minaprine

{{Short description|Chemical compound}}

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{{Multiple issues|

{{globalize|date=July 2016}}

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{{Drugbox

| IUPAC_name = 4-methyl-N-(2-morpholin-4-ylethyl)-6-phenylpyridazin-3-amine

| image =Minaprine.svg

| image_class = skin-invert-image

| tradename =

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

| pregnancy_category =

| legal_AU =

| legal_BR = C1

| 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 =

| legal_DE =

| legal_NZ =

| legal_UK =

| legal_US =

| legal_EU =

| legal_UN =

| legal_status = Rx-only

| routes_of_administration = Oral

| bioavailability =

| metabolism =

| elimination_half-life = 2-2.5 hours

| excretion =

| CAS_number_Ref = {{cascite|correct|CAS}}

| CAS_number = 25905-77-5

| ATC_prefix = N06

| ATC_suffix = AX07

| PubChem = 4199

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

| DrugBank =

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

| ChemSpiderID = 4054

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

| UNII = 00U7GX0NLM

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

| KEGG = D05039

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

| ChEMBL = 278819

| C=17 | H=22 | N=4 | O=1

| smiles = CC1=CC(=NN=C1NCCN2CCOCC2)C3=CC=CC=C3

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

|StdInChI = 1S/C17H22N4O/c1-14-13-16(15-5-3-2-4-6-15)19-20-17(14)18-7-8-21-9-11-22-12-10-21/h2-6,13H,7-12H2,1H3,(H,18,20)

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

|StdInChIKey = LDMWSLGGVTVJPG-UHFFFAOYSA-N

}}

Minaprine (INN, USAN, BAN; brand names Brantur, Cantor) is a monoamine oxidase inhibitor antidepressant drug that was used in France for the treatment of depression until it was withdrawn from the market in 1996 because it caused convulsions.{{cite journal | vauthors = Wermuth CG, Schlewer G, Bourguignon JJ, Maghioros G, Bouchet MJ, Moire C, Kan JP, Worms P, Biziere K | title = 3-aminopyridazine derivatives with atypical antidepressant, serotonergic, and dopaminergic activities | journal = Journal of Medicinal Chemistry | volume = 32 | issue = 3 | pages = 528–537 | date = March 1989 | pmid = 2563772 | doi = 10.1021/jm00123a004 }}{{cite journal| vauthors = Fung M, Thornton A, Mybeck K, Wu JH, Hornbuckle K, Muniz E |title=Evaluation of the Characteristics of Safety Withdrawal of Prescription Drugs from Worldwide Pharmaceutical Markets-1960 to 1999|journal=Therapeutic Innovation & Regulatory Science|date=1 January 2001|volume=35|issue=1|pages=293–317|doi=10.1177/009286150103500134|s2cid=73036562}}

A study found that it acts as a reversible inhibitor of MAO-A (RIMA) in rats.{{cite journal | vauthors = Kan JP, Mouget-Goniot C, Worms P, Biziere K | title = Effect of the antidepressant minaprine on both forms of monoamine oxidase in the rat | journal = Biochemical Pharmacology | volume = 35 | issue = 6 | pages = 973–978 | date = March 1986 | pmid = 3954800 | doi = 10.1016/0006-2952(86)90085-7 }} It has also been found to weakly inhibit acetylcholinesterase in rat brain (striatum) homogenates.{{cite journal | vauthors = Contreras JM, Rival YM, Chayer S, Bourguignon JJ, Wermuth CG | title = Aminopyridazines as acetylcholinesterase inhibitors | journal = Journal of Medicinal Chemistry | volume = 42 | issue = 4 | pages = 730–741 | date = February 1999 | pmid = 10052979 | doi = 10.1021/jm981101z }}

It has demonstrated significant antibiotic activity against M. chelonae and M. abscessus in tests with antibiotic resistant bacteria.{{cite journal | vauthors = Chopra S, Matsuyama K, Hutson C, Madrid P | title = Identification of antimicrobial activity among FDA-approved drugs for combating Mycobacterium abscessus and Mycobacterium chelonae | journal = The Journal of Antimicrobial Chemotherapy | volume = 66 | issue = 7 | pages = 1533–1536 | date = July 2011 | pmid = 21486854 | doi = 10.1093/jac/dkr154 | doi-access = free }}