Phenytoin sodium

Sodium channel stabilizer CAS# 630-93-3

Phenytoin sodium

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Chemical structure

Phenytoin sodium

3D structure

Chemical Properties of Phenytoin sodium

Cas No. 630-93-3 SDF Download SDF
PubChem ID 657302 Appearance Powder
Formula C15H11N2NaO2 M.Wt 274.25
Type of Compound N/A Storage Desiccate at -20°C
Synonyms 5,5-Diphenylhydantoin sodium salt
Solubility DMSO : 50 mg/mL (182.32 mM; Need ultrasonic)
H2O : < 0.1 mg/mL (insoluble)
Chemical Name sodium;5,5-diphenylimidazolidin-3-ide-2,4-dione
SMILES C1=CC=C(C=C1)C2(C(=O)[N-]C(=O)N2)C3=CC=CC=C3.[Na+]
Standard InChIKey FJPYVLNWWICYDW-UHFFFAOYSA-M
Standard InChI 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
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 sodium

DescriptionPhenytoin sodium is an inactive voltage-gated sodium channel stabilizer. Target: Sodium Channel Phenytoin sodium 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 sodium Dilution Calculator

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Phenytoin sodium Molarity Calculator

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Preparing Stock Solutions of Phenytoin sodium

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 3.6463 mL 18.2315 mL 36.4631 mL 72.9262 mL 91.1577 mL
5 mM 0.7293 mL 3.6463 mL 7.2926 mL 14.5852 mL 18.2315 mL
10 mM 0.3646 mL 1.8232 mL 3.6463 mL 7.2926 mL 9.1158 mL
50 mM 0.0729 mL 0.3646 mL 0.7293 mL 1.4585 mL 1.8232 mL
100 mM 0.0365 mL 0.1823 mL 0.3646 mL 0.7293 mL 0.9116 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 sodium

Phenytoin is an inactive voltage-gated sodium channel stabilizer.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 se

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References on Phenytoin sodium

Drug release, cell adhesion and wound healing evaluations of electrospun carboxymethyl chitosan/polyethylene oxide nanofibres containing phenytoin sodium and vitamin C.[Pubmed:26224348]

IET Nanobiotechnol. 2015 Aug;9(4):191-200.

In this work, N, O-carboxymethyl chitosan (CMCS) samples from virgin chitosan (CS) were synthesised and CMCS/polyethylene oxide (PEO) (50/50) blend nanofibrous samples were successfully electrospun from their aqueous solution. The electrospinning conditions to achieve smooth and fine diameter nanofibrous mats were optimised via D-optimal design approach. Afterwards, vitamin C and Phenytoin sodium (PHT-Na) were added to these samples for producing wound dressing materials. H-nuclear magnetic resonance, scanning electron microscopy and Fourier transform infrared tests for the evaluation of functionalised CS, morphology and biodegradability studies of CMCS/PEO blend nanofibrous samples were applied. The kinetic and drug release mechanism for vitamin C and PHT-Na drug-loaded electrospun samples were also investigated by UV-vis spectrophotometer and high performance liquid chromatography, respectively. The results showed an approximately similar drug release rate of the two drugs and followed Higuchi's kinetic model. The stem cells viability and their adhesion on the surface of the samples containing PHT-Na and vitamin C were carried out using MTT assay and the best cells' biocompatibility was obtained using both drugs into the CMCS/PEO nanofibrous samples. Moreover, the in vivo animal wound model results revealed that the electrospun samples containing vitamin C and PHT-Na (1%) had a remarkable efficiency in the wounds' closure and their healing process compared with vitamin C/PHT-Na (50/50) ointment. Finally, the histology observations showed that the wound treated with optimised electrospun samples containing two drugs enabled regeneration of epidermis layers due to collagen fibres accumulation followed by granulating tissues formation without necrosis.

The antiepileptic medications carbamazepine and phenytoin inhibit native sodium currents in murine osteoblasts.[Pubmed:27440235]

Epilepsia. 2016 Sep;57(9):1398-405.

OBJECTIVE: Fracture risk is a serious comorbidity in epilepsy and may relate to the use of antiepileptic drugs (AEDs). Many AEDs inhibit ion channel function, and the expression of these channels in osteoblasts raises the question of whether altered bone signaling increases bone fragility. We aimed to confirm the expression of voltage-gated sodium (NaV ) channels in mouse osteoblasts, and to investigate the action of carbamazepine and phenytoin on NaV channels. METHODS: Immunocytochemistry was performed on primary calvarial osteoblasts extracted from neonatal C57BL/6J mice and additional RNA sequencing (RNASeq) was included to confirm expression of NaV . Whole-cell patch-clamp recordings were made to identify the native currents expressed and to assess the actions of carbamazepine (50 mum) or phenytoin (50 mum). RESULTS: NaV expression was demonstrated with immunocytochemistry, RNA sequencing, and functionally, with demonstration of robust tetrodotoxin-sensitive and voltage-activated inward currents. Application of carbamazepine or phenytoin resulted in significant inhibition of current amplitude for carbamazepine (31.6 +/- 5.9%, n = 9; p < 0.001), and for phenytoin (35.5 +/- 6.9%, n = 7; p < 0.001). SIGNIFICANCE: Mouse osteoblasts express NaV , and native NaV currents are blocked by carbamazepine and phenytoin, supporting our hypothesis that AEDs can directly influence osteoblast function and potentially affect bone strength.

Effect of phenytoin on sodium conductances in rat hippocampal CA1 pyramidal neurons.[Pubmed:27489371]

J Neurophysiol. 2016 Oct 1;116(4):1924-1936.

The antiepileptic drug phenytoin (PHT) is thought to reduce the excitability of neural tissue by stabilizing sodium channels (NaV) in inactivated states. It has been suggested the fast-inactivated state (IF) is the main target, although slow inactivation (IS) has also been implicated. Other studies on local anesthetics with similar effects on sodium channels have implicated the NaV voltage sensor interactions. In this study, we reexamined the effect of PHT in both equilibrium and dynamic transitions between fast and slower forms of inactivation in rat hippocampal CA1 pyramidal neurons. The effects of PHT were observed on fast and slow inactivation processes, as well as on another identified "intermediate" inactivation process. The effect of enzymatic removal of IF was also studied, as well as effects on the residual persistent sodium current (INaP). A computational model based on a gating charge interaction was derived that reproduced a range of PHT effects on NaV equilibrium and state transitions. No effect of PHT on IF was observed; rather, PHT appeared to facilitate the occupancy of other closed states, either through enhancement of slow inactivation or through formation of analogous drug-bound states. The overall significance of these observations is that our data are inconsistent with the commonly held view that the archetypal NaV channel inhibitor PHT stabilizes fast inactivation states, and we demonstrate that conventional slow activation "IS" and the more recently identified intermediate-duration inactivation process "II" are the primary functional targets of PHT. In addition, we show that the traditional explanatory frameworks based on the "modulated receptor hypothesis" can be substituted by simple, physiologically plausible interactions with voltage sensors. Additionally, INaP was not preferentially inhibited compared with peak INa at short latencies (50 ms) by PHT.

Description

Phenytoin sodium is an inactive voltage-gated sodium channel stabilizer.

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