Homochiral drugs: A demanding tendency of the pharmaceutical industry

Current Medicinal Chemistry

Volumn 16, Issue 16, 2009, Pages 2064-2074

  Núñez, Mariá C ^a   García Rubiño, M Eugenia ^a   Conejo García, Ana ^a   Cruz López, Olga ^a   Kimatrai, María ^a   Gallo, Miguel A ^a   Espinosa, Antonio ^a   Campos, Joaquín M ^a  

^a Facultad de Farmacia   (Spain)

Author keywords

Asymmetric synthesis; Chiral pool; Chiral switch; Homochiral; Racemates; Separation of racemates

Indexed keywords

ANGIOTENSIN 2 RECEPTOR ANTAGONIST; ANTICONVULSIVE AGENT; BENZODIAZEPINE DERIVATIVE; BETA ADRENERGIC RECEPTOR BLOCKING AGENT; CALCIUM CHANNEL BLOCKING AGENT; CAPTOPRIL; CITALOPRAM; CYCLOPHOSPHAMIDE; DEXIBUPROFEN; DIPEPTIDYL CARBOXYPEPTIDASE INHIBITOR; ESOMEPRAZOLE; FLECAINIDE; FLUOXETINE; IBUPROFEN; KETOPROFEN; LEVALBUTEROL; LEVOBUPIVACAINE; METHADONE; NONSTEROID ANTIINFLAMMATORY AGENT; OMEPRAZOLE; PROPRANOLOL; SALBUTAMOL; SECOBARBITAL; THALIDOMIDE; VALSARTAN; VERAPAMIL;

BRONCHODILATING ACTIVITY; CANCER PAIN; CHIRALITY; CRYSTALLIZATION; DRUG BLOOD LEVEL; DRUG EFFICACY; DRUG ELIMINATION; DRUG POTENCY; DRUG RECEPTOR BINDING; DRUG RESEARCH; DRUG SAFETY; DRUG STRUCTURE; DRUG SYNTHESIS; DRUG TOLERABILITY; EMBRYOTOXICITY; ENANTIOMER; GASTROESOPHAGEAL REFLUX; HUMAN; MORNING SICKNESS; NONHUMAN; PEPTIC ULCER; RACEMIC MIXTURE; REFLUX ESOPHAGITIS; REVIEW; RHEUMATOID ARTHRITIS; STEREOCHEMISTRY; STOMACH ACID SECRETION; STOMACH IRRITATION; STRUCTURE ACTIVITY RELATION; STRUCTURE ANALYSIS; TERATOGENICITY;

ANIMALS; DRUG DISCOVERY; DRUG INDUSTRY; HUMANS; PHARMACEUTICAL PREPARATIONS; STEREOISOMERISM; TECHNOLOGY, PHARMACEUTICAL; THALIDOMIDE;

EID: 68449088253     PISSN: 09298673     EISSN: None     Source Type: Journal    
DOI: 10.2174/092986709788682173     Document Type: Review

References (74)

1. Collins, A.N.; Sheldrake, G.N.; Crosby, J. Chirality in industry. The commercial manufacture and applications of optically active compounds. John Wiley & Sons: New York, 1992.
2. Testa, B.; Trager, W.F. Racemates versus enantiomers in drug development: Dogmatism or pragmatism. Chirality, 1990, 2, 129-33.
3. Horn, A.S.; De Ranter, C.J. X-Ray crystallography and drug action. Clarendon: Oxford, 1984.
4. Ahlberg, P. The Nobel Prize in Chemistry 2001 - presentation speech. The Royal Swedish Academy of Science [Online] 2001, (accessed Aug 26, 2002).
5. Blaschke, G.; Kraft, H.P.; Fikentscher, K.; Köhler, F. Chromatographic separation of racemic thalidomide and teratogenic activity of its enantiomers. Arzneimittelforschung, 1979, 29, 1640-2.
6. Fabro, S.; Smith, R.L.; Williams, R.T. Toxicity and teratogenicity of optical isomers of thalidomide. Nature, 1967, 215, 296-7.
7. Reist, M.; Carrupt, P.A.; Francotte, E.; Testa, B. Chiral inversion and hydrolysis of thalidomide: Mechanisms and catalysis by bases and serum albumin, and chiral stability of teratogenic metabolites. Chem. Res. Toxicol., 1998, 11, 1521-8.
8. Eriksson, T.; Bjorkman, S.; Roth, B.; Fyge, A.; Höuglund, P. Stereopecific determination, chiral inversion in vitro and pharmacokinetics in humans of the enantiomers of thalidomide. Chirality, 1995, 7, 44-52.
9. Agranat, I.; Caner, H.; Caldwell, J. Putting chirality to work: The strategy of chiral switches. Nat. Rev. Drug Discov., 2002, 10, 753-68.
10. (a) Meyring, M.; Muhlbacher, J.; Messer, K.; Kastner-Pustet, N.; Bringmann, G.; Mannschreck, A.; Blaschke, G. In vitro biotransformation of (R)- and (S)-thalidomide: Application of circular dichroism spectroscopy to the stereochemical characterization of the hydroxylated metabolites. Anal. Chem., 2002, 74, 3726-35
11. (b) Eriksson, T.; Bjorkman, S.; Hoglund, P. Clinical pharmacology of thalidomide. Eur. J. Clin. Pharmacol., 2001, 57, 365-76
12. (c) Eriksson, T.; Bjorkman, S.; Roth, B.; Bjork, H.; Hoglund, P. Hydroxy-lated metabolites of thalidomide: Formation in-vitro and in-vivo in man. J. Pharm. Pharmacol., 1998, 5, 1409-16.
13. (a) Gordon, J.N.; Goggin, P.M. Thalidomide and its derivatives: Emerging from the wilderness. Postgrad. Med. J., 2003, 79, 127-32.
14. (b) Weeber, M.; Vos, R.; Klein, H.; de Jong-van den Berg, L.; Aronson, A.R.; Molema, G. Generating hypotheses by discovering implicit associations in the literature: A case report of a search for new potential therapeutic uses of thalidomide. J. Am. Med. Inform. Assoc., 2003, 10, 252-9.
15. (c) Weber, D.; Rankin, K.; Gavino, M.; Delasalle, K.; Alexanian, R. Thalidomide Alone or With Dexamethasone for Previously Untreated Multiple Myeloma. J. Clin. Oncol., 2003, 21, 16-9
16. (d) Friedrich, M.J. Despite Checkered Past, Thalidomide and its Analogues Show Potential. J. Natl. Cancer. Inst., 2002, 94, 1270-2.
17. (e) Lewis, R. The Return of Thalidomide. Scientist, 2001, 15, 1.
18. Stoschitzky, K.; Lindner, W.; Zernig, G. Racemic beta-blockers-fixed combinations of different drugs. J. Clin. Basic Cardiol., 1998, 1, 15-9.
19. Barrett, A.; Cullum, C. The biological properties of the optical isomers of propranolol and their own cardiac arrhytmias. Br. J. Pharmacol., 1968, 34, 43-55.
20. Echizen, H.; Manz, M.; Eichelbaum, M. Electrophysiologic effects on dextro- and levo- verapamil on sinus node and AV node function in humans. J. Cardiovasc. Pharm., 1988, 12, 543-6
21. Satoh, K.; Yanagisawa, T.; Taira, N. Coronary vasodilatator and cardiac effects of optical isomers of verapamil in the dog. J. Cardiovasc. Pharm., 1980, 2, 309-18.
22. Patocka, J.; Dvorak, A. Biomedical aspects of chiral molecules. J. Appl. Med., 2004, 2, 95-100.
23. Nowak, R. Single-isomer levalbuterol: A review for the acute data. Curr. Allergy Asthma Rep., 2003, 3, 172-8.
24. Asmus, M.J.; Hendeles, L. Levalbuterol nebulizer solution: Is it worth five times the cost of Albuterol? Pharmacotherapy, 2000, 20, 123-9.
25. Drayer, D.E. Pharmacodynamic and pharmacokinetic differences between drug enantiomers in human: An overview. Clin. Pharmacol. Ther., 1986, 40, 125-33.
26. Ho, I.I.; Harris, R.A. Mechanism of action of barbiturates. Annu. Rev. Pharmacol., 1988, 37, 1919-26.
27. Katzung, B.G. Basic and clinical pharmacology. Lange Medical Books/McGraw Hill: New York, 2004.
28. Lee, E.J.D.; Williams, K.M. Chirality. Clinical pharmacokinetic and pharmacodynamic considerations. Clin. Pharmacokinet., 1990, 18, 339-45.
29. Rentsch, K,M. The importance of stereoselective determination of drugs in the clinical laboratory. J. Biochem. Bioph. Meth., 2002, 54, 1-9.
30. Pham-Huy, C.; Chikhi-Chorfi, N.; Galons, H.; Sadeg, N.; Laqueille, X.; Aymard, N.; Massicot, F.; Warnet, J.M.; Claude, J.R. Enantioselective high-performance liquid chromatography determination of methadone enantiomers and its major metabolite in human biologic fluids using a new derivatized cyclodextrin-bonded phase. J. Chromatogr. B., 1997, 700, 155-63.
31. Davies, N.M.; Teng, X.V. Importance of chirality in drug therapy and pharmacy practice. Implication for psychiatry. Adv. Pharm., 2003, 1, 242-52.
32. Marzo, A.; Heftman, E. Enantioselective analytical methods in pharmacokinetics with specific reference to genetic polymorphic metabolism. J. Biochem. Bioph. Meth., 2002, 54, 57-70.
33. Jamali, F.; Mehver, R.; Pasutto, F.M. Enantioselective aspects of drug action and disposition: Therapeutic pitfalls. J. Pharm. Sci. USA, 1989, 78, 695-715.
34. (a) Gristwood, R.W. Cardiac and CNS toxicity of levobupivacaine: strength of evidence for advantage over bupivacaine. Drugs Saf., 2002, 25, 153-63.
35. (b) Gristwood, R.W.; Greaves, J.L. Levobupivacaine: A new safer long acting local anaesthetic agent. Expert Opin. Inv. Drugs, 1999, 8, 861-76.
36. Bardsley, H.; Gristwood, R.; Baker, H.; Watson, N.; Nimmo, W. A comparison of the cardiovascular effects of levobupivacaine and rac-bupivacaine following intravenous administration to healthy volunteers. Br. J. Clin. Pharmacol., 1998, 46, 245-9.
37. Lindberg, P.; Brandstrom, A.; Wallmark, B.; Mattsson, H.; Rikner, L.; Hoffmann, K.J. Omeprazole: The first proton pump inhibitor. Med. Res. Rev., 1990, 10, 1-60.
38. Lindberg, P.; Weidolf, L. Method for the treatment of gastric acid-related diseases and production of medication using the (-)-enantiomer of omeprazole. U.S. Patent 5877192, 1999.
39. (a) Olbe, L.; Carlsson, E.; Lindberg, P. A proton-pump inhibitor expedition: The case histories of omeprazole and esomeprazole. Nat. Rev. Drug Discov., 2003, 2, 132-9.
40. (b) Kale-Pradhan, P.B.; Landry, H.K.; Sypula, W.T. Esomeprazole for acid peptic disorders. Ann. Pharmacother., 2002, 36, 655-63.
41. (c) Lindberg, P.; Keeling, D.; Frylund, J.; Andersson, T.; Lundborg, P.; Carlsson, E. Esomeprazole-enhanced bio-availability, specificity for the proton pump and inhibition of acid secretion. Aliment. Pharmacol. Ther., 2003, 17, 481-8.
42. (d) Chong, E.; Ensom, M.H. Pharmacogenetics of the proton pump inhibitors: A systematic review. Pharmacotherapy, 2003, 23, 460-71.
43. (a) Jenkins, D.J.; Sancilio, F.D.; Stowell, G.W.; Whittall, L.B.; Whittle, R.R. Alkoxy substituted benzimidazole compounds, pharmaceutical preparations containing the same, and methods of using the same, U.S. Patent 6,262,085, 2001.
44. (b) Jenkins, D.J.; Sancilio, F.D.; Stowell, G.W.; Whittall, L.B.; Whittle, R.R. Alkoxy substituted benzimidazole compounds, pharmaceutical preparations containing the same, and methods of using the same, U.S. Patent 6,369,087, 2002.
45. Pham-Huy, C.; Villain-Pautet, G.; He, H.; Chikhi-Chorfi, N.; Galons, H.; Thevenin, M.; Claude, J.R.; Warnet, J.M. Separation of oxazepam, lorazepam and temazepam enantiomers by HPLC on a derivatized cyclodextrin-bonded phase: Application to the determination in plasma. J. Biochem. Bioph. Meth., 2002, 54, 287-99.
46. He, H.; Liu, Y.; Sun, C.; Wang, X.; Pham-Huy, C. Effect of temperature on enantiomer separation of oxazepam and lorazepam by HPLC on a β-cyclodextrin derivatized bonded chiral stationary phase. J. Chromatogr. Sc., 2004, 42, 62-6.
47. Mohler, H.; Richards, J.C. The benzodiazepines. From molecular biology to clinical practice. Raven Press: New York, 1983.
48. Miller, L.; Orihuela, C.; Fronek, R.; Honda, D.; Dapremont, O. Chromatographic resolution of the enantiomers of a pharmaceutical intermediate from the milligram to the kilogram scale. J. Chromatogr. A., 1999, 849, 309-17.
49. Williams, K.L.; Sander, L.C. Enantiomer separations on chiral stationary phases in supercritical fluid chromatography. J. Chromatogr. A., 1997, 785, 149-58.
50. Liu, Y.; Lantz, A.W.; Armstrong, D.W. High efficiency liquid and super-subcritical fluid-based enantiomeric separations: An overview. J. Liq. Chromatogr. Relat. Technol., 2004, 27, 1121-78.
51. Welch, C.J.; Leonard, W.R.; DaSilva, J.O.; Biba, M., Albaneze-Walker, J.; Henderson, D.W.; Laing, B.; Mathre, D.J. Preparative chiral SFC as a green technology for rapid access to enantiopurity in pharmaceutical process research. LC-GC Eur., 2005, 18, 264-6, 270, 272.
52. Zhang, Y.; Wu, D.; Wang-Iverson, D.B.; Tymiak, A.A. Enantioselective chromatography in drug discovery. Drug Discov. Today., 2005, 10, 571-7.
53. Maftouh, M.; Granier-Loyaux, C.; Chavana, E.; Marini, J.; Pradines, A.; Heyden, Y.W.; Picard, C. Screening approach for chiral separation of pharmaceuticals. Part III. Supercritical fluid chromatography for analysis and purification in drug discovery. J. Chromatogr. A., 2005, 1088, 67-81.
54. Amanullah, M.; Mazzotti, M. Optimization of a hybrid chromatography-crystallization process for the separation of Troeger's base enantiomers. J. Chromatogr. A., 2006, 1107, 36-45.
55. Lorenz, H.; Polenske, D.; Seidel-Morgenstern, A. Application of preferential crystallization to resolve racemic compounds in a hybrid process. Chirality, 2006, 18, 828-40.
56. Jacques, J.; Collet, A.; Wilen, S.H. Enantiomers, racemates and resolutions. Wiley: New York, 1981.
57. Kozma, D. DRC Handbook of optical resolutions via diastereomeric salt formation. CRC Press: Florida, 2002.
58. Fogassy, E.; Nogradi, M.; Kozma, D.; Egri, G.; Pálovics, E.; Kiss, V. Optical resolution methods. Org. Biomol. Chem., 2006, 4, 3011-30.
59. Kinbara, K. Design of resolving agents based on crystal engineering. Synletters, 2005, 5, 732-43.
60. Borghese, A.; Libert, V.; Zhang, T.; Alt, C.A. Efficient fast screening methodology for optical resolution agents: Solvent effects are used to affect the efficiency of the resolution process. Org. Process. Res. Dev., 2004, 8, 532-4.
61. Toda, F. Isolation and optical resolution of materials utilizing inclusion crystallization. Top Curr. Chem., 1987, 140, 43-69.
62. Eliel, E.; Wilen, S.H.; Mander, L.N. Stereochemistry of organic compounds. Wiley: New York, 1994.
63. Kinbara, K.; Hashimoto, Y.; Sukegawa, M.; Nohira, H.; Saigo, K. Crystal structures of the salts of chiral primary amines with achiral carboxylic acids: Recognition of the commonly-occurring supramolecular assemblies of hydrogen-bond networks and their role in the formation of conglomerates. J. Am. Chem. Soc., 1996, 118, 3441-9.
64. Sakai, K.; Hirayama, R.; Tamura, R. Novel optical resolution technologies. Springer-Verlag Berlin: Heidelberg, 2007.
65. Ushio, T.; Tamura, R.; Takahashi, H.; Azuma, N.; Yamamoto, K. Unusual enantiomeric resolution phenomenon observed upon Recrystallization of a Racemic compound. Angew. Chem. Int. Ed. Engl., 1996, 35, 2372-4.
66. Tamura, R.; Fujimoto, D.; Lepp, Z.; Misaki, K.; Miura, H.; Takahashi, H.; Ushio, T.; Nakai, T.; Hirotsu, K. Mechanism of preferential enrichment, an unusual enantiomeric resolution phenomenon caused by polymorphic transition during crystallization of mixed crystals composed of two enantiomers. J. Am. Chem. Soc.; 2002, 124, 13139-53.
67. Yokota, M.; Doki, N.; Shimizu, K. Chiral separation of a racemic compound induced by transformation of racemic crystal structures: DL-glutamic acid. Cryst. Growth Des., 2006, 6, 1588-90.
68. Mughal, R.K.; Davey, R.J.; Blanden, N. Application of crystallization inhibitors to chiral separations. 1. Design of additives to discriminate between the racemic compound and the pure enantiomer of mandelic acid. Cryst. Growth Des., 2007, 7, 218-24
69. Mughal, R.K.; Davey, R.J.; Blagden, N. Application of crystallization inhibitors to chiral separations. 2. Enhancing the chiral purity of mandelic acid by crystallization. Cryst. Growth Des., 2007, 7, 225-8.
70. Collins, A.N.; Sheldrake, G.N.; Crosby, J. Chirality in industry II: Developments in the manufacture and applications of optically active compounds. John Wiley & Sons: New York, 1997.
71. Patel, R.N. Biocatalysis and biotechnology for functional foods and industrial products. CRC Press LLC: Boca Raton, Florida, 2007.
72. Colonna, S.; Richelmi, C. Organic biotransformations. Chimica e l'Industria, 2004, 86, 58-62.
73. Eggert, T. Industrial biotransformations. Wiley-VCH Verlag GmbH & Co. KGaA: Weinheim, 2006.
74. Miller, C.P.; Ullrich, J.W. A Consideration of the patentability of enantiomers in the pharmaceutical industry in the United States. Chirality, 2008, 20, 762-70.