Basic information
- CAS
630-93-3- Standard SMILES
O=C1[N-]C(=O)C(c2ccccc2)(c2ccccc2)N1.[Na+]- InChIKey
FJPYVLNWWICYDW-UHFFFAOYSA-M- Molecular formula
- C15H11N2NaO2
- Average molar mass
- 274.25 g/mol
- Monoisotopic mass
- 274.07182188
Overview
Diphenylhydantoin (Phenytoin), Sodium Salt can cause cancer according to an independent committee of scientific and health experts.
Names & identifiers
- Preferred name
- Phenytoin Sodium
- IUPAC
- sodium 5,5-diphenylimidazolidin-3-ide-2,4-dione
- English name
- Phenytoin sodium
- Molecular formula
- C15H13N2NaO2
- Molecular weight
- 276.27
Names & synonyms
PHENYTOIN SODIUM630-93-35,5-Diphenylhydantoin sodium saltDiphenylhydantoin SodiumTacosalAntisacerPhenytoin sodium saltDiphenylan sodiumPHENYTEKPrompt Phenytoin SodiumPhenytexDTXSID2023775
Show more names
DILANTINSODIUM DIPHENYLHYDANTOINdi-lenditoinepelinepinateptoinenkefalalepsin
Extended Phenytoin SodiumPHENYTOIN SODIUM, PROMPTPhenytoin sodium,promptPhenytoin sodium extendedPhenytoin sodium,extended4182431BJH2,4-Imidazolidinedione, 5,5-diphenyl-, monosodium saltDTXCID803775
Database identifiers
- CAS
630-93-3- PubChem CID
- 657302
- DTXSID
DTXSID2023775- ChEMBL
CHEMBL1611- UNII
- 4182431BJH
- EC Number
- 211-148-2
Properties
Computed structural properties
- Topological polar surface area
- 47.2 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 3
- Rotatable bonds
- 2
- Heavy atoms
- 20
- Formal charge
- 0
- Complexity
- 356
Experimental & physicochemical properties
Human Drugs
FDA approved drugs -> Active ingredient
FDA approved drugs -> Active ingredient
Animal DrugsFDA approved animal drugs -> Active ingredient
Collision Cross Section158.4 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
Physicochemical properties
- storage temp.
- Inert atmosphere,Room Temperature
- solubility
- aqueous base: soluble
- form
- Crystalline Powder
- color
- White to almost white
- Merck
- 14 · 14,7322
- BCS Class
- 2 · 2
- Stability
- Hygroscopic
- InChI
- InChI=1S/C15H12N2O2.Na.H/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);;
- InChIKey
- FJPYVLNWWICYDW-UHFFFAOYSA-M
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Danger
H301 (18.6%): Toxic if swallowed [Danger Acute toxicity, oral]
P203, P260, P261, P264, P270, P272, P280, P301+P316, P301+P317, P302+P352, P318, P319, P321, P330, P333+P317, P362+P364, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 194 reports by companies from 11 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Regulatory Information
Hazard Traits - Carcinogenicity
REACH registered substance: Phenytoin sodium (EC: 211-148-2)
Phenytoin sodium: Does not have an individual approval but may be used under an appropriate group standard
Other Safety InformationIMAP assessments - 2,4-Imidazolidinedione, 5,5-diphenyl-, monosodium salt: Human health tier I assessment
Hazard Classes and CategoriesAcute Tox. 3 (18.6%)
Toxicology
Treatment
Treatment is nonspecific since there is no known antidote. The adequacy of the respiratory and circulatory systems should be carefully observed and appropriate supportive measures employed. Hemodialysis can be considered since phenytoin is not completely bound to plasma proteins. Total exchange transfusion has been used in the treatment of severe intoxication in pediatric patients. (L1712)
Health EffectsMay cause a potentially dangerous rash that may develop into Stevens Johnson syndrome, an extremely rare but potentially fatal skin disease.
Chemistry & industry
Pharmacology
Metabolism/Metabolites
Primarily hepatic. The majority of the dose (up to 90%) is metabolized to 5-(4'-hydroxyphenyl)-5-phenylhydantoin (p-HPPH). This metabolite undergoes further glucuronidation and is excreted into the urine. CYP2C19 and CYP2C9 catalyze the aforementioned reaction. Route of Elimination: Most of the drug is excreted in the bile as inactive metabolites which are then reabsorbed from the intestinal tract and excreted in the urine. Urinary excretion of phenytoin and its metabolites occurs partly with glomerular filtration but, more importantly, by tubular secretion. Half Life: 22 hours (range of 7 to 42 hours)
FDA Pharmacological Classification
EXTENDED PHENYTOIN SODIUM
Cytochrome P450 2C9 Inducers [MoA]; Decreased Central Nervous System Disorganized Electrical Activity [PE]; Anti-epileptic Agent [EPC]; Cytochrome P450 2B6 Inducers [MoA]; Cytochrome P450 3A Inducers [MoA]; Cytochrome P450 2C8 Inducers [MoA]; Cytochrome P450 1A2 Inducers [MoA]; Cytochrome P450 2C19 Inducers [MoA]; Cytochrome P450 2D6 Inducers [MoA]
PHENYTOIN SODIUM
Cytochrome P450 2D6 Inducers [MoA]; Cytochrome P450 1A2 Inducers [MoA]; Cytochrome P450 2C19 Inducers [MoA]; Cytochrome P450 2C8 Inducers [MoA]; Cytochrome P450 2B6 Inducers [MoA]; Cytochrome P450 3A Inducers [MoA]; Anti-epileptic Agent [EPC]; Decreased Central Nervous System Disorganized Electrical Activity [PE]; Cytochrome P450 2C9 Inducers [MoA]
MeSH Pharmacological Classification
Drugs used to prevent SEIZURES or reduce their severity.
A class of drugs that inhibit the activation of VOLTAGE-GATED SODIUM CHANNELS.
Drugs and compounds that induce the synthesis of CYTOCHROME P-450 CYP1A2.
Uses & manufacturing
UsesFor the control of generalized tonic-clonic (grand mal) and complex partial (psychomotor, temporal lobe) seizures and prevention and treatment of seizures occurring during or following neurosurgery.
Related reactions
2 records
Compound notes
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