Central and Peripheral Sympatholytics and Vasodilators
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1 Central and Peripheral Sympatholytics and Vasodilators Chapter 24, page 781 You are expected to read these pages before you come to the lecture Morten Grøtli Department of Chemistry and Molecular Biology verview β-adrenergic blocking drugs α-adrenergic blocking drugs Mixed α/β-adrenergic blocking drugs Centrally acting sympatholytics Adrenergic neuron blocking drugs Vasodilator Phosphodiesterase inhibitors itrodilator Ganglionic blocker drugs Endothelial antagonists 1
2 Mechanism of vascular smooth muscle and relaxation β-adrenergic blocking drugs eart Blood vessels 2
3 -Adrenergic Receptor Blockers onselctive -Adrenergic Receptor Blockers 1-selective 3
4 -Adrenergic Blockers Drugs Mechanism of action C 3 C 3 2 R Doxazosin R = Prazosin R = Terazosin R = C 3 C 3 C 3 2 Alfuzosin Mixed / -Selective Adrenergic Blockers 4
5 Centrally Acting Sympatholytics Centrally Acting Sympatholytics Cl Cl Clonidine Cl 2 Cl Guanabenz Cl Cl Guanfacine 2 C 3 Cl 3 C 2 2 Moxonidine Rilmenidine Agmatine C 2 5 Efaroxan 5
6 Metabolites Adrenergic euron Blocking Agents 6
7 Direct-Acting Vasodilators Potassium Channel peners 7
8 Potassium Channel peners Potassium Channel peners 8
9 Phosphordiesterase Inhibitors itrodilators itroglycerin Isosorbide dinitrate 9
10 Ganglinic Blockers Endotheline Receptor Blockers CYP3A4 (major) CYP2C9 (minor) S C 3 S S 10
11 Endotheline Receptor Blockers C(C 3 ) 3 3 C S C 3 C 3 C C 3 Ph Ph Bosentan S Cl S 3 C 3 C a Sitaxentan Ambrisentan Angiotensin-Converting Enzyme Inhibitors, Antagonists and Calcium Blockers Chapter 23, page 747 You are expected to read these pages before you come to the lecture Morten Grøtli Department of Chemistry and Molecular Biology (grotli@chem.gu.se) 11
12 verviwe Renin inhibitors Angiotensin-converting enzyme (ACE) inhibitors Angiotensin II receptor blockers Calcium channel blockers Asp Arg Val Tyr Ile is Pro Phe is Leu Val Ile R Angiotensinogen Renin Asp Arg Val Tyr Ile is Pro Phe is Leu Angiotensin I Angiotensin II Angiotensin Converting Enzyme Asp Arg Val Tyr Ile is Pro Phe Aminopeptidase The Reninangiotensin pathway Arg Val Tyr Ile is Pro Phe Angiotensin III Endo- and Exopeptidase Inactive Peptides Asp Arg Val Tyr Ile is Pro Angiotensin
13 Renin release and effects Bradykinin pathway 13
14 rally Active Renin Inhibitors S is 9 3 C S S Compound A Phe 8 Leu 10 Zankiren (A-72517) X 3 C R 2 R 1 3 C onpeptide Template Aliskiren ACE inhibitors General structure: R 3 R2 RIG R 1 Benazepril C2 5 C 2C Compounds Ring R 1 R 2 R 3 Lisinopril C 2 (C 2) 4 2 C 3 Moexipril C 3 C 3 C 2C 3 2C Perindopril C 3 C 2C 3 C 3 2C Quinapril C 3 C 2C 3 2C Ramipril C 3 C 2C 3 2C S Spirapril S C 3 C 2C 3 2C Trandolapril C 3 C 2C 3 2C 14
15 A model of substrate binding to carboxypeptidase A and ACE Inhibitor binding 15
16 Transition state Bioactivation of enapril 16
17 Model of ACE inhibitor binding Bioactivation of fosinopril ACE Zn 2+ X P 3 ACE ydrophobic site 17
18 SAR Metabolic routes 18
19 Peptide Mimetics: Design of Antagonists/Agonists Structural comparison Cl S
20 Structures of losartan analogues C 2 2 C C 3 C 3 Valsartan Irbesartan Telmisartan 3 C C 3 C 3 C 3 Candesartan cilexetil lmesartan medoxomil Metabolism 20
21 Cellular mechanism for influx, efflux and sequestering of Ca 2+ Chemical classes 21
22 Structure of Ca 2+ Channel Blockers General structure: R 1 R 2 5 X C R 3 Isradipine: 3 C (C 3 ) 2 C 2 C C 3 C 2 C 3 Compounds R 1 R 2 R 3 X Amlodipine C 2 (C 2 ) 2 2 C 2 C 2 C 3 C 2 C 3 2-Cl Clevidipine C 3 C 2 C 2 C nc 3 7 C 2 C 3 2,3-Cl 2 Felodipine C 3 C 2 C 2 C 3 C 2 C 3 2,3-Cl 2 icardipine C 3 C 2 (C 2 ) 2 C3 2 C C 6 5 C 2 C ifedipine C 3 C 2 C 3 C 2 C C 3 imodipine C 3 C 2 C 2 C 2 C 3 C 2 CC isoldipine C 3 C 2 C 2 C(C 3 ) 2 C 2 C Structures of isradipine and its analogous 3-nitro derivatives 3 C C 3 3 C C 3 (C 3 ) 2 C 2 C C 2 C 3 (C 3 ) 2 C 2 C 2 Isradipine (Calcium channel blocker) P (Calcium channel activator) 22
23 Conformation 3 C 6 2 C 3 C Ar C 3 R ring 5 ring ring ring 3 R Antiperiplanar relationship between carbonyl and double bond Synplanar relationship between carbonyl and double bond xidation 23
24 Ziconotide Questions 1.Läkemedel Y består av två aktiva substanser 1 och 2. Föreslå farmakologisk effekt av läkemedel Y. 2.Förklara verkningsmekanismen för 1. 3.Förklara verkningsmekanismen för 2. 4.Förklara struktur-aktivitetssambanden för den läkemedelsgrupp som 2 tillhör. 5.ar 3 tilsvarande/ olik farmakologisk effekt sammanliknat med 1? Förklara. 24
25 Questions 1.Förklara vilka strukturelement som är viktiga för aktiviteten av läkemedel 4. 2.Förklara hur strukturen för 4 kan modifieras för att ge ökad aktivitet och receptorspecificitet. Vilka modifikationer ska man undgå att göra? Questions 1. ur måste strukturen för 5 ändras för att bli ett kalciumantagonistiskt 1,4- dihydropyridinderivat? Förklara struktur-effektsambanden för 1,4-dihydropyridinderivat. Illustrera med en figur. 25
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