Selegilin

Selegilin
(IUPAC) ime
	(R)-N-metil-N-(1-fenilpropan-2-il)prop-1-in-3-amin
Klinički podaci
Robne marke	Eldepryl
AHFS/Drugs.com	Monografija
MedlinePlus	a697046
Identifikatori
CAS broj	14611-51-9 [14611-52-0] (HCl)
ATC kod	N04BD01 QN06AX90
PubChem	26757
DrugBank	DB01037
ChemSpider	24930
UNII	2K1V7GP655
KEGG	D03731
ChEBI	CHEBI:9086
ChEMBL	CHEMBL972
Hemijski podaci
Formula	C13H17N
Mol. masa	187,281 g/mol
SMILES	eMolekuli & PubHem
InChI
	InChI=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 ; Key: MEZLKOACVSPNER-GFCCVEGCSA-N
Farmakokinetički podaci
Bioraspoloživost	4,4% (oralno, na prazan stomak), 20% (oralno, nakon jela), 18% (flaster)
Vezivanje za proteine plazme	90%
Metabolizam	jetra
Poluvreme eliminacije	1,5 sata (oralno, jedna doza), 9 sata (oralno, hronično)
Izlučivanje	urin
Farmakoinformacioni podaci
Trudnoća	?
Pravni status	samo na recepat (SAD)
Način primene	Oralno, transdermalno, bukalno

Selegilin (Anipril, L-deprenil, Eldepril, Emsam, Zelapar. Jumex) je lek koji se koristio za tretman ranih stupnjeva Parkinsonove bolesti, depresije i senilne demencije. Pri normalnim kliničkim dozama on je selektivni ireverzibilni 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.^[6] Isto i važi i za standarne doze kad se lek primenjuje putem transdermalnog flastera.^[7] Selegilin pripada klasi lekova koji se nazivaju fenetilamini. Selegilin je metamfetaminski derivat sa propargilnom grupom vezanom za atom azota.

Hemija

Selegilin, N-metil-N-(2-propinil)-2-metil-1-feniletil-2-amin, se sintetiše putem alkilacije (–)-metamfetamina koristeći propargil bromid.^[8]^[9]^[10]^[11]

Reference

↑ Li Q, Cheng T, Wang Y, Bryant SH (2010). „PubChem as a public resource for drug discovery.”. Drug Discov Today 15 (23-24): 1052-7. DOI:10.1016/j.drudis.2010.10.003. PMID 20970519. edit
↑ Evan E. Bolton, Yanli Wang, Paul A. Thiessen, Stephen H. Bryant (2008). „Chapter 12 PubChem: Integrated Platform of Small Molecules and Biological Activities”. Annual Reports in Computational Chemistry 4: 217-241. DOI:10.1016/S1574-1400(08)00012-1.
↑ Hettne KM, Williams AJ, van Mulligen EM, Kleinjans J, Tkachenko V, Kors JA. (2010). „Automatic vs. manual curation of a multi-source chemical dictionary: the impact on text mining”. J Cheminform 2 (1): 3. DOI:10.1186/1758-2946-2-3. PMID 20331846. edit
↑ Joanne Wixon, Douglas Kell (2000). „Website Review: The Kyoto Encyclopedia of Genes and Genomes — KEGG”. Yeast 17 (1): 48–55. DOI:10.1002/(SICI)1097-0061(200004)17:1<48::AID-YEA2>3.0.CO;2-H.
↑ Gaulton A, Bellis LJ, Bento AP, Chambers J, Davies M, Hersey A, Light Y, McGlinchey S, Michalovich D, Al-Lazikani B, Overington JP. (2012). „ChEMBL: a large-scale bioactivity database for drug discovery”. Nucleic Acids Res 40 (Database issue): D1100-7. DOI:10.1093/nar/gkr777. PMID 21948594. edit
↑ Amsterdam, J. D. (2003). „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 of Clinical Psychiatry 64 (2): 208–14. DOI:10.4088/JCP.v64n0216. PMID 12633131.
↑ Cascade EF, Kalali AH (June 2007). „EMSAM: The First Year”. Psychiatry 2007. Arhivirano iz originala na datum 2010-02-28. Pristupljeno 2009-11-30.
↑ J. Knoll, E. Sanfai, DE 1568277 (1966).
↑ J. Hermann Nee Voeroes, Z. Ecsery, G. Sabo, L. Arvai, L. Nagi, O. Orban, E. Sanfai, 4564706 SAD patent 4564706 (1986)
↑ B. Brunova, M. Ferenc, EP 344675 (1989)
↑ Fowler, Joanna S. (1977). „2-Methyl-3-butyn-2-ol as an acetylene precursor in the Mannich reaction. A new synthesis of suicide inactivators of monoamine oxidase”. The Journal of Organic Chemistry 42 (15): 2637–7. DOI:10.1021/jo00435a026. PMID 874623.

Literatura

Nicholas C. Price, Lewis Stevens (1999). Fundamentals of Enzymology: The Cell and Molecular Biology of Catalytic Proteins (Third izd.). USA: Oxford University Press. ISBN 019850229X.
Eric J. Toone (2006). Advances in Enzymology and Related Areas of Molecular Biology, Protein Evolution (Volume 75 izd.). Wiley-Interscience. ISBN 0471205036.
Branden C, Tooze J.. Introduction to Protein Structure. New York, NY: Garland Publishing. ISBN: 0-8153-2305-0.
Irwin H. Segel. Enzyme Kinetics: Behavior and Analysis of Rapid Equilibrium and Steady-State Enzyme Systems (Book 44 izd.). Wiley Classics Library. ISBN 0471303097.
Robert A. Copeland (2013). Evaluation of Enzyme Inhibitors in Drug Discovery: A Guide for Medicinal Chemists and Pharmacologists (2nd izd.). Wiley-Interscience. ISBN 111848813X.
Gerhard Michal, Dietmar Schomburg (2012). Biochemical Pathways: An Atlas of Biochemistry and Molecular Biology (2nd izd.). Wiley. ISBN 0470146842.

Povezano

Vanjske veze

Deprenyl (Selegiline) Can Slow Parkinson's Disease Safely Arhivirano 2012-03-14 na Wayback Machine-u According to the British Medical Journal
FDA Approves Emsam (Selegiline) as First Drug Patch for Depression

[1] Li Q, Cheng T, Wang Y, Bryant SH (2010). „PubChem as a public resource for drug discovery.”. Drug Discov Today 15 (23-24): 1052-7. DOI:10.1016/j.drudis.2010.10.003. PMID 20970519. edit

[2] Evan E. Bolton, Yanli Wang, Paul A. Thiessen, Stephen H. Bryant (2008). „Chapter 12 PubChem: Integrated Platform of Small Molecules and Biological Activities”. Annual Reports in Computational Chemistry 4: 217-241. DOI:10.1016/S1574-1400(08)00012-1.

[3] Hettne KM, Williams AJ, van Mulligen EM, Kleinjans J, Tkachenko V, Kors JA. (2010). „Automatic vs. manual curation of a multi-source chemical dictionary: the impact on text mining”. J Cheminform 2 (1): 3. DOI:10.1186/1758-2946-2-3. PMID 20331846. edit

[4] Joanne Wixon, Douglas Kell (2000). „Website Review: The Kyoto Encyclopedia of Genes and Genomes — KEGG”. Yeast 17 (1): 48–55. DOI:10.1002/(SICI)1097-0061(200004)17:1<48::AID-YEA2>3.0.CO;2-H.

[5] Gaulton A, Bellis LJ, Bento AP, Chambers J, Davies M, Hersey A, Light Y, McGlinchey S, Michalovich D, Al-Lazikani B, Overington JP. (2012). „ChEMBL: a large-scale bioactivity database for drug discovery”. Nucleic Acids Res 40 (Database issue): D1100-7. DOI:10.1093/nar/gkr777. PMID 21948594. edit

[6] Amsterdam, J. D. (2003). „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 of Clinical Psychiatry 64 (2): 208–14. DOI:10.4088/JCP.v64n0216. PMID 12633131.

[Cascade01-7] Cascade EF, Kalali AH (June 2007). „EMSAM: The First Year”. Psychiatry 2007. Arhivirano iz originala na datum 2010-02-28. Pristupljeno 2009-11-30.

[8] J. Knoll, E. Sanfai, DE 1568277 (1966).

[9] J. Hermann Nee Voeroes, Z. Ecsery, G. Sabo, L. Arvai, L. Nagi, O. Orban, E. Sanfai, 4564706 SAD patent 4564706 (1986)

[10] B. Brunova, M. Ferenc, EP 344675 (1989)

[11] Fowler, Joanna S. (1977). „2-Methyl-3-butyn-2-ol as an acetylene precursor in the Mannich reaction. A new synthesis of suicide inactivators of monoamine oxidase”. The Journal of Organic Chemistry 42 (15): 2637–7. DOI:10.1021/jo00435a026. PMID 874623.

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