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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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the CDK toolkit. All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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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
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

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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)
InChI Key XWLUWCNOOVRFPX-UHFFFAOYSA-N
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.
External links Click here for help
For extended ADME data see the following:

Electronic Medicines Compendium (eMC)
Drugs.com