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phenobarbital   Click here for help

GtoPdb Ligand ID: 2804

Synonyms: fenobarbital | Luminal® | phenobarb | phenobarbital sodium | phenobarbitone | phenylethylbarbiturate
Approved drug PDB Ligand
phenobarbital is an approved drug (FDA (no date available))
Compound class: Synthetic organic
Comment: Phenobarbital is also a component of the approved drug barbexaclone
IUPHAR Pharmacology Education Project (PEP) logo

View more information in the IUPHAR Pharmacology Education Project: phenobarbital

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 5
Hydrogen bond donors 2
Rotatable bonds 2
Topological polar surface area 75.27
Molecular weight 232.08
XLogP 1.32
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 CCC1(C(=O)NC(=O)NC1=O)c1ccccc1
Isomeric SMILES CCC1(C(=O)NC(=O)NC1=O)c1ccccc1
InChI InChI=1S/C12H12N2O3/c1-2-12(8-6-4-3-5-7-8)9(15)13-11(17)14-10(12)16/h3-7H,2H2,1H3,(H2,13,14,15,16,17)
InChI Key DDBREPKUVSBGFI-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 (0)
WHO Essential Medicine WHO Essential Medicines List (EML) (23rd List, 2023). Access PDF version.
Click to view more information about the WHO Model Lists of Essential Medicines.
IUPAC Name Click here for help
5-ethyl-5-phenyl-1,3-diazinane-2,4,6-trione
International Nonproprietary Names Click here for help
INN number INN
414 phenobarbital
Synonyms Click here for help
fenobarbital | Luminal® | phenobarb | phenobarbital sodium | phenobarbitone | phenylethylbarbiturate
Database Links Click here for help
BindingDB Ligand 50021437
CAS Registry No. 50-06-6 (source: Scifinder)
ChEBI CHEBI:8069
ChEMBL Ligand CHEMBL40
DrugBank Ligand DB01174
DrugCentral Ligand 2134, 2134
GtoPdb PubChem SID 135650817
Immunopaedia Search phenobarbital
PubChem CID 4763
RCSB PDB Ligand UQA
Search Google for chemical match using the InChIKey DDBREPKUVSBGFI-UHFFFAOYSA-N
Search Google for chemicals with the same backbone DDBREPKUVSBGFI
Search PubMed clinical trials phenobarbital
Search PubMed titles phenobarbital
Search PubMed titles/abstracts phenobarbital
UniChem Compound Search for chemical match using the InChIKey DDBREPKUVSBGFI-UHFFFAOYSA-N
UniChem Connectivity Search for chemical match using the InChIKey DDBREPKUVSBGFI-UHFFFAOYSA-N
Wikipedia Phenobarbital