Introduction to Medicinal Chemistry. CHEM 5720 Dr. James J. Kiddle. Course Goals
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1 Introduction to Medicinal Chemistry CEM 5720 Dr. James J. Kiddle Course Goals To introduce the basic chemical principles which control drug action in biological systems To demonstrate the application of chemical principles to the design and development of drugs in therapeutic use. To examine the pharmacology of specific drug classes and their site of action in biological systems. To highlight the interdisciplinary nature of medicinal chemistry in its efforts to develop new therapeutics for treating diseases. 1
2 What is Medicinal Chemistry? The Definitions: Medicinal Chemistry: The Development of biochemical rationales for the action of chemicals in a biological system. Pharmaceutical Chemistry: The modification of structures with known physiologic or pharmacological effects and the analysis of drugs. Double, double toil and trouble; Fire burn, and cauldron bubble. Fillet of a fenny snake, In the cauldron boil and bake; Eye of newt and toe of frog, Wool of bat and tongue of dog, Adder's fork and blind-worm's sting, Lizard's leg and owlet's wing, For a charm of powerful trouble, Like a hell-broth boil and bubble. Double, double toil and trouble; Fire burn and cauldron bubble. Scale of dragon, tooth of wolf, Witches' mummy, maw and gulf f the ravin'd salt-sea shark, Root of hemlock digg'd i' the dark, Liver of blaspheming Jew, Gall of goat, and slips of yew Silver'd in the moon's eclipse, ose of Turk and Tartar's lips, Finger of birth-strangled babe Ditch-deliver'd by a drab, Make the gruel thick and slab: Add thereto a tiger's cauldron, For the ingredients of our cauldron. Double, double toil and trouble; Fire burn and cauldron bubble. Cool it with a baboon's blood, Then the charm is firm and good. Macbeth, IV, i 2
3 istory 3100 B.C. Medicines described in Chinese book of herbs (Pentsao), some of which contain constituents of modern medicine (Ma huang ephedra sinica) 2000 B.C. it was written that hemp fruit would result in the user seeing devils through communication with less malevolent spirits. It is now known that the active component in hemp plant (Cannibis sativa) is tetrahydrocannabinol (TC) B.C. Compilation of 811 Egyptian formulas for fighting disease (Ebers Papyrus, 1862) istory 30 B.C. When Cleopatra decided to take her life, she first experimented with various plant extracts, using her slaves in toxicity tests. enbane (yoscyamus niger); scopalomine rapid but painful Deadly ightshade (Atropa belladonna); atropine rapid but painful Strychnine (ux vomica) rapid but left the face contorted Asp s venom rapid and tranquil passage to the afterworld 3 C Scopolamine 3 C Atropine Strychnine C 2-3
4 istory 150 Writings of Galen (Greece) assert imbalance of four humors cause disease herbs with opposing qualities should cure disease (contraria contrariis curantur). istory 600 Chinese recognize the effects of puffer fish (liver, ovaries and roe) as toxic. Deliberate consumption of these parts was a common method of suicide in China and Japan [tetrodotoxin] Swiss physician Paracelus urged alchemists to seek the arcanum, healing essence within effective pharmaceutical preparations. Also points out all substances are poisons; there is none which is not a poison. The right dose differentiates a poison from a remedy. 4
5 istory 1805 morphine extracted from poppy by Sertürner (not widely recognized until 1817, when he reported that a dose of 100 mg produced sever opium poisoning to himself). C 3 Morphine Isolated from opium in 1805 by Serturner narcotic, cough suppressent 3 C 3 C Emetine isolated from ipecacuanha in 1817 by Pelletier and Magendie emetic, specific remedy for dysentery oscapine isolated from opium in 1803 by Derosne cough suppressent C 3 C 3 C 3 C 3 3 C C 3 istory 1820 quinine isolated as active component of Cinchona tree bark originally brought to Europe by Calancha (monk) accompanying Spanish Conquistadors to Central and South America. Effective antimalarial drug First mass production of a pharmaceutical agent. Pelletier s factory processes 150,000 kg of cinchona bark to produce 3600 kg of quinine sulfate concept of biological receptor formulated by British pharmacologist John Langley studying the effect of atropine and pilocarpine on cat salivary flow first alkaloid synthesized, coniine (from emlock) Ehrlich described side chain theory; germicidal capability of a molecule depends on its structure, particularly its side chain, which binds disease causing organisms. 5
6 istory 1898 First mass-produced synthetic drug, Aspirin (Bayer 1898). Compound first reported in 1853, and could not be patented, process was patented and name was proprietary. First mass mailing of pharmaceutical information (30,000 doctors). The Bayer Process 3 C a C 2 - a + 2 S 4 3 C C 3 Aspirin istory 1940 DA ligands leading to cell death are first cancer chemotherapeutics First protein structure solved Merrifield method of solid-phase peptide synthesis reported, later adapted for combinatorial synthesis (mid 1980 s) 1965 Receptor families and selectivity of agents for different family members reported First report of computing interactions between a drug and its biological target (ethidium bromide and derivatives with DA fragment) igh throughput screening allows rapid evaluation of compounds (interleukin-1) Drug likeness used as an in silico screening strategy. 6
7 The ature of Drugs (C 2 C 3 ) Procaine itrous oxide Both are anesthetics. What about the route of administration? The ature of Drugs Li + 2 Cl Lithium Clonazepam Both are Mood-stabilizing ote the difference in charge. 7
8 The ature of Drugs Electrostatic Interactions vs. ydrophobic Carboxylic acids Amines Alkyl chains Phenyl rings The ature of Drugs C 3 Metabolism C 3 2 (+)-S-Deprenyl S-Amphetamine [Potent CS Stimulant] Monoamine xidase Inhibitor (used to treat Parkinson's disease C 3 (-)-R-Deprenyl Metabolism C 3 2 R-Amphetamine [Weak CS Stimulant] 8
9 Top Twenty Prescribed Drugs in umira 2. Sovaldi 3. Remicade 4. Rituxan 5. Enbrel 6. Lantus 7. Avastin 8. erceptin 9. Advar 10. Crestor 11.eulasta 12. Abilify 13. Lyrica 14. Revlimid 15. Gleevec 16. Prevnar 17.Copaxone 18. Zetia/Vytorin 19. Januvia 20. Symbicort 9
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