Receptor Sites and Drug Design
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1 Receptor Sites and Drug Design Case Study: piates use for Anesthesia & analgesia 1
2 PAI 2
3 The functional groups and their placement in three-dimensional space determines to a large degree a molecule s biological activity. The portion of a molecule that determines the biological effects of a drug is called the pharmacophore. 3
4 Medicinal Uses for Morphine: as an adjunct to general anesthesia in epidural anesthesia or intrathecal analgesia for palliative care (i.e. to alleviate pain without curing the underlying reason for it, usually because the latter is found impossible) as an antitussive for severe cough; (Codeine is better) Codeine 4
5 H CH 3 Codeine (1832) H Morphine (~1805) xycodone (1916) Heroin (1874) 5
6 An analgesic (also known as a painkiller) is any member of the group of drugs used to relieve pain (achieve analgesia). The word analgesic derives from Greek an- ("without") and algos ("pain"). A general anesthetic is a drug that brings about a reversible loss or alteration of consciousness. Local anesthesia is any technique to render part of the body insensitive to pain without affecting consciousness. 6
7 Why do humans have receptor sites for such a complex structure? 7
8 Endorphins ("endogenous morphine") are endogenous opioid peptides (discovered in 1974) An enkephalin is a pentapeptide involved in regulating perception of pain in the body 8
9 piate antagonist-reversal agent CH 3 piate reversal agent (competitive antagonist) -high affinity for μ-receptor site H CH 3 xycodone 9
10 piate antagonist-reversal agent piate reversal agent (blocks pleasure centers) -used for treatment of alcohol dependence (alcoholism) & opiate addiction 10
11
12 3 12
13 a new opiate, which was based on the piperidine structure was introduced: Fentanyl is about 100 X the potency of morphine 13
14 How does fentanyl and morphine compare? 3 14
15 Commercial Synthesis of Fentanyl Cl H 2 Br H 2 K 2 C 3 abh 4 H H H Fentanyl 15
16 Anaquest Approach to 4,4-Disubstituted Piperdines: H 2 C HCl reflux KC H CH H EtH H 3 + C 2 Et H Et 3 Cl C 2 Et C 2 Et H 2 Pd(H) 2 /C H 2 16
17 C 2 Et Medicinal rganic Lecture Chemistry Series H 2 S K 2 C 3 Br Br K 2 C 3 S C 2 Et C 2 Et C 2 Et Br 5-10X more potent than fentanyl 10,000 X more potent K 2 C 3 than morphine Modify ester- ew class of drugs? Fast acting-less potent than fentanyl 17
18 rganic compounds are transformed to molecules of increasing polarity, then excreted by the kidneys: activation B inactivation A inactivation inactivation C B ase I: xidation-reduction Hydrolysis Demethylation ase II: Synthesis (acylation, methylation etc.) Conjugation-covalent bonding with carbohydrates, AA or sulfates 18
19 Metabolism of Piperidine Analgetics 19
20 C 2 H H Known to be inactive metabolite LAH Cl H R Et 3 Et 3 Cl R 20
21 R armacological Profile: MHP: ED 50 =0.06 potent analgetic MHP: >15 min long acting analgetic K i = 3-9 (strength of μ receptor binding) Anesthesia 2-3 Minutes-short acting 21
22 Esters & Carbonates 22
23 Ultra short acting analgesic Remifentanil is a specific μ-receptor agonist. It is potent & short acting- (1/2 life~4 min) a reduction in sympathetic nervous system tone, Slight respiratory depression and analgesia. dose-dependent decrease in heart rate arterial pressure respiratory rate and tidal volume near normal 23
Case Study: Opiates use for Anesthesia & analgesia
rganic Lecture Series Receptor Sites and Drug Design Case Study: piates use for Anesthesia & analgesia 52 rganic Lecture Series PAI 53 Drug interactions at the cellular level rganic Lecture Series The
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