Chiral resolution by Vamsi Anil Krishna Chandu
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This document discusses chiral drug technology and its importance in the pharmaceutical industry. It begins by introducing resolution methods like chromatography and kinetic resolution used to separate chiral compounds. It then discusses resolving agents and how they demonstrate stereoselectivity. Examples are given of major drug products that were originally racemates but are now only marketed as single enantiomers. Chiral drug sales have grown significantly in therapeutic areas like cardiovascular and cancer. The document concludes by stating that chiral technology represents a large commercial opportunity and that consideration of chirality is important in drug research and development due to regulatory guidelines.
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Molecules that form nonsuperimposable mirror images, and thus exist as enantiomers, are said to be chiral molecules.
For a molecule to be chiral, it cannot contain a plane of symmetry.
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Have identical properties.
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Have distinct physical properties.
Have different molecular shapes.
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Characterization of penicillin.pptx
Penicillin, one of the first and still one of the most widely used antibiotic agents, is derived from the penicillium mold. In 1928 Scottish bacteriologist alexander fleming in a contaminated green mold penicillium notatum. He isolated the mold, grew it in a fluid medium, and found that it produced a substance capable of killing many of the common bacteria that infect humans. Australian pathologist howard florey and British biochemist ernst Boris chain isolated and purified penicillin in the late 1930s, and by 1941 an injectable form of the drug was available for therapeutic use.
Penicillin's are beta lactam antibiotics and characterized by three fundamental structural requirements
The fused beta-lactam and thiazolidine ring structure.
free carboxylic acid group.
And one or more substituted acylamino side chain.
Penam nucleus: 7-oxo-l-thia-4-azabicyclo [3.2.0] heptane
Absolute configuration: 3-S, 5-R, 6-R.
Instrumental methods of characterization:
FTIR
MASS
C13-NMR
1H-NMR
FTIR: -
Penicillin G molecule and its IR spectra in D2 O and in DMSO. Spectra are characterized by the presence of three intense bands.
β- lactam CO stretching observe at 1761 cm-1 in D2O and 1762 cm-1 in DMSO solution.
Amide group is observe at 1640 cm-1 in D2O and 1674 cm-1 in DMSO solution.
Asymmetric stretching of carboxylate group is observe at 1601 cm-1 in D20 and 1615 cm-1 in DMSO solution.
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Mass selecting the precursor ions using the first mass spectrometer.
Injecting the ions into the first quadrupole (collision cell) where they undergo CID.
Mass-analyzing the fragment ions produced using the second quadrupole.
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- 1. Presented by Ch.Vamsi Anil Krishna(10AB1R0026) Adderss: Dept of Pharmaceutical Chemistry Vignan Pharmacy College,Vadlamudi, Guntur, Andhra Pradesh, India.
- 2. Introduction Resolution Methods Resolving agents Stereoselectivity of action Chiral drug sales Chiral BIOCKBUSTER DRUGS Conclusion
- 6. Chromatography Widely used in development laboratories Applicable to >99% of small molecules at analytical scale Used in manufacturing scale
- 7. Methods for Preparing Chiral Compounds Chromatography
- 8. A small scale separation of the chiral compounds in labs.
- 10. Kinetic Resolution Evalution of an historical process(> 100 years) Based upon different reaction rates of the isomers Theoretically 100% yield Technology applied on limited scale to date
- 11. Diastereomer Crystallisation Most widely used technique in industry Widely used in development Cheap additives Only one isomer recovered per stage
- 12. Resolving Agents
- 15. Out 100 drugs sold in 1994: Pure enantiomer 20% Racemate 21% No chiral 33% Out 100 drugs sold in 1997: Pure enantiomer 30% Racemate 9% No chiral 57%
- 16. Racemic Mixture Single-enantiomer Amphetamine(Benzedrine) Dextroamphetamine(Dexedrine) Bupivacaine(Marcain) Levobupivacaine (Chirocaine) Cetirizine(Zyrtec/ Reactine) Levocetirizine(Xyzal) Citalopram(Celexa/ Cipramil) Escitalopram(Lexapro/ Cipralex) Methylphinidate(Ritalin) Dexmethylphenidate(Focalin)
- 17. Racemic Mixture Single-enantiomer Modafinil(Provigil) Armodafinil(Nuvigil) Ofloxacin(Floxin) Levofloxacin(Levaquin) Omeprazole(Prilosec) Esomeprazole(Nexium) Salbutamol(Ventolin) Levalbuterol(Xopenex) Zopiclone(Imovane) Eszopliclone(Lunesta)
- 18. $ MILLIONS 1998 1999 2000 Cardio vascular $21,906 $24,805 $26,012 Antibiotics 19,756 20,907 23,265 Cancer 8,006 9,420 13,360 Central Nervous System 7,027 8,592 13,720 Antiviral 6,131 7,540 13,446 Gastrointestinal 1,718 2,998 5,355 TOTAL $6,45,44 $74,262 $95,198
- 19. Chiral technology is a rapidly developing area Chiral technology represents a huge commercial business opportunity that has yet to be fully realised
- 21. MARKET OF CHIRAL DRUGS Single–enantiomer drug sales show a continuous growth worldwide and many of the top selling drugs are marketed as single enantiomers Annual sales of chiral drugs: $133billion(2000), $172billion(2005)
- 22. It is necessary to consider the chiral nature of a com-pound in drug Research. Enantiomers of all chiral bioactive molecules must be separated and tested. The FDA and regulatory authorities in Europe, China, and Japan have provided guidelines indicating that only the active enantiomer of a chiral drug should be brought to market.
- 23. Chiral drug separation Bingyun LiDonald T. Haynie Engineering and Physics, Bionano systems Engineering Labo Biomedical ratory, Center for Applied Physics Studies, Louisiana Tech University, Ruston, Louisiana, U.S.A The impact of chiral technology on the pharmaceutical industry ANDY RICHARDS & RAY McCAGUE
- 24. This work was supported by A.VISWANATH M.pharm (Ph.D) Dept of Pharamaceutical chemisrty. My beloved PRINCIPAL Dr.P.SRINIVASA BABU
- 26. Thank you