mephenytoin   Click here for help

GtoPdb Ligand ID: 7223

Synonyms: Mesantoin®
Approved drug
mephenytoin is an approved drug (FDA (1946))
Compound class: Synthetic organic
Comment: Mephenytoin is a hydantoin class drug. It is no longer available in the US or the UK.
2D Structure
Click here for help

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.

✖
Click here for structure editor
Physico-chemical Properties
Click here for help

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.

✖
Hydrogen bond acceptors 4
Hydrogen bond donors 1
Rotatable bonds 2
Topological polar surface area 52.9
Molecular weight 218.11
XLogP 1.85
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
Click here for help

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/)

✖
Canonical SMILES CCC1(N=C(N(C1=O)C)O)c1ccccc1
Isomeric SMILES CCC1(N=C(N(C1=O)C)O)c1ccccc1
InChI InChI=1S/C12H14N2O2/c1-3-12(9-7-5-4-6-8-9)10(15)14(2)11(16)13-12/h4-8H,3H2,1-2H3,(H,13,16)
InChI Key GMHKMTDVRCWUDX-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 (FDA (1946))
IUPAC Name Click here for help
4-ethyl-2-hydroxy-1-methyl-4-phenyl-4,5-dihydro-1H-imidazol-5-one
International Nonproprietary Names Click here for help
INN number INN
1463 mephenytoin
Synonyms Click here for help
Mesantoin®
Database Links Click here for help
CAS Registry No. 50-12-4
ChEMBL Ligand CHEMBL861
DrugBank Ligand DB00532
DrugCentral Ligand 1695
GtoPdb PubChem SID 178103797
PubChem CID 4060
Search Google for chemical match using the InChIKey GMHKMTDVRCWUDX-UHFFFAOYSA-N
Search Google for chemicals with the same backbone GMHKMTDVRCWUDX
Search PubMed clinical trials mephenytoin
Search PubMed titles mephenytoin
Search PubMed titles/abstracts mephenytoin
UniChem Compound Search for chemical match using the InChIKey GMHKMTDVRCWUDX-UHFFFAOYSA-N
UniChem Connectivity Search for chemical match using the InChIKey GMHKMTDVRCWUDX-UHFFFAOYSA-N
Wikipedia Mephenytoin