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Handedness in Anesthetic Pharmacology

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Anesthesia for the New Millennium

Part of the book series: Developments in Critical Care Medicine and Anesthesiology ((DCCA,volume 34))

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Abstract

The historical beginnings of stereochemistry are a fascinating piece of scientific detective work dating back to the early career of French chemist Louis Pasteur in the 1840s. Pasteur, then a young man, was interested in crystallography. While examining the crystals of tartaric acid salts with a hand lens, he serendipitously noticed that sodium ammonium tartrate existed as two distinct kinds of crystals that were mirror images of each other. After laboriously separating the right and left handed forms of the crystals into two piles, Pasteur discovered that, while the original mixture had been optically inactive, each individual pile of crystals rotated polarized light when dissolved in solution. Furthermore, the specific rotations of the two solutions were exactly equal but opposite in direction!

Authors Note: This chapter was adapted with permission from Egan TD: Stereochemistry and Anesthetic Pharmacology: Joining Hands With the Medicinal Chemists. Anesth Analg 1996; 83:447–50

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References

  1. Mason S: The origin of chirality in nature. Trends Pharmacol Sci 1986;7:20–23

    Article  CAS  Google Scholar 

  2. Hegstrom RA. Konderpudi DK: The handedness of the universe. Sci American 1990;262:98–105

    Article  Google Scholar 

  3. Morrison RT. Boyd RN: Organic Chemistry. 3rd Edition. Boston: Allyn and Bacon, 1973

    Google Scholar 

  4. Testa B: Mechanisms of chiral recognition in xenobiotic metabolism and drug-receptor interaction. Chirality 1989;1:7–9

    Article  PubMed  CAS  Google Scholar 

  5. Ariens EJ: Chirality in bioactive agents and its pitfalls. Trends Pharmacol Sci 1986;7:200–205

    Article  CAS  Google Scholar 

  6. Tucker GT, Lennard MS: Enantiomer specific pharmacokinetics. Pharmac Ther 1990;45:309–329

    Article  CAS  Google Scholar 

  7. Williams KM: Chirality: pharmacokinetics and pharmacodynamics in 3 dimensions. Clin Exp Pharmacol Physiol 1989:16:465–470

    Article  PubMed  CAS  Google Scholar 

  8. Drayer DE: Pharmacodynamic and pharmacokinetic differences between drug enantiomers in humans: an overview. Clin Pharmacol Ther 1986;40:125–133

    Article  PubMed  CAS  Google Scholar 

  9. Lee EJD, Williams KM: Chirality. Clinical pharmacokinetic and pharmacodynamic considerations. Clin Pharmacokinet 1990;18:339–345

    Article  PubMed  CAS  Google Scholar 

  10. Wahlstrom G, Norberg L: A comparative investigation in the rat of the anesthetic effects of the isomers of two barbiturates. Brain Res 1984;310:261–267

    Article  PubMed  CAS  Google Scholar 

  11. Kaiser DG, van Geissen GJ, Reisher RJ, Wechter WJ: Isomeric inversion of ibuprofen (R)-enantiomer in humans. J Pharma Sci 1976;65:269–273

    Article  CAS  Google Scholar 

  12. O’reilly RA, Trager WF, Rettie AE, Goulart DA: Interaction of amiodarone with racemic warfarin and its separated enantiomorphs in humans. Clin Pharmacol Ther 1987;42:290–294

    Article  CAS  Google Scholar 

  13. Whelan E, Wood AJ, Koshakji R, Shay S, Wood M: Halothane inhibition in propranolol metabolism is stereoselective. Anesthesiology 1989;71:561–564

    Article  PubMed  CAS  Google Scholar 

  14. Schuttler J, Stanski DR, White PF, Trevor AJ, Horai Y, Verotta D, Sheiner LB: Pharmacodynamic modeling of the EEG effects of ketamine and its enantiomers in man. J Pharmacokin Biopharm 1987;15:241–253

    CAS  Google Scholar 

  15. White PF, Ham J, Way WL, Trevor AJ: Pharmacology of ketamine isomers in surgical patients. Anesthesiology 1980; 52:231–239

    Article  PubMed  CAS  Google Scholar 

  16. White PF, Schuttler J, Shafer A, Stanski DR, Horai Y, Trevor AJ: Comparative pharmacology of the ketamine isomers-studies in volunteers. Br J Anaesth 1985;57:197–203

    Article  PubMed  CAS  Google Scholar 

  17. Rutten AJ, Mather LE, McLean CF: Cardiovascular effects and regional clearances of IV bupivacaine in sheep: enantiomeric analysis. Br J Anaesth 1991;67:247–256

    Article  PubMed  CAS  Google Scholar 

  18. Denson DD, Behbehani MM, Gregg RV: Enantiomer-specific effects of an intravenously administered arrhythmogenic dose of bupivacaine on neurons of the nucleus tractus solitarius and the cardiovascular system in the anesthetized rat. Regional Anesth 1992;17:311–316

    CAS  Google Scholar 

  19. Rutten AJ, Mather LE, McLean CF, Nancarrow C: Tissue distribution of bupivacaine enantiomers in sheep. Chirality 1993;5:485–491

    Article  PubMed  CAS  Google Scholar 

  20. McClure JH: Ropivacaine. Br J Anaesth 1996;76:300–307

    Article  PubMed  CAS  Google Scholar 

  21. Lien CA, Belmont MR, Abalos A, Eppich L, Quessy S, Abou-Donia MM, Savarese JJ: The cardiovascular effects and histamine-releasing properties of 51W89 in patients receiving nitrous oxide/opioid/ barbiturate anesthesia. Anesthesiology 1995;82:1131–1138

    Article  PubMed  CAS  Google Scholar 

  22. Smith I, Nathanson M, White PF: Sevoflurane a long awaited volatile anaesthetic. Br J Anaesth 1996;76(3):435–45

    Article  PubMed  CAS  Google Scholar 

  23. Egan TD: Remifentanil pharmacokinetics and pharmacodynamics: a preliminary appraisal. Clin Pharmacokinet 1995;29:80–94

    Article  PubMed  CAS  Google Scholar 

  24. Millership JS, Fitzpatrick A: Commonly used chiral drugs: a survey. Chirality 1993;5:573–576

    Article  PubMed  CAS  Google Scholar 

  25. Lennard MS: Clinical pharmacology through the looking glass: reflections on the racemate vs. enantiomer debate. Br J Clin Pharmacol 1991;31:623–625

    Article  PubMed  CAS  Google Scholar 

  26. Gross M, Cartwright A, Campbell B, Bolton R, Holmes K, Kirkland K, Salmonson T, Robert JL: Regulatory requirements for chiral drugs. Drug Info J 1993;27:453–457

    Article  Google Scholar 

  27. Nation RL: Chirality in new drug development-clinical pharmacokinetic considerations. Clin Pharmacokinet 1994;27:249–255

    Article  PubMed  CAS  Google Scholar 

  28. Wainer IW, Caldwell J, Testa B: Joining hands. Chirality 1989;1:1

    Article  Google Scholar 

  29. Bulls, pills and patents. The Economist. June 28, 1997 pg. 69

    Google Scholar 

  30. Hermansson J, Grahn A: Optimization of the separation of enantiomers of basic drugs-retention mechanisms and dynamic modification of the chiral bonding properties on an alpha 1-acid glycoprotein column. J Chromatog 1995;694:57–69

    Article  CAS  Google Scholar 

  31. Soini H, Riekkola ML, Novotny MV: Chiral separations of basic drugs and quantitation of bupivacaine enantiomers in serum by capillary electrophoresis with modified cyclodextrin buffers. J Chromatog 1992;608:265–274

    Article  CAS  Google Scholar 

  32. Cook CE, Seltzman TB, Tallent CR, Wooten JD III: Immunoassay of racemic drugs: a problem of enantioselective antisera and a solution. J Pharmacol Exp Ther 1982;220:568–573

    PubMed  CAS  Google Scholar 

  33. Sheldon RA: The industrial synthesis of pure enantiomers. Drug Info J 1990;24:129–139

    Article  Google Scholar 

  34. Mosher HS, Morrison JD: Current status of asymmetric synthesis. Science 1983;221:1013–1019

    Article  PubMed  CAS  Google Scholar 

  35. Egan TD: Stereochemistry and anesthetic pharmacology: joining hands with the medicinal chemists. [editorial] Anesth Analg 1996;83:447–450

    PubMed  CAS  Google Scholar 

  36. Ariens EJ: Stereochemistry, a basis for sophisticated nonsense in pharmacokinetics and clinical pharmacology. Eur J Clin Pharmacol 1984;26:663–668

    Article  PubMed  CAS  Google Scholar 

  37. Mather LE: “Chirality is in your hands” Bull Aust NZ College of Anaesthetists 1994;3:26–32

    Google Scholar 

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© 1999 Springer Science+Business Media Dordrecht

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Egan, T.D. (1999). Handedness in Anesthetic Pharmacology. In: Stanley, T.H., Egan, T.D. (eds) Anesthesia for the New Millennium. Developments in Critical Care Medicine and Anesthesiology, vol 34. Springer, Dordrecht. https://doi.org/10.1007/978-94-011-4566-4_3

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  • DOI: https://doi.org/10.1007/978-94-011-4566-4_3

  • Publisher Name: Springer, Dordrecht

  • Print ISBN: 978-94-010-5935-0

  • Online ISBN: 978-94-011-4566-4

  • eBook Packages: Springer Book Archive

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