Phenytoin

CAS# 57-41-0

Phenytoin

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Chemical structure

Phenytoin

3D structure

Chemical Properties of Phenytoin

Cas No. 57-41-0 SDF Download SDF
PubChem ID 1775 Appearance Powder
Formula C15H12N2O2 M.Wt 252.27
Type of Compound N/A Storage Desiccate at -20°C
Synonyms 5,5-Diphenylhydantoin
Solubility DMSO : 100 mg/mL (396.40 mM; Need ultrasonic)
Chemical Name 5,5-diphenylimidazolidine-2,4-dione
SMILES C1=CC=C(C=C1)C2(C(=O)NC(=O)N2)C3=CC=CC=C3
Standard InChIKey CXOFVDLJLONNDW-UHFFFAOYSA-N
Standard InChI 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)
General tips For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.
We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months.
Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it.
About Packaging 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial.
2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial.
3. Try to avoid loss or contamination during the experiment.
Shipping Condition Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request.

Biological Activity of Phenytoin

DescriptionPhenytoin is an inactive voltage-gated sodium channel stabilizer. Target: Sodium Channel Phenytoin is an antiepileptic drug. It is useful to treat partial seizures and generalized tonic-clonic seizures but not primary generalized seizures such as absence seizures or myoclonic seizures. Phenytoin is believed to protect against seizures by causing voltage-dependent block of voltage-gated sodium channels [1]. Phenytoin has low affinity for resting sodium channels at hyperpolarized membrane potentials [2]. When neurons are depolarized and the channels transition into the open and inactivated states, greater binding and block occur. The inhibitory potency is strongly use dependent, so that block accumulates with prolonged or repetitive activation, such as occurs during a seizure discharge. The blocking of sodium channels by phenytoin is of slow onset. The time course of fast sodium currents is therefore not altered in the presence of the drug and action potentials evoked by synaptic depolarizations of ordinary duration are not blocked. Thus phenytoin is able to selectively inhibit pathological hyperexcitability in epilepsy without unduly impairing ongoing activity. Phenytoin also blocks persistent sodium current and this may be of particular importance in seizure control. Phenytoin is a class 1b antiarrhythmic [3].

References:
[1]. Rogawski, M.A. and W. Loscher, The neurobiology of antiepileptic drugs. Nat Rev Neurosci, 2004. 5(7): p. 553-64. [2]. Porter, R.J., et al., Mechanisms of action of antiseizure drugs. Handb Clin Neurol, 2012. 108: p. 663-81. [3]. Balaji, S., Medical therapy for sudden death. Pediatr Clin North Am, 2004. 51(5): p. 1379-87.

Phenytoin Dilution Calculator

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Phenytoin Molarity Calculator

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Preparing Stock Solutions of Phenytoin

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 3.964 mL 19.82 mL 39.6401 mL 79.2801 mL 99.1002 mL
5 mM 0.7928 mL 3.964 mL 7.928 mL 15.856 mL 19.82 mL
10 mM 0.3964 mL 1.982 mL 3.964 mL 7.928 mL 9.91 mL
50 mM 0.0793 mL 0.3964 mL 0.7928 mL 1.5856 mL 1.982 mL
100 mM 0.0396 mL 0.1982 mL 0.3964 mL 0.7928 mL 0.991 mL
* Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations.

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Background on Phenytoin

Phenytoin is an inactive voltage-gated sodium channel stabilizer.

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References on Phenytoin

A prospective study to assess the association between genotype, phenotype and Prakriti in individuals on phenytoin monotherapy.[Pubmed:28302415]

J Ayurveda Integr Med. 2017 Jan - Mar;8(1):37-41.

BACKGROUND: Genetic polymorphisms in drug metabolizing enzymes (DMEs) impart distinct drug metabolizing capacity and a unique phenotype to an individual. Phenytoin has large inter-individual variability in metabolism due to polymorphisms in CYP2C9 and CYP2C19. As per Ayurveda, Prakriti imparts a unique phenotype to an individual. OBJECTIVE: To assess whether Prakriti can substitute phenotyping [therapeutic drug monitoring (TDM)] and genotyping in individualizing therapy with Phenytoin in epilepsy patients. METHODS AND MATERIALS: This was a cross-sectional study conducted over a period of three years. Prakriti was assessed using standardized and validated software. Polymorphisms in CYP2C9 and CYP2C19 were assessed using Polymerase Chain Reaction (PCR)-Restriction fragment length polymorphism (PCR-RFLP). Plasma concentrations of Phenytoin (phenotype) were determined using reverse phase-high performance liquid chromatography (RF-HPLC). RESULTS: Total 351 patients were enrolled for the study. Kapha vata (KV) (39%) was the predominantly observed Prakriti followed by vata kapha (VK) (20.8%) and vata pitta (VP) (8.83%) among the patients. The CYP2C9 and CYP2C19 genotype distributions were in accordance with Hardy-Weinberg equilibrium. There was no association between Prakriti and genotypes and Prakriti and phenotype (p > 0.05 each). Patients with CYP2C9 *1/*3 genotype were thrice more likely to have toxic plasma concentrations of Phenytoin as compared to those with wild-type genotype (*1/*1) (Adjusted odds ratio - 3.36; 95% C.I. 1.61, 7.01). However, no such association was observed between polymorphisms of CYP2C19 and phenotype. CONCLUSIONS: We did not find any association between Prakriti and either phenotype or genotypes suggesting that Prakriti assessment would be of limited utility in individualizing Phenytoin therapy in epilepsy patients.

Description

Phenytoin is an inactive voltage-gated sodium channel stabilizer.

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