MedKoo Cat#: 592266 | Name: Phenytoin
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Description:

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

Phenytoin is an anticonvulsant that is used to treat a wide variety of seizures. It is also an anti-arrhythmic and a muscle relaxant. Phenytoin has been proposed for several other therapeutic uses, but its use has been limited by its many adverse effects and interactions with other drugs.

Chemical Structure

Phenytoin
Phenytoin
CAS#57-41-0 (free base)

Theoretical Analysis

MedKoo Cat#: 592266

Name: Phenytoin

CAS#: 57-41-0 (free base)

Chemical Formula: C15H12N2O2

Exact Mass: 252.0899

Molecular Weight: 252.27

Elemental Analysis: C, 71.42; H, 4.79; N, 11.10; O, 12.68

Price and Availability

Size Price Availability Quantity
25g USD 250.00 2 weeks
100g USD 460.00 2 weeks
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Synonym
Phenytoin; NCI-C55765; NCI C55765; NCIC55765
IUPAC/Chemical Name
2,4-Imidazolidinedione, 5,5-diphenyl-
InChi Key
CXOFVDLJLONNDW-UHFFFAOYSA-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)
SMILES Code
O=C1NC(C(C2=CC=CC=C2)(C3=CC=CC=C3)N1)=O
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
>3 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
2934.99.03.00
More Info
Product Data
Biological target:
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/
Solvent mg/mL mM comments
Solubility
DMSO 41.7 165.16
DMSO:PBS (pH 7.2) (1:1) 0.5 1.98
Ethanol 14.0 55.50
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 252.27 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:
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:
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.
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.