oxypertine
{{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]-1H-indole
| image = Oxypertine.svg
| image_class = skin-invert-image
| width = 225px
| tradename = Oxypertine, others
| Drugs.com = {{drugs.com|international|oxypertine}}
| 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}}
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| legal_DE =
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| legal_US =
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| legal_status = Rx-only
| routes_of_administration = By mouth
| bioavailability =
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| elimination_half-life =
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| 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
| 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.{{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 }} It was also evaluated for the treatment of anxiety.{{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 = }}
Pharmacology
=Pharmacodynamics=
The drug shows high affinity for the serotonin 5-HT2 and dopamine D2 receptors (Ki = 8.6{{nbsp}}nM and 30{{nbsp}}nM, respectively).{{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 }} It antagonizes the behavioral effects of tryptamine, a serotonin receptor agonist, and apomorphine, a dopamine receptor agonist, in animals.{{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 }} Like reserpine and tetrabenazine, oxypertine depletes catecholamines, though not serotonin, possibly contributing to its antipsychotic effectiveness.{{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 }}
Chemistry
Chemically, it is a substituted tryptamine and phenylpiperazine derivative.{{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 }} Its chemical structure is similar to other "pertines" including alpertine, milipertine, and solypertine.{{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.}}{{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}}
History
Oxypertine was first described in the scientific literature by 1962.
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}}.{{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}}{{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}}{{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}}{{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 }} It is also known by its former developmental code name WIN-18501. The drug has been sold under brand names including Equipertine, Forit, Integrin, Lanturil, Lotawin, Opertil, and Oxypertine.
See also
References
{{Reflist}}
{{Antipsychotics}}
{{Dopamine receptor modulators}}
{{Serotonin receptor modulators}}
{{Tryptamines}}
Category:Indole ethers at the benzene ring