flutazolam

{{Short description|Benzodiazepam}}

{{distinguish|Fluetizolam}}

{{Drugbox

| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid = 461102637

| IUPAC_name = 10-chloro-11b-(2-fluorophenyl)-7-(2-hydroxyethyl)-3,5-dihydro-2H-[1,3]oxazolo[3,2-d][1,4]benzodiazepin-6-one

| image = Flutazolam.svg

| width = 155

| image2 = Flutazolam ball-and-stick.png

| width2 = 160

| tradename = Coreminal (JP)

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

| legal_US = Unscheduled

| legal_status = In general: unscheduled, Rx-only in Japan

| bioavailability =

| metabolism = Hepatic

| elimination_half-life = 3.5 hours (parent compound); 47-100 hours (major metabolite)

| routes_of_administration = Oral

| excretion =

| CAS_number_Ref = {{cascite|changed|??}}

| CAS_number = 27060-91-9

| ATC_prefix =

| PubChem = 3398

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

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

| ChemSpiderID = 3281

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

| UNII = 5G2K7O5D8S

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

| KEGG = D01286

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

| ChEMBL = 1697836

| C=19 | H=18 | Cl=1 | F=1 | N=2 | O=3

| smiles = Fc1ccccc1C42OCCN2CC(=O)N(c3c4cc(Cl)cc3)CCO

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

| StdInChI = 1S/C19H18ClFN2O3/c20-13-5-6-17-15(11-13)19(14-3-1-2-4-16(14)21)22(8-10-26-19)12-18(25)23(17)7-9-24/h1-6,11,24H,7-10,12H2

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

| StdInChIKey = WMFSSTNVXWNLKI-UHFFFAOYSA-N

| synonyms = 13-chloro- 2-(2-fluorophenyl)- 9-(2-hydroxyethyl)- 3-oxa- 6,9-diazatricyclo[8.4.0.0^2,6] tetradeca-1(10),11,13- trien- 8-one

}}

Flutazolam{{cite patent | country = DE | number = 1952486 }} (Coreminal, MS-4101) is a drug which is a benzodiazepine derivative. It was invented in Japan, and this is the main country in which it has been used medically. It has sedative, muscle relaxant, anticonvulsant, and anxiolytic effects similar to those produced by other benzodiazepine derivatives, and though it is around the same potency as diazepam, it produces a more marked sedation and impaired coordination. It is indicated for the treatment of insomnia.Mitsushima T, Ueki S. Psychopharmacological effects of flutazolam (MS-4101). Nippon Yakurigaku Zasshi. 1978 Nov;74(8):959-79. (Japanese). Its major active metabolite is n-desalkylflurazepam, also known as norflurazepam, which is also a principal metabolite of flurazepam (trade name 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 }} While flutazolam has a very short half-life of only 3.5 hours, n-desalkylflurazepam has a long half-life of between 47–100 hours.{{cite web |title=Dalmane Prescribing Information |url=https://www.accessdata.fda.gov/drugsatfda_docs/label/2007/016721s076lbl.pdf |archive-url=https://web.archive.org/web/20170118191529/http://www.accessdata.fda.gov/drugsatfda_docs/label/2007/016721s076lbl.pdf |url-status=dead |archive-date=January 18, 2017 |website=Prescribing Information for Dalmane |publisher=FDA |access-date=3 April 2022}}

Flutazolam is closely related in structure to another benzodiazepine, haloxazolam.{{cite journal | vauthors = Kuwayama T, Kurono Y, Muramatsu T, Yashiro T, Ikeda K | title = The behavior of 1,4-benzodiazepine drugs in acidic media. V. Kinetics of hydrolysis of flutazolam and haloxazolam in aqueous solution. | journal = Chemical and Pharmaceutical Bulletin | date = January 1986 | volume = 34 | issue = 1 | pages = 320–6 | doi = 10.1248/cpb.34.320 | pmid = 2870816 | doi-access = free }}{{cite journal | vauthors = Yashiro T, Kuwayama T, Kawazura H, Suzuki T | title = [The behavior of 1,4-benzodiazepine drugs in acidic media. IX. Effect of hydrolyzate of flutazolam on the central nervous system] | language = ja | journal = Yakugaku Zasshi: Journal of the Pharmaceutical Society of Japan | volume = 107 | issue = 10 | pages = 830–4 | date = October 1987 | pmid = 2894449 | doi = 10.1248/yakushi1947.107.10_830 | doi-access = free }}