Fludiazepam

Title: Fludiazepam
CAS Registry Number: 3900-31-0
CAS Name: 7-Chloro-5-(2-fluorophenyl)-1,3-dihydro-1-methyl-2H-1,4-benzodiazepin-2-one
Manufacturers' Codes: ID-540; Ro-5-3438
Trademarks: Erispan (Sumitomo)
Molecular Formula: C16H12ClFN2O
Molecular Weight: 302.73
Percent Composition: C 63.48%, H 4.00%, Cl 11.71%, F 6.28%, N 9.25%, O 5.29%
Literature References: Fluorinated analog of diazepam, q.v. Prepn: E. Reeder et al., DE 1136709; E. Reeder, L. H. Sternbach, US 3371085 (1962, 1968 both to Hoffmann-LaRoche); L. H. Sternbach et al., J. Org. Chem. 27, 3788 (1962). Synthesis and pharmacology: Y. Asami et al., Arzneim.-Forsch. 24, 1563 (1974). Pharmacodynamics: M. Nakamura, H. Fukushima, J. Pharm. Pharmacol. 30, 56, 254 (1978); T. Tsuchiya, H. Fukushima, Eur. J. Pharmacol. 48, 421 (1978). Anxiolytic vs sedative properties: M. Babbini et al., Life Sci. 25, 15 (1979).
Properties: Colorless prisms from n-hexane/isopropanol, mp 88-92°, (Asami); also reported as mp 69-72° (Sternbach). LD50 in mice (mg/kg): 910 orally; 360 i.p.; 1150 s.c. (Asami).
Melting point: mp 88-92°; mp 69-72° (Sternbach)
Toxicity data: LD50 in mice (mg/kg): 910 orally; 360 i.p.; 1150 s.c. (Asami)
NOTE: This is a controlled substance (depressant): 21 CFR, 1308.14.
Therap-Cat: Anxiolytic.
Keywords: Anxiolytic; Benzodiazepine Derivatives.
Fludioxonil Fludrocortisone Flufenacet Flufenamic Acid Flufenoxuron

Fludiazepam
Fludiazepam.svg
Fludiazepam3d.png
Systematic (IUPAC) name
9-chloro-6-(2-fluorophenyl)- 2-methyl-2,5-diazabicyclo [5.4.0]undeca- 5,8,10,12-tetraen-3-one
Clinical data
AHFS/Drugs.com International Drug Names
Pregnancy cat.  ?
Legal status Schedule IV(US)
Routes Oral
Pharmacokinetic data
Bioavailability  ?
Metabolism Hepatic
Half-life  ?
Excretion Renal
Identifiers
CAS number 3900-31-0
ATC code N05BA17
PubChem CID 3369
DrugBank DB01567
ChemSpider 3252 YesY
UNII 7F64A2K16Z YesY
KEGG D01354 YesY
ChEBI CHEBI:31618 YesY
ChEMBL CHEMBL13291 YesY
Chemical data
Formula C16H12ClFN2O 
Mol. mass 302.7
 YesY (what is this?)  (verify)

Fludiazepam was developed by Hoffman-LaRoche in the 1960s[1] and is marketed in Japan and Taiwan in 0.25mg tablets under the brand name Erispan[2][3] is a drug which is a benzodiazepine derivative and is closely related to diazepam.[4] It exerts its pharmacological properties via enhancement of GABAergic inhibition.[5] Fludiazepam has 4 times more binding affinity for benzodiazepine receptors than diazepam.[6] It possesses anxiolytic,[7][8][9] anticonvulsant, sedative, hypnotic and skeletal muscle relaxant properties.[10]

Fludiazepam has drug abuse potential.[11]