Flutoprazepam

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 checkY
  • Key:OFVXPDXXVSGEPX-UHFFFAOYSA-N checkY
 ☒NcheckY (what is this?)  (verify)

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 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.
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