Phenytoin-d10 | CAS#65854-97-9 | Phenytoin quantification internal standard

MedKoo Cat#: 463881 | Name: Phenytoin-d10

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Description:

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

Phenytoin-d10 is intended for use as an internal standard for the quantification of phenytoin by GC- or LC-MS. Phenytoin is an anticonvulsant agent and active metabolite of fosphenytoin. Phenytoin is formed from fosphenytoin by tissue phosphatases. It inhibits neuronal voltage-gated sodium channels in a voltage-dependent manner. Phenytoin reduces the neuronal firing frequency and decreases the amplitude of excitatory post-synaptic potentials (EPSPs) in electrically stimulated rat corticostriatal slices. It protects against seizures induced by maximal electroshock (MES) in mice. Formulations containing phenytoin have been used in the treatment of tonic-clonic seizures and status epilepticus.

Chemical Structure

Phenytoin-d10

CAS#65854-97-9 (deuterated forms)

Theoretical Analysis

MedKoo Cat#: 463881

Name: Phenytoin-d10

CAS#: 65854-97-9 (deuterated forms)

Chemical Formula: C15H2D10N2O2

Exact Mass: 262.1526

Molecular Weight: 262.33

Elemental Analysis: C, 68.68; H, 8.45; N, 10.68; O, 12.20

Price and Availability

Size	Price	Availability	Quantity
5mg	USD 450.00	2 Weeks
10mg	USD 750.00	2 Weeks

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Related CAS #

57-41-0 (free base) 630-93-3 (sodium) 65854-97-9 (deuterated forms)

Synonym

Phenytoin-d10; Phenytoin d10; 5,5-Diphenylhydantoin-d10; 5,5-Diphenylhydantoin d10;

IUPAC/Chemical Name

5,5-bis(phenyl-d5)imidazolidine-2,4-dione

InChi Key

CXOFVDLJLONNDW-LHNTUAQVSA-N

InChi Code

InChI=1S/C15H12N2O2/c18-13-15(17-14(19)16-13,11-7-3-1-4-8-11)12-9-5-2-6-10-12/h1-10H,(H2,16,17,18,19)/i1D,2D,3D,4D,5D,6D,7D,8D,9D,10D

SMILES Code

O=C1C(C2=C(C([2H])=C(C([2H])=C2[2H])[2H])[2H])(NC(N1)=O)C3=C(C([2H])=C(C([2H])=C3[2H])[2H])[2H]

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

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:

Phenytoin-d10 is the deuterium labeled Phenytoin. Phenytoin (5,5-Diphenylhydantoin) is a potent Voltage-gated Na+ channels (VGSCs) blocker.

In vitro activity:

Accordingly, this study aimed to compare the effect of phenytoin on the growth rate of gingival fibroblast cells and PDL in the cell culture medium. In the experimental group, 20 mg/ml phenytoin dissolved in sodium hydroxide was added to Dulbecco's modified Eagle's medium (DMEM). After 48 hours, fibroblast cell proliferation was assessed through a 1-WST cell proliferation kit by ELISA. The proliferation of gingival fibroblast cells and PDL in both test and control groups were statistically analyzed by the independent t-test. The results showed that the effect of phenytoin on the proliferation of gingival fibroblast cells and PDL fibroblast cells is significant. Also, the proliferation of PDL cells was significantly different from gingival cells in the experimental group (P <0.001) and was higher in PDL cells. Reference: Cell Mol Biol (Noisy-le-grand). 2022 May 31;68(5):141-145. https://pubmed.ncbi.nlm.nih.gov/36029507/

In vivo activity:

This study aimed to evaluate whether phenytoin promotes myelin recovery of the corpus callosum of demyelinated adult mice. The oligodendroglial lineage (Olig2 + cells, NG2 + cells, and RIP + cells) significantly increases by the phenytoin administration when compared to the control-vehicle group. The phenytoin-treated group also showed an increased expression of MBP in the corpus callosum and better functional scores in the horizontal bar test. These findings suggest that phenytoin stimulates the proliferation of OPCs, re-establishes the oligodendroglial population, promotes myelin recovery in the corpus callosum, and improves motor coordination and muscle strength. Reference: Exp Brain Res. 2022 May;240(5):1617-1627. https://pubmed.ncbi.nlm.nih.gov/35362723/

Preparing Stock Solutions

The following data is based on the product molecular weight 262.33 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.

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:

1. Zhang L, Gao Q, Peng X, Deng S, Zhang L. The effect of phenytoin on the proliferative ability of periodontal and gingival ligament fibroblasts in cell culture medium. Cell Mol Biol (Noisy-le-grand). 2022 May 31;68(5):141-145. doi: 10.14715/cmb/2022.68.5.19. PMID: 36029507. 2. Na J, Zheng L, Wang L, Shi Q, Yang Z, Liu N, Guo Y, Fan Y. Phenytoin Regulates Migration and Osteogenic Differentiation by MAPK Pathway in Human Periodontal Ligament Cells. Cell Mol Bioeng. 2021 Sep 10;15(1):151-160. doi: 10.1007/s12195-021-00700-0. PMID: 35096190; PMCID: PMC8761188. 3. Vega-Riquer JM, Campos-Ordonez T, Galvez-Contreras AY, Gonzalez-Castañeda RE, Gonzalez-Perez O. Phenytoin promotes the proliferation of oligodendrocytes and enhances the expression of myelin basic protein in the corpus callosum of mice demyelinated by cuprizone. Exp Brain Res. 2022 May;240(5):1617-1627. doi: 10.1007/s00221-022-06356-0. Epub 2022 Apr 1. PMID: 35362723. 4. Nelson M, Yang M, Dowle AA, Thomas JR, Brackenbury WJ. The sodium channel-blocking antiepileptic drug phenytoin inhibits breast tumour growth and metastasis. Mol Cancer. 2015 Jan 27;14(1):13. doi: 10.1186/s12943-014-0277-x. PMID: 25623198; PMCID: PMC4320839.

In vitro protocol:

In vivo protocol:

1. Vega-Riquer JM, Campos-Ordonez T, Galvez-Contreras AY, Gonzalez-Castañeda RE, Gonzalez-Perez O. Phenytoin promotes the proliferation of oligodendrocytes and enhances the expression of myelin basic protein in the corpus callosum of mice demyelinated by cuprizone. Exp Brain Res. 2022 May;240(5):1617-1627. doi: 10.1007/s00221-022-06356-0. Epub 2022 Apr 1. PMID: 35362723. 2. Nelson M, Yang M, Dowle AA, Thomas JR, Brackenbury WJ. The sodium channel-blocking antiepileptic drug phenytoin inhibits breast tumour growth and metastasis. Mol Cancer. 2015 Jan 27;14(1):13. doi: 10.1186/s12943-014-0277-x. PMID: 25623198; PMCID: PMC4320839.

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Evaluation of tissue stem cell derived human intestinal organoids, a physiologically relevant model to evaluate cytochrome P450 induction in gut. Drug Metab Dispos. 2020 Dec 18:DMD- AR-2020-000281. doi: 10.1124/dmd.120.000281. Epub ahead of print. PMID: 33355212. 15: Unnikrishnan G, Jacob NS, Salim S, Jose M, Salini RA, Pavithran V, Jeemon P, Thomas SV. Enduring language deficits in children of women with epilepsy and the potential role of intrauterine exposure to antiepileptic drugs. Epilepsia. 2020 Nov;61(11):2442-2451. doi: 10.1111/epi.16685. Epub 2020 Oct 14. PMID: 33345345. 16: Hussain SA, Heesch J, Weng J, Rajaraman RR, Numis AL, Sankar R. Potential induction of epileptic spasms by nonselective voltage-gated sodium channel blockade: Interaction with etiology. Epilepsy Behav. 2020 Dec 16:107624. doi: 10.1016/j.yebeh.2020.107624. Epub ahead of print. PMID: 33341392. 17: Chu MT, Wang CW, Chang WC, Chen CB, Chung WH, Hung SI. Granulysin-Based Lymphocyte Activation Test for Evaluating Drug Causality in Antiepileptics- Induced Severe Cutaneous Adverse Reactions. J Invest Dermatol. 2020 Dec 17:S0022-202X(20)32398-8. doi: 10.1016/j.jid.2020.11.027. Epub ahead of print. PMID: 33340500. 18: Łukawski K, Czuczwar SJ. Developing precision treatments for epilepsy using patient and animal models. Expert Rev Neurother. 2020 Dec 29:1-10. doi: 10.1080/14737175.2021.1866989. Epub ahead of print. PMID: 33339471. 19: Sathe AG, Mishra U, Ivaturi V, Brundage RC, Cloyd JC, Elm JJ, Chamberlain JM, Silbergleit R, Kapur J, Lowenstein DH, Shinnar S, Cock HR, Fountain NB, Babcock L, Coles LD. Early Exposure of Fosphenytoin, Levetiracetam, and Valproic Acid After High-Dose Intravenous Administration in Young Children With Benzodiazepine-Refractory Status Epilepticus. J Clin Pharmacol. 2020 Dec 17. doi: 10.1002/jcph.1801. Epub ahead of print. 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