Flutoprazepam

Flutoprazepam (Restas) is a drug which is a benzodiazepine. It was patented in Japan by Sumitomo in 1972[1] and its medical use remains mostly confined to that country. Its muscle relaxant properties are approximately equivalent to those of diazepam - however, it has more powerful sedative, hypnotic, anxiolytic and anticonvulsant effects and is around four times more potent by weight compared to diazepam.[2] It is longer acting than diazepam due to its long-acting active metabolites,[3] which contribute significantly to its effects.[4] Its principal active metabolite is n-desalkylflurazepam, also known as norflurazepam, which is also a principal metabolite of flurazepam (trade name Dalmane).[5][6]

Flutoprazepam
Clinical data
Trade namesRestas
AHFS/Drugs.comInternational Drug Names
Routes of
administration		Oral, Intravenous
ATC code
  • none
Legal status
Legal status
Pharmacokinetic data
Bioavailability80-90%
MetabolismHepatic
Elimination half-life60-90 hours
ExcretionRenal
Identifiers
IUPAC name
  • 7-chloro-1-(cyclopropylmethyl)-5-(2-fluorophenyl)-3H-1,4-benzodiazepin-2-one
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC19H16ClFN2O
Molar mass342.795 g·mol−1
3D model (JSmol)
SMILES
  • FC1=CC=CC=C1C2=NCC(N(CC3CC3)C4=C2C=C(C=C4)Cl)=O
InChI
  • InChI=1S/C19H16ClFN2O/c20-13-7-8-17-15(9-13)19(14-3-1-2-4-16(14)21)22-10-18(24)23(17)11-12-5-6-12/h1-4,7-9,12H,5-6,10-11H2 Y
  • Key:OFVXPDXXVSGEPX-UHFFFAOYSA-N Y
 NY (what is this?)  (verify)

Flutoprazepam is typically used for the treatment of severe insomnia and may also be used for treating stomach ulcers.[7]

Flutoprazepam does not fall under the international Convention on Psychotropic Substances of 1971, and is currently unscheduled in the United States.[8]

  • In Singapore, flutoprazepam is a Class C-Schedule II drug under the Misuse of Drugs Act.
  • In Thailand, flutoprazepam is a Schedule III psychotropic substance.
  • In Hong Kong, flutoprazepam is regulated under Schedule 1 of Hong Kong's Chapter 134 Dangerous Drugs Ordinance. Flutoprazepam can only be used legally by health professionals and for university research purposes. The substance can be given by pharmacists under a prescription. Anyone who supplies the substance without prescription can be fined $10000 (HKD). The penalty for trafficking or manufacturing the substance is a $5,000,000 (HKD) fine and life imprisonment. Possession of the substance for consumption without license from the Department of Health is illegal with a $1,000,000 (HKD) fine and/or 7 years of jail time.[9]

See also

References
  1. US patent 3632574, Hisao Yamamoto et al, "PROCESS FOR PRODUCING BENZODIAZEPINE DERIVATIVES", published 1968-29-04, issued 1972-04-01
  2. Sukamoto T, Aikawa K, Itoh K, Nose T (September 1980). "[Psychopharmacological and general pharmacological studies of 7-chloro-1-cyclopropylmethyl-1, 3-dihydro-5-(2-fluorophenyl)-2H-1, 4-benzodiazepin-2-one (KB-509) (author's transl)]". Nihon Yakurigaku Zasshi. Folia Pharmacologica Japonica. 76 (6): 447–68. doi:10.1254/fpj.76.447. PMID 7203280.
  3. Ueki S, Sukamoto T, Watanabe S, Yamamoto T, Kataoka Y, Shibata S, et al. (July 1982). "[Behavioral effects of flutoprazepam (KB-509) and its metabolites]". Nihon Yakurigaku Zasshi. Folia Pharmacologica Japonica. 80 (1): 15–30. doi:10.1254/fpj.80.15. PMID 6890927.
  4. Barzaghi N, Leone L, Monteleone M, Tomasini G, Perucca E (1989). "Pharmacokinetics of flutoprazepam, a novel benzodiazepine drug, in normal subjects". European Journal of Drug Metabolism and Pharmacokinetics. 14 (4): 293–8. doi:10.1007/BF03190114. PMID 2633923. S2CID 20710732.
  5. Miyaguchi H, Kuwayama K, Tsujikawa K, Kanamori T, Iwata YT, Inoue H, Kishi T (February 2006). "A method for screening for various sedative-hypnotics in serum by liquid chromatography/single quadrupole mass spectrometry". Forensic Science International. 157 (1): 57–70. doi:10.1016/j.forsciint.2005.03.011. PMID 15869852.
  6. Barzaghi N, Leone L, Monteleone M, Tomasini G, Perucca E (1989). "Pharmacokinetics of flutoprazepam, a novel benzodiazepine drug, in normal subjects". European Journal of Drug Metabolism and Pharmacokinetics. 14 (4): 293–8. doi:10.1007/BF03190114. PMID 2633923. S2CID 20710732.
  7. Fukuda T, Itoh K, Nose T (March 1981). "[Antiulcerogenic action of 7-chloro-1-cyclopropylmethyl-1,3-dihydro-5-(2-fluorophenyl)-2H-1,4-benzodiazepin-2-one (KB-509), a new benzodiazepine derivative]". Nihon Yakurigaku Zasshi. Folia Pharmacologica Japonica. 77 (3): 273–80. doi:10.1254/fpj.77.273. PMID 7052359.
  8. "Green List—List of psychotropic substances under international control" (PDF) (26th ed.). International Narcotics Control Board. August 2016. Archived from the original (PDF) on 2017-04-21. Retrieved 2017-07-30.
  9. "Bilingual Laws Information System" (English). The Government of the Hong Kong Special Administrative Region of the People's Republic of China.
This article is issued from Wikipedia. The text is licensed under Creative Commons - Attribution - Sharealike. Additional terms may apply for the media files.