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Importance of Chirality

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Valliappan Kannappan
Valliappan Kannappan
VALLIAPPAN K
Professor of Quality Assurance (Retd.)
Department of Pharmacy
Annam...

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Valliappan Kannappan
Valliappan Kannappan
S
K
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T
C
H
 Behavior of chiral molecules
Importance of Chirality
Importance of...

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Valliappan Kannappan
Valliappan Kannappan
O
L
D
C
H
I
R
A
L
D
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unichiral / homochiral
unichiral / homochiral-
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Hallmark ...

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Importance of Chirality

  1. 1. Valliappan Kannappan Valliappan Kannappan VALLIAPPAN K Professor of Quality Assurance (Retd.) Department of Pharmacy Annamalai University INDIA vallikonnect@gmail.com Importance of Chirality 2021 10 min.
  2. 2. Valliappan Kannappan Valliappan Kannappan S K E T C H  Behavior of chiral molecules Importance of Chirality Importance of Chirality  Molecules of nature  Molecules of life Regulatory Environment Importance of Chirality 2021  Regulatory Environment  Unichiral drugs employed in Drug therapy
  3. 3. Valliappan Kannappan Valliappan Kannappan O L D C H I R A L D R unichiral / homochiral unichiral / homochiral- - Hallmark of many molecules from nature Look @ Molecules of @ Molecules of Nature Nature - - is not even-handed (-)-morphine N H3C H 32 16 N Importance of Chirality 2021 R U G S (5R,6S,9R,13S,14R) - analgesic Of the possible 32 stereoisomers only the levo- morphine has the desired analgesic activity. Poppy plant; papever sommniferum O OH HO (3R,4S,8S,9R) - anti-malarial (-)-quinine OH H O N
  4. 4. Valliappan Kannappan Valliappan Kannappan Proteins H H O M O C H I R A L I T Y S DNA, RNA Sugars Amino Acids D D- - L L- - Look @ Molecules of Life @ Molecules of Life most of the Biological macromolecules: Chiral Importance of Chirality 2021 S I G N A T U R E O F L I F E  Enzymes  Receptors  Carbohydrates  Nucleic acids  Transmitters  Hormones
  5. 5. Valliappan Kannappan Valliappan Kannappan N E W M O L E N T I T e-mcc 47% e-scc 18% rac- 5% Major proportion of medicines are chiral Chiral drugs Importance of Chirality 2021 T I E S ach 28% m-dia 2% 67% chiral 67% chiral http:// www. fda.gov/cder/rdmt/ Approved Jan 2004 to June 2006 Approved Jan 2004 to June 2006
  6. 6. Valliappan Kannappan Valliappan Kannappan Biological targets are chiral and so are the molecules (drugs) that interact with them Importance of Chirality 2021 molecules (drugs) that interact with them Source: Christopher Welch, Chiral India, 2016. Hence, mirror-image perspective is important when the molecule under study is chiral.
  7. 7. Valliappan Kannappan Valliappan Kannappan Regulatory Environment Regulatory Environment Importance of Chirality 2021
  8. 8. Valliappan Kannappan Valliappan Kannappan Enantiopure Drugs employed in drug therapy (select) Enantiopure Enantiopure drug drug Therapeutic indication Therapeutic indication Therapeutic area Therapeutic area S-amlodipine Antianginal / Antihypertensive Cardiology S-metoprolol Antihypertensive S-atenolol Antihypertensive Esomeprazole Proton pump inhibitor U N I C H I R A L D R Importance of Chirality 2021 Gastroenterology S-pantoprazole Proton pump inhibitor Dexrabiprazole Proton pump inhibitor Levosalbutamol Bronchodilator Pulmonology Levocetrizine Antihistaminic R-formetrol Antihistaminic Levofloxacin Antibacterial Infectious diseases R U G S
  9. 9. Valliappan Kannappan Valliappan Kannappan Enantiopure Enantiopure drug drug Therapeutic indication Therapeutic area Therapeutic area S-penicillamine Rheumatoid Arthritis Rheumatology / Pain/ Inflammation S-etodolac NSAID Dexketoprofen; (S-) NSAID Dexibuprofen; (S-) NSAID S-ketamine Anesthetic U N I C H I R A L D R Enantiopure Drugs employed in drug therapy (select) Importance of Chirality 2021 S-ketamine Anesthetic Anesthesiology Levobupivacaine Local anesthetic Ropivacaine Local anesthetic Cisatracurium Skeletal muscle relaxant Levothyroxine Anti-hypothyroidism Endocrinology Levodopa Anti-Parkinson Neuropsychiatry R U G S
  10. 10. Valliappan Kannappan Valliappan Kannappan  Stereochemistry is a key characteristic of life science, and chirality is often crucial for specific BA.  Appeal to academia to provide more space for chirality in their deliberations on life science research/teaching and also try to mitigate the so called “stereophobia” Concluding Remarks Concluding Remarks Importance of Chirality 2021 and also try to mitigate the so called “stereophobia” that exist both among faculty and students (debatable !!!).  Call upon teachers to empower the student community with chiral science, which is an integral part of drug discovery and development process.
  11. 11. Valliappan Kannappan Valliappan Kannappan Thanks for you time Thanks for you time Importance of Chirality 2021 valliappan valliappan Chirally Yours Chirally Yours

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