Alemannische Wikipedia

Benutzer:Mathieu Kappler/Sandkaste/7

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Strukturformel
Struktur von Mianserin
1:1-Gmìsch vum (R)-Isomer (owa) un em (S)-Isomer (unter)
Allgemeines
Freiname Mianserin
Andere Namen

(RS)-2-Methyl-1,2,3,4,10,14b-hexahydrodibenzo[c,f]pyrazino[1,2-a]azepin

Summeformle C18H20N2
CAS-Nummer
PubChem 4184
ATC-Code

N06AX03

DrugBank DB06148
Arzneistoffaagoobe
Wirkstoffklass

Narvahailmìttel (Antidepressivum)

Äigeschafte
Molari Masse 264,36 g·mol−1
Aggregatzuestand

fäscht

Schmelzpunkt

282–284 °C (Mianserin·Hydrochlorid)[1]

Sicherhäitshiiwiis
Mä sött Acht gee, ass d Gültigkäit vo dr Gfaarstoffkennzäichnig bi Arzneimiddel iigschränkt isch
GHS-Gfoorstoffkennzäichnig [2]

Vorlage:GHS-Piktogramme-klein Achtung

H- und P-Sätze H: 302
P: käini P-Setz [2]
Toxikologischi Date
Sowit wie möglig, wärde SI-Äihäite verwändet. Wenn nüt anders stoot, gälte d Date wo aagee si bi Standardbedingige.

{[{Dialäkt|Elsässisch|Elsassisch|Owerelsassisch}}

D’ Mianserin ìsch a Àrznäischtoff vu dr Grupp vu da tretraziklischa Narvahailmìttel. ’S ìsch a Ànàloogon vu dr Mirtazapin.

Gschìcht

ändere

Ìm Vergliich mìt da triziklischa Substànza han d’ äältra tretraziklischa kä ärheebliga Fortschrìtt ìn Vertragligkait un Wìrksàmkait. D’ Mirtazapin, a Vàrianta vu dr Mianserin, ìsch àwwer àls Vertratter vun’ra bschtìmmta Grupp, d’ NaSSA. D’ Mianserin, wo sehr ahnlig wia d’ Mirtazapin wìrkt, gheert eewafàlls züa dara Grupp. D’ Mianserin ìsch ànna 1967 vun Organon patentiart worra.[4] Züagloo ìsch sa ànna 1975 ìm Ditschlànd unter’m Màrkanàmma Tolvin, un ìn dr Schwiz un ìm Eeschtriich àls Tolvon. D’rzüa ìsch sa vu zàhlriicha Handler àls Hailmìttel vum äffentliga Gebiat vermarktet. It is also available throughout the world under a variety of other brand names including Athymil, Bonserin, Bolvidon, Deprevon, Lantanon, Lerivon, Miansan, Serelan, Tetramide, and Tolvin among others.[5][6][7]

Mianserin is not approved for use in the United States, but is available in the United Kingdom and other European countries.[8][9] A mianserin generic drug received Vorlage:Abbrlink approval in May 1996 and is available in Australia.[10]

[11]Vorlage:Rp[12]Vorlage:Rp

[13]

Latin [7][5][14][6]

D’ Mianserin ìsch ainer vu da äärschta Narvahailmìttel gsìì, wo-n-uff’m britischa Màrkt ààkumma ìsch, un wo weniger gfoohrlig gsìì ìsch àss d’ triziklika Narvahailmìttel, wänn man ’s ìn Ìwwerdoosa nìmmt. Jedoch ìsch d’ Mianserin numma salta verschrìewa ìm Verainigta Keenigraich.[15]

Wackselwìrkung

ändere
Mianserin[16]
Site Ki (nM) Species Ref
Vorlage:Abbrlink 4,000 Human [17]
Vorlage:Abbrlink 71 Human [17]
Vorlage:Abbrlink 9,400 Human [17]
5-HT1A 400–2,600 Human [18][19]
5-HT1B ≥2,800 Rat [20]
5-HT1D 220–400 Human [21][22]
5-HT1E Vorlage:Abbr Vorlage:Abbr Vorlage:Abbr
5-HT1F 13 Human [18]
5-HT2A 1.6–55 Human [23][24]
5-HT2B 1.6–20 Human [25][26]
5-HT2C 0.63–6.5 Human [23][27]
5-HT3 5.8–300 Rodent [28][19]
5-HT4 Vorlage:Abbr Vorlage:Abbr Vorlage:Abbr
5-HT5A Vorlage:Abbr Vorlage:Abbr Vorlage:Abbr
5-HT6 55–81 Human [29][30]
5-HT7 48–56 Human [31][32][33]
α1 34 Human [34]
α2 73 Human [34]
  α2A 4.8 Human [31]
  α2B 27 Human [35]
  α2C 3.8 Human [31]
D1 426–1,420 Human [19][31]
D2 2,100–2,700 Human [34][36]
D3 2,840 Human [34]
D4 Vorlage:Abbr Vorlage:Abbr Vorlage:Abbr
D5 Vorlage:Abbr Vorlage:Abbr Vorlage:Abbr
H1 0.30–1.7 Human [37][34][31]
H2 437 Human [38]
H3 95,500 Human [38]
H4 >100,000 Human [38][39]
Vorlage:Abbrlink 820 Human [34]
Vorlage:Abbrlink 21,000 Human [40]
Vorlage:Abbrlink 30,200 Human [40]
Vorlage:Abbrlink 530 (Vorlage:Abbrlink) Human [40]
Values are Ki (nM), unless otherwise noted. The smaller the value, the more strongly the drug binds to the site.

Mianserin appears to exert its effects via antagonism of histamine and serotonin receptors, and inhibition of norepinephrine reuptake. More specifically, it is an antagonist/inverse agonist at most or all sites of the histamine H1 receptor, serotonin 5-HT1D, 5-HT1F, 5-HT2A, 5-HT2B, 5-HT2C, 5-HT3, 5-HT6, and 5-HT7 receptors, and adrenergic α1- and α2-adrenergic receptors, and additionally a norepinephrine reuptake inhibitor.[41][42] As an H1 receptor inverse agonist with high affinity, mianserin has strong antihistamine effects (e.g., sedation). Conversely, it has low affinity for the muscarinic acetylcholine receptors, and hence lacks anticholinergic properties.[34] Mianserin has been found to be a low affinity but potentially significant partial agonist of the κ-opioid receptor (Ki = 1.7 μM; EC50 = 0.53 μM),[40] similarly to some tricyclic antidepressants (TCAs).[43]

Blockade of the H1 and possibly α1-adrenergic receptors has sedative effects,[44] and also antagonism of the 5-HT2A and α1-adrenergic receptors inhibits activation of intracellular phospholipase C (PLC), which seems to be a common target for several different classes of antidepressants.[45] By antagonizing the somatodendritic and presynaptic α2-adrenergic receptors which function predominantly as inhibitory autoreceptors and heteroreceptors, mianserin disinhibits the release of norepinephrine, dopamine, serotonin, and acetylcholine in various areas of the brain and body.

Along with mirtazapine, although to a lesser extent in comparison, mianserin has sometimes been described as a noradrenergic and specific serotonergic antidepressant (NaSSA).[46] However, the actual evidence in support of this label has been regarded as poor.[47]



Àm Ààfàng wìrkt d’ Mianserin maischt dämpfend. D’ Ìndikàzioona vu dr Mianserin sìnd fascht d’ gliicha wia da vu da triziklischa Narvahailmìttel vu dr Imipramin-Typ. D’ mìttlera Tàgesmänga ìsch vu 30 bis 90 mg. Waga da meeglischa Naawawìkunga soll ma wahrend uff a reegelmassiga-n-Àrt s’ Blutbìld lüaga. D’ Hàlbwartzitt vu dr Mianserin ìsch äbb 17 Schtunda.[48] Wänn dr Pàziant grippa-n-ahnliga Symptooma hàt, Agranulozytose soll ma s’ Medikamant sofort .

Ma hàt schun aimol versüacht, d’ Laaweszitt vu Fààdawìrm dur mehrera Sübschtànza z’ verlängra. Doo drbi ìsch d’ Mianserin wìrklig gsìì.[49]

Naawawìrkunga

ändere

Uffheerung vu dr Behàndlung dur Mianserin kààt mìt verschìedena Wìrkunga: Narvazammabruch, Àngschtzäschtànd, Panikattacke,[50] nìedra Appetit odd’r sogàr Anorexie, Insomnie, Durchfall, Übelkeit, Erbrechen, so wia grippa-n-ahnliga Symptooma, wia Allergie un Juckreiz, unteràndrem.

A Ìwwerdoosa vu Mianserin kààt Schmarzruckgàng, tiafa Bewusstloosigkait, nìedra Blüatdruck, hoocha Blüatdruck, Harzjààga verursàcha, so wia-n-a Verlängerung vu dr QT-Zitt.[51]

Gegahailààzaiga un Wàrn

ändere

àndra Narvahailmìttel ìsch d’ Mianserin fìr d’ Behàndlung vu Narvakrànkhaita nìt ààgazaigt. D’ Mianserin màcht weeniger vegetàtiva Naawawìrkunga wia maischt triziklischa Narvahailmìttel. Trotzdam kààt sa laawendsgfoohrliga Schteerunga verursàcha, wia Blutbìldungsschteerunga, drunter Agranulozytose, odd’r Schaada àm Knochamàrk). Wagadam ìsch d’ Mianserin ìwwerhàuipt nìt àls Ärschtwàhlmìttel fìr d’ Behandlung vu dr Narvazammabruch bnutzt.

[52]

Kemii

ändere

Stereoisomerii

ändere

D’ Mianserin sätzt ma-n-àls a Ràzemàt ii, so zu sààga, àls a 1:1-Gmìsch vu dr (S)-Form un vu dr (R)-Form, obwohl d’ (S)-Form fàrmàkoloogisch àktiver ìsch.[53] A Ràzemàtschpàltung mìt Hìlf vu (+)- odd’r (–)-p-Ditoluoylwiisiira hàt ma-n-ànna 1999 bschrìewa.[54]

wia man ’s härschtällt

ändere

A Ìwwerblìck vu da Methooda fìr d’ Härschtällung vu dr Mianserin kààt ma ìn’ma Nohschlààgwark fìnda.[55]. Àui bi dr Ärschtààmäldung hàt d’ Firma Organon mehrera Methooda fìr d’ Härschtällung vu dam Medikamant vorgschlààga.[4] Mìt dr Zitt han sìch zwai Schtràtegia fìr dr Uffbàui vu dr Mianserin un wara hìttz’tàgs ààgwandet:

Uffbàui vum 7-Rìng üss Benzylanilin

ändere

Dr Waag ìwwer d’ 2-Benzylanilin (1) hàt dr Ärfìnder un wìrd àui ìn dr friahjera Literàtüür zitiart.[56] S’ Dibenzoazepin wìrd ìwwer a Imidchlorid (4) üss’m äntschpraachenda Chloracetanilid (3) mìt Phosphoroxychlorid uffbàuia. Dr Piperazinrìng vum tetraziklischa Rìngsyschteem vu dr Mianserin wìrd üss’m 1,2-Diamin (5), wo dur d’ Umsätzung mìt Methylamin äntschtànda ìsch, mìt Hìlf vu Oxalsiiradiethylester (6) un anschließender Reduktion der Piperazindion-Zwischenstufe (7) mit Diboran zum Zielmolekül (8) gschlossa. Dia Syntheesa vu Piperazin ìsch uffwandig àwwer selektiv, ìsch noch hìtt ààgwandt.[57]

 
D’ Härschtällung vu dr Mianserin ìwwer d’ Benzylanilin

Ànders kààt ma dr Piperazinrìng mìt Hìlf vum 1,2-Dibromethan uffbàuia.[58] S’ Lätscht ìsch àwwer schtàrk krabsärragend. D’ 2-Benzylanilin ìsch àui s’ Màteriàl, wo ma-n-àm Ààfàng bnutzt, fìr d’ kirààla Syntheesa vu dr Mianserin, wo-n-ànna 2015 veräffentligt worra ìsch.[59] Schtàtt Methylamin wìrd Phthalimid iigsätzt un s’ Dibenzazepin, wo ma bikummt, wìrd kirààl hydriart

Uffbàui vum 7-Rìng dur d’ Iifiahrung vun’ra Methyylagrupp

ändere

Dia Meegligkait fìr dr Uffbàui vum 7-Rìng mìt Hìlf vu 2-Aminobenzylalkohol hàt ma ìn dr schpeetera Pàtantaliteràtüür bschrìewa. Schun ànna 1975 hàt d’ Firma Akzo (wo bis 2007 d’ Mutterunternamma vun Organon gsìì ìsch), a Verfàhra ààgmäldet,[60] wo dia Methooda ààgwandt worra ìsch. Dia Methooda brüücht numma viar Etàppa: z’äärscht sätzt ma Styroloxid (1) mìt N-Methylaminoethanol (2) um, dernooh chloriert ma ìn dr Zwìscha-n-etàppa (4). Dernooh Umsetzung mìt 2-Aminobenzylalkohol (5) zur Diphenylpiperazin-Zwischenstufe (6) un Ringschluss mit Polyphosphorsäure zum Mianserin (7) synthetisiert.

 
D’ Härschtällung vu dr Miansering üss Styroloxid (ohna d’ Schutzgruppa)

 
D’ Härschtällung vu dr Miansering üss Styroloxid (mìt da Schutzgruppa)


[61]. </ref> [62]. </ref> [63] [64]

Wittera Forschung

ändere

D’ Nutzung vu dr Mianserin, fìr d’ Litt mìt Wohrnammungsschteerung halfa, wo düan mìt Narvapìllala bhàndelt wara, hàt ma-n-ìn klinischa Schtudia ; ìsch unklààr gsìì.[65][66]

z’ lasa

ändere

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Literàtüür

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ändere
  Commons: Mianserin – Sammlig vo Multimediadateie

Ainzelnohwiisa

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  1. ↑ The Merck Index: An Encyclopedia of Chemicals, Drugs, and Biologicals. 14. Auflage. Merck & Co., Whitehouse Station NJ 2006, ISBN 978-0-911910-00-1, S. 1064.
  2. ↑ 2,0 2,1 Vorlage:Linktext-Check in dr Datebank vu Sigma-Aldrich, abgruefen am 10. April 2011 (PDF).
  3. ↑ 3,0 3,1 Mianserin. In: Römpp Online. Georg Thieme Verlag, abgrüeft am 29. August 2021.
  4. ↑ 4,0 4,1 S’ Pàtant ìsch doo z’ fìnda: DE 1 695 556 (1967). In: Verfahren zur Herstellung von Piperazinderivaten. Willem Jacob van der Burg, Jaques Delobelle (Organon), abgruefen am 29. August 2021 (änglisch).
  5. ↑ 5,0 5,1 Index Nominum 2000: International Drug Directory. Taylor & Francis, 2000, ISBN 978-3-88763-075-1, S. 689 u. ff. (englisch, google.com).
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  19. ↑ 19,0 19,1 19,2 : Standard binding and functional assays related to medications development division testing for potential cocaine and opiate narcotic treatment medications. In: NIDA Res. Monogr.. 178, 1998, S. 440–66
  20. ↑ : Characterization of 5-hydroxytryptamine1B receptors in rat spinal cord via [125I]iodocyanopindolol binding and inhibition of [3H]-5-hydroxytryptamine release. In: J. Pharmacol. Exp. Ther.. 260, Nr. 2, 1992, S. 614–26
  21. ↑ : Identification of 5-hydroxytryptamine1D binding sites in human brain membranes. In: Synapse. 3, Nr. 1, 1989, S. 61–6
  22. ↑ : Molecular pharmacology of 5-HT1D recognition sites: radioligand binding studies in human, pig and calf brain membranes. In: Naunyn Schmiedebergs Arch. Pharmacol.. 337, Nr. 6, 1988, S. 595–601
  23. ↑ 23,0 23,1 : Agonist and antagonist actions of yohimbine as compared to fluparoxan at alpha(2)-adrenergic receptors (AR)s, serotonin (5-HT)(1A), 5-HT(1B), 5-HT(1D) and dopamine D(2) and D(3) receptors. Significance for the modulation of frontocortical monoaminergic transmission and depressive states. In: Synapse. 35, Nr. 2, 2000, S. 79–95
  24. ↑ : Comparison of [125I]iodolysergic acid diethylamide binding in human frontal cortex and platelet tissue. In: J. Neurochem.. 53, Nr. 1, 1989, S. 191–6
  25. ↑ : RS-127445: a selective, high affinity, orally bioavailable 5-HT2B receptor antagonist. In: Br. J. Pharmacol.. 127, Nr. 5, 1999, S. 1075–82
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  52. ↑ Mianserin 30 mg film-coated tablets. In: UK Electronic Medicines Compendium. Januar 2014, abgruefen am 29. August 2021 (änglisch).
  53. ↑ R. M. Pinder, A. M. L. Van Delft: The Potential Therapeutic Role of the Enantiomers And Metabolites Of Mianserin. In: Br.J.clin.Pharmac. Band 15, 1983, PMC 1427891 (freie Volltext) – (englisch).
  54. ↑ Pàtant: Jackson Roy William, Subasinghe Kamani Rupika (Monash University, Australia; Polychip Pharmaceuticals Pty. Ltd.): WO 99 16 769. In: Resolution of optically-active compounds. Abgruefen am 29. August 2021 (änglisch).
  55. ↑ Axel Kleemann, Jürgen Engel, Bernd Kutscher, Dietmar Reichert: Pharmaceutical Substances. 4. Auflage. Thieme-Verlag, Stuttgart 2000, ISBN 978-1-58890-031-9 (englisch).
  56. ↑ W J Van der Burg, I L Bonta, J Delobelle, C Ramon, B Vargaftig: Novel type of substituted piperazine with high antiserotonin potency. In: Journal of Medicinal Chemistry. Band 13, 1970, S. 35–39, doi:10.1021/jm00295a010 (englisch).
  57. ↑ Hulinska Hana, Polivka Zdenek, Jilek Jiri et al.: Experimental antiulcer agents: N-substituted 2-(4-methyl-1-piperazinyl)acetamides as pirenzepine models and some related compounds. In: Collection of Czechoslovak Chemical Communications. Band 53, 1988, S. 1820 (englisch, cas.cz).
  58. ↑ Pàtant: Olivie Jacques (Akzono): US 4 217 452 (1980). In: Synthesis for the preparation of tetracyclic compounds. Abgruefen am 29. August 2021 (änglisch).
  59. ↑ Piotr Roszkowski, Jan. K. Maurin, Zbigniew Czarnocki: The enantioselective synthesis of (S)-(+)-mianserin and (S)-(+)-epinastine. In: Beilstein Journal of Organic Chemistry. Band 11, 2015, S. 1509 (englisch, beilstein-journals.org).
  60. ↑ Pàtant: Olivie Jaques (AKZO N V Neth): DE 2 505 239 (1975). In: Verfahren zur Herstellung tetracyclischer Verbindungen. Abgruefen am 29. August 2021 (änglisch).
  61. ↑ Pàtant: Lypacewicz Maria K, Poslinska-bucewka Halina, Smolinska Jadwiga et al. (Instytut Farmaceutyczny, Warszawa): PL 175 287 (1998). In: Preparation of 1,2,3,4,10,14b-hexahydro-2-methyldibenzo[c,f]pyrazino[1,2-a]azepine.; Chem.Abstr. 130, 296 698 (1999). Abgruefen am 29. August 2021 (änglisch).
  62. ↑ Pàtant: Kisielowski-Ruppert, Lothar; Mörsdorf, Johann Peter; Grafe, Ingomar; Ahrens, Kurt-Henning (HEUMANN Pharma GmbH & Co): Verfahren zur Herstellung von 1,2,3,4,10,14b-Hexahydro-2-methyl-dibenzo[c,f]- pyrazino[1,2-a]azepin und seiner Salze (DE 4 305 659 (1993)). Abgruefen am 29. August 2021 (änglisch).
  63. ↑ Pàtant: Zhao, Zhenqiao (Shandong Renhetang Pharmaceutical Co., Ltd., Peop. Rep. China): Process for preparation of mianserin hydrochloride. (CN 101 544 644 (2009)). In: Chem.Abstr. Band 1 216 535, 2009 (englisch, espacenet.com [abgerufen am 29. August 2021]).
  64. ↑ Pàtant: Haider Akhtar, Bollinger Heinrich, Fischer Alan (S. A. SOCHINAZ, Switz.): Procédé de Preparation d’un composé tetracyclique (CH 678 623 (1990)). Abgruefen am 29. August 2021 (änglisch).
  65. ↑ V. Terevnikov, G. Joffe, J. H. Stenberg: Randomized Controlled Trials of Add-On Antidepressants in Schizophrenia. In: International Journal of Neuropsychopharmacology. Band 18, Nr. 9, 19. Mai 2015, S. pyv049, doi:10.1093/ijnp/pyv049, PMID 25991654, PMC 4576515 (freie Volltext) – (englisch).
  66. ↑ J. A. Vernon, E. Grudnikoff, A. J. Seidman, T. W. Frazier, M. S. Vemulapalli, P. Pareek, T. E. Goldberg, J. M. Kane, C. U. Correll: Antidepressants for cognitive impairment in schizophrenia--a systematic review and meta-analysis. In: Schizophrenia Research. Band 159, Nr. 2–3, November 2014, S. 385–94, doi:10.1016/j.schres.2014.08.015, PMID 25240772, PMC 4252251 (freie Volltext) – (englisch).
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