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Maprotiline
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{{Short description|Antidepressant}} {{cs1 config|name-list-style=vanc}} {{infobox drug | Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 477169275 | IUPAC_name = ''N''-Methyl-9,10-ethanoanthracene-9(10''H'')-propanamine | image = Maprotiline structure.svg | image_class = skin-invert-image | width = 200px | image2 = Maprotiline ball-and-stick model.png | width2 = 200px <!--Clinical data--> | tradename = Ludiomil, others | Drugs.com = {{drugs.com|monograph|maprotiline-hydrochloride}} | MedlinePlus = a682158 | pregnancy_US_comment = B3<sup>[in US?]</sup><!-- B3 is AU? --> | legal_AU = S4 | legal_BR = C1 | legal_BR_comment = <ref>{{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}}</ref> | legal_US = Rx-only | routes_of_administration = [[Oral administration|Oral]], [[intramuscular injection|intramuscular]], [[intravenous therapy|intravenous]] <!--Pharmacokinetic data--> | bioavailability = 66–70% | protein_bound = 88% | metabolism = hepatic | onset = 6 hours | elimination_half-life = 27–58 hours | excretion = [[Urine]] (57%) and [[bile]] (30%) as [[glucuronide]]s, 3–4% as unchanged drug <!--Identifiers--> | CAS_number_Ref = {{cascite|correct|??}} | CAS_number = 10262-69-8 | CAS_supplemental = <br />10347-81-6 ([[hydrochloride]])<br /> 58902-67-3 ([[mesylate]]) | ATC_prefix = N06 | ATC_suffix = AA21 | ATC_supplemental = | PubChem = 4011 | IUPHAR_ligand = 2402 | DrugBank_Ref = {{drugbankcite|correct|drugbank}} | DrugBank = DB00934 | ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}} | ChemSpiderID = 23719117 | UNII_Ref = {{fdacite|correct|FDA}} | UNII = 2U1W68TROF | KEGG_Ref = {{keggcite|correct|kegg}} | KEGG = D02566 | ChEMBL_Ref = {{ebicite|correct|EBI}} | ChEMBL = 21731 | synonyms = Maprotiline hydrochloride; Maprotiline methanesulfonate; Ba 34276<ref name="Elks2014" /><ref name="IndexNominum2000" /><ref name="Drugs.com" /> <!--Chemical data--> | C=20 | H=23 | N=1 | SMILES = CNCCC[C@]12CC[C@H](c3ccccc31)c1ccccc12 | StdInChI_Ref = {{stdinchicite|changed|chemspider}} | StdInChI = 1S/C20H23N/c1-21-14-6-12-20-13-11-15(16-7-2-4-9-18(16)20)17-8-3-5-10-19(17)20/h2-5,7-10,15,21H,6,11-14H2,1H3/t15-,20+ | StdInChIKey_Ref = {{stdinchicite|changed|chemspider}} | StdInChIKey = QSLMDECMDJKHMQ-GSXCWMCISA-N }} '''Maprotiline''', sold under the brand name '''Ludiomil''' among others, is a [[tetracyclic antidepressant]] (TeCA) that is used in the treatment of [[depression (mood)|depression]].<ref name="LemkeWilliams2012" /> It may alternatively be classified as a [[tricyclic antidepressant]] (TCA), specifically a [[secondary amine]].<ref name="LemkeWilliams2012" /> In terms of its [[chemistry]] and [[pharmacology]], maprotiline is closely related to such-other secondary-amine TCAs as [[nortriptyline]] and [[protriptyline]] and has similar effects to them,<ref name="Zhou2013" /><ref name="LemkeWilliams2012" /> albeit with more distinct [[anxiolytic]] effects.<ref>{{cite journal | vauthors = Guimarães FS, Zuardi AW, Graeff FG | title = Effect of chlorimipramine and maprotiline on experimental anxiety in humans | journal = Journal of Psychopharmacology | volume = 1 | issue = 3 | pages = 184–192 | date = January 1987 | doi = 10.1177/026988118700100305 | pmid = 22158980 | s2cid = 8444656 }}</ref><ref>{{cite journal | vauthors = Vinader-Caerols C, Martos AJ, Monleón S, Arenas MC, Parra A | title = Acute effects of maprotiline on learning, anxiety, activity and analgesia in male and female mice | journal = Acta Neurobiologiae Experimentalis | date = 2006 | volume = 66 | issue = 1 | pages = 23–31 | doi = 10.55782/ane-2006-1584 | pmid = 16617674 | doi-access = free }}</ref><ref>{{cite journal | vauthors = Pecknold JC, Familamiri P, McClure DJ, Elie R, Chang H | title = Trimipramine and maprotiline: antidepressant, anxiolytic, and cardiotoxic comparison | journal = The Journal of Clinical Psychiatry | volume = 46 | issue = 5 | pages = 166–171 | date = May 1985 | pmid = 2859273 }}</ref> Additionally, whereas [[protriptyline]] tends to be somewhat more stimulating and in any case is distinctly more-or-less non-sedating,<ref name="pmid6360257">{{cite journal | vauthors = Brownell LG, Perez-Padilla R, West P, Kryger MH | title = The role of protriptyline in obstructive sleep apnea | journal = Bulletin Européen de Physiopathologie Respiratoire | volume = 19 | issue = 6 | pages = 621–4 | date = 1983 | pmid = 6360257 | doi = | url = }}</ref> mild degrees of sedation may be experienced with maprotiline.<ref name="pmid3044007">{{cite journal | vauthors = Holmberg G | title = Sedative effects of maprotiline and amitriptyline | journal = Acta Psychiatrica Scandinavica | volume = 77 | issue = 5 | pages = 584–6 | date = May 1988 | pmid = 3044007 | doi = 10.1111/j.1600-0447.1988.tb05171.x | s2cid = 41977086 | url = }}</ref>
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