Basic information
- CAS
92134-98-0- Standard SMILES
O=C1NC(c2ccccc2)(c2ccccc2)C(=O)N1COP(=O)([O-])[O-].[Na+].[Na+]- InChIKey
GQPXYJNXTAFDLT-UHFFFAOYSA-L- Molecular formula
- C16H13N2Na2O6P
- Average molar mass
- 406.24 g/mol
- Monoisotopic mass
- 406.0306617
Overview
Fosphenytoin Sodium is the sodium salt form of fosphenytoin, a prodrug that is hydrolyzed to the anticonvulsant phenytoin upon parental administration. Phenytoin exerts its effect most likely through an enhancement of sodium efflux from neurons in the motor cortex. This leads to a suppression of excessive neuronal firing and spread of seizure activity. Other physiologic effects from actions of phenytoin include modulation of the voltage-dependent calcium channels of neurons, inhibition of calcium flux across neuronal membranes and enhancement of sodium-potassium ATPase activity of neurons and glial cells. (NCI05)
Names & identifiers
- Preferred name
- Fosphenytoin Sodium
- IUPAC
- disodium;(2,5-dioxo-4,4-diphenylimidazolidin-1-yl)methyl phosphate
- English name
- Fosphenytoin sodium
- Molecular formula
- C16H16N2NaO6P
- Molecular weight
- 386.28
Names & synonyms
Fosphenytoin sodium92134-98-0Fosphenytoin disodium saltPro-EpanutinCI 982CI-982ACC-9653-010 (sodium salt)7VLR55452ZACC-9653-010DTXSID1044271Sesquient2,4-Imidazolidinedione, 5,5-diphenyl-3-((phosphonooxy)methyl)-, disodium salt
Show more names
Sodium (2,5-dioxo-4,4-diphenylimidazolidin-1-yl)methyl phosphateCetebyxACC-9653FOSPENYTOINFosphenytion SodiuMPhenytoin Impurity 11
RefChem:57122DTXCID9024271Fosphenytoin disodiumCerebyxFosphenytoin_SodiumFosphenytoin (disodium)ACC 9653-010ACC 9653
Database identifiers
- CAS
92134-98-0- PubChem CID
- 56338
- DTXSID
DTXSID1044271- ChEMBL
CHEMBL919- UNII
- 7VLR55452Z
- EC Number
- 618-823-4
Properties
Computed structural properties
- Topological polar surface area
- 122 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 6
- Rotatable bonds
- 4
- Heavy atoms
- 27
- Formal charge
- 0
- Complexity
- 535
Experimental & physicochemical properties
Human Drugs
FDA approved drugs -> Active ingredient
FDA approved drugs -> Active ingredient
Physicochemical properties
- Melting point
- 220 ° · 220° (softens)
- storage temp.
- 2 · Inert atmosphere,2-8°C
- solubility
- 2 O: · H2O: ≥15mg/mL
- form
- powder
- color
- white to tan
- Water Solubility
- 2 O: · H2O: ≥15mg/mL
- InChI
- InChI=1S/C16H15N2O6P.Na.H/c19-14-16(12-7-3-1-4-8-12,13-9-5-2-6-10-13)17-15(20)18(14)11-24-25(21,22)23;;/h1-10H,11H2,(H,17,20)(H2,21,22,23);;
- InChIKey
- JOJPAZCANKNCBW-UHFFFAOYSA-N
- SMILES
- O=C1N(C(=O)NC1(C1C=CC=CC=1)C1C=CC=CC=1)COP(O)(O)=O.[NaH]
- FDA UNII
- 7 VLR55452Z · 7VLR55452Z
- NCI Drug Dictionary
- fosphenytoin sodium
- UNSPSC Code
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 (97.5%): Toxic if swallowed [Danger Acute toxicity, oral]
P264, P270, P301+P316, P321, P330, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 40 reports by companies from 2 notifications to the ECHA C&L Inventory.
Hazard information
Hazard Classes and CategoriesAcute Tox. 3 (97.5%)
Toxicology
Drug Induced Liver Injury
Drug Induced Liver Injury Rank (DILIrank 2.0)
Fosphenytoin sodium
vMost-DILI-concern
8
Warnings & precautions
DOI:10.1016/j.drudis.2016.02.015
Safety data
- wgk
- 3
- ridadr
- UN 2811 6.1 / PGIII
- hs_code
- 2933290000
- Toxicity
- LD50 in mice, rats (mg/kg): 234, 363 i.v. (Smith)
- risk_code
- 45-61-22
- Signal word
- Danger
- Symbol(GHS)
- GHS07,GHS08
- hazard_code
- T
- safety_code
- 53-36/37-45
- Storage Class
- 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects
Chemistry & industry
Pharmacology
FDA Pharmacological Classification
FOSPHENYTOIN SODIUM
Cytochrome P450 2C8 Inducers [MoA]; Cytochrome P450 2B6 Inducers [MoA]; Cytochrome P450 3A Inducers [MoA]; Cytochrome P450 2D6 Inducers [MoA]; Cytochrome P450 1A2 Inducers [MoA]; Cytochrome P450 2C19 Inducers [MoA]; Decreased Central Nervous System Disorganized Electrical Activity [PE]; Cytochrome P450 2C9 Inducers [MoA]; Anti-epileptic Agent [EPC]
MeSH Pharmacological Classification
Drugs used to prevent SEIZURES or reduce their severity.
A class of drugs that act by inhibition of sodium influx through cell membranes. Blockade of sodium channels slows the rate and amplitude of initial rapid depolarization, reduces cell excitability, and reduces conduction velocity.
Uses & manufacturing
UsesUse (kg) in USA (2002): 278
Applications
UsesPDE3 (phosphodiesterase 3) inhibitor
UsesAnti epileptic
UsesFosphenytoin sodium is used in the treatment of epileptic seizures.
Upstream & downstream products
Upstream raw materials
Suppliers79 total
国药集团化学试剂有限公司86-21-63210123 · [email protected]
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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