U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C16H12ClFN2O
Molecular Weight 302.731
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of FLUDIAZEPAM

SMILES

CN1C2=C(C=C(Cl)C=C2)C(=NCC1=O)C3=CC=CC=C3F

InChI

InChIKey=ROYOYTLGDLIGBX-UHFFFAOYSA-N
InChI=1S/C16H12ClFN2O/c1-20-14-7-6-10(17)8-12(14)16(19-9-15(20)21)11-4-2-3-5-13(11)18/h2-8H,9H2,1H3

HIDE SMILES / InChI

Molecular Formula C16H12ClFN2O
Molecular Weight 302.731
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

Fludiazepam is a potent benzodiazepine and 2ʹ-fluoro derivative of diazepam,[3] originally developed by Hoffman-La Roche in the 1960s. Fludiazepam is marketed in Japan and Taiwan under the brand name Erispan. Fludiazepam exerts its pharmacological properties via enhancement of GABAergic inhibition. Fludiazepam has 4 times more binding affinity for benzodiazepine receptors than diazepam. Fludiazepam possesses anxiolytic, anticonvulsant, sedative, hypnotic and skeletal muscle relaxant properties.

CNS Activity

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
1.23 nM [Ki]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Erispan

PubMed

Sample Use Guides

In Vivo Use Guide
PO 0.75 mg/day in 3 divided doses.
Route of Administration: Oral
In Vitro Use Guide
An aliquot (1 ml) of synaptosomal membrane suspension (1 mg protein) was added to the assay tubes containing FLUDIAZEPAM at varying concentrations (from 0.1 nM to 104 nM) and [3H]-diazepam (0.6 nM) in 2 ml of 50 mM Tris-HCl buffer (pH 7.4). The assay mixtures were incubated at 4 ° C for 15 min. The incubation was terminated by adding ice-cold 50 mM Tris-HCl buffer (5 ml) followed by rapid filtration through a Whatman GF/B filter. Each filter was immediately washed twice with ice-cold 50 mM Tris-HCl buffer (5 ml) The bound [3H]-diazepam retained on the filter was extracted with ACS II (Amersham)(10 ml) and counted. All incubations were done in triplicate. Nonspecific binding was determined in tubes containing diazepam at a final concentration of 103 nM.
Substance Class Chemical
Record UNII
7F64A2K16Z
Record Status Validated (UNII)
Record Version