Doxefazepam

Title: Doxefazepam
CAS Registry Number: 40762-15-0
CAS Name: 7-Chloro-5-(2-fluorophenyl)-1,3-dihydro-3-hydroxy-1-(2-hydroxyethyl)-2H-1,4-benzodiazepin-2-one
Additional Names: N-1-hydroxyethyl-3-hydroxyflurazepam
Manufacturers' Codes: SAS-643
Trademarks: Doxans (Schiapparelli)
Molecular Formula: C17H14ClFN2O3
Molecular Weight: 348.76
Percent Composition: C 58.55%, H 4.05%, Cl 10.17%, F 5.45%, N 8.03%, O 13.76%
Literature References: Prepn: G. F. Tamagnone et al., Arzneim.-Forsch. 25, 720 (1975); eidem, J. Pharm. Pharmacol. 26, 566 (1974); F. De Marchi, G. F. Tamagnone, DE 2338058 (1974 to Schiapparelli), C.A. 80, 121016v (1974). Comparison with flurazepam, q.v., and pharmacology, toxicity studies: M. Babbini et al., Arzneim.-Forsch. 25, 1294 (1975). Structure-activity studies: eidem, Pharmacol. Res. Commun. 7, 337 (1975). GC determn in blood and tissue: F. Marcucci et al., J. Chromatogr. 198, 180 (1980); in plasma, urine: S. Mardente et al., Ther. Drug Monit. 3, 351 (1981). Quantitative EEG, behavioral effects: W. G. Sanita et al., ibid. 341. Effect on sleep: G. Rodriguez et al., Neuropsychobiology 11, 133 (1984).
Properties: Crystals from methylene chloride/petr ether, mp 138-140°. LD50 in rats, mice (mg/kg): 2550, >1500 orally; 586, 774 i.p. (Babbini).
Melting point: mp 138-140°
Toxicity data: LD50 in rats, mice (mg/kg): 2550, >1500 orally; 586, 774 i.p. (Babbini)
Therap-Cat: Sedative, hypnotic.
Keywords: Sedative/Hypnotic; Benzodiazepine Derivatives.
Doxenitoin Doxepin Doxercalciferol Doxifluridine Doxofylline

Doxefazepam
Doxefazepam.svg
Doxefazepam3d.png
Systematic (IUPAC) name
9-chloro-6-(2-fluorophenyl)-4-hydroxy
-2-(2-hydroxyethyl)-2,5-diazabicyclo
[5.4.0]undeca-5,8,10,12-tetraen-3-one
Clinical data
Pregnancy cat.  ?
Legal status Schedule IV(US)
Routes Oral
Pharmacokinetic data
Bioavailability  ?
Metabolism Hepatic
Half-life 3-4 hours[1]
Excretion Renal
Identifiers
CAS number 40762-15-0 N
ATC code N05CD12
PubChem CID 38668
DrugBank ?
ChemSpider 35431 YesY
UNII verifiedrevid = 457288969 231RV72C8L verifiedrevid = 457288969 N
KEGG D07327 YesY
ChEMBL CHEMBL64677 YesY
Chemical data
Formula C17H14ClFN2O3 
Mol. mass 348.8
 N (what is this?)

Doxefazepam (marketed under brand name Doxans) is a benzodiazepine derivative drug developed by Schiapparelli in the 1970s.[2] It possesses anxiolytic, anticonvulsant, sedative and skeletal muscle relaxant properties. It is used therapeutically as a hypnotic.[3] According to Babbini and colleagues in 1975, this derivative of flurazepam was between 2 and 4 times more potent than the latter while at the same time being half as toxic in laboratory animals.[4]