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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).
IUPHAR Pharmacology Education Project (PEP) logo

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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Click here for structure editor
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 Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/). 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

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
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.

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

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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

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes. US FDA (1996)
Is prodrug? Yes
Active form phenytoin
IUPAC Name Click here for help
[(2-hydroxy-5-oxo-4,4-diphenyl-4,5-dihydro-1H-imidazol-1-yl)methoxy]phosphonic acid
International Nonproprietary Names Click here for help
INN number INN
6484 fosphenytoin
Synonyms Click here for help
ACC-9653-010 | Cerebyx® | CI-982 | Sesquient®
Database Links Click here for help
CAS Registry No. 93390-81-9
ChEMBL Ligand CHEMBL1201336
DrugBank Ligand DB01320
DrugCentral Ligand 1247
GtoPdb PubChem SID 178103765
PubChem CID 56339
Search Google for chemical match using the InChIKey XWLUWCNOOVRFPX-UHFFFAOYSA-N
Search Google for chemicals with the same backbone XWLUWCNOOVRFPX
Search PubMed clinical trials fosphenytoin
Search PubMed titles fosphenytoin
Search PubMed titles/abstracts fosphenytoin
UniChem Compound Search for chemical match using the InChIKey XWLUWCNOOVRFPX-UHFFFAOYSA-N
UniChem Connectivity Search for chemical match using the InChIKey XWLUWCNOOVRFPX-UHFFFAOYSA-N
Wikipedia Fosphenytoin