrimidone "Medi-Pets"
  34. Pyrimidone Medi-Pets
  35. Resimatil
  36. Sertan
Brand Mixtures Not Available
Chemical IUPAC Name 5-ethyl-5-phenyl-1,3-diazinane-4,6-dione
Chemical Formula C12H14N2O2
Chemical Structure Structure
CAS Registry Number 125-33-7
InChI Identifier InChI=1/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)/f/h13-14H
InChI Key DQMZLTXERSFNPB-KGCNKATMCR
KEGG Drug D00474 Link Image
KEGG Compound C07371 Link Image
PubChem Compound 4909 Link Image
PubChem Substance 173378 Link Image
ChEBI ID Not Available
PharmGKB ID PA451105 Link Image
HET ID Not Available
GenBank ID Not Available
Drug ID Number [DIN] 00396761 Link Image
RxList Link http://www.rxlist.com/cgi/generic2/primid.htm Link Image
PDRhealth Link Not Available
Wikipedia Link http://en.wikipedia.org/wiki/Primidone Link Image
FDA Label
Material Safety Data Sheet (MSDS)
Synthesis Reference Boon et al., Brit. pat. 666,027 (1952 to I.C.I.)
Average Molecular Weight 218.2518
Monoisotopic Molecular Weight 218.1055
State Solid
Melting Point 281.5 oC
Experimental Water Solubility 500 mg/L Source: PhysProp
Predicted Water Solubility 1.04e+00 mg/mL Calculated using ALOGPS
Experimental LogP/Hydrophobicity 1.6 Source: PhysProp
Predicted LogP 0.62 Calculated using ALOGPS
Experimental LogS -2.64 [ADME Research, USCD]
Predicted LogS -2.32 Calculated using ALOGPS
Experimental Caco2 Permeability Not Available
pKa/Isoelectric Point Not Available
Mass Spectrum Not Available
MOL File Show Link Image | Download Link Image
SDF File Show Link Image | Download Link Image
PDB File Show Link Image | Download Link Image
2D Structure
3D Structure
Experimental PDB ID Not Available
Isomeric SMILES CCC1(C(=O)NCNC1=O)C1=CC=CC=C1
Canonical SMILES CCC1(C(=O)NCNC1=O)C1=CC=CC=C1
Drug Category
  • Anticonvulsants
  • Barbiturates
ATC Codes
AHFS Codes
  • 28:12.04
Indication For the treatment of epilepsy
Pharmacology Primidone is a barbiturate with anticonvulsant properties. Primidone, either alone or used concomitantly with other anticonvulsants, is indicated in the control of grand mal, psychomotor, and focal epileptic seizures. It may control grand mal seizures refractory to other anticonvulsant therapy. Primidone raises electro- or chemoshock seizure thresholds or alters seizure patterns in experimental animals. Primidone per se has anticonvulsant activity as do its two metabolites, phenobarbital and phenylethylmalonamide (PEMA). In addition to its anticonvulsant activity, Primidone potentiates that of phenobarbital in experimental animals.
Mechanism of Action Primidone is a GABA receptor agonist. The mechanism of Primidone's antiepileptic action is not known.
Absorption 90 to 100%
Toxicity Not Available
Protein Binding 70%
Biotransformation Hepatic
Half Life 3-23 hours
Dosage Forms
Form Route
Tablet Oral
Patient Information Show Link Image
Contraindications Show Link Image
Interactions Show Link Image
Drug Interactions
Drug Interaction
Acenocoumarol The barbiturate decreases the anticoagulant effect
Aminophylline The barbiturate decreases the effect of theophylline
Anisindione The barbiturate decreases the anticoagulant effect
Betamethasone The barbiturate decreases the effect of the corticosteroid
Chlorotrianisene The enzyme inducer decreases the effect of hormones
Clomifene The enzyme inducer decreases the effect of hormones
Conjugated Estrogens The enzyme inducer decreases the effect of hormones
Cortisone acetate The barbiturate decreases the effect of the corticosteroid
Cyclosporine The barbiturate increases the effect of cyclosporine
Dexamethasone The barbiturate decreases the effect of the corticosteroid
Dicumarol The barbiturate decreases the anticoagulant effect
Diethylstilbestrol The enzyme inducer decreases the effect of hormones
Divalproex sodium Valproic acid increases the effect of the barbiturate
Doxycycline The anticonvulsant decreases the effect of doxycycline
Dyphylline The barbiturate decreases the effect of theophylline
Estradiol The enzyme inducer decreases the effect of hormones
Estriol The enzyme inducer decreases the effect of hormones
Estrone The enzyme inducer decreases the effect of hormones
Estropipate The enzyme inducer decreases the effect of hormones
Ethinyl Estradiol This product may cause a slight decrease of contraceptive effect
Felbamate Felbamate increases the effect and toxicity of primidone
Felodipine The barbiturate decreases the effect of felodipine
Fludrocortisone The barbiturate decreases the effect of the corticosteroid
Folic Acid Folic acid decreases the effect of anticonvulsant
Gefitinib This CYP3A4 inducer may reduce gefitinib plasma concentrations and pharmacological effects
Griseofulvin The barbiturate decreases the effect of griseofulvine
Hydrocortisone The barbiturate decreases the effect of the corticosteroid
Levonorgestrel Phenobarbital decreases the effect of levonorgestrel
Medroxyprogesterone The enzyme inducer decreases the effect of hormones
Megestrol The enzyme inducer decreases the effect of hormones
Mestranol This product may cause a slight decrease of contraceptive effect
Methadone The barbiturate decreases the effect of methadone
Methoxyflurane The barbiturate increases the renal toxicity of methoxyflurane
Methylprednisolone The barbiturate decreases the effect of the corticosteroid
Metoprolol The barbiturate decreases the effect of metabolized beta-blocker
Metronidazole The barbiturate decreases the effect of metronidazole
Nifedipine The barbiturate decreases the effect of the calcium channel blocker
Norethindrone This product may cause a slight decrease of contraceptive effect
Oxtriphylline The barbiturate decreases the effect of theophylline
Paramethasone The barbiturate decreases the effect of the corticosteroid
Prednisolone The barbiturate decreases the effect of the corticosteroid
Prednisone The barbiturate decreases the effect of the corticosteroid
Propranolol The barbiturate decreases the effect of metabolized beta-blocker
Quinestrol The enzyme inducer decreases the effect of hormones
Quinidine The anticonvulsant decreases the effect of quinidine
Theophylline The barbiturate decreases the effect of theophylline
Triamcinolone The barbiturate decreases the effect of the corticosteroid
Verapamil The barbiturate decreases the effect of the calcium channel blocker
Voriconazole The barbiturate decreases the effect of voriconazole
Warfarin The barbiturate decreases the anticoagulant effect
Food Interactions
  • Avoid alcohol.
  • Avoid high doses of caffeine.
  • Take with food to reduce gastric irritation.
Pathways Not Available
General References
  1. Schaffer LC, Schaffer CB, Caretto J: The use of primidone in the treatment of refractory bipolar disorder. Ann Clin Psychiatry. 1999 Jun;11(2):61-6. [PubMed Link Image]
  2. Murphy K, Delanty N: Primary Generalized Epilepsies. Curr Treat Options Neurol. 2000 Nov;2(6):527-542. [PubMed Link Image]
  3. Kagitani-Shimono K, Imai K, Okamoto N, Ono J, Okada S: Unverricht-Lundborg disease with cystatin B gene abnormalities. Pediatr Neurol. 2002 Jan;26(1):55-60. [PubMed Link Image]
  4. Young MC, Hughes IA: Loss of therapeutic control in congenital adrenal hyperplasia due to interaction between dexamethasone and primidone. Acta Paediatr Scand. 1991 Jan;80(1):120-4. [PubMed Link Image]
  5. Brown GM, Stone GH, Rathbone MP: Primidone and rapid cycling affective disorders. Lancet. 1993 Oct 9;342(8876):925. [PubMed Link Image]
  6. Drugs.com Link Image
  7. Wikipedia Link Image
  8. RxList Link Image
Organisms Affected
  • Humans and other mammals
Phase 1 Metabolizing Enzymes
  1. Cytochrome P450 2C19 (CYP2C19)
Targets
  1. Gamma-aminobutyric-acid receptor subunit alpha-1
Phase 1 Metabolizing Enzyme 1 [top]
Enzyme 1 Name Cytochrome P450 2C19 (CYP2C19)
Enzyme 1 Gene Name CYP2C19
Enzyme 1 SwissProt ID P33261 Link Image
Enzyme 1 SNPs SNPJam Report Link Image
Enzyme 1 Protein Sequence >sp|P33261|CP2CJ_HUMAN Cytochrome P450 2C19 (EC 1.14.13.80) 
MDPFVVLVLCLSCLLLLSIWRQSSGRGKLPPGPTPLPVIGNILQIDIKDVSKSLTNLSKI
YGPVFTLYFGLERMVVLHGYEVVKEALIDLGEEFSGRGHFPLAERANRGFGIVFSNGKRW
KEIRRFSLMTLRNFGMGKRSIEDRVQEEARCLVEELRKTKASPCDPTFILGCAPCNVICS
IIFQKRFDYKDQQFLNLMEKLNENIRIVSTPWIQICNNFPTIIDYFPGTHNKLLKNLAFM
ESDILEKVKEHQESMDINNPRDFIDCFLIKMEKEKQNQQSEFTIENLVITAADLLGAGTE
TTSTTLRYALLLLLKHPEVTAKVQEEIERVVGRNRSPCMQDRGHMPYTDAVVHEVQRYID
LIPTSLPHAVTCDVKFRNYLIPKGTTILTSLTSVLHDNKEFPNPEMFDPRHFLDEGGNFK
KSNYFMPFSAGKRICVGEGLARMELFLFLTFILQNFNLKSLIDPKDLDTTPVVNGFASVP
PFYQLCFIPV
Drug Target 1 [top]
Target 1 ID 872
Target 1 Name Gamma-aminobutyric-acid receptor subunit alpha-1
Target 1 Synonyms
  1. Gamma-aminobutyric-acid receptor subunit alpha-1 precursor
Target 1 Gene Name GABRA1
Target 1 Protein Sequence >Gamma-aminobutyric-acid receptor subunit alpha-1 precursor 
MRKSPGLSDCLWAWILLLSTLTGRSYGQPSLQDELKDNTTVFTRILDRLLDGYDNRLRPG
LGERVTEVKTDIFVTSFGPVSDHDMEYTIDVFFRQSWKDERLKFKGPMTVLRLNNLMASK
IWTPDTFFHNGKKSVAHNMTMPNKLLRITEDGTLLYTMRLTVRAECPMHLEDFPMDAHAC
PLKFGSYAYTRAEVVYEWTREPARSVVVAEDGSRLNQYDLLGQTVDSGIVQSSTGEYVVM
TTHFHLKRKIGYFVIQTYLPCIMTVILSQVSFWLNRESVPARTVFGVTTVLTMTTLSISA
RNSLPKVAYATAMDWFIAVCYAFVFSALIEFATVNYFTKRGYAWDGKSVVPEKPKKVKDP
LIKKNNTYAPTATSYTPNLARGDPGLATIAKSATIEPKEVKPETKPPEPKKTFNSVSKID
RLSRIAFPLLFGIFNLVYWATYLNREPQLKAPTPHQ
Target 1 Number of Residues 463
Target 1 Molecular Weight 51802
Target 1 Theoretical pI 9.61
Target 1 GO Classification
Function
neurotransmitter receptor activity
transporter activity
ion transporter activity
ion channel activity
ligand-gated ion channel activity
extracellular ligand-gated ion channel activity
signal transducer activity
receptor activity
transmembrane receptor activity
GABA receptor activity
GABA-A receptor activity
Process
cellular process
cell communication
signal transduction
cell surface receptor linked signal transduction
G-protein coupled receptor protein signaling pathway
gamma-aminobutyric acid signaling pathway
anion transport
inorganic anion transport
chloride transport
physiological process
cellular physiological process
transport
ion transport
Component
postsynaptic membrane
cell
membrane
intrinsic to membrane
integral to membrane
Target 1 General Function Involved in GABA-A receptor activity
Target 1 Specific Function GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel
Target 1 Pathways Not Available
Target 1 Reactions Not Available
Target 1 Pfam Domain Function
Target 1 Signals
  • 1-27
Target 1 Transmembrane Regions
  • 252-273
  • 279-300
  • 313-334
  • 422-443
Target 1 Essentiality Non-Essential
Target 1 GenBank ID Protein 31631 Link Image
Target 1 UniProtKB/Swiss-Prot ID P14867 Link Image
Target 1 UniProtKB/Swiss-Prot Entry Name GBRA1_HUMAN Link Image
Target 1 PDB ID Not Available
Target 1 Cellular Location
  • Membrane
  • multi-pass membrane protein
Target 1 Gene Sequence >1371 bp 
ATGAGGAAAAGTCCAGGTCTGTCTGACTGTCTTTGGGCCTGGATCCTCCTTCTGAGCACA
CTGACTGGAAGAAGCTATGGACAGCCGTCATTACAAGATGAACTTAAAGACAATACCACT
GTCTTCACCAGGATTTTGGACAGACTCCTAGATGGTTATGACAATCGCCTGAGACCAGGA
TTGGGAGAGCGTGTAACCGAAGTGAAGACTGATATCTTCGTCACCAGTTTCGGACCCGTT
TCAGACCATGATATGGAATATACAATAGATGTATTTTTCCGTCAAAGCTGGAAGGATGAA
AGGTTAAAATTTAAAGGACCTATGACAGTCCTCCGGTTAAATAACCTAATGGCAAGTAAA
ATCTGGACTCCGGACACATTTTTCCACAATGGAAAGAAGTCAGTGGCCCACAACATGACC
ATGCCCAACAAACTCCTGCGGATCACAGAGGATGGCACCTTGCTGTACACCATGAGGCTG
ACAGTGAGAGCTGAATGTCCGATGCATTTGGAGGACTTCCCTATGGATGCCCATGCTTGC
CCACTAAAATTTGGAAGTTATGCTTATACAAGAGCAGAAGTTGTTTATGAATGGACCAGA
GAGCCAGCACGCTCAGTGGTTGTAGCAGAAGATGGATCACGTCTAAACCAGTATGACCTT
CTTGGACAAACAGTAGACTCTGGAATTGTCCAGTCAAGTACAGGAGAATATGTTGTTATG
ACCACTCATTTCCACTTGAAGAGAAAGATTGGCTACTTTGTTATTCAAACATACCTGCCA
TGCATAATGACAGTGATTCTCTCACAAGTCTCCTTCTGGCTCAACAGAGAGTCTGTACCA
GCAAGAACTGTCTTTGGAGTAACAACTGTGCTCACCATGACAACATTGAGCATCAGTGCC
AGAAACTCCCTCCCTAAGGTGGCTTATGCAACAGCTATGGATTGGTTTATTGCCGTGTGC
TATGCCTTTGTGTTCTCAGCTCTGATTGAGTTTGCCACAGTAAACTATTTCACTAAGAGA
GGTTATGCATGGGATGGCAAAAGTGTGGTTCCAGAAAAGCCAAAGAAAGTAAAGGATCCT
CTTATTAAGAAAAACAACACTTACGCTCCAACAGCAACCAGCTACACCCCTAATTTGGCC
AGGGGCGACCCGGGCTTAGCCACCATTGCTAAAAGTGCAACCATAGAACCTAAAGAGGTC
AAGCCCGAAACAAAACCACCAGAACCCAAGAAAACCTTTAACAGTGTCAGCAAAATTGAC
CGACTGTCAAGAATAGCCTTCCCGCTGCTATTTGGAATCTTTAACTTAGTCTACTGGGCT
ACGTATTTAAACAGAGAGCCTCAGCTAAAAGCCCCCACACCACATCAATAG
Target 1 GenBank Gene ID
Target 1 GeneCard ID GABRA1 Link Image
Target 1 GenAtlas ID GABRA1 Link Image
Target 1 HGNC ID HGNC:4075 Link Image
Target 1 Chromosome Location 5
Target 1 Locus 5q34-q35
Target 1 SNPs SNPJam Report Link Image
Target 1 General References
  1. Cossette P, Liu L, Brisebois K, Dong H, Lortie A, Vanasse M, Saint-Hilaire JM, Carmant L, Verner A, Lu WY, Wang YT, Rouleau GA: Mutation of GABRA1 in an autosomal dominant form of juvenile myoclonic epilepsy. Nat Genet. 2002 Jun;31(2):184-9. Epub 2002 May 6. [PubMed Link Image]
  2. Schofield PR, Pritchett DB, Sontheimer H, Kettenmann H, Seeburg PH: Sequence and expression of human GABAA receptor alpha 1 and beta 1 subunits. FEBS Lett. 1989 Feb 27;244(2):361-4. [PubMed Link Image]
  3. Garrett KM, Duman RS, Saito N, Blume AJ, Vitek MP, Tallman JF: Isolation of a cDNA clone for the alpha subunit of the human GABA-A receptor. Biochem Biophys Res Commun. 1988 Oct 31;156(2):1039-45. [PubMed Link Image]
Target 1 Drug References
  1. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed Link Image]
  2. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed Link Image]

This project is supported by Genome Alberta & Genome Canada, a not-for-profit organization that is leading Canada's national genomics strategy with $600 million in funding from the federal government. This project is also supported in part by GenomeQuest, Inc., an enterprise genomic information company serving the life science community.