flurazepam   Click here for help

GtoPdb Ligand ID: 7188

Synonyms: Dalmane® | Ro-5-6901 | Ro-56901
Approved drug PDB Ligand
flurazepam is an approved drug (FDA (1970))
Compound class: Synthetic organic
Comment: Flurazepam is a benzodiazepine drug.
Marketed formulations may contain flurazepam hydrochloride (PubChem CID 37368).
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View more information in the IUPHAR Pharmacology Education Project: flurazepam

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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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 0
Rotatable bonds 6
Topological polar surface area 35.91
Molecular weight 387.15
XLogP 3.78
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 CCN(CCN1C(=O)CN=C(c2c1ccc(c2)Cl)c1ccccc1F)CC
Isomeric SMILES CCN(CCN1C(=O)CN=C(c2c1ccc(c2)Cl)c1ccccc1F)CC
InChI InChI=1S/C21H23ClFN3O/c1-3-25(4-2)11-12-26-19-10-9-15(22)13-17(19)21(24-14-20(26)27)16-7-5-6-8-18(16)23/h5-10,13H,3-4,11-12,14H2,1-2H3
InChI Key SAADBVWGJQAEFS-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/)
No information available.
Summary of Clinical Use Click here for help
Flurazepam is used to treat insomnia.
Mechanism Of Action and Pharmacodynamic Effects Click here for help
Flurazepam binds to the benzodiazepine (BZD) binding sites on GABAA receptor complexes in the central nervous system. This acts to increase binding of inhibitory GABA at these sites and results in overall neuro-inhibition and this is responsible for the drug's sedative action.
External links Click here for help
For extended ADME data see the following:

Electronic Medicines Compendium (eMC)
Drugs.com