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phenacemide   Click here for help

GtoPdb Ligand ID: 7265

Synonyms: Phenurone®
Approved drug
phenacemide is an approved drug (FDA (1951))
Compound class: Synthetic organic
Comment: Phenacemide is a ureide (acetylurea) anticonvulsant. It is a congener and ring-opened analogue of the hydantoin phenytoin, and is structurally related to the barbiturate family of drugs and other hydantoins. Use of phenacemide was widely discontinued due to toxic side-effects.
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 4
Hydrogen bond donors 3
Rotatable bonds 3
Topological polar surface area 76.67
Molecular weight 178.07
XLogP 1.35
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 OC(=NC(=N)O)Cc1ccccc1
Isomeric SMILES OC(=NC(=N)O)Cc1ccccc1
InChI InChI=1S/C9H10N2O2/c10-9(13)11-8(12)6-7-4-2-1-3-5-7/h1-5H,6H2,(H3,10,11,12,13)
InChI Key XPFRXWCVYUEORT-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 (1951)
IUPAC Name Click here for help
1-[(C-hydroxycarbonimidoyl)imino]-2-phenylethan-1-ol
International Nonproprietary Names Click here for help
INN number INN
92 phenacemide
Synonyms Click here for help
Phenurone®
Database Links Click here for help
CAS Registry No. 63-98-9
ChEMBL Ligand CHEMBL918
DrugBank Ligand DB01121
DrugCentral Ligand 2114
GtoPdb PubChem SID 178103839
PubChem CID 4753
Search Google for chemical match using the InChIKey XPFRXWCVYUEORT-UHFFFAOYSA-N
Search Google for chemicals with the same backbone XPFRXWCVYUEORT
Search PubMed clinical trials phenacemide
Search PubMed titles phenacemide
Search PubMed titles/abstracts phenacemide
UniChem Compound Search for chemical match using the InChIKey XPFRXWCVYUEORT-UHFFFAOYSA-N
UniChem Connectivity Search for chemical match using the InChIKey XPFRXWCVYUEORT-UHFFFAOYSA-N
Wikipedia Phenacemide