fosphenytoin   Click here for help

GtoPdb Ligand ID: 7190

Synonyms: ACC-9653-010 | Cerebyx® | CI-982 | Sesquient®
Approved drug
fosphenytoin is an approved drug (FDA (1996))
Compound class: Synthetic organic
Comment: Fosphenytoin is a prodrug of phenytoin. This drug is an anticonvulsant.
Marketed formulations may contain fosphenytoin sodium (PubChem CID 56338).
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View more information in the IUPHAR Pharmacology Education Project: fosphenytoin

2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 8
Hydrogen bond donors 3
Rotatable bonds 5
Topological polar surface area 129.47
Molecular weight 362.07
XLogP 1.15
No. Lipinski's rules broken 0
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Canonical SMILES O=C1N(COP(=O)(O)O)C(=NC1(c1ccccc1)c1ccccc1)O
Isomeric SMILES O=C1N(COP(=O)(O)O)C(=NC1(c1ccccc1)c1ccccc1)O
InChI InChI=1S/C16H15N2O6P/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)
No information available.
Summary of Clinical Use Click here for help
Fosphenytoin is used to treat grand mal seizures and seizures associated with brain trauma (surgical or accidental). The FDA approved use of Sesquient® as a treatment for status epilepticus in adults and children in November 2020.
Mechanism Of Action and Pharmacodynamic Effects Click here for help
This drug blocks sodium channel α subunits (genes SNC1A-SNC11A are listed in this database in the Voltage-gated sodium channels section). This appears to reduce seizure propagation and limit the spread of seizure activity in the brain. See the DrugBank link for further details.
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