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Doxefazepam
Clinical data
Routes of; administration	Oral
ATC code	N05CD12 (WHO) ;
Legal status
Legal status	CA: Schedule IV; US: Schedule IV;
Pharmacokinetic data
Metabolism	Hepatic
Elimination half-life	3-4 hours
Excretion	Renal
Identifiers
	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;
CAS Number	40762-15-0 ;
PubChem CID	38668;
ChemSpider	35431 ;
UNII	231RV72C8L;
KEGG	D07327 ;
ChEMBL	ChEMBL64677 ;
CompTox Dashboard (EPA)	DTXSID2020551 ;
Chemical and physical data
Formula	C17H14ClFN2O3
Molar mass	348.76 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES FC1=CC=CC=C1C2=NC(C(N(CCO)C3=C2C=C(C=C3)Cl)=O)O;
	InChI InChI=1S/C17H14ClFN2O3/c18-10-5-6-14-12(9-10)15(11-3-1-2-4-13(11)19)20-16(23)17(24)21(14)7-8-22/h1-6,9,16,22-23H,7-8H2 ; Key:VOJLELRQLPENHL-UHFFFAOYSA-N ;
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Doxefazepam (marketed under brand name Doxans) is a benzodiazepine medication It possesses anxiolytic, anticonvulsant, sedative and skeletal muscle relaxant properties. It is used therapeutically as a hypnotic.^[2] 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.^[3]

It was patented in 1972 and came into medical use in 1984.^[4]

Side effects

Section 5.5 of the article Doxefazepam in volume 66 of the World Health Organization's (WHO) and International Agency for Research on Cancer's (IARC) IARC Monographs On The Evaluation Of Carcinogenic Risks To Humans, an article describing the carcinogenic/toxic effects of doxefazepam on humans and experimental animals, states that there is "inadequate evidence in humans for the carcinogenicity of doxefazepam" and limited evidence in experimental for the carcinogenicity of doxefazepam," and concluded that the overall evaluation of the substance's carcinogenicity to humans is "not classifiable."^[5]

References

^ "Doxefazepam". IPCS INTOX. Archived from the original on 24 July 2008.
^ Rodriguez G, Rosadini G, Sannita WG, Strumia E (1984). "Effects of doxefazepam on normal sleep. An EEG and neuropsychological study". Neuropsychobiology. 11 (2): 133–139. doi:10.1159/000118066. PMID 6483162.
^ Babbini M, Torrielli MV, Strumia E, Gaiardi M, Bartoletti M, De Marchi F (August 1975). "Sedative-hypnotic properties of a new benzodiazepine in comparison with flurazepam. Pharmacological and clinical findings". Arzneimittel-Forschung. 25 (8): 1294–1300. PMID 241364.
^ Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 539. ISBN 9783527607495.
^ "Doxefazepam" (PDF). IARC Monographs on the Evaluation of Carcinogenic Risks to Humans. 66. International Agency For Research On Cancer (IARC): 97–104. 13–20 Feb 1996. PMC 7681544. PMID 9097119. Retrieved 10 July 2014.