{{Short description|Antipsychotic medication}} {{cs1 config|name-list-style=vanc|display-authors=6}} {{Drugbox | Verifiedfields = verified | Watchedfields = verified | verifiedrevid = 444739401 | IUPAC_name = 5,6-Dimethoxy-2-methyl-3-[2-(4-phenylpiperazin-1-yl)ethyl]-1''H''-indole | image = Oxypertine.svg | image_class = skin-invert-image | width = 225px
<!--Clinical data--> | tradename = Oxypertine, others | Drugs.com = {{drugs.com|international|oxypertine}} | pregnancy_category = | legal_AU = <!-- Unscheduled / S2 / S3 / S4 / S5 / S6 / S7 / S8 / S9 --> | 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_CA = <!-- / Schedule I, II, III, IV, V, VI, VII, VIII --> | legal_DE = <!-- Anlage I, II, III or Unscheduled --> | legal_NZ = <!-- Class A, B, C --> | legal_UK = <!-- GSL / P / POM / CD / Class A, B, C --> | legal_US = <!-- OTC / Rx-only / Schedule I, II, III, IV, V --> | legal_EU = | legal_UN = <!-- N I, II, III, IV / P I, II, III, IV --> | legal_status = Rx-only | routes_of_administration = By mouth
<!--Pharmacokinetic data--> | bioavailability = | metabolism = | elimination_half-life = | excretion =
<!--Identifiers--> | CAS_number_Ref = {{cascite|correct|??}} | CAS_number = 153-87-7 | ATC_prefix = N05 | ATC_suffix = AE01 | PubChem = 4640 | UNII_Ref = {{fdacite|correct|FDA}} | UNII = 5JGL4G25R7 | KEGG_Ref = {{keggcite|correct|kegg}} | KEGG = D01219 | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID = 4479 | synonyms = WIN-18501; WIN18501; WIN-18,501, Win-18501; Win-18501-2
<!--Chemical data--> | C=23 | H=29 | N=3 | O=2 | SMILES = CC1=C(C2=CC(=C(C=C2N1)OC)OC)CCN3CCN(CC3)C4=CC=CC=C4 | StdInChI_Ref = {{stdinchicite|changed|chemspider}} | StdInChI = 1S/C23H29N3O2/c1-17-19(20-15-22(27-2)23(28-3)16-21(20)24-17)9-10-25-11-13-26(14-12-25)18-7-5-4-6-8-18/h4-8,15-16,24H,9-14H2,1-3H3 | StdInChIKey_Ref = {{stdinchicite|changed|chemspider}} | StdInChIKey = XCWPUUGSGHNIDZ-UHFFFAOYSA-N }}
'''Oxypertine''', sold under the brand name '''Oxypertine''' among others, is an antipsychotic medication of the pertine group which was previously used in the treatment of schizophrenia but is no longer marketed.<ref name="isbn0-412-54090-8">{{cite book | title = Dictionary of organic compounds | publisher = Chapman & Hall | location = London | year = 1996 | isbn = 0-412-54090-8 | url = https://books.google.com/books?id=5S_uhYzKWisC&q=oxypertine%20forit&pg=PA5038 | vauthors = Hall C, Rhodes PH }}</ref> It was also evaluated for the treatment of anxiety.<ref name="pmid12484">{{cite journal | vauthors = Somohano MD, Broissin MC, Sobrino ZA | title = [Clinical evaluation of oxypertine in anxiety conditions] | language = es | journal = Neurologia, Neurocirugia, Psiquiatria | volume = 17 | issue = 3 | pages = 171–180 | date = 1976 | pmid = 12484 | doi = }}</ref>
==Pharmacology== ===Pharmacodynamics=== The drug shows high affinity for the serotonin 5-HT<sub>2</sub> and dopamine D<sub>2</sub> receptors (K<sub>i</sub> = 8.6{{nbsp}}nM and 30{{nbsp}}nM, respectively).<ref name="MegensKennis1996">{{cite journal | vauthors = Megens AA, Kennis LE | title = Risperidone and related 5HT2/D2 antagonists: a new type of antipsychotic agent? | volume = 33 | issue = | pages = 185–232 | date = 1996 | pmid = 8776944 | doi = 10.1016/s0079-6468(08)70306-0 | isbn = 978-0-444-82310-6 | series = Progress in Medicinal Chemistry }}</ref> It antagonizes the behavioral effects of tryptamine, a serotonin receptor agonist, and apomorphine, a dopamine receptor agonist, in animals.<ref name="MegensKennis1996" /><ref name="NiemegeersJanssen1979">{{cite journal | vauthors = Niemegeers CJ, Janssen PA | title = A systematic study of the pharmacological activities of dopamine antagonists | journal = Life Sciences | volume = 24 | issue = 24 | pages = 2201–2216 | date = June 1979 | pmid = 388130 | doi = 10.1016/0024-3205(79)90096-1 | publisher = Elsevier BV }}</ref> Like reserpine and tetrabenazine, oxypertine depletes catecholamines, though not serotonin, possibly contributing to its antipsychotic effectiveness.<ref name="pmid5362847">{{cite journal | vauthors = Bak IJ, Hassler R, Kim JS | title = Differential monoamine depletion by oxypertine in nerve terminals. Granulated synaptic vesicles in relation to depletion of norepinephrine, dopamine and serotonin | journal = Zeitschrift für Zellforschung und Mikroskopische Anatomie | volume = 101 | issue = 3 | pages = 448–462 | year = 1969 | pmid = 5362847 | doi = 10.1007/BF00335580 | s2cid = 32583722 }}</ref>
==Chemistry== Chemically, it is a substituted tryptamine and phenylpiperazine derivative.<ref name="pmid4972600">{{cite journal | vauthors = Breulet M, Labar P, Delree C, Collard J, Bobon J | title = [Oxypertine, peperazine derivative of tryptophan with neuroleptic and dynamogenic properties] | language = fr | journal = Acta Neurologica et Psychiatrica Belgica | volume = 68 | issue = 2 | pages = 116–127 | date = February 1968 | pmid = 4972600 }}</ref> Its chemical structure is similar to other "pertines" including alpertine, milipertine, and solypertine.<ref name="EllisLuscombe1996">{{cite book | vauthors = Ellis GP, Luscombe DK | title=Progress in Medicinal Chemistry | publisher=Elsevier Science | issue=v. 33 | year=1996 | isbn=978-0-08-086281-1 | url=https://books.google.com/books?id=SDaZ4qcemf8C&pg=PA219 | access-date=30 October 2024 | page=219 | quote=Pertines (class 7; Table 5.12) The pertines oxypertine, solypertine, milipertine, and alpertine are piperazinylethylindoles.}}</ref><ref name="LednicerMitscher1980">{{cite book | vauthors = Lednicer D, Mitscher LA | title=The Organic Chemistry of Drug Synthesis, Volume 2 | publisher=Wiley | series=Organic Chemistry Series of Drug Synthesis | year=1980 | isbn=978-0-471-04392-8 | url=https://books.google.com/books?id=r-eqWrMoO18C&pg=PA341 | access-date=30 October 2024 | pages=341–343}}</ref>
==History== Oxypertine was first described in the scientific literature by 1962.<ref name="Elks2014" />
==Society and culture== ===Names=== ''Oxypertine'' is the generic name of the drug and its {{Abbrlink|INN|International Nonproprietary Name}}, {{Abbrlink|USAN|United States Adopted Name}}, {{Abbrlink|BAN|British Approved Name}}, {{Abbrlink|DCF|Dénomination Commune Française}}, and {{Abbrlink|JAN|Japanese Accepted Name}}.<ref name="Elks2014">{{cite book | vauthors = Elks J | title=The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies | publisher=Springer US | year=2014 | isbn=978-1-4757-2085-3 | url=https://books.google.com/books?id=0vXTBwAAQBAJ&pg=PA924 | access-date=2 November 2024 | page=924}}</ref><ref name="IndexNominum2000">{{cite book | author=Schweizerischer Apotheker-Verein | title=Index Nominum 2000: International Drug Directory | publisher=Medpharm Scientific Publishers | year=2000 | isbn=978-3-88763-075-1 | url=https://books.google.com/books?id=5GpcTQD_L2oC&pg=PA779 | access-date=2 November 2024 | page=779}}</ref><ref name="MortonHall2012">{{cite book | vauthors = Morton IK, Hall JM | title=Concise Dictionary of Pharmacological Agents: Properties and Synonyms | publisher=Springer Netherlands | year=2012 | isbn=978-94-011-4439-1 | url=https://books.google.com/books?id=tsjrCAAAQBAJ&pg=PA212 | access-date=2 November 2024 | page=212}}</ref><ref name="Drugs.com-International">{{cite web | url=https://drugs.com/international/oxypertine.html | archive-url=https://web.archive.org/web/20160303222344/https://drugs.com/international/oxypertine.html | archive-date=2016-03-03 | title=List of Antipsychotics }}</ref> It is also known by its former developmental code name ''WIN-18501''.<ref name="Elks2014" /><ref name="IndexNominum2000" /><ref name="MortonHall2012" /><ref name="Drugs.com-International" /> The drug has been sold under brand names including ''Equipertine'', ''Forit'', ''Integrin'', ''Lanturil'', ''Lotawin'', ''Opertil'', and ''Oxypertine''.<ref name="Elks2014" /><ref name="IndexNominum2000" /><ref name="MortonHall2012" /><ref name="Drugs.com-International" />
==See also== * Pertine
==References== {{Reflist}}
{{Antipsychotics}} {{Dopamine receptor modulators}} {{Serotonin receptor modulators}} {{Tryptamines}}
Category:Abandoned drugs Category:2-Alkyltryptamines Category:Antipsychotics Category:Catechol ethers Category:Indole ethers Category:Monoamine-depleting agents Category:Pertines