bentazepam

{{Short description|Chemical compound}}

{{Drugbox

| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid = 439545413

| IUPAC_name = 5-phenyl-3,4,6,7,8,9-hexahydro-[1]benzothiolo[2,3-e][1,4]diazepin-2-one

| image = Bentazepam.svg

| width = 150

| tradename = Tiadipona (ES)

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

| pregnancy_category =

| legal_US = Unscheduled

| routes_of_administration = Oral (tablets)

| bioavailability =

| metabolism = Hepatic

| elimination_half-life = 2–4 hours

| excretion = Renal

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

| CAS_number = 29462-18-8

| ATC_prefix = N05

| ATC_suffix = BA24

| ATC_supplemental =

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

| ChEMBL = 1521495

| PubChem = 34592

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

| DrugBank =

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

| ChemSpiderID = 11248641

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

| UNII = 66JKK43S1Z

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

| KEGG = D03083

| C = 17

| H = 16

| N = 2

| O = 1

| S = 1

| smiles = O=C1CN=C(C2=CC=CC=C2)C3=C(N1)SC4=C3CCCC4

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

| StdInChI = 1S/C17H16N2OS/c20-14-10-18-16(11-6-2-1-3-7-11)15-12-8-4-5-9-13(12)21-17(15)19-14/h1-3,6-7H,4-5,8-10H2,(H,19,20)

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

| StdInChIKey = AIZFEOPQVZBNGH-UHFFFAOYSA-N

}}

Bentazepam{{cite patent | country = DE | number = 2005276 }} (also known as Thiadipone, Tiadipona) is a thienodiazepine which is a benzodiazepine analog.

It possesses anxiolytic, anticonvulsant, sedative and skeletal muscle relaxant properties.

Peak plasma rates are achieved in around 2,5 hours after oral administration.{{cite journal | vauthors = Mariño EL, Fernandez Lastra C, Gonzalez Lopez F, Dominguez-Gil A, Garcia Santalla JL, Vorca G, Izquierdo JA, Ledesma-Jimeno A | display-authors = 6 | title = Parametrization by non-linear regression and bayesian estimation of bentazepam in a multiple dosage regimen in humans | journal = International Journal of Clinical Pharmacology, Therapy, and Toxicology | volume = 25 | issue = 11 | pages = 627–32 | date = November 1987 | pmid = 3429066 }} The elimination half-life is between approximately 2–4 hours.{{cite journal | vauthors = Gonzalez López F, Mariño EL, Dominguez-Gil A | title = Pharmacokinetics of tiadipone: a new anxiolytic | journal = International Journal of Clinical Pharmacology, Therapy, and Toxicology | volume = 24 | issue = 9 | pages = 482–4 | date = September 1986 | pmid = 2877954 }}{{cite journal | vauthors = Colino CI, Lastra CF, López FG, Ledesma A, Mariño EL | title = Open-loop feedback control of serum bentazepam concentrations and Bayesian estimation in multiple dosage regimens in patients | journal = International Journal of Clinical Pharmacology, Therapy, and Toxicology | volume = 29 | issue = 11 | pages = 457–62 | date = November 1991 | pmid = 1800395 }} Bentazepam is effective as an anxiolytic.

A severe benzodiazepine overdose with bentazepam may result in coma and respiratory failure.{{cite journal | vauthors = Rivas López FA, López Soriano F, Mendoza Cerezo A, Jiménez Ferré J, Azurmendi Rodríguez JI, de la Rubia Nieto MA | title = [Mixed benzodiazepine poisoning and reversal with flumazenil (Ro 15-1788)] | journal = Revista Espanola de Anestesiologia y Reanimacion | volume = 36 | issue = 1 | pages = 48–50 | year = 1989 | pmid = 2565591 }} Adverse effects include dry mouth, somnolence, asthenia, dyspepsia, constipation, nausea{{cite journal | vauthors = Honorato J, Rubio A, Tristán C, Otero FJ, Garrido J | title = [A pharmacovigilance study with bentazepam in a sample of 1046 psychiatric outpatients] | journal = Revista de Medicina de la Universidad de Navarra | volume = 34 | issue = 2 | pages = 80–8 | year = 1990 | pmid = 1983365 }} and drug-induced lymphocytic colitis has been associated with bentazepam.{{cite journal | vauthors = Fernández-Bañares F, Salas A, Esteve M, Espinós J, Forné M, Viver JM | title = Collagenous and lymphocytic colitis. evaluation of clinical and histological features, response to treatment, and long-term follow-up | journal = The American Journal of Gastroenterology | volume = 98 | issue = 2 | pages = 340–7 | date = February 2003 | doi = 10.1111/j.1572-0241.2003.07225.x | pmid = 12591052 | s2cid = 1983209 }}{{cite journal | vauthors = de-la-Serna C, Gil-Grande LA, Sanromán AL, Gonzalez M, Ruiz-del-Arbol L, Garcia Plaza A | title = Bentazepam-induced hepatic bridging necrosis | journal = Journal of Clinical Gastroenterology | volume = 25 | issue = 4 | pages = 710–1 | date = December 1997 | pmid = 9451703 | doi = 10.1097/00004836-199712000-00042 }} Severe liver damage and hepatitis has also been associated with bentazepam.{{cite journal | vauthors = Andrade RJ, Lucena MI, Kaplowitz N, García-Muņoz B, Borraz Y, Pachkoria K, García-Cortés M, Fernández MC, Pelaez G, Rodrigo L, Durán JA, Costa J, Planas R, Barriocanal A, Guarner C, Romero-Gomez M, Muņoz-Yagüe T, Salmerón J, Hidalgo R | display-authors = 6 | title = Outcome of acute idiosyncratic drug-induced liver injury: Long-term follow-up in a hepatotoxicity registry | journal = Hepatology | volume = 44 | issue = 6 | pages = 1581–8 | date = December 2006 | pmid = 17133470 | doi = 10.1002/hep.21424 | s2cid = 9067701 | doi-access = free }}{{cite journal |url=http://www.elsevier.es/revistas/ctl_servlet?_f=7064&ip=90.221.211.72&articuloid=13047309&revistaid=2 |language=Spanish |journal=Medicina Clínica |title=Utilidad clinica del acetato de megestrol para la ganancia de peso en los enfermos con neoplasia y caquexia |volume=120 |issue=17 |pages=678 |year=2003 |doi=10.1157/13047309 |last1=Tuca |first1=Albert |name-list-style=vanc |access-date=2009-09-18 |archive-date=2018-09-16 |archive-url=https://web.archive.org/web/20180916024925/http://www.elsevier.es/revistas/ctl_servlet?_f=7064&ip=90.221.211.72&articuloid=13047309&revistaid=2 |url-status=dead |url-access=subscription }}{{cite journal | vauthors = Andrade RJ, Lucena MI, Alcantara R, Fraile JM | title = Bentazepam-associated chronic liver disease | journal = Lancet | volume = 343 | issue = 8901 | pages = 860 | date = April 1994 | pmid = 7908109 | doi = 10.1016/S0140-6736(94)92065-6 | s2cid = 33991843 }} Whilst liver failure from bentazepam is considered to be rare, liver function monitoring has been recommended for all patients taking bentazepam.{{cite journal | vauthors = Andrade RJ, Lucena MI, Aguilar J, Lazo MD, Camargo R, Moreno P, García-Escaño MD, Marquez A, Alcántara R, Alcáin G | display-authors = 6 | title = Chronic liver injury related to use of bentazepam: an unusual instance of benzodiazepine hepatotoxicity | journal = Digestive Diseases and Sciences | volume = 45 | issue = 7 | pages = 1400–4 | date = July 2000 | pmid = 10961721 | doi = 10.1023/A:1005520523502 }}