ija 3 m Adrenergični č sistem 2 adrenergični agonisti/antagonisti č ska ke acevt Farm Izr. Izr prof pr. of dr. dr Marko Mark o Anderluh 4.
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1 acevts ska kem mija 3 Farm Adrenergični sistem 2 adrenergični agonisti/antagonisti Izr. prof. dr. Marko Anderluh 4. april 2013
2 adrenergični agonisti Agonisti 2 aktivirajo presinaptične receptorje in zavrejo nadaljnje sproščanje noradrenalina Učinek? Antihipertenzivi, proti glavkomu, analgetiki, mišični relaksanti
3 adrenergični agonisti Prototip Cl Klonidin HN HN N Cl
4 adrenergični agonisti apraklonidin brimonidin tizanidin Cl N N NH 2 Cl NH 2 guanabenz guanfacin
5 adrenergični agonisti SAR NH namesto CH 2 mostu gvanidin ali obročni ekvivalent pka 8.3 pri fiziološkem ph 80% v ionizirani obliki Cl substitucija na o poziciji Ar, lahko tudi Me: KAJ SE SPREMENI?! logp = 1,6
6 adrenergični antagonisti
7 adrenergični antagonisti Fenoksibenzamin: ireverzibilni neselektivni antagonist N Cl + N O O nukleofil
8 NA NA + Fenoksibenzamin Sam Fenoksibenzamin Izguba receptorjev Ni več Maksimalnega učinka [Agonist], mg/kg
9 Neselektivni adrenergični Preteklost antagonisti strukturno podobni imidazolinskim α agonistom antihipertenziva (feokromocitom) tolazolin N H N Me HO N N H N Ne razlikujejo med 1 in 2 fentolamin
10 adrenergični antagonisti kinazolini O N N N O O O N NH 2 Prazosin
11 adrenergični antagonisti kinazolini N O R MeO N N MeO N t1/2 [ur] trajanje [ur] prazosin terazosin 12 >18 doksazosin O O NH 2 Prazosin Terazosin Doksazosin O O
12 adrenergični antagonisti kinazolini Selektivni na -prostata
13 adrenergični antagonisti simptomatsko zdravljenje benigne hiperplazije prostate blokatorji α1 receptorjev odgovorni za kontrakcijo gl. mišic prostate, uretre in vratu mehurja olajša uriniranje Terapija hipertenzije
14 SAR adrenergični antagonisti
15 Johimbin adrenergični antagonisti Ni v klinični uporabi, prehaja v CŽS => povečana č srčna č frekvenca, krvni pritisk, tremor, psihične motnje, tahikardija, slabost, bruhanje v raznih produktih za hujšanje
16 Johimbin adrenergični antagonisti v raznih produktih za hujšanje, še kaj?
17 adrenergični antagonisti Mirtazapin Tetraciklični antidepresiv Številne tarče; 5 HT, privzem NA, tudi 2 NA, tudi 2 Centralno delujoč
18 Compound SERT NET DAT Amoxapine Loxapine Maprotiline Mianserin Mirtazapine i 2,40 0 5,80 0 4, ,31 0 9,00 2, ,00 0 9, mac α 1 α 2 D 2 H HT 1 1A HT 2A h , ,60 0 2,40 0 9, , ,19 7 >100 1,64 >100 >5,4? ,000 0, Oxaprotiline 3, , ,0 00 2, ,0 00? 21 2,90 0
19 adrenergični agonisti/antagonisti 1 : Srce stimulacija preko camp Ca ++ kanal srčni utrip in moč 2 : Gladke mišice žil, bronhov, uterusa, GIT: inhibicja preko camp MLCK kontrakcija krvni pritisk, bronhokonstrikcija ij V prečnoprogastih mišicah obraten učinek
20 adrenergični agonisti Sklopljeni s proteinom G (G s ); aktivira adenilat ciklazo, biosinteza camp Povezani s Ca2+ kanalčki zaviranje V gladkih mišicah bronhijev, maternici, iigit ( motilitete), jetrih Relaksacija gladkih mišic širjenje dihalnih poti, relaksacija maternice Agonisti ANTIASTMATIKI, TOKOLITIKI Antagonisti ne v terapiji
21 adrenergični agonisti SAR fenetilaminov Pomemben del za beta učinke Vedno prisotna OH H O NH-R 1 R HO R Razlikovanje med Splošnimi, beta in 2 učinki Če je R= CH 3 se učinek premakne na 2
22 adrenergični agonisti Izoprenalin (izoproterenol) Izoetarin 1, 2 neselektiven Str. učinkič 1 < 2 razmeroma selektiven lk Problem kateholov? COMT!
23 adrenergični agonisti Problem kateholov: COMT Bioizosterne zamenjave m OH Karboksilna skupina Ester Amid O O H OH H OH O H H H OH N Me N HO O H 2 N HO HO HO A B C H N neaktiven 2 -antagonist 2 -antagonist
24 adrenergični agonisti Soterenol Salbutamol Sulfonamidna skupina: Daljši t1/2 (ni COMT substrat) Slaba 2 selektivnost Hidroksimetilenska skupina t butilna skupina Daljši Dljši1/2 t1/2 (4h) prvi i selektivni i 2 agonist! 2000x selektivnejši od izoprenalina Možno podaljšanje do R enantiomer hidroksietilenske sk. 68x učinkovitejši
25 adrenergični agonisti selektivnost OH OH OH OH OH NHSO 2 CH 3 HO HN HO HN HO HN Izoproterenol Soterenol Salbutamol 2 / 1 = 1 2 / 1 = 6 2 / 1 = 59
26 adrenergični agonisti terbutalin fenoterol 3,5 dihidroksi derivat Daljši t1/2 (slab COMT substrat) dobra 2 selektivnost Bronhodilatator, tokolitik N podaljšanje Dodaten stereogeni center ni bistvenega podaljšanja delovanja, je pa!
27 adrenergični agonisti formoterol N podaljšanje + bioizoster Dodaten stereogeni center Do 12 h delovanja (salbutamol 4 h) salmeterol Biiiistveno N podaljšanje Vezava v hidrofobno regijo Podaljšano delovanje, 12 h Večja selektivnost Advair - prodaja 2010
28 adrenergični agonisti indakaterol N podaljšanje Izjemno podaljšano delovanje, 1x/dan
29 adrenergični agonisti Ritodrin Relaksacija gladkih mišic uterusa preprečevanje prezgodnjega rojevanja/splava N voluminozen substituent: velika 2 selektivnost lkti t Str. učinki glukoneogeneza (hiperglikemija)
30 adrenergični agonisti SAR m mesto; mesto; bioizosteri OH p mesto; OH ni nujna N voluminozen substituent: velika 2 selektivnost Dodatno N podaljšanje daljši t1/2, daljše zadrževanje dž v telesu tl Dobra BU, tudi per os
31 adrenergični agonisti Mirabegron Prvotno terapija debelosti (+lipoliza) Terapija prekomernega uriniranja/inkontinence i i FDA dovoljenje j julij j2012 ( drug approvals 2012 pt xiv.html )
32 adrenergični agonisti solabegron Podobno kot mirabegron, II faza KT amibegron Centralni učinek anksiolitik, antidepresiv Prekinjena klinična testiranja 2008
33 adrenergični ant/agonisti ws/neurotrans.html 1 receptorji aktivirajo adenilat ciklazo, biosinteza camp Lokacija na srčnomišičnih celicah, 4 je učinki sekrecija iz žlez slinavk sekrecija k renina iz celic jukstaglomerularnega l aparata lipoliza v maščobnem tkivu
34 adrenergični agonisti Agonisti uporabni? Kardiostimulatorno delovanje terapija srčnega popuščanja OH OH OH Prenalterol l 1 / 2 = 13 O OH H N HO HN
35 adrenergični agonisti Razlikovanje med podtipi receptorjev HO HN HO HN HO O N H OH OH HO OH OH Izoproterenol: Terbutalin: Prenalterol: 1 = 2 2 >> 1 1 >> 2
36 adrenergični antagonisti Prehod iz agonista v antagonist Izoprenalin (izoproterenol) dikloroizoprenalin 1, 2 neselektiven lki Str. učinki DELNI AGONIST neselektiven
37 adrenergični antagonisti 1. generacija ariloksipropanolamini dikloroizoprenalin pronetalol DELNI AGONIST propranolol Delni AGONIST z nižjo intrinzično č aktivnostjo Še vedno neselektiven ANTAGONIST! (10 20x učinkovitejši) ( j ) Še vedno neselektiven
38 adrenergični antagonisti 1. generacija ariloksipropanolamini pronetalol l propranolol l Učinkovit R enantiomer Učinkovit S enantiomer!!!
39 adrenergični antagonisti 1. generacija ariletanolamini pronetalol l sotalol tll Tudi kot antiaritmik deluje na K+ kanalčke
40 adrenergični antagonisti 1. generacija ariloksipropanolamini: modifikacija naftilnega substituenta timolol pindolol O OH N H N H
41 adrenergični antagonisti 1. generacija učinki: Proti angini pectoris, proti aritmijam Antihipertenzivi! Srce zmanjšan output Ledvice izločanje renina CŽS dejavnost simpa ka Učinek odvisen od dejavnosti pacienta!
42 adrenergični antagonisti Heart rate recorded continuously in a spectator watching a live y p g football match, showing the effect of the beta-adrenoceptor antagonist oxprenolol.
43 adrenergični antagonisti 2. generacija prva generacija str. učinki; utrujenost, bronhokonstrikcija, CŽS učinki (sedacija, nočne more, vrtoglavica) 1 selektivne učinkovine
44 adrenergični antagonisti 2. generacija praktolol atenolol metoprolol O N H OH H O NH 2 Selektivni, povečana polarnost ne prehajajo HEB v večji meri manj CŽS učinkov
45 adrenergični antagonisti 2. generacija bisoprolol nebivolol Dolg t1/2 aplikacija 1x dnevno, še povečana selektivnost
46 adrenergični antagonisti 2. generacija Od kod selektivnost?
47 adrenergični antagonisti 3. Generacija jakost vezave na receptorje esmolol ksamoterol Selektivni, povečana polarnost, ester izjemno kratek t1/2 Selektivni, povečana polarnost, delni agonist?!?
48 SAR adrenergični antagonisti
49 adrenergični antagonisti FK parametri t1/2: esmolol (9 min), propranolol (1 6 ur), atenolol (7 ur), sotalol (12 ur), nadolol(22ur) vezava na proteine: propranolol, labetalol (90), pindolol (50) bisoprolol, nadolol (30) atenolol (10), sotalol(5) metabolizem: maščobotopne spojine razgradnja pri prvem prehodu skozi jetra. Variira. propranolol in acebutolol aktivni metaboliti
50 adrenergični antagonisti Metabolizem? Primer propranolol
51 Biosinteza A, NA metiltirozin -metildopa karbidopa Zaviralec tirozin hidroksilaze terapija feokromocitoma Lažni substrat terapija hude hipertenzije Zaviralec DOPA dk dekarboksilaze bkl terapija parkinsonizma
52 Biosinteza A, NA metiltirozin mesto delovanja
53 Shranjevanje A, NA v veziklih Rezerpin Zavira transport NA v vezikle (vezikularni prenašalec) antihipertenziv gvanetidin Zavira sproščanje NA iz veziklov antihipertenziv
54 Zaviralci privzema A, NA Triciklični antidepresivi (imipramin) Efedrin Amfetamin
55 Skrivnosti učinka kokaina Agonistični adrenergični učinek na periferiji zaviranje (ponovnega) privzema CŽS zaviralec privzema DA, NA in S
56 Zaviralci metabolizma A, NA Zaviralci MAO Vpliv na vse monoamine Tranilcipromin moklobemid
57 Zaviralci metabolizma A, NA Ostali zaviralci MAO Vpliv na vse monoamine, terapija Parkinsonove bolezni
58 Zanimivost udarec zafarmacevtske velikane novartis izgubil v indiji/305717
59 Literatura predavanj G. L. Patrick: An introduction i to medicinal i chemistry, Oxford University press, 4. izdaja: 23. poglavje Foye s Principles of Medicinal Chemistry, 6. izdaja: 13. poglavje
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