93390-81-9
Chemical Structure
Fosphenytoin
- CAS No.: 93390-81-9
- Formula:C16H15N2O6P
- Molecular Weight:362.27
IUPAC Name: (2,5-dioxo-4,4-diphenylimidazolidin-1-yl)methyl dihydrogen phosphate
InChIKey: XWLUWCNOOVRFPX-UHFFFAOYSA-N
SMILES: O=C1N(COP(O)(O)=O)C(C(C2=CC=CC=C2)(C3=CC=CC=C3)N1)=O
Biological Activity: Fosphenytoin is a prodrug of Phenytoin (HY-B0448). Fosphenytoin can be converted to Phenytoin in vivo, which blocks voltage-gated sodium channels in a voltage- and use-dependent manner, prolonging inactivation and slowing recovery. Fosphenytoin enhances GABA responses and, at higher concentrations, mildly modulates calcium channels and increases sodium-potassium ATPase activity. Fosphenytoin raises the afterdischarge threshold, reduces the severity and duration of seizures, alleviates pain-like behavior, and protects hippocampal pyramidal neurons after ischemia without altering GFAP immunoreactivity. Fosphenytoin can be used in research on acute herpes zoster pain, epilepsy, and cerebral ischemia[1][2][3][4][5].
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Fosphenytoin | Fosphenytoin is a prodrug of Phenytoin (HY-B0448). Fosphenytoin can be converted to Phenytoin in vivo, which blocks voltage-gated sodium channels in a voltage- and use-dependent manner, prolonging inactivation and slowing recovery. Fosphenytoin enhances GABA responses and, at higher concentrations, mildly modulates calcium channels and increases sodium-potassium ATPase activity. Fosphenytoin raises the afterdischarge threshold, reduces the severity and duration of seizures, alleviates pain-like behavior, and protects hippocampal pyramidal neurons after ischemia without altering GFAP immunoreactivity. Fosphenytoin can be used in research on acute herpes zoster pain, epilepsy, and cerebral ischemia. | |||||||||||||||||||||
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References
- [1]. Varia SA, et al. Phenytoin prodrugs III: water-soluble prodrugs for oral and/or parenteral use. J Pharm Sci. 1984;73(8):1068-1073. [Content Brief]
- [2]. Takasaki I, et al. Fosphenytoin Alleviates Herpes Simplex Virus Infection-Induced Provoked and Spontaneous Pain-Like Behaviors in Mice. Biol Pharm Bull. 2022 Mar 1;45(3):360-363. [Content Brief]
- [3]. Aleyadeh R, et al. Fosphenytoin. 2023 Aug 28. In: StatPearls [Internet]. Treasure Island (FL): StatPearls Publishing; 2023 Jan–. [Content Brief]
- [4]. Löscher W, et al. Anticonvulsant effect of fosphenytoin in amygdala-kindled rats: comparison with phenytoin. Epilepsy Res. 1998 Mar;30(1):69-76. [Content Brief]
- [5]. Chan SA, et al. Fosphenytoin reduces hippocampal neuronal damage in rat following transient global ischemia. Acta Neurochir (Wien). 1998;140(2):175-80. [Content Brief]
