diazepam   

GtoPdb Ligand ID: 3364

Synonyms: Diastat® | LA-III | Valium® | WY-3467
diazepam is an approved drug (FDA (1986))
Compound class: Synthetic organic
Comment: Diazepam is a benzodiazepine drug with long acting anticonvulsant, anxiolytic, sedative, muscle relaxant, and amnesic properties.

Ligand Activity Visualisation Charts

These are box plot that provide a unique visualisation, summarising all the activity data for a ligand taken from ChEMBL and GtoPdb across multiple targets and species. Click on a plot to see the median, interquartile range, low and high data points. A value of zero indicates that no data are available. A separate chart is created for each target, and where possible the algorithm tries to merge ChEMBL and GtoPdb targets by matching them on name and UniProt accession, for each available species. However, please note that inconsistency in naming of targets may lead to data for the same target being reported across multiple charts.

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View interactive charts of activity data across species

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2D Structure

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

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 3
Hydrogen bond donors 0
Rotatable bonds 1
Topological polar surface area 32.67
Molecular weight 284.07
XLogP 2.92
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey

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 Clc1ccc2c(c1)C(=NCC(=O)N2C)c1ccccc1
Isomeric SMILES Clc1ccc2c(c1)C(=NCC(=O)N2C)c1ccccc1
InChI InChI=1S/C16H13ClN2O/c1-19-14-8-7-12(17)9-13(14)16(18-10-15(19)20)11-5-3-2-4-6-11/h2-9H,10H2,1H3
InChI Key AAOVKJBEBIDNHE-UHFFFAOYSA-N
Classification
Compound class Synthetic organic
Approved drug? Yes (FDA (1986))
WHO Essential Medicine WHO Model List of Essential Medicines (21st List, 2019). Access PDF version.
IUPAC Name
7-chloro-1-methyl-5-phenyl-2,3-dihydro-1H-1,4-benzodiazepin-2-one
International Nonproprietary Names
INN number INN
1295 diazepam
Synonyms
Diastat® | LA-III | Valium® | WY-3467
Database Links
CAS Registry No. 439-14-5 (source: Scifinder)
ChEMBL Ligand CHEMBL12
DrugBank Ligand DB00829
DrugCentral Ligand 852
GtoPdb PubChem SID 178100389
PubChem CID 3016
RCSB PDB Ligand DZP
Search Google for chemical match using the InChIKey AAOVKJBEBIDNHE-UHFFFAOYSA-N
Search Google for chemicals with the same backbone AAOVKJBEBIDNHE
Search PubMed clinical trials diazepam
Search PubMed titles diazepam
Search PubMed titles/abstracts diazepam
Search UniChem for chemical match using the InChIKey AAOVKJBEBIDNHE-UHFFFAOYSA-N
Search UniChem for chemicals with the same backbone AAOVKJBEBIDNHE
Wikipedia Diazepam

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Tocris
Diazepam
Cat. No. 2805