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MedKoo Cat#: 318569 | Name: Primidone
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Primidone is an anticonvulsant. It is a compound that potentiates GABA receptor function.

Chemical Structure

Primidone
CAS#125-33-7

Theoretical Analysis

MedKoo Cat#: 318569

Name: Primidone

CAS#: 125-33-7

Chemical Formula: C12H14N2O2

Exact Mass: 218.1055

Molecular Weight: 218.26

Elemental Analysis: C, 66.04; H, 6.47; N, 12.84; O, 14.66

Price and Availability

Size Price Availability Quantity
1g USD 150.00
2g USD 250.00
5g USD 450.00
10g USD 650.00
20g USD 950.00
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Related CAS #
No Data
Synonym
Primidone; Primaclone; Mylepsinum; Mizodin; Mysoline; Resimatil; Sanofi-Synthelabo Brand of Primidone; Sertan; XcelBrand of Primidone;
IUPAC/Chemical Name
5-ethyl-5-phenyl-1,3-diazinane-4,6-dione
InChi Key
DQMZLTXERSFNPB-UHFFFAOYSA-N
InChi Code
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)
SMILES Code
CCC1(C(=O)NCNC1=O)C2=CC=CC=C2
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO, not in water
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info
Product Data
Product Data
Instruction
View handling instruction
Biological target:
Primidone is a neuronal voltage-gated sodium channel (VGSC) blocker.
In vitro activity:
Mechanistically, primidone treatment suppressed activation and phosphorylation of RIPK1 (p-S166), RIPK3 (p-S227), and MLKL (p-S358) in U937 cells (Fig. 1C). Notably, primidone not only inhibited TNFα-induced activation of the necrosome members RIPK1, RIPK3, and MLKL in U937 cells, but also in human HT-29 cells (Fig. 1D), and murine NIH3T3 (Fig. 1E) and L929 cells (Fig. 1F). The inhibitory properties of the drug on TNFα-mediated cell death were also evident in primary MEFs (Fig. 1G), expanding this observation to multiple cell types and species. Reference: Cell Death Differ. 2021 May;28(5):1610-1626. https://pubmed.ncbi.nlm.nih.gov/33273695/
In vivo activity:
Results indicate that primidone impaired copulation but not sexual motivation. Specifically, rats receiving primidone displayed fewer ejaculations, required more time to achieve an intromission, and displayed fewer intromissions per attempted mount as evidenced by a lower intromission ratio. However, animals treated with primidone also chose a goal box containing a sexually-receptive female in an x-maze as often as animals receiving vehicle. Reference: Pharmacol Biochem Behav. 2009 Aug;93(2):160-4. https://pubmed.ncbi.nlm.nih.gov/19447126/
Solvent mg/mL mM comments
Solubility
DMSO 47.0 215.34
Ethanol 3.0 13.75
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 218.26 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
Krügel U, Straub I, Beckmann H, Schaefer M. Primidone inhibits TRPM3 and attenuates thermal nociception in vivo. Pain. 2017 May;158(5):856-867. doi: 10.1097/j.pain.0000000000000846. PMID: 28106668; PMCID: PMC5402713. 3. Westerman AT, Roma PG, Creed ET, Hurwitz ZE, Dominguez JM. The antiepileptic primidone impairs male rat sexual behavior. Pharmacol Biochem Behav. 2009 Aug;93(2):160-4. doi: 10.1016/j.pbb.2009.05.006. Epub 2009 May 15. PMID: 19447126.
In vitro protocol:
Krügel U, Straub I, Beckmann H, Schaefer M. Primidone inhibits TRPM3 and attenuates thermal nociception in vivo. Pain. 2017 May;158(5):856-867. doi: 10.1097/j.pain.0000000000000846. PMID: 28106668; PMCID: PMC5402713.
In vivo protocol:
1. Westerman AT, Roma PG, Creed ET, Hurwitz ZE, Dominguez JM. The antiepileptic primidone impairs male rat sexual behavior. Pharmacol Biochem Behav. 2009 Aug;93(2):160-4. doi: 10.1016/j.pbb.2009.05.006. Epub 2009 May 15. PMID: 19447126. 2. Krügel U, Straub I, Beckmann H, Schaefer M. Primidone inhibits TRPM3 and attenuates thermal nociception in vivo. Pain. 2017 May;158(5):856-867. doi: 10.1097/j.pain.0000000000000846. PMID: 28106668; PMCID: PMC5402713.
1: Nida A, Alston J, Schweinfurth J. Primidone Therapy for Essential Vocal Tremor. JAMA Otolaryngol Head Neck Surg. 2016 Feb 1;142(2):117-21. doi: 10.1001/jamaoto.2015.2849. PubMed PMID: 26660910. 2: Louis ED, Hernandez N, Dyke JP, Ma R, Dydak U. Effect of Primidone on Dentate Nucleus γ-Aminobutyric Acid Concentration in Patients With Essential Tremor. Clin Neuropharmacol. 2016 Jan-Feb;39(1):24-8. doi: 10.1097/WNF.0000000000000127. PubMed PMID: 26757316; PubMed Central PMCID: PMC4764876. 3: Celik S, Kecel-Gunduz S, Ozel AE, Akyuz S. Structural and vibrational study of primidone based on monomer and dimer calculations. J Biomol Struct Dyn. 2015;33(4):911-23. doi: 10.1080/07391102.2014.913505. Epub 2014 May 7. PubMed PMID: 24712318. 4: Dong MM, Trenholm R, Rosario-Ortiz FL. Photochemical degradation of atenolol, carbamazepine, meprobamate, phenytoin and primidone in wastewater effluents. J Hazard Mater. 2015 Jan 23;282:216-23. doi: 10.1016/j.jhazmat.2014.04.028. Epub 2014 Apr 21. PubMed PMID: 24798495. 5: Anagnostou E, Kararizou E, Evdokimidis I. Ocular flutter in essential tremor: clinical course and response to primidone. J Neurol. 2013 Oct;260(10):2672-4. doi: 10.1007/s00415-013-7109-6. Epub 2013 Sep 24. PubMed PMID: 24061767. 6: Arjunan V, Santhanam R, Subramanian S, Mohan S. Primidone--an antiepileptic drug--characterisation by quantum chemical and spectroscopic (FTIR, FT-Raman, 1H, 13C NMR and UV-Visible) investigations. Spectrochim Acta A Mol Biomol Spectrosc. 2013 May 15;109:282-97. doi: 10.1016/j.saa.2013.03.025. Epub 2013 Mar 14. PubMed PMID: 23542519. 7: Tanoshima R, 't Jong GW, Merlocco A, Simpson J, Friedman JN, Colantonio D, Koren G. A child exposed to primidone not prescribed for her. Ther Drug Monit. 2013 Apr;35(2):145-9. doi: 10.1097/FTD.0b013e3182843206. Review. PubMed PMID: 23503440. 8: Serralheiro A, Alves G, Fortuna A, Rocha M, Falcão A. First HPLC-UV method for rapid and simultaneous quantification of phenobarbital, primidone, phenytoin, carbamazepine, carbamazepine-10,11-epoxide, 10,11-trans-dihydroxy-10,11-dihydrocarbamazepine, lamotrigine, oxcarbazepine and licarbazepine in human plasma. J Chromatogr B Analyt Technol Biomed Life Sci. 2013 Apr 15;925:1-9. doi: 10.1016/j.jchromb.2013.02.026. Epub 2013 Feb 27. PubMed PMID: 23507454. 9: Naderi F, Javadi SA, Motamedi M, Sahraian MA. The efficacy of primidone in reducing severe cerebellar tremors in patients with multiple sclerosis. Clin Neuropharmacol. 2012 Sep-Oct;35(5):224-6. doi: 10.1097/WNF.0b013e31826249bb. PubMed PMID: 22821064. 10: Bentué-Ferrer D, Verdier MC, Tribut O. [Therapeutic drug monitoring of primidone and phenobarbital]. Therapie. 2012 Jul-Aug;67(4):381-90. doi: 10.2515/therapie/2012036. Epub 2012 Nov 1. French. PubMed PMID: 23110839. 11: Rezaei B, Jafari MT, Khademi R. Selective separation and determination of primidone in pharmaceutical and human serum samples using molecular imprinted polymer-electrospray ionization ion mobility spectrometry (MIP-ESI-IMS). Talanta. 2009 Aug 15;79(3):669-75. doi: 10.1016/j.talanta.2009.04.046. Epub 2009 May 3. PubMed PMID: 19576428. 12: Westerman AT, Roma PG, Creed ET, Hurwitz ZE, Dominguez JM. The antiepileptic primidone impairs male rat sexual behavior. Pharmacol Biochem Behav. 2009 Aug;93(2):160-4. doi: 10.1016/j.pbb.2009.05.006. Epub 2009 May 15. PubMed PMID: 19447126. 13: Lopez-Gomez M, Ramirez-Bermudez J, Campillo C, Sosa AL, Espinola M, Ruiz I. Primidone is associated with interictal depression in patients with epilepsy. Epilepsy Behav. 2005 May;6(3):413-6. PubMed PMID: 15820351. 14: de Haan GJ, Carpay JA, van Donselaar CA. [Antiepileptic primidone shortly to be withdrawn from sale: change medication now]. Ned Tijdschr Geneeskd. 2003 Nov 22;147(47):2325-6. Review. Dutch. PubMed PMID: 14669538. 15: Serrano-Dueñas M. Use of primidone in low doses (250 mg/day) versus high doses (750 mg/day) in the management of essential tremor. Double-blind comparative study with one-year follow-up. Parkinsonism Relat Disord. 2003 Oct;10(1):29-33. PubMed PMID: 14499204. 16: Queiroz ME, Silva SM, Carvalho D, Lanças FM. Determination of lamotrigine simultaneously with carbamazepine, carbamazepine epoxide, phenytoin, phenobarbital, and primidone in human plasma by SPME-GC-TSD. J Chromatogr Sci. 2002 Apr;40(4):219-23. PubMed PMID: 12004942. 17: Ferranti V, Chabenat C, Marchais H, Ménager S, Hue H, Orecchioni AM, Lafont O. Effects of encapsulation of primidone on its oxidative metabolism in rats. Drug Metabol Drug Interact. 2001;18(3-4):191-208. PubMed PMID: 11791884. 18: Katano H, Fukushima T, Karasawa K, Sugiyama N, Ohkura A, Kamiya K. Primidone-induced hyperammonemic encephalopathy in a patient with cerebral astrocytoma. J Clin Neurosci. 2002 Jan;9(1):79-81. PubMed PMID: 11749025. 19: Kanner AM, Parra J, Frey M. The "forgotten" cross-tolerance between phenobarbital and primidone: it can prevent acute primidone-related toxicity. Epilepsia. 2000 Oct;41(10):1310-4. PubMed PMID: 11051127. 20: Nagaki S, Ratnaraj N, Patsalos PN. 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. PubMed PMID: 10716065.

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