fludiazepam

{{Short description|Chemical compound}}

{{Drugbox

| Watchedfields = changed

| verifiedrevid = 443821344

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

| image = Fludiazepam.svg

| image_class = skin-invert-image

| width = 170

| image2 = Fludiazepam ball-and-stick model.png

| tradename = Erispan (JP, TW)

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

| pregnancy_category =

| legal_BR = B1

| legal_BR_comment = {{Cite web |author=Anvisa |author-link=Brazilian Health Regulatory Agency |date=2023-03-31 |title=RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial |trans-title=Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control|url=https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-784-de-31-de-marco-de-2023-474904992 |url-status=live |archive-url=https://web.archive.org/web/20230803143925/https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-784-de-31-de-marco-de-2023-474904992 |archive-date=2023-08-03 |access-date=2023-08-16 |publisher=Diário Oficial da União |language=pt-BR |publication-date=2023-04-04}}

| legal_CA = Schedule IV

| legal_DE = Anlage III

| legal_US = Schedule IV

| routes_of_administration = Oral (tablets)

| class = Benzodiazepine

| bioavailability =

| metabolism = Hepatic

| elimination_half-life =

| excretion = Renal

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

| CAS_number = 3900-31-0

| ATC_prefix = N05

| ATC_suffix = BA17

| PubChem = 3369

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

| DrugBank = DB01567

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

| ChemSpiderID = 3252

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

| UNII = 7F64A2K16Z

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

| KEGG = D01354

| ChEBI_Ref = {{ebicite|correct|EBI}}

| ChEBI = 31618

| ChEMBL_Ref = {{ebicite|correct|EBI}}

| ChEMBL = 13291

| C=16 | H=12 | Cl=1 | F=1 | N=2 | O=1

| smiles = O=C1CN=C(C2=CC=CC=C2F)C3=CC(Cl)=CC=C3N1C

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

| StdInChI = 1S/C16H12ClFN2O/c1-20-14-7-6-10(17)8-12(14)16(19-9-15(20)21)11-4-2-3-5-13(11)18/h2-8H,9H2,1H3

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

| StdInChIKey = ROYOYTLGDLIGBX-UHFFFAOYSA-N

}}

Fludiazepam, US Patent 3371085 5-aryl-3h-1,4-benzodiazepin-2(1h)-ones marketed under the brand name Erispan (エリスパン){{cite journal | vauthors = Su TP, Chen TJ, Hwang SJ, Chou LF, Fan AP, Chen YC | title = Utilization of psychotropic drugs in Taiwan: an overview of outpatient sector in 2000 | journal = Zhonghua Yi Xue Za Zhi (Chinese Medical Journal; Free China Ed) | volume = 65 | issue = 8 | pages = 378–91 | date = August 2002 | pmid = 12455808 }}{{cite web|url=http://www.non-benzodiazepines.org.uk/benzodiazepine-names.html |title=Benzodiazepine Names |access-date=2008-12-29 |publisher=non-benzodiazepines.org.uk |url-status=dead |archive-url=https://web.archive.org/web/20081208054743/http://www.non-benzodiazepines.org.uk/benzodiazepine-names.html |archive-date=2008-12-08 }} is a potent benzodiazepine and 2ʹ-fluoro derivative of diazepam,{{cite journal | vauthors = Neville GA, Beckstead HD, Shurvell HF | title = A Fourier transform-Raman and infrared vibrational study of delorazepam, fludiazepam, flurazepam, and tetrazepam | journal = Journal of Pharmaceutical Sciences | volume = 83 | issue = 2 | pages = 143–51 | date = February 1994 | pmid = 7909552 | doi = 10.1002/jps.2600830207 }} originally developed by Hoffmann-La Roche in the 1960s.US Patent 3299053 -ARYL-JH-L,X-BENZODIAZEPIN-Z(LH)-ONES It is marketed in Japan and Taiwan. {{cn|date=March 2016}} It exerts its pharmacological properties via enhancement of GABAergic inhibition.{{cite journal | vauthors = Tsuchiya T, Fukushima H | title = Effects of benzodiazepines and pentobarbitone on the gaba-ergic recurrent inhibition of hippocampal neurons | journal = European Journal of Pharmacology | volume = 48 | issue = 4 | pages = 421–4 | date = April 1978 | pmid = 648585 | doi = 10.1016/0014-2999(78)90169-3 }} Fludiazepam has 4 times more binding affinity for benzodiazepine receptors than diazepam.{{cite journal | vauthors = Nakatsuka I, Shimizu H, Asami Y, Katoh T, Hirose A, Yoshitake A | title = Benzodiazepines and their metabolites: relationship between binding affinity to the benzodiazepine receptor and pharmacological activity | journal = Life Sciences | volume = 36 | issue = 2 | pages = 113–9 | date = January 1985 | pmid = 2857046 | doi = 10.1016/0024-3205(85)90089-X }} It possesses anxiolytic,{{cite journal | vauthors = Okada S, Ichiki K, Tanokuchi S, Ishii K, Hamada H, Ota Z | title = Effect of an anxiolytic on lipid profile in non-insulin-dependent diabetes mellitus | journal = The Journal of International Medical Research | volume = 22 | issue = 6 | pages = 338–42 | year = 1994 | pmid = 7895897 | doi = 10.1177/030006059402200605 | s2cid = 9591519 }}{{cite journal | vauthors = Okada S, Ichiki K, Tanokuchi S, Ishii K, Hamada H, Ota Z | title = Improvement of stress reduces glycosylated haemoglobin levels in patients with type 2 diabetes | journal = The Journal of International Medical Research | volume = 23 | issue = 2 | pages = 119–22 | year = 1995 | pmid = 7601294 | doi = 10.1177/030006059502300205 | s2cid = 12865838 }}{{cite journal | vauthors = Okada S, Ichiki K, Tanokuchi S, Ishii K, Hamada H, Ota Z | title = How blood pressure in patients with non-insulin-dependent diabetes mellitus is influenced by stress | journal = The Journal of International Medical Research | volume = 23 | issue = 5 | pages = 377–80 | year = 1995 | pmid = 8529781 | doi = 10.1177/030006059502300508 | s2cid = 42485678 }} anticonvulsant, sedative, hypnotic and skeletal muscle relaxant properties.{{cite journal | vauthors = Inoue H, Maeno Y, Iwasa M, Matoba R, Nagao M | title = Screening and determination of benzodiazepines in whole blood using solid-phase extraction and gas chromatography/mass spectrometry | journal = Forensic Science International | volume = 113 | issue = 1–3 | pages = 367–73 | date = September 2000 | pmid = 10978650 | doi = 10.1016/S0379-0738(00)00226-7 }} Fludiazepam has been used recreationally.{{cite journal | vauthors = Shimamine M, Masunari T, Nakahara Y | title = [Studies on identification of drugs of abuse by diode array detection. I. Screening-test and identification of benzodiazepines by HPLC-DAD with ICOS software system] | journal = Eisei Shikenjo Hokoku. Bulletin of National Institute of Hygienic Sciences | issue = 111 | pages = 47–56 | year = 1993 | pmid = 7920567 }}