Bioequivalence of chiral drugs: Stereospecific versus non-stereospecific methods

Clinical Pharmacokinetics

Volumn 33, Issue 2, 1997, Pages 122-141

  Mehvar, Reza ^a   Jamali, Fakhreddin ^b  

^a DRAKE UNIVERSITY   (United States)

^b UNIVERSITY OF ALBERTA   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

DISOPYRAMIDE; DOXEPIN; FLURBIPROFEN; IBUPROFEN; NADOLOL; NORTRIPTYLINE; PROPAFENONE; VERAPAMIL;

BIOEQUIVALENCE; CHIRALITY; DRUG FORMULATION; ENANTIOMER; PHARMACODYNAMICS; PRIORITY JOURNAL; RACEMIC MIXTURE; REVIEW; STEREOCHEMISTRY;

EID: 0030851895     PISSN: 03125963     EISSN: None     Source Type: Journal    
DOI: 10.2165/00003088-199733020-00004     Document Type: Review

References (88)

1. Some views from the Medical Product Agency of the documentation forchiral drugs. Uppsala: Registration Division, Medical Product Agency, 1991
2. EC-Note for guidance: investigation of chiral active substances, CPMP Working party on quality of medicinal products, CPMP Working party on safely of medicinal products. CPMP Working party on efficacy of medicinal products. 1993 Oct. III/350I/9IEN
3. Ariens E. Stereochemistry, a basis for sophisticated nonsense in pharmacokinetics and clinical pharmacology, Eur J Clin Pharmacol 1984; 26: 663-8
4. Jamnli F, Mehvar R, Pasutto FM. Enantioselective aspects of drug action and disposition: therapeutic pitfalls. J Phurm Sci 1989; 78: 695-715
5. Tucker GT, Lennard MS. Enantiomer specific pharmacokinetics. Pharmacol Ther 1990; 45: 309-29
6. Drayer DE. Pharmacodynamic and pharmacokinetic differences between drug enantiomers in humans: an overview. Clin Pharmacol Ther 1986; 40: 125-33
7. Lee EJD, Williams KM, Chirulity: clinical pharmacokinetic and pharmacodynamic considerations. Clin Pharmacokinet 1990; 18: 339-45
8. Eichelbaum M, Gross AS. Stereochemical aspects of drug action and disposition. In: Testa B, Meyer UA. editors. Advances in drug research, Vol. 28. London: Academic Press, 1996: 1-64
9. Jamali F, Collins DS, Berry BW, et al. Comparative bioavailahility of two flurbiprofen products: stereoselective versus conventional approach. Biopharm Drug Dispos 1991; 12: 435-45
10. Koytchev R, Alken RG, Mayer O, et al. Bioequhalence studies of two oral propafenone preparations [in German]. Arzneimittel Forschung 1995; 45: 542-5
11. Midha KK, Hubbard JW, Rawson MJ, et al. The roles of stereochemistry and partial areas in a parallel design study to assess the bioequivalence of two formulations of hydroxychloroquine: a drug with a very long half life. Eur J Phurm Sci 1996; 4: 283-92
12. Srinivas NR, Barr WH, Shyu WC, et al. Bioequivalenee of two tablet formulations of nadolol using single and multiple dose data: assessment using stereospecific and nonstereospecific assays. J Pharm Sci 1996; 85: 299-303
13. Nerurkar SG, Dighe SV, Williams RL. Bioequivalenee of racemic drugs. J Clin Pharmacol 1992; 32: 935-43
14. Shah VP, Midha KK, Dighe S, et al. Analytical methods validation: bioavailability, bioequivalenee, and pharmacokinetics. J Pharm Sci 1992; 81: 309-12
15. Blume HH, Midha KK. Bio-internationul 92, conference on bioavailability, bioequivalence, and pharmacokinetic studies. Eur J Drug Metab Pharmacokinet 1993 Jul-Sep: 18: 225-12
16. Ariens E. Racemic therapeutics: ethical and regulatory aspects. Eur J Clin Pharmacol 1991; 41: 89-93
17. Cox SR, Brown MA, Squires DJ, et al. Comparative human study of ibuprofen enantiomer plasma concentrations produced by two commercially available ibuprofen tablets. Biopharm Drug Dispos 1988; 9: 539-49
18. Nitchuk WM. Regulatory requirements for generic chiral drugs. J Clin Pharmacol 1992; 32: 953-4
19. Jamali F, Wechter WJ. From controversy to resolution: bioequivalenee of racemic drugs (abstract). J Clin Pharmacol 1992; .12: 955-62
20. Jamali F. Stereochemistry and bioequivalence. J Clin Pharmacol 1992; 32: 930-4
21. Hooper WD, Dickinson RG, Gal J. Enantioselective versus non-enantioselective assays in comparative bioavailability studies with racemic drugs. Biopharm Drug Dispos 1992; 13: 383-5
22. Jamali F. Enantioselective versus non-enantioselective assays in comparative bioavailability studies for racemic drugs. Biopharm Drug Dispos 1992; 13: 385-7
23. Wright MR, Jamali F. Bioequivalence: stereochomical considerations. Clin Res Reg Affairs 1993; 10: 1-11
24. Ravis WR, Owen JS, Stercochemical considerations in bioavailability studies. In: Jackson AJ, editor. Generica, and bioequivalenee. Ann Arbor (MI): CRC Press. 1994: 113-37
25. Midha KK, Hubbard JW, Mckay G, et al. Stercoselectivity in bioequivalence studies of nortriptyline. J Pharm Sci 1995; 84: 1265-6
26. Midha KK, Hubbard JW, Rawson M, et al. The impact of stereoisomerism in a bioequivalenee study on two formulations of doxepin. Eur J Pharm Sci 1996; 4: 133-8
27. Thompson GA, Barker SH, Brezovic CP, et al. Ihuprofen pharmacokinetics are stereoselectively altered by food [abstract]. Pharm Res 1996; 13 Suppl.: S-413
28. Pasutto FM. Mirror images: the analysis of pharmaceutical enanliomers. J Clin Pharmacol 1992; 32: 917-24
29. Richmond B, Pelerson S, Vescuso P. An academic user's guide to STELLA, Lyme (NH): High Performance Systems. 1987
30. Mehvar R. Input rate-dependent stereoselective pharmacokinetics: enantiomeric oral bioavailability and blood concentration ratios after constant oral input. Biopharm Drug Dispos 1992; 13: 597-615
31. Mehvur R. Input rule-dependent stereoseleetive pharmacokinctics: effect of pulsatile oral input. Chirality 1994; 6: 185-95
32. Gill TS, Hopkins KJ, Rowland M, Stereospecific assay of nicoumalone: application to pharmacokinetic studies in man. Br J Clin Pharmacol 1988; 25: 591-8
33. Gupta SK, Hwang S, Alkinson L, et al. Simultaneous first-order and capacity-limited elimination kinetics after oral administration of verapamil. J Clin Phurmacol 1996; 36: 25-34
34. Eichelbaurn M, Mikus G, Vogelgesang B. Pharmacokinetics of (+)-, (-)-, and (±)-verupamil after intravenous administration. Br J Clin Pharmacol 1984; 17: 453-8
35. Wagner J. Predictability of verapamil steady-slate plasma levels from single-dose data explained. Clin Pharmacol Ther 1984; 36: 1-4
36. Kroemur HK, Funek-Brentano C, Silberstein DJ, et al. Stereoselective disposition and pharmacologic activity of propafenone enantiomers. Circulation 1989; 79; 1068-76
37. Grosehner K, Linder W, Schnedl H, et al. The effects of the stereoisomers of propafenone and diprafenone in guinea-pig heart. Br J Pharmacol 1991; 102: 669-74
38. Stoschitzky K, Klein W, Stark G, et al. Different Stereoselective effects of (R)- and (S)-propafenone: clinical pharmacologic, electrophysiologic. and radioligand binding studies. Clin Phurmueol Ther 1990; 47: 740-6
39. Stark U, Stark G, Stoschitzky K, et al. Stereoselective electrophysiological effects of propufenone in Langendorff perfused guinea pig hearts, Basic Res Cardiol 1992; 87: 87-97
40. Piquette-Miller M, Foster RT, Kappagodu CT, et al. Pharmacokinetics of acebutolol enantiomers in humans. J Pharm Sci 1991; 80: 313-6
41. Piquette-Miller M, Foster RT, Kappagoda CT, et al. Effect of aging on the pharmacokinetics of acebutolol enantiomers. J Clin Pharmacol 1992; 32: 148-56
42. Mehvur R, Gross ME, Kreamer RN. Pharmacokineties of alenolol enantiomers in humans and rats. J Pharm Sci 1990; 79: 881-5
43. Villen T, Burtilsson L, Sjoqvist F. Nonstereoselectivc disposition of ethosuximide in humans. Ther Drug Monit 1990; 12: 514-6
44. Kroemer HK, Turgeon J, Parker RA, et al. Flecainide enanliomers: disposition in human subjects and electrophysiologic actions in vitro. Clin Pharmacol Ther 1989; 46: 584-90
45. Jumuli F, Berry BW, Tehrani MR, et al. Stereoselctive pharmacokinetics of flurbiprofen in humans and rats. J Pharm Sci 1988; 77: 666-9
46. Jamali F, Brocks DR. Clinical pharmacokinetics of ketoprofen and its enantiomers. Clin Pharmacokinet 1990; 19: 197-217
47. Aholfathi Z, Fiset C, Gilbert M, et al. Role of polymorphic debrisoquin 4-hydroxylase activity in the Stereoselective disposition of mexiletine in humans. J Pharmacol Exp Ther 1993; 266: 1196-201
48. Carr RA, Foster RT, Lewanczuk RZ, et al. Pharmacokinetics of sotalol enantiomers in humans J Clin Pharmacol 1992; 32: 1105-9
49. Fiset C, Philippon F, Gilbert M, et al. Stereosclcetive disposition of (±)-Notulol at steady-state conditions. Br J Clin Pharmacol 1993; 36: 75-7
50. Singh NN, Jamali F, Pasutto FM, et al. Pharmacokinetics of the enantiomers of tiaprofenic acid in humans. J Phurm Sci 1986; 75: 439-42
51. Gross AS, Mikus G, Fischer C, et al. Stereoselective disposition of flecainidc in relation to the sparteine/dehrisoquine metaboliser phenotype. Br J Clin Pharmacol 1989; 28: 555-66
52. Brocks DR, Jamali E, Russell AS, et al. The stereoselective pharmacokinetics of etodolae in young und elderly subjects, and after cholecystectomy. J Clin Pharmacol 1992; 32: 982-9
53. Smith DA, Chandler MH, Shedlofsky SI, et al. Age-dependent stcreoselective increase in the oral clearance of hexoharbitone isomers caused by rifampicin. Br J Clin Pharmacol 1991; 32: 735-9
54. Hooper WD, Qing MS. The influence of age and gender on the stereoselective metabolism and pharmacokinetics of mephobarbital in humans. Clin Pharmacol Ther 1990; 48: 633-40
55. Mehvar R, Reynolds JM. Input rate-dependent stereoselective pharmacokinetics: experimental evidence in verapamil-infused isolated rat livers. Drug Metab Dispos 1995; 23: 637-41
56. Karim A, Piergies A. Veraptimil stereoisomerism: enantioineric ratios in plasma dependent on peak concentrations, oral input rale, or both. Clin Pharmacol Ther 1995; 58: 174-84
57. Bleske BE, Welage LS, Rose S, et al. The effect of dosage release formulations on the pharmacokinetics of propranolol slereoisomers in humans. J Clin Pharmacol 1995; 35: 374-8
58. Tukuhashi H, Ogala H, Shimizu M, et al. Comparaitive pharmacokinetics of unbound disopyramide enantiomers following oral administration of racemic disopyramide in humans. J Pharm Sci 1991; 80: 709-11
59. Paliwal JK, Smith DE, Cox SR, et al. Stereoselective, competitive, and nonlinear plasma protein binding of ibuprophen enantiomers as determined in vivo in healthy subjects. J Pharmacokinet Biopharm 1993:21: 145-61
60. Aoyama T, Kotaki H, Sasaki T, et al. Nonlinear kinetics of threometylphenidate enantiomers in a patient with narcolepsy and in healthy volunteers. Eur J Clin Pharmacol 1993; 44: 79-84
61. Silber B, Holford NHG, Riegclmim S. Stereoselective disposition and glucuronidation of propranolol in humans. J Pharm Sci 1982; 71: 699-704
62. Welterich U, Spahn-Langguth H, Mutschler F., et al. Evidence for intestinal secretion as an additional clearance pathway of talinolol enantiomers: concentration- and dose-dependent absorption in vitro and in vivo. Pharm Res 1996; 13: 514-22
63. Wade DN, Mearrick PT, Morris JL. Active transport of L-dopa in the intestine. Nature 1973; 242: 463-5
64. Hendel J, Brodthagen H. Entero-hepatic cycling of methotrexate estimated by use of the D-isomer as a reference marker. Eur J Clin Pharmacol 1984; 26: 103-7
65. Tamai I, Ling H-Y, Timbul S-M, et al. Stereospecific absorption and degradation of eephalexin. J Pharm Pharmacol 1988; 40: 320-4
66. Kroemur HK, Echizen H, Heidemann H, et al. Predictability of the in vivo metabolism of verapumil from in vitro data: contribution of individual pathways and stereosclective aspects. J Pharmacol Exp Ther 1992; 260: 1052-7
67. Woodcock B, Menke G, Fischer A, et al. Drug input rate from the Gl-tract. Michaelis-Menten kinetics and the bioavailability of slow release verapamil and nifedipine. Drug Des Deliv 1988; 2: 299-310
68. Takahashi H, Ogata H. Plasma protein binding and blood cell distribution of propranolol enantiomers in rats. Biochem Pharmacol 1990; 39: 1495-8
69. Jamali F, Singh NN, Pasutto FM, et al. Pharmacokinetics of ibuprofen enantiomers in humans following oral administration of tablets with different absorption rates. Pharm Res 1988; 5:40-3
70. Avgerinos A, Noormohammadi A, Hutt AJ. Disposition of ibuprofen following administration of a novel controlled release formulation to healthy volunteers. Int J Pharm 1991; 68: 97-103
71. Kroemer HK, Fischer C, Meese CO, et al. Enantiomer/enantiomer interaction of (S)- and (R)-propafenonc for cytochrome P450IID6-catalyzed 5-hydroxylation: in vitro evaluation of the mechanism. Mol Pharmacol 1991; 40: 135-42
72. Mast V, Fischer C, Mikus O, et al. Use of pseudoracemic nitrendipine to elucidate the metabolic steps responsible for stereoselective disposition of nitrendipine enantiomers. Br J Clin Pharmacol 1992; 33: 51-9
73. Giacomini KM, Nelson WL, Pershe RA, et al. In vivo interaction of the enantiomers of disopyramide in human subjects. J Pharmacokinet Biopharm 1986; 14: 335-55
74. Duddu SP, Vakilynejud M, Jamali F, et al. Stereoselective dissolution of propranolol hydrochloride from hydroxypropyl methylcellulose matrices. Pharm Res 1993; 10: 1648-53
75. Auhry A-F, Wainer IW, An in vitro study of the stereoselective dissolution of (rac)-verapamil from two sustained release formulation. Chirality 1993; 5: 84-90
76. Carr RA, Pasutto FM, Longstreth JA, et al. Stereospecific determination of the in vitro dissolution of modified release formulations of (±)-verapumil. Chirality 1993; 5: 443-7
77. Vakily M, Jamali F. Human pharmacokinetics of tiaprofenic acid after regular and sustained release formulations: lack of chiral inversion and stereoselective release. J Pharm Sci 1994; 83: 495-8
78. Echizcn H, Manz M, Eichelbaum M. Electrophysiologic effects of dextro- and levo-verapamil on sinus node and AV node function in humans. J Cardiovasc Pharmacol 1988; 12: 543-6
79. Hamann SR, Blouin RA, McAllister Jr RG. Clinical pharmacokinetics of verapamil. Clin Pharmacokinet 1984; 9: 26-41
80. Longstreth JA, Verapamil, a chiral challenge to the pharmacokinetic and pharmacodynamic assessment of bioavailability and bioequivalence. In: Wainer IW, editor, Drug stereochemistry, analytical methods and pharmacology. New York: Marcel Dekker, 1993:315-36
81. Shibukawa A, Wainer IW. Simultaneous direct determination of the enantiomers of verapamil and norverapamil in plasma using a derivalized amylose high-performance liquid chromutographic chiral stationary phase. J Chromatogr Biomed Appl 1992; 574: 85-92
82. Walker SE, Hardy BO. Alterations in apparent bioequivaleney of ibuprofen based on isomer analysis (abstract). J Clin Pharmacol 1992; 32: 957
83. Kaiser DG, VanGiessen GJ, Reischer RJ, et al. Isomeric inversion of ibuprofen (R)-enantiomer in humans. J Pharm Sci 1976; 65: 269-73
84. Takahashi H, Ogata H, Shimizu M, et al. Relative bioavailability of two disopyramide capsules in humans based on total, unbound, and unbound enanliomer concentrations. Biopharm Drug Dispos 1993; 14: 409-18
85. Lima JJ, Wenzke SC, Boudoulas H, et al. Antiarrhythmic activity and unbound concentrations of disopyramide enantiomers in patients. Ther Drug Monit 1990; 12: 23-8
86. Midha KK, Hubbard JWm McKay G, et al. Stereoselective pharmacokinetics of doxepin isomers. Eur J Clin Pharmacol 1992; 42: 539-44
87. Ducharme J, Fieger H, Ducharme MP, et al. Enantioselective disposition of hydroxychloroquine after a single oral dose of the racemate to healthy subjects. Br J Clin Pharmacol 1995; 40: 127-33
88. Karim A, Enantioselective assays in comparative bioavailahility studies of racemic drug formulations: nice to know or need to know? J Clin Pharmacol 1996; 36: 490-9