Referencia número: HY-B0448

Phenytoin

(Synonyms: 5,5-Diphenylhydantoin)

6 Cited Publications

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Based on 6 publication(s) in Google Scholar

Phenytoin (5,5-Diphenylhydantoin) is a potent Voltage-gated Na⁺ channels (VGSCs) blocker. Phenytoin has antiepileptic activity and reduces breast tumour growth and metastasis in mice.

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Pureza: 99.95%
No. CAS: 57-41-0
Fòrmula: C₁₅H₁₂N₂O₂
Peso molecular:252.27

Almacenamiento:

Powder -20°C, 3 years , 4°C, 2 years ; In solvent -80°C, 2 years , -20°C, 1 year

Phenytoin Chemical Structure

No. CAS: 57-41-0

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Actividad biológica
- Descripciòn
- Cellular Effect
- In Vitro
- Induced Disease Models
- Ensayo clínico
Chemical Information
Publications (6)
Solvente y solubilidad
- In Vitro
- In Vivo
Pureza y Documentación
Referencias
Help & FAQs
Bioz

Actividad biológica

Descripciòn

Phenytoin (5,5-Diphenylhydantoin) is a potent Voltage-gated Na⁺ channels (VGSCs) blocker. Phenytoin has antiepileptic activity and reduces breast tumour growth and metastasis in mice^[1]^[2].

Ver todos los productos específicos de isoformas Sodium Channel :

Cellular Effect

Cell Line	Type	Value	Description	References
CHO	IC₅₀	21.9 μM Compound: phenytoin	Inhibition of Cav1.2 current measured using QPatch automatic path clamp system in CHO cells expressing Cav1.2, beta-2 and alpha-2/delta-1 subunits Inhibition of Cav1.2 current measured using QPatch automatic path clamp system in CHO cells expressing Cav1.2, beta-2 and alpha-2/delta-1 subunits	[PMID: 23812503]
HEK293	IC₅₀	>100 μM Compound: 24	Inhibition of human Nav1.2 channel expressed in HEK cells by patch-clamp electrophysiology method Inhibition of human Nav1.2 channel expressed in HEK cells by patch-clamp electrophysiology method	[PMID: 19394229]
HEK293	IC₅₀	>100 μM Compound: phenytoin	Inhibition of human NaV1.2 expressed in HEK cells at -60 mV holding potential by patch clamp recording technique Inhibition of human NaV1.2 expressed in HEK cells at -60 mV holding potential by patch clamp recording technique	[PMID: 20943396]
HEK293	IC₅₀	49 μM Compound: Phenytoin	Inhibition of sodium current measured using whole-cell patch clamp experiments in HEK-293 cells stably transfected with hNaV1.5 cDNA Inhibition of sodium current measured using whole-cell patch clamp experiments in HEK-293 cells stably transfected with hNaV1.5 cDNA	[PMID: 21300721]
HEK293	IC₅₀	>100 μM Compound: DPH	Inhibition of human voltage-gated sodium channel 1.5 expressed in HEK293 cells assessed as changes in membranre potential after 45 mins by FRET analysis Inhibition of human voltage-gated sodium channel 1.5 expressed in HEK293 cells assessed as changes in membranre potential after 45 mins by FRET analysis	[PMID: 22364743]
HEK293	IC₅₀	>100 μM Compound: DPH	Inhibition of human voltage-gated sodium channel 1.7 expressed in HEK293 cells assessed as changes in membranre potential after 45 mins by FRET analysis Inhibition of human voltage-gated sodium channel 1.7 expressed in HEK293 cells assessed as changes in membranre potential after 45 mins by FRET analysis	[PMID: 22364743]
HEK293	IC₅₀	125 μM Compound: Phenytoin	Inhibition of L-type calcium channel measured using 2-electrode voltage-clamp in human embryonic kidney cells heterologically expressing alpha-1C subunit Inhibition of L-type calcium channel measured using 2-electrode voltage-clamp in human embryonic kidney cells heterologically expressing alpha-1C subunit	[PMID: 22761000]
HT-29	EC₅₀	500 μM Compound: 91	Anti-necroptic activity in TNF alpha induced cell death in human HT-29 cells preincubated for 1 hr with compound and measured after 15 hrs in presence of TNFalpha/zVAD Anti-necroptic activity in TNF alpha induced cell death in human HT-29 cells preincubated for 1 hr with compound and measured after 15 hrs in presence of TNFalpha/zVAD	[PMID: 36346971]
L929	EC₅₀	500 μM Compound: 91	Anti-necroptic activity in mouse L929 cells incubated for 2 hrs in presence of TNF/vVAD-fmk Anti-necroptic activity in mouse L929 cells incubated for 2 hrs in presence of TNF/vVAD-fmk	[PMID: 36346971]
Oocyte	IC₅₀	9.8 μM Compound: 5	Inhibition of human aquaporin 4 M23 isoform expressed in Xenopus laevis oocytes Inhibition of human aquaporin 4 M23 isoform expressed in Xenopus laevis oocytes	[PMID: 18178093]
Ventricular myocyte	IC₅₀	103 μM Compound: Phenytoin	Inhibition of calcium current (ICaL) measured using whole-cell patch clamp experiments in isolated guinea pig ventricular myocytes Inhibition of calcium current (ICaL) measured using whole-cell patch clamp experiments in isolated guinea pig ventricular myocytes	[PMID: 21300721]
Ventricular myocyte	IC₅₀	103 μM Compound: Phenytoin	Inhibition of L-type calcium channel measured using whole-cell patch clamp in guinea pig ventricular myocytes Inhibition of L-type calcium channel measured using whole-cell patch clamp in guinea pig ventricular myocytes	[PMID: 22761000]

In Vitro

Phenytoin is an antiepileptic drug. It is useful to 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^[2].
Phenytoin has low affinity for resting sodium channels at hyperpolarized membrane potentials^[3].
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^[4].

MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.

Induced Disease Models

Note:
Please do not refer to only one article to determine the experimental conditions. It is recommended to determine the optimal experimental conditions (animal strain, age, dosage, frequency and cycle, detection time and indicators, etc.) through preliminary experiments before the formal experiment.

Phenytoin (60 mg/kg; once daily for 28 days) sodium reduces MDA-MB-231 cells in six-week-old female Rag2^-/-Il2rg^-/- mice^[1].
Phenytoin can induce a model of gingival hyperplasia in mice^[6].

Induction of Gingival Hyperplasia in Mice^[5]

Background

Phenytoin induced gingival overgrowth, a side effect with multifactorial aetiology, is characterized by an increase in the volume of extracellular tissues, particularly collagenous components, with varying degrees of inflammation.

Specific Modeling Methods

Mice: BALB/cByJ • male • 8 week old
Administration: 30 mg/kg • miniosmotic pumps • 0.5-μL/h • 2 weeks

Note

(1) Mice are housed for 1 week before any procedure for acclimation.
(2) Pumps are replaced every 2 weeks throughout the 12-week experimental period.
(3) Mice are then euthanized and heads are immediately placed in freshly made 4% paraformaldehyde for 24 hours for fixation.

Modeling Indicators

Morphology: Gingival overgrowth was apparent in the maxillary anterior gingival tissue of mice; Increased the papillary height and area.
Histomorphometry: Increased epithelial thickness and area in the maxillary anterior zone.
Molecular changes: Ccn2 is overexpressed in all regions of the epithelium; TGF-β1 and LOXL2 is overexpressed in both epithelial and connective tissues.

Correlated Product(s): Cyclosporine A (HY-B0579)

Opposite Product(s): Lovastatin (HY-N0504)

MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.

Ensayo clínico

NCT Number	Sponsor	Condition	Start Date	Phase A549
NCT01329991	Plexxikon\|		2011-05	PHASE1

Chemical Information

No. CAS 57-41-0
Appearance Solid
Peso molecular 252.27
Fòrmula C₁₅H₁₂N₂O₂
Color White to off-white
SMILES

O=C1NC(C(C2=CC=CC=C2)(C3=CC=CC=C3)N1)=O
Synonyms

5,5-Diphenylhydantoin
Envío

Room temperature in continental US; may vary elsewhere.

Almacenamiento

Powder	-20°C	3 years
	4°C	2 years
In solvent	-80°C	2 years
	-20°C	1 year

Publications (6)

All In Vivo Efficacy Study

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Journal Impact Factor

Emerg Contam

2026 Feb 23.
Int Immunopharmacol

Lidocaine inhibits influenza a virus replication by up-regulating IFNα4 via TBK1-IRF7 and JNK-AP1 signaling pathways. [Abstract]

2023 Feb:115:109706. PMID: 36638664
Cell Rep Methods

RECOVER identifies synergistic drug combinations in vitro through sequential model optimization. [Abstract]

2023 Oct 23;3(10):100599. PMID: 37797618
Regen Ther

Phenytoin regulates osteogenic differentiation of human bone marrow stem cells by PI3K/Akt pathway. [Abstract]

2023 Jul 6:24:201-210. PMID: 37448850
University of Glasgow

2023.
Oxid Med Cell Longev

Ageing Increases Cardiac Electrical Remodelling in Rats and Mice via NOX4/ROS/CaMKII-Mediated Calcium Signalling. [Abstract]

2022 Mar 28;2022:8538296. PMID: 35387264

Phenytoin purchased from MedChemExpress. Usage Cited in: Oxid Med Cell Longev. 2022 Mar 28;2022:8538296. [Abstract]

Phenytoin (Isoproterenol, ISO, 1 mg/kg, i.p.). The typical ECG recording showing that ageing increased susceptibility to ISO-induced arrhythmias using PES with PCL from 90 ms to 30 ms.

Phenytoin purchased from MedChemExpress. Usage Cited in: Oxid Med Cell Longev. 2022 Mar 28;2022:8538296. [Abstract]

Histogram of the VT occurrence rate in young and old mice with or without treatment of Phenytoin (Isoproterenol, ISO, 1 mg/kg, i.p.) (∗∗P < 0.01 and ∗∗∗P < 0.001).

Phenytoin purchased from MedChemExpress. Usage Cited in: Oxid Med Cell Longev. 2022 Mar 28;2022:8538296. [Abstract]

The typical APD80 map and AP trace (young: black line; old: red line) in intact Langendorff perfused young and old mouse hearts before and following Phenytoin (Isoproterenol, ISO, 1μM) challenge in pacing at 10 Hz.

Phenytoin purchased from MedChemExpress. Usage Cited in: Oxid Med Cell Longev. 2022 Mar 28;2022:8538296. [Abstract]

Quantitative analysis of APD80 from individual hearts in young and old mice before and following Phenytoin (Isoproterenol, ISO, 1μM) (∗P < 0.05, ∗∗P < 0.01, and ∗∗∗P < 0.001).

Phenytoin purchased from MedChemExpress. Usage Cited in: Oxid Med Cell Longev. 2022 Mar 28;2022:8538296. [Abstract]

Ageing induced fractional increases in APD80 challenged by Phenytoin (Isoproterenol, ISO, 1μM) (ΔAPD80) (P > 0.05).

Phenytoin purchased from MedChemExpress. Usage Cited in: Oxid Med Cell Longev. 2022 Mar 28;2022:8538296. [Abstract]

The typical CaTD50 map and calcium transient trace (young: black line; old: red line) in intact Langendorff perfused young and old mouse hearts before and following Phenytoin (Isoproterenol, ISO, 1μM) challenge in pacing at 10 Hz.

Phenytoin purchased from MedChemExpress. Usage Cited in: Oxid Med Cell Longev. 2022 Mar 28;2022:8538296. [Abstract]

Histogram showing the τ30–90 in young and old mice before and following Phenytoin (Isoproterenol, ISO, 1μM) pacing at 10 Hz (∗P < 0.05 and ∗∗P < 0.01). n = 5 (each group).

Solvente y solubilidad

In Vitro:

DMSO : 50 mg/mL (198.20 mM; Need ultrasonic; Hygroscopic DMSO has a significant impact on the solubility of product, please use newly opened DMSO)

View the Complete Stock Solution Preparation Table

Preparing Stock Solutions

View the Complete Stock Solution Preparation Table

Concentration Solvent Mass

1 mg

5 mg

10 mg

Concentration

Solvent

Mass

1 mM

3.9640 mL

19.8200 mL

39.6401 mL

5 mM

0.7928 mL

3.9640 mL

7.9280 mL

10 mM

0.3964 mL

1.9820 mL

3.9640 mL

Please refer to the solubility information to select the appropriate solvent. Once prepared, please aliquot and store the solution to prevent product inactivation from repeated freeze-thaw cycles.

Storage method and period of stock solution: -80°C, 2 years; -20°C, 1 year. When stored at -80°C, please use it within 2 years. When stored at -20°C, please use it within 1 year.

Calculadora de molaridad

Mass (g) = Concentration (mol/L) × Volume (L) × Molecular Weight (g/mol)

Mass Mass

Concentration Concentration

Volume Volume

Molecular Weight Molecular Weight

Calculadora de dilución

Concentration _(start) × Volume _(start) = Concentration _(final) × Volume _(final)

Concentration _(start) Concentration _(start)

Volume _(start) Volume _(start)

Concentration _(final) Concentration _(final)

Volume _(final) Volume _(final)

In Vivo:

Select the appropriate dissolution method based on your experimental animal and administration route.

Stock Solution Working Solution

For the following dissolution methods, please ensure to first prepare a clear stock solution using an In Vitro approach and then sequentially add co-solvents:
To ensure reliable experimental results, the clarified stock solution can be appropriately stored based on storage conditions. As for the working solution for In Vivo experiments, it is recommended to prepare freshly and use it on the same day.
The percentages shown for the solvents indicate their volumetric ratio in the final prepared solution. If precipitation or phase separation occurs during preparation, heat and/or sonication can be used to aid dissolution.

Protocol 1

Add each solvent one by one: 10% DMSO 40% PEG300 5% Tween-80 45% Saline

Solubility: ≥ 2.5 mg/mL (9.91 mM); Clear solution

This protocol yields a clear solution of ≥ 2.5 mg/mL (saturation unknown).

Taking 1 mL working solution as an example, add 100 μL DMSO stock solution (25.0 mg/mL) to 400 μL PEG300, and mix evenly; then add 50 μL Tween-80 and mix evenly; then add 450 μL Saline to adjust the volume to 1 mL.

Protocol 2

Add each solvent one by one: 10% DMSO 90% (20% SBE-β-CD in Saline)

Solubility: ≥ 2.5 mg/mL (9.91 mM); Clear solution

This protocol yields a clear solution of ≥ 2.5 mg/mL (saturation unknown).

Taking 1 mL working solution as an example, add 100 μL DMSO stock solution (25.0 mg/mL) to 900 μL 20% SBE-β-CD in Saline, and mix evenly.

Protocol 3

Add each solvent one by one: 10% DMSO 90% Corn Oil

Solubility: ≥ 2.5 mg/mL (9.91 mM); Clear solution

This protocol yields a clear solution of ≥ 2.5 mg/mL (saturation unknown). If the continuous dosing period exceeds half a month, please choose this protocol carefully.

Taking 1 mL working solution as an example, add 100 μL DMSO stock solution (25.0 mg/mL) to 900 μL Corn oil, and mix evenly.

In Vivo Dissolution Calculator

Please enter the basic information of animal experiments:

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Recommended: Prepare an additional quantity of animals to account for potential losses during experiments.

Recommended: Prepare an additional quantity of animals to account for potential losses during experiments.

Please enter your animal formula composition:

%
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Recommended: Keep the proportion of DMSO in working solution below 2% if your animal is weak.
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+
+
%
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The co-solvents required include: DMSO, . All of co-solvents are available by MedChemExpress (MCE). , Tween 80. All of co-solvents are available by MedChemExpress (MCE).

Working solution concentration: 0.22 mg/mL

Pureza y Documentación

Select Batch:

Pureza: 99.98%

Assay: 99.98%

ee.: 99.98%

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COA (2659 KB)
Elemental Analysis Report (2659 KB)
HNMR (2659 KB)
CNMR (2659 KB)
RP-HPLC (2659 KB)
NP-HPLC (2659 KB)
MS (2659 KB)
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IR (2659 KB)
GC (2659 KB)
OR (2659 KB)
SDS-PAGE (2659 KB)
SEC-HPLC (2659 KB)
Other Report (2659 KB)
Instrucciones de manejo (2659 KB)

Referencias

[1]. Michaela Nelson, et al. The sodium channel-blocking antiepileptic drug phenytoin inhibits breast tumour growth and metastasis. Mol Cancer. 2015 Jan 27;14(1):13. [Content Brief]

[2]. Rogawski, M.A. and W. Loscher, The neurobiology of antiepileptic drugs. Nat Rev Neurosci, 2004. 5(7): p. 553-64. [Content Brief]

[3]. Porter, R.J., et al., Mechanisms of action of antiseizure drugs. Handb Clin Neurol, 2012. 108: p. 663-81. [Content Brief]

[4]. Balaji, S., Medical therapy for sudden death. Pediatr Clin North Am, 2004. 51(5): p. 1379-87. [Content Brief]

[5]. Assaggaf MA, et al. Prevention of phenytoin-induced gingival overgrowth by lovastatin in mice. Am J Pathol. 2015 Jun;185(6):1588-99. [Content Brief]

Help & FAQs

How should lyophilized recombinant proteins be reconstituted and stored?

1. Before opening the cap, centrifuge the vial at 13000 rpm for 20-30 seconds. This step will ensure that any lyophilized powder that may have adhered to the cap or walls is collected at the bottom of the vial, minimizing the risk of product loss.

Complete Stock Solution Preparation Table

Storage method and period of stock solution: -80°C, 2 years; -20°C, 1 year. When stored at -80°C, please use it within 2 years. When stored at -20°C, please use it within 1 year.

Optional Solvent	Concentration Solvent Mass	1 mg	5 mg	10 mg	25 mg
DMSO	1 mM	3.9640 mL	19.8200 mL	39.6401 mL	99.1002 mL
	5 mM	0.7928 mL	3.9640 mL	7.9280 mL	19.8200 mL
	10 mM	0.3964 mL	1.9820 mL	3.9640 mL	9.9100 mL
	15 mM	0.2643 mL	1.3213 mL	2.6427 mL	6.6067 mL
	20 mM	0.1982 mL	0.9910 mL	1.9820 mL	4.9550 mL
	25 mM	0.1586 mL	0.7928 mL	1.5856 mL	3.9640 mL
	30 mM	0.1321 mL	0.6607 mL	1.3213 mL	3.3033 mL
	40 mM	0.0991 mL	0.4955 mL	0.9910 mL	2.4775 mL
	50 mM	0.0793 mL	0.3964 mL	0.7928 mL	1.9820 mL
	60 mM	0.0661 mL	0.3303 mL	0.6607 mL	1.6517 mL
	80 mM	0.0496 mL	0.2478 mL	0.4955 mL	1.2388 mL
	100 mM	0.0396 mL	0.1982 mL	0.3964 mL	0.9910 mL

Keywords

Phenytoin

6 Cited Publications

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Phenytoin

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Publications Citing Use of MedChemExpress (MCE) Phenytoin

Ver todos los productos específicos de isoformas Sodium Channel

Actividad biológica

Chemical Information

Publications (6)

Solvente y solubilidad

Pureza y Documentación

Referencias

Help & FAQs

Complete Stock Solution Preparation Table

Phenytoin Related Classifications

Referencia número: HY-B0448