Phenytoin
5,5-Diphenylhydantoin
CAS: 57-41-0
Molecular Formula: C15H12N2O2
Phenytoin - Names and Identifiers
| Name | 5,5-Diphenylhydantoin |
| Synonyms | Dantinal Phenytoin Dantoinal PHENYTOIN,USP Dantoinalklinos Dantoinal klinos 5,5-Diphenylhydantoin 4,5-Diphenyl-4-imidazoline-2-one 5,5-Diphenylhydantoin-2-13C, 3-15N 5,5-Diphenyltetrahydroglyoxalin-4-one sodium 5-oxo-4,4-diphenyl-4,5-dihydro-1H-imidazol-2-olate |
| CAS | 57-41-0 |
| EINECS | 200-328-6 |
| InChI | InChI=1/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 |
| InChIKey | CXOFVDLJLONNDW-UHFFFAOYSA-N |
Phenytoin - Physico-chemical Properties
| Molecular Formula | C15H12N2O2 |
| Molar Mass | 252.27 |
| Density | 1.1562 (rough estimate) |
| Melting Point | 293-295 °C (lit.) |
| Boling Point | 395.45°C (rough estimate) |
| Flash Point | 11°C |
| Water Solubility | <0.01 g/100 mL at 19 ºC |
| Solubility | DMSO 50 mg/mL Water <1 mg/mL Ethanol 13 mg/mL |
| Vapor Presure | 4.29E-08mmHg at 25°C |
| Appearance | White crystal or powder |
| Color | White to almost white |
| Merck | 14,7322 |
| BRN | 384532 |
| pKa | pKa 8.43(H2O,t =25,I=0.025) (Uncertain) |
| Storage Condition | 2-8°C |
| Stability | Stable. Combustible. Incompatible with strong oxidizing agents, strong bases. |
| Refractive Index | 1.5906 (estimate) |
| MDL | MFCD00005264 |
| Use | Used as antiepileptic drugs, antiarrhythmic drugs |
| In vitro study | 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. Phenytoin has low affinity for resting sodium channels at hyperpolarized membrane potentials. 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. |
| In vivo study | Phenytoin (5,5-Diphenylhydantoin; 60 mg/kg; daily; 28 days ) reduces tumour growth in six week-old female Rag2 -/- Il2rg -/- mice with MDA-MB-231 cells. |
Phenytoin - Risk and Safety
| Risk Codes | R45 - May cause cancer R61 - May cause harm to the unborn child R22 - Harmful if swallowed R63 - Possible risk of harm to the unborn child R40 - Limited evidence of a carcinogenic effect R39/23/24/25 - R23/24/25 - Toxic by inhalation, in contact with skin and if swallowed. R11 - Highly Flammable R20/21/22 - Harmful by inhalation, in contact with skin and if swallowed. |
| Safety Description | S53 - Avoid exposure - obtain special instructions before use. S45 - In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.) S36/37 - Wear suitable protective clothing and gloves. S16 - Keep away from sources of ignition. S7 - Keep container tightly closed. |
| UN IDs | 2811 |
| WGK Germany | 3 |
| RTECS | MU1050000 |
| HS Code | 29332100 |
| Hazard Class | 6.1(b) |
| Packing Group | II |
| Toxicity | LD50 in mice (mg/kg): 92 i.v.; 110 s.c. (Stille, Brunckow) |
Phenytoin - Reference Information
| (IARC) carcinogen classification | 2B (Vol. Sup 7, 66) 1996 |
| NIST chemical information | information provided by: webbook.nist.gov (external link) |
| EPA chemical substance information | information provided by: ofmpeb.epa.gov (external link) |
| biological activity | Diphenylhydantoin is an inactivated voltage-gated sodium channel stabilizer. |
| Target | Value |
| Use | used as antiepileptic drug, antiarrhythmic drug |
| spontaneous combustion temperature | 550°C |
| toxic substance data | information provided by: pubchem.ncbi.nlm.nih.gov (external link) |
Last Update：2024-04-09 21:04:16
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