5-ethyl-5-phenyl-1,3-diazinane-4,6-dione

• ChemBase ID: 673
• Molecular Formular: C12H14N2O2
• Molecular Mass: 218.25176
• Monoisotopic Mass: 218.1055277
• SMILES: O=C1NCNC(=O)C1(CC)c1ccccc1
• Canonical SMILES: CCC1(C(=O)NCNC1=O)c1ccccc1
• InChI: 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

NAMES AND DATABASE IDS

Names

• IUPAC name: 5-ethyl-5-phenyl-1,3-diazinane-4,6-dione
• IUPAC Traditional name: primidone
• Brand Name: Apo-Primidone; Cyral; Desoxyphenobarbitone; Hexadiona; Hexamidine; Lepimidin; Lepsiral; Liskantin; Majsolin; Medi-Pets; Midone; Milepsin; Misodine; Misolyne; Mizodin; Mizolin; Myidone; Mylepsin; Mylepsinum; Mysedon; Mysoline; Neurosyn; Pms Primidone; Prilepsin; Primacione; Primaclone; Primacone; Primakton; Primidon; Primidone Methanol Solution; Primoline; Prysoline; Pyrimidone "Medi-Pets"; Pyrimidone Medi-Pets; Resimatil; Sertan
• Synonyms: Primidone; Primidone; 2-Desoxyphenobarbital; primaclone; 5-Ethyl-5-phenylhexahydropyrimidine-4,6-dione; Mysoline; Neurosyn; Mylepsin; 5-Ethyldihydro-5-phenyl-4,6(1H,5H)-pyrimidinedione; Liskantin; Mylepsinum; Mysoline; Resimatil; Sertan; 2-脱氧苯巴比妥; 5-乙基-5-苯基六氢嘧啶-4,6-二酮; 普里米酮

Database IDs

• CAS Number: 125-33-7
• EC Number: 204-737-0
• MDL Number: MFCD00038662
• PubChem SID: 46507775; 160964136; 24277732
• PubChem CID: 4909
• ATC CODE: N03AA03
• CHEMBL: 856
• Chemspider ID: 4740
• DrugBank ID: DB00794
• KEGG ID: D00474
• Unique Ingredient Identifier: 13AFD7670Q
• Wikipedia Title: Primidone

CALCULATED PROPERTIES

JChem

• Acid pKa: 11.497226
• H Acceptors: 2
• H Donor: 2
• LogD (pH = 5.5): 1.1182984
• LogD (pH = 7.4): 1.1182681
• Log P: 1.1182989
• Molar Refractivity: 59.0376 cm^3
• Polarizability: 23.068121 Å^3
• Polar Surface Area: 58.2 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 0.62
• LOG S: -2.32
• Solubility (Water): 1.04e+00 g/l

PROPERTIES

Physical Property

• Solubility: 500 mg/L; DMSO
• Apperance: White Solid
• Melting Point: 279 - 281°C; 281-282°C
• Auto Ignition Point: > 360°C
• Hydrophobicity(logP): 1.6

Safety Information

• Storage Condition: -20°C; Refrigerator; Room Temperature (15-30°C)
• RTECS: UV9100000
• European Hazard Symbols: Harmful (Xn)
• UN Number: 2811
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: III
• Australian Hazchem: 2X
• Risk Statements: 22-40; R:22
• Safety Statements: 22-36-45; S:36/37/39
• EU Classification: T2
• EU Hazard Identification Number: 6.1B
• Emergency Response Guidebook(ERG) Number: 154
• GHS Pictograms: GHS07; GHS08
• GHS Signal Word: Warning
• GHS Hazard statements: H302-H351
• GHS Precautionary statements: P281
• Personal Protective Equipment: Eyeshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges

Pharmacology Properties

• Admin Routes: oral
• Bioavailability: ~100%
• Excretion: Renal
• Half Life: Primidone: 5-18 hours,; Phenobarbital: 75-120 hours,; PEMA: 16 hours; Time to reach steady state:; Primidone: 2-3 days,; Phenobarbital&PEMA 1-4weeks
• Metabolism: Hepatic
• Protein Bound: 25%
• Legal Status: POM (UK); Rx-only (US)
• Pregnancy Category: D (US)

Product Information

• Grade: analytical standard, for drug analysis
• Salt Data: Free Base

DETAILS

MP Biomedicals - 02151948

Shows activity as an anticonvulsant.

DrugBank - DB00794

• Drug Groups: approved
• 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)
• 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.
• Toxicity: Symptoms of an overdose typically include sluggishness, incoordination, difficulty in thinking, slowness of speech, faulty judgment, drowsiness or coma, shallow breathing, staggering, and in severe cases coma and death.
• Affected Organisms: Humans and other mammals
• Biotransformation: Hepatic
• Absorption: 90 to 100%
• Half Life: 3-23 hours
• Protein Binding: 70%
• References: Murphy K, Delanty N: Primary Generalized Epilepsies. Curr Treat Options Neurol. 2000 Nov;2(6):527-542. [Pubmed] ; 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] ; Brown GM, Stone GH, Rathbone MP: Primidone and rapid cycling affective disorders. Lancet. 1993 Oct 9;342(8876):925. [Pubmed] ; 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] ; 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]
• External Links: Wikipedia; RxList; Drugs.com

Selleck Chemicals - S1965

Research Area: Neurological Disease
Biological Activity:
Primidone(Mysoline) is an anticonvulsant of the pyrimidinedione class, the active metabolites of which, phenobarbital (major) and phenylethylmalonamide (PEMA) (minor), are also anticonvulsants. It is used mainly to treat complex partial, simple partials, generalized tonic-clonic seizures, myoclonic, akinetic seizures. [1]

Sigma Aldrich - P7295

Biochem/physiol Actions
抗惊厥药
Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. P7295.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

Toronto Research Chemicals - P734000

Anticonvulsant.

REFERENCES

• Murphy K, Delanty N: Primary Generalized Epilepsies. Curr Treat Options Neurol. 2000 Nov;2(6):527-542. Pubmed
• 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
• Brown GM, Stone GH, Rathbone MP: Primidone and rapid cycling affective disorders. Lancet. 1993 Oct 9;342(8876):925. Pubmed
• 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
• 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
• http://en.wikipedia.org/wiki/Primidone
• Bogue, C., et al.: Br. J. Pharmacol., 8, 230 (1953)
• Daley, R.D., Anal. Profiles Drug Subs., 2, 409 (1953)