flutoprazepam

{{Short description|Benzodiazepam}}

{{Drugbox

| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid = 447931828

| IUPAC_name = 7-chloro-1-(cyclopropylmethyl)-5-(2-fluorophenyl)-3H-1,4-benzodiazepin-2-one

| image = Flutoprazepam.svg

| width = 175

| image2 = Flutoprazepam ball-and-stick.png

| width2 = 180

| tradename = Restas

| Drugs.com = {{drugs.com|international|flutoprazepam}}

| pregnancy_US = X

| legal_CA = Schedule IV

| legal_UK = PSA

| legal_DE = NpSG

| legal_US = Unscheduled

| legal_status =

| routes_of_administration = Oral, Intravenous

| bioavailability = 80-90%

| metabolism = Hepatic

| elimination_half-life = 60-90 hours

| excretion = Renal

| CAS_number_Ref = {{cascite|correct|??}}

| CAS_number = 25967-29-7

| ChEMBL_Ref = {{ebicite|changed|EBI}}

| ChEMBL = 2106743

| ATC_prefix = none

| PubChem = 3400

| DrugBank_Ref = {{drugbankcite|correct|drugbank}}

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = 3283

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = 2GHY1101MM

| KEGG_Ref = {{keggcite|correct|kegg}}

| KEGG = D01279

| C=19 | H=16 | Cl=1 | F=1 | N=2 | O=1

| smiles = FC1=CC=CC=C1C2=NCC(N(CC3CC3)C4=C2C=C(C=C4)Cl)=O

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChI = 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

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = OFVXPDXXVSGEPX-UHFFFAOYSA-N

}}

Flutoprazepam (Restas) is a drug which is a benzodiazepine. It was patented in Japan by Sumitomo in 1972{{ cite patent

| country = US

| number = 3632574

| status = patent

| title = PROCESS FOR PRODUCING BENZODIAZEPINE DERIVATIVES

| pubdate = 1968-29-04

| gdate = 1972-04-01

| inventor = Hisao Yamamoto et al

}} 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.{{cite journal | vauthors = Sukamoto T, Aikawa K, Itoh K, Nose T | title = [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)] | journal = Nihon Yakurigaku Zasshi. Folia Pharmacologica Japonica | volume = 76 | issue = 6 | pages = 447–68 | date = September 1980 | pmid = 7203280 | doi = 10.1254/fpj.76.447 | doi-access = free }} It is longer acting than diazepam due to its long-acting active metabolites,{{cite journal | vauthors = Ueki S, Sukamoto T, Watanabe S, Yamamoto T, Kataoka Y, Shibata S, Suwandi D, Shibata K, Takano M, Sato Y | display-authors = 6 | title = [Behavioral effects of flutoprazepam (KB-509) and its metabolites] | journal = Nihon Yakurigaku Zasshi. Folia Pharmacologica Japonica | volume = 80 | issue = 1 | pages = 15–30 | date = July 1982 | pmid = 6890927 | doi = 10.1254/fpj.80.15 | doi-access = free }} which contribute significantly to its effects.{{cite journal | vauthors = Barzaghi N, Leone L, Monteleone M, Tomasini G, Perucca E | title = Pharmacokinetics of flutoprazepam, a novel benzodiazepine drug, in normal subjects | journal = European Journal of Drug Metabolism and Pharmacokinetics | volume = 14 | issue = 4 | pages = 293–8 | year = 1989 | pmid = 2633923 | doi = 10.1007/BF03190114 | s2cid = 20710732 }} Its principal active metabolite is n-desalkylflurazepam, also known as norflurazepam, which is also a principal metabolite of flurazepam (trade name Dalmadorm/Dalmane).{{cite journal | vauthors = Miyaguchi H, Kuwayama K, Tsujikawa K, Kanamori T, Iwata YT, Inoue H, Kishi T | title = A method for screening for various sedative-hypnotics in serum by liquid chromatography/single quadrupole mass spectrometry | journal = Forensic Science International | volume = 157 | issue = 1 | pages = 57–70 | date = February 2006 | pmid = 15869852 | doi = 10.1016/j.forsciint.2005.03.011 }}{{cite journal | vauthors = Barzaghi N, Leone L, Monteleone M, Tomasini G, Perucca E | title = Pharmacokinetics of flutoprazepam, a novel benzodiazepine drug, in normal subjects | journal = European Journal of Drug Metabolism and Pharmacokinetics | volume = 14 | issue = 4 | pages = 293–8 | year = 1989 | pmid = 2633923 | doi = 10.1007/BF03190114 | s2cid = 20710732 }}

Flutoprazepam is typically used for the treatment of severe insomnia and may also be used for treating stomach ulcers.{{cite journal | vauthors = Fukuda T, Itoh K, Nose T | title = [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] | journal = Nihon Yakurigaku Zasshi. Folia Pharmacologica Japonica | volume = 77 | issue = 3 | pages = 273–80 | date = March 1981 | pmid = 7052359 | doi = 10.1254/fpj.77.273 | doi-access = free }}

Flutoprazepam does not fall under the international Convention on Psychotropic Substances of 1971, and is currently unscheduled in the United States.{{cite web |title=Green List—List of psychotropic substances under international control |url=https://www.incb.org/documents/Psychotropics/greenlist/2016/V1604744_Eng.pdf |date=August 2016 |edition=26th |publisher=International Narcotics Control Board |access-date=2017-07-30 |archive-url=https://web.archive.org/web/20170421003842/https://www.incb.org/documents/Psychotropics/greenlist/2016/V1604744_Eng.pdf |archive-date=2017-04-21 |url-status=dead }}

• 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.{{cite web |title=Bilingual Laws Information System |url=http://www.legislation.gov.hk/eng/index.htm |format=English |publisher=The Government of the Hong Kong Special Administrative Region of the People's Republic of China}}