Phenytoin Sodium | CAS#630-93-3 | K+ Channel Blocker

MedKoo Cat#: 318489 | Name: Phenytoin Sodium

Description:

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

Phenytoin Sodium is a potent K+ channel block. It also is a potent multi-channel blockers, blocking Na+ and Ca 2+ channels. It selectively blocks persistent INaP over shorter INaP actions and blocks high frequency repetitive firing of action potentials. Phenytoin Sodium is an anticonvulsant that is used to treat a wide variety of seizures. It is also an anti-arrhythmic and a muscle relaxant. The mechanism of therapeutic action is not clear, although several cellular actions have been described including effects on ion channels, active transport, and general membrane stabilization.

Chemical Structure

Phenytoin Sodium

CAS#630-93-3 (sodium)

Theoretical Analysis

MedKoo Cat#: 318489

Name: Phenytoin Sodium

CAS#: 630-93-3 (sodium)

Chemical Formula: C15H11N2NaO2

Exact Mass: 0.0000

Molecular Weight: 274.25

Elemental Analysis: C, 65.69; H, 4.04; N, 10.21; Na, 8.38; O, 11.67

Price and Availability

Size	Price	Availability
200mg	USD 150.00	Ready to ship
1g	USD 250.00	Ready to ship
5g	USD 450.00	Ready to ship
10g	USD 550.00	Ready to ship
20g	USD 650.00	Ready to ship
50g	USD 850.00	2 weeks

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Related CAS #

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

Synonym

Phenytoin Sodium; Dilantin sodium; Diphenylhydantoin Sodium; 5,5-Diphenylhydantoin sodium salt; Diphantoine; Phizer Brand of Phenytoin; Sodium Diphenylhydantoinate; Phenytoin; Phenytoin Pfizer Brand; Phenytoin Phizer Brand;

IUPAC/Chemical Name

sodium;5,5-diphenylimidazolidin-3-ide-2,4-dione

InChi Key

FJPYVLNWWICYDW-UHFFFAOYSA-M

InChi Code

InChI=1S/C15H12N2O2.Na/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);/q;+1/p-1

SMILES Code

C1=CC=C(C=C1)C2(C(=O)[N-]C(=O)N2)C3=CC=CC=C3.[Na+]

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

Certificate of Analysis

View CoA: current batch, Lot#TC70329

Safety Data Sheet (SDS)

View Safety Data Sheet (SDS)

Instruction

View handling instruction

Biological target:

Phenytoin sodium (5,5-Diphenylhydantoin sodium salt) is a potent Voltage-gated Na+ channels (VGSCs) blocker that has antiepileptic activity.

In vitro activity:

The effect of phenytoin sodium on the quantal content of e.p.ps was investigated in excised mouse sternomastoid nerve-muscle preparations. On exposure to a solution containing phenytoin sodium (10 pg/ml) the mean amplitude of e.p.ps was reduced. It was found that the concentration of phenytoin sodium tested significantly reduced the time constant of decay of m.e.p.cs but had little effect on their amplitude. Decay of m.e.p.cs there appeared to be a reduction in the growth time of m.e.p.cs in the presence of the phenytoin. In the three experiments, the growth time fell from 175 + 19 ms in control solution to 146 + 10 ms in the solution containing phenytoin. A. The results show that phenytoin has two types of depressant action at the neuromuscular junction. Reference: Br J Pharmacol. 1980 May;69(1):119-21 https://pubmed.ncbi.nlm.nih.gov/6247003

In vivo activity:

In this study, the effects of local and systemic use of phenytoin sodium on dural healing were investigated. Thirty-six male Wistar rats were divided into control, local phenytoin and systemic phenytoin groups with 12 rats in each. The values of all the parameters were statistically significantly higher in 6th week than in the 1st week in the systemic phenytoin group based on the results of Wilcoxon test as well as Kruskal Wallis test. In the local phenytoin group, all the parameters were concurrently increased in the 1st week. The maximum increase was observed in granulation formation in the 1st week for the systemic phenytoin group with a less but similar increase in the rates of collagen and neovascularization. Evaluation of these results showed that the local and systemic uses of phenytoin had statistically significant positive effects on dura mater healing, particularly in the in systemic phenytoin group than in the local phenytoin group. Reference: Turk Neurosurg . 2011;21(4):471-6. https://pubmed.ncbi.nlm.nih.gov/22194102/

	Solvent	mg/mL	mM	comments
Solubility
	DMSO	53.0	193.25

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 274.25 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. Gage PW, Lonergan M, Torda TA. Presynaptic and postsynaptic depressant effects of phenytoin sodium at the neuromuscular junction. Br J Pharmacol. 1980 May;69(1):119-21. doi: 10.1111/j.1476-5381.1980.tb10890.x. PMID: 6247003; PMCID: PMC2044177. 2. Ergun E, Kurt G, Tonge M, Aytar H, Tas M, Baykaner K, Ceviker N. Effects of phenytoin sodium on dura mater healing in a rat model of CSF leakage. Turk Neurosurg. 2011;21(4):471-6. PMID: 22194102.

In vitro protocol:

In vivo protocol:

1. Ergun E, Kurt G, Tonge M, Aytar H, Tas M, Baykaner K, Ceviker N. Effects of phenytoin sodium on dura mater healing in a rat model of CSF leakage. Turk Neurosurg. 2011;21(4):471-6. PMID: 22194102.

1: Mundlamuri RC, Sinha S, Subbakrishna DK, Prathyusha PV, Nagappa M, Bindu PS, Taly AB, Umamaheswara Rao GS, Satishchandra P. Management of generalised convulsive status epilepticus (SE): A prospective randomised controlled study of combined treatment with intravenous lorazepam with either phenytoin, sodium valproate or levetiracetam--Pilot study. Epilepsy Res. 2015 Aug;114:52-8. doi: 10.1016/j.eplepsyres.2015.04.013. Epub 2015 May 1. PubMed PMID: 26088885. 2: Zarandi MA, Zahedi P, Rezaeian I, Salehpour A, Gholami M, Motealleh B. Drug release, cell adhesion and wound healing evaluations of electrospun carboxymethyl chitosan/polyethylene oxide nanofibres containing phenytoin sodium and vitamin C. IET Nanobiotechnol. 2015 Aug;9(4):191-200. doi: 10.1049/iet-nbt.2014.0030. PubMed PMID: 26224348. 3: Lavandier N, Tourniaire D. [Follow-up of a cohort of patients after substitution of phenytoin for phenytoin sodium in an epilepsy center]. Rev Neurol (Paris). 2015 Feb;171(2):181-8. doi: 10.1016/j.neurol.2014.09.006. Epub 2015 Jan 6. French. PubMed PMID: 25575610. 4: Kaucher KA, Acquisto NM, Rao GG, Kaufman DC, Huntress JD, Forrest A, Haas CE. Relative bioavailability of orally administered fosphenytoin sodium injection compared with phenytoin sodium injection in healthy volunteers. Pharmacotherapy. 2015 May;35(5):482-8. doi: 10.1002/phar.1589. PubMed PMID: 26011141. 5: Sehgal VN, Prasad PV, Kaviarasan PK, Rajan D. Trophic skin ulceration in leprosy: evaluation of the efficacy of topical phenytoin sodium zinc oxide paste. Int J Dermatol. 2014 Jul;53(7):873-8. doi: 10.1111/ijd.12457. Epub 2014 Mar 6. PubMed PMID: 24601869. 6: Erenberk U, Dundaroz R, Gok O, Uysal O, Agus S, Yuksel A, Yilmaz B, Kilic U. Melatonin attenuates phenytoin sodium-induced DNA damage. Drug Chem Toxicol. 2014 Apr;37(2):233-9. doi: 10.3109/01480545.2013.838777. Epub 2013 Oct 30. PubMed PMID: 24171672. 7: Doshi MS, Naik AA, Mehta MR, Gogtay NJ, Thatte UM, Menon MD. Three-way, three-period, crossover bioequivalence study of single oral dose of three brands of 300 mg phenytoin sodium tablets marketed in India, on healthy Indian human volunteers. J Pharmacol Pharmacother. 2013 Oct;4(4):243-6. doi: 10.4103/0976-500X.119709. PubMed PMID: 24250200; PubMed Central PMCID: PMC3825999. 8: Onuki Y, Ikegami-Kawai M, Ishitsuka K, Hayashi Y, Takayama K. A 5% glucose infusion fluid provokes significant precipitation of phenytoin sodium injection via interruption of the cosolvent effect of propylene glycol. Chem Pharm Bull (Tokyo). 2012;60(1):86-93. PubMed PMID: 22223379. 9: National Toxicology Program. Phenytoin and phenytoin sodium. Rep Carcinog. 2011;12:345-7. PubMed PMID: 21863082. 10: Ergun E, Kurt G, Tonge M, Aytar H, Tas M, Baykaner K, Ceviker N. Effects of phenytoin sodium on dura mater healing in a rat model of CSF leakage. Turk Neurosurg. 2011;21(4):471-6. doi: 10.5137/1019-5149.JTN .4165-11.2. PubMed PMID: 22194102. 11: Fonseka HF, Ekanayake SM, Dissanayake M. Two percent topical phenytoin sodium solution in treating pyoderma gangrenosum: a cohort study. Int Wound J. 2010 Dec;7(6):519-23. doi: 10.1111/j.1742-481X.2010.00725.x. Epub 2010 Aug 17. PubMed PMID: 20722769. 12: Yi T, Zhan XC, Li CR, He N. Application of highly accurate nephelometric titration in the assaying of phenytoin sodium. Yao Xue Xue Bao. 2006 Apr;41(4):370-5. PubMed PMID: 16856486. 13: Kaushal S, Rani A, Chopra SC, Singh G. Safety and efficacy of clobazam versus phenytoin-sodium in the antiepileptic drug treatment of solitary cysticercus granulomas. Neurol India. 2006 Jun;54(2):157-60. PubMed PMID: 16804259. 14: Yi T, Zhan XC, Li CR, He N. Determination of phenytoin sodium injection and tablets by highly accurate nephelometric titration. Chem Pharm Bull (Tokyo). 2006 Mar;54(3):384-6. PubMed PMID: 16508198. 15: Rhodes RS Pharmd, Kuykendall JR Phd Pharmd, Heyneman CA Pharmd Ms, May MP Ms, Bhushan A Msc Phd. Stability of phenytoin sodium suspensions for the treatment of open wounds. Int J Pharm Compd. 2006 Jan-Feb;10:74-8. PubMed PMID: 23974120. 16: Wijnberg ID, Ververs FF. Phenytoin sodium as a treatment for ventricular dysrhythmia in horses. J Vet Intern Med. 2004 May-Jun;18(3):350-3. PubMed PMID: 15188823. 17: Muchohi SN, Kokwaro GO, Maitho TE, Munenge RW, Watkins WM, Edwards G. Pharmacokinetics of phenytoin following intravenous and intramuscular administration of fosphenytoin and phenytoin sodium in the rabbit. Eur J Drug Metab Pharmacokinet. 2002 Apr-Jun;27(2):83-9. PubMed PMID: 12064376. 18: Wijnberg ID, Back W, van der Kolk JH. [The use of electromyographic examination as a diagnostic tool and phenytoin sodium as treatment in a case of classic springhalt in a Dutch warmblood horse]. Tijdschr Diergeneeskd. 2000 Dec 15;125(24):743-7. Dutch. PubMed PMID: 11189905. 19: Suthisisang C, Payakachat N, Chulavatnatol S, Towanabut S. Bioavailability of phenytoin sodium capsules available in Thailand. Part II: In vivo study. J Med Assoc Thai. 1998 Jan;81(1):64-70. PubMed PMID: 9470324. 20: Lewis WG, Rhodes RS. Systemic absorption of topical phenytoin sodium. Ann Pharmacother. 1994 Jul-Aug;28(7-8):961. PubMed PMID: 7949521.