Izvorni kod stranice Selegilin

{{Drugbox-lat
| verifiedrevid = 464388442
| IUPAC_name = (''R'')-''N''-metil-''N''-(1-fenilpropan-2-il)prop-1-in-3-amin
| image = Selegilin.svg
| image2 = Selegiline-3D-balls.png

<!--Clinical data-->
| tradename = Eldepryl
| Drugs.com = {{drugs.com-lat|monograph|selegiline-hydrochloride}}
| MedlinePlus = a697046
| pregnancy_category = C <small>([[US]])</small>
| legal_status = samo na recepat <small>([[SAD]])</small>
| routes_of_administration = Oralno, transdermalno, [[Obraz|bukalno]]

<!--Pharmacokinetic data-->
| bioavailability = 4,4% (oralno, na prazan stomak), 20% (oralno, nakon jela), 18% (flaster)
| protein_bound = 90%
| metabolism = jetra
| elimination_half-life = 1,5 sata (oralno, jedna doza), 9 sata (oralno, hronično)
| excretion = urin

<!--Identifiers-->
| CASNo_Ref = {{cascite|correct|CAS}}
| CAS_number_Ref = {{cascite|correct|}}
| CAS_number = 14611-51-9
| CAS_supplemental = [14611-52-0] <small>(HCl)</small>
| ATC_prefix = N04
| ATC_suffix = BD01
| ATC_supplemental =  {{ATCvet|N06|AX90}}
| PubChem = 26757
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
 | DrugBank = DB01037
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 24930
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 2K1V7GP655
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = D03731
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 9086
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 972

<!--Chemical data-->
| C=13 | H=17 | N=1 
| molecular_weight = 187,281 g/mol
| smiles = C#CCN([C@@H](Cc1ccccc1)C)C
| InChI = 1/C13H17N/c1-4-10-14(3)12(2)11-13-8-6-5-7-9-13/h1,5-9,12H,10-11H2,2-3H3/t12-/m1/s1
| InChIKey = MEZLKOACVSPNER-GFCCVEGCBI
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C13H17N/c1-4-10-14(3)12(2)11-13-8-6-5-7-9-13/h1,5-9,12H,10-11H2,2-3H3/t12-/m1/s1
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = MEZLKOACVSPNER-GFCCVEGCSA-N
}}

'''Selegilin''' (''Anipril'', ''L-deprenil'', ''Eldepril'', ''Emsam'', ''Zelapar''. ''Jumex'') je [[lek]] koji se koristio za tretman ranih stupnjeva [[Parkinsonova bolest|Parkinsonove bolesti]], [[klinička depresija|depresije]] i [[senilna demencija|senilne demencije]]. Pri normalnim kliničkim dozama on je selektivni ireverzibilni [[Inhibitor monoaminske oksidaze|MAO-B inhibitor]]. Međutim, u većim dozama on gubi svoju specifičnost i takođe je inhibir MAO-A. Dijetarne restrikcije su uobičajene za MAOI tretmane, ali je utvrđeno da one nisu neophodne pri primeni niskih doza.<ref>{{cite journal | last = Amsterdam | first = J. D. | title = A double-blind, placebo-controlled trial of the safety and efficacy of selegiline transdermal system without dietary restrictions in patients with major depressive disorder | journal = Journal of Clinical Psychiatry | volume = 64 | issue = 2 | pages = 208–14 | publisher = | date = 2003 | url = | doi =10.4088/JCP.v64n0216 | id = | accessdate = | pmid = 12633131}}</ref> Isto i važi i za standarne doze kad se lek primenjuje putem transdermalnog flastera.<ref name=Cascade01>{{cite journal
|author=Cascade EF, Kalali AH
|journal=Psychiatry 2007
|month=June
|year=2007
|title=EMSAM: The First Year
|url=http://www.psychiatrymmc.com/emsam-the-first-year/
|accessdate=2009-11-30
|archive-date=2010-02-28
|archive-url=https://web.archive.org/web/20100228220220/http://www.psychiatrymmc.com/emsam-the-first-year/
|dead-url=yes
}}</ref> Selegilin pripada klasi lekova koji se nazivaju [[fenetilamin]]i. Selegilin je [[levometamfetamin|metamfetaminski]] [[derivat (hemija)|derivat]] sa [[propargil]]nom grupom vezanom za atom azota.

== Hemija ==
Selegilin, N-metil-N-(2-propinil)-2-metil-1-feniletil-2-amin, se sintetiše putem alkilacije (–)-[[metamfetamin]]a koristeći [[propargil bromid]].<ref>J. Knoll, E. Sanfai, {{Cite patent|DE|1568277}} (1966).</ref><ref>J. Hermann Nee Voeroes, Z. Ecsery, G. Sabo, L. Arvai, L. Nagi, O. Orban, E. Sanfai, {{US patent| 4564706}} (1986)</ref><ref>B. Brunova, M. Ferenc, {{Cite patent|EP|344675}} (1989)</ref><ref>{{cite journal |doi=10.1021/jo00435a026 |title=2-Methyl-3-butyn-2-ol as an acetylene precursor in the Mannich reaction. A new synthesis of suicide inactivators of monoamine oxidase |year=1977 |last1=Fowler |first1=Joanna S. |journal=The Journal of Organic Chemistry |volume=42 |issue=15 |pages=2637–7 |pmid=874623}}</ref>
:[[Datoteka:Selegiline synthesis.png|500px|center]]

== Reference ==
{{reflist}}

== Literatura ==
{{refbegin|2}}
* {{PriceEnzymology3rd}}
* {{TooneAdvancesInEnzymology}}
* {{Branden ProteinStructure2nd}}
* {{SegelEnzymeKinetics}}
* {{CopelandEvaluationOfEnzymeInhibitors2nd}}
* {{MichalBiochemicalPathways}}
{{refend}}

== Povezano ==
* [[D-Deprenil]]
* [[Rasagilin]]

== Spoljašnje veze ==
* [http://www.antiaging-magazine.com/news/news_1.html Deprenyl (Selegiline) Can Slow Parkinson's Disease Safely] {{Webarchive|url=https://web.archive.org/web/20120314075845/http://www.antiaging-magazine.com/news/news_1.html |date=2012-03-14 }} According to the British Medical Journal
* [http://www.fda.gov/bbs/topics/NEWS/2006/NEW01326.html FDA Approves Emsam (Selegiline) as First Drug Patch for Depression]
{{-}}
{{Antidepresivi}}
{{Antioksidansi}}
{{Dopaminergici}}

[[Kategorija:Nootropici]]
[[Kategorija:Inhibitori monoaminske oksidaze]]
[[Kategorija:Antiparkinsonski lekovi]]
[[Kategorija:Amfetamini]]
[[Kategorija:Alkini]]
[[Kategorija:Enantiomerno čisti lekovi]]