Sympathomimetic enantiomers and asthma

Chirality

Volumn 10, Issue 3, 1998, Pages 262-272

  Handley, D A ^a   McCullough, J R ^a   Crowther, S D ^b   Morley, J ^b  

^a SUNOVION PHARMACEUTICALS INC   (United States)

^b KING S COLLEGE HOSPITAL   (United Kingdom)

Author keywords

Airway; Beta2 agonist; Bronchospasm; Distomer; Eutomer; Hyperreactivity; Racemic

Indexed keywords

ADRENERGIC RECEPTOR STIMULATING AGENT; BRONCHODILATING AGENT; ISOPRENALINE; SALBUTAMOL; TERBUTALINE;

AIRWAY OBSTRUCTION; ARTICLE; ASTHMA; BRONCHOSPASM; BRONCHUS HYPERREACTIVITY; CARDIOVASCULAR RESPONSE; DRUG ANTAGONISM; DRUG EFFICACY; ENANTIOMER; HUMAN; PRIORITY JOURNAL; RECEPTOR BLOCKING; STIMULUS RESPONSE;

ALBUTEROL; ANTI-ASTHMATIC AGENTS; ASTHMA; BRONCHIAL SPASM; CLINICAL TRIALS; HUMANS; ISOPROTERENOL; STEREOISOMERISM; SYMPATHOMIMETICS;

EID: 0031939353     PISSN: 08990042     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1520-636X(1998)10:3<262::AID-CHIR9>3.0.CO;2-B     Document Type: Article

References (95)

1. Anonymous. Deaths from asthma. JAMA 199:81, 1967.
2. Speizer, F.E., Doll, R., Heaf, P., Strang, L.B. Investigation into use of drugs preceding death from asthma. Br. Med. J. 1:339-343, 1968.
3. Pearce, N., Grainger, J., Atkinson, M., Crane, J., Burgess, C., Culling, C., Windom, H., Beasley, R. Case-control study of prescribed fenoterol and death from asthma in New Zealand, 1977-1981. Thorax 45:170-175, 1990.
4. Grainger, J., Woodman, K., Pearce, N., Crane, J., Burgess, C., Keane, A., Beasley, R. Prescribed fenoterol and death from asthma in New Zealand, 1981-7: A further case-control study. Thorax 46:105-111, 1991.
5. Suissa, S., Ernst, P., Boivin, J-F., Horwitz, R.I., Habbick, B., Cockcroft, D.W., Blais, L., McNutt, M., Buist, A.S., Spitzer, W.O. A cohort analysis of excess mortality in asthma and the use of inhaled beta-agonists. Am. J. Respir. Crit. Care. Med. 149:604-610, 1994.
6. Yu, S.S., Lefkowitz, R.J., Hausdorff, W.P. Beta-adrenergic receptor sequestration. A potential mechanism of receptor resensitization. J. Biol. Chem. 268:337-341, 1993.
7. Lipworth, B.J., Struthers, A.D., McDevitt, D.G. Tachyphylaxis to systemic but not to airway responses during prolonged therapy with high dose inhaled salbutamol in asthmatics. Am. Rev. Respir. Dis. 140:586-592, 1989.
8. Bai, T.R., Mak, J.C., Barnes, P.J. A comparison of beta-adrenergic receptors and in vitro relaxant responses to isoproterenol in asthmatic airway smooth muscle. Am. J. Resp. Cell. Mol. Biol. 6:647-651, 1992.
9. Karlsson, J.-A., Persson, C.G.A. Influence of tracheal contraction on relaxant effects in vitro of theophylline and isoprenaline. Br. J. Pharmacol. 74:73-79, 1981.
10. Nials, A.T., Coleman, R.A., Johnson, M., Magnussen, H., Rabe, K.F., Vardey, C.J. Effect of beta-adrenoceptor agonists in human bronchial smooth muscle. Br. J. Pharmacol. 110:1112-1116, 1993.
11. Lowell, F.C., Curry, J.J., Schiller, I.W. A clinical and experimental study of Isuprel in spontaneous and induced asthma. New. Eng. J. Med. 240:45-51, 1949.
12. Stolley, P.D. Asthma mortality. Why the United States was spared an epidemic of deaths due to asthma. Am. Rev. Respir. Dis. 105:883-890, 1972.
13. Reisman, R.E. Asthma induced by adrenergic aerosols. J. Allergy 46: 162-177, 1970.
14. Trautlein, J., Allegra, J., Field, J., Gillin, M. Paradoxic bronchospasm after inhalation of isoproterenol. Chest. 70:711-714, 1976.
15. Paterson, J.W., Courtney Evans, R.J., Prime, F.J. Selectivity of bronchodilator action of salbutamol in asthmatic patients. Br. J. Dis. Chest. 65:21-38, 1971.
16. van Metre, T. Jr. Adverse effects of inhalation of excessive amounts of nebulized isoproterenol in status asthmaticus. J. Allergy Clin. Immunol. 43:101-113, 1969.
17. Eisenstadt, W.S., Nicholas, S.S. The adverse effects of adrenergic aerosols in bronchial asthma. Ann. Allergy 27:283-288, 1969.
18. Fraser, P.M., Speizer, F.E., Waters, S.D.M., Doll, R., Mann, N.M. The circumstances preceding death from asthma in young people in 1968 to 1969. Br. J. Dis. Chest. 65:71-84, 1969.
19. Conolly, M.E., Davies, D.S., Dollery, C.T., George, C.F. Resistance to beta-adrenoceptor stimulants (a possible explanation for the rise in asthma deaths). Br. J. Pharmacol. 43:389-402, 1971.
20. Rocha e Silva, M. Release of histamine in anaphylaxis. In: Handbook of Experimental Pharmacology. Eichler, O., Farah, A., eds. Berlin: Springer Verlag, 1966:430-480.
21. 2-adrenoceptor agonists in asthma: Help or hindrance? Br. J. Clin. Pharmacol. 33:129-138, 1992.
22. Pearce, N., Crane, J., Burgess, C., Jackson, R., Beasley, R. Beta agonists and asthma mortality: Déjà vu. Clin. Exp. Allergy 21:401-410, 1991.
23. Cockcroft, D.W., McParland, C.P., Britto, S.A., Swystun, V.A., Rutherford, B.C. Regular inhaled salbutamol and airway responsiveness to allergen. Lancet 342:833-838, 1993.
24. Morley, J. Anomalous effects of albuterol and other sympathomimetics in the guinea pig. Clin. Rev. Allergy Immunol. 14:65-89, 1996.
25. Kerrebijn, K.F. Beta agonists. In: Asthma, Its Pathology and Treatment. Kaliner, M.A., Barnes, P.J., Persson, C.G.A., eds. New York: Marcel Dekker Inc., 1991:523-559.
26. Barnes, P.J., Pride, N.B. Dose-response curves to inhaled beta-adrenoceptor agonists in normal and asthmatic subjects. Br. J. Pharmacol. 15:677-682, 1983.
27. Ahrens, R.C., Bonham, A.C., Maxwell, G.A., Wienburger, M.M. A method for comparing the peak intensity and duration of action of aerosolized bronchodilators using bronchoprovocation with methacholine. Am. Rev. Respir. Dis. 129:903-906, 1984.
28. Ahrens, R.C., Harris, J.B., Milavetz, G., Annis, L., Ries, R. Use of bronchial provocation with histamine to compare the pharmacodynamics of inhaled albuterol and metaproterenol in patients with asthma. J. Allergy Clin. Immunol. 79:876-882, 1987.
29. Jenne, J.W., Ahrens, R.C. Pharmacokinetics of beta-adrenergic compounds. In: Drug Therapy for Asthma: Research and Clinical Practice. Jenne, J.W., Murphy, S., eds. New York: Marcel Dekker, 1987:213-258.
30. Gibson, G.J., Greenacre, J.K., Konig, P., Conolly, M.E., Pride, N.B. Use of exercise challenge to investigate possible tolerance to beta-adrenoceptor stimulation in asthma. Br. J. Dis. Chest. 72:199-206, 1978.
31. Tashkin, D.P., Conolly, M.E., Deutsch, R.I., Hui, K.K., Littner, M., Scarpace, P., Abrass, I. Subsensitization of beta-adrenoceptors in airways and lymphocytes of healthy and asthmatic subjects. Am. Rev. Respir. Dis. 125:185-193, 1982.
32. 2 agonists. Thorax 51:1051-1056, 1996.
33. Peel, E.T., Gibson, G.J. Effects of long-term administration of inhaled salbutamol therapy on the provocation of asthma by histamine. Am. Rev. Respir. Dis. 121:973-976, 1980.
34. van Schayck, C.P., Graafsma, S.J., Visch, M.B., Dompeling, E., van Weel, C., van Herwaardeen, C.L.A. Increased bronchial hyperresponsiveness after inhaling salbutamol during 1 year is not caused by sub-sensitization to salbutamol. J. Allergy. Clin. Immunol. 86:793-800, 1990.
35. 2-agonist on lung function, airway hyperresponsiveness and symptoms in children with asthma. Am. Rev. Respir. Dis. 146:547-554, 1992.
36. 2,-agonist treatment. Am. Rev. Respir. Dis. 148:707-712, 1993.
37. 2 agonist against excessive airway narrowing in response to bronchoconstrictor stimuli in asthma and chronic obstructive disease. Thorax 46:9-14, 1991.
38. Crowther, S.D., Page, C.P., Costello, J.F., Morley, J. High incidence of increased sensitivity to airway spasmogens following inhalation of racemic salbutamol. Am. J. Respir. Crit. Care. Med. 155:A345, 1997.
39. Mitchell, E.A. Is current treatment increasing asthma mortality and morbidity? Thorax 44:81-84, 1989.
40. Van-Schayck, C.P., Dompeling, E., Van-Herwaarden, C.L., Wever, A.M., Van-Weel, C. Interacting effects of atopy and bronchial hyperresponsiveness on the annual decline in lung function and the exacerbation rate in asthma. Am. Rev. Respir. Dis. 144:1297-1301, 1991.
41. Fuhrman, C., Ernst, P., Kauffmann, F. Long-term effects of therapy on respiratory health. Eur. Respir. J. 9:436-443, 1996.
42. Spitzer, W.O., Suissa, S., Ernst, P., Horwitz, R.I., Habbick, B., Cockcroft, D., Boivin, J-F., McNutt, M., Buist, A.S., Rebuck, A.S. Asthma death and near-fatal asthma in relation to beta-agonist use. N. Engl. J. Med. 326:501-506, 1992.
43. Sears, M.R. Dose reduction of beta agonists in asthma. Lancet. ii:1331-1332, 1991.
44. 2-adrenoceptor agonist, salmeterol, on airway hyperresponsiveness in patients with mild asthma. N. Engl. J. Med. 327:1198-1203, 1992.
45. 2-agonists in asthma. N. Engl. J. Med. 327:1204-1208, 1992.
46. Pearlman, D.S., Chervinsky, P., LaForce, C., Seltzer, J.M., Southern, D.L., Kemp, J.P., Dockhorn, R.J., Grossman, J., Liddle, R.F., Yancey, S.W., Cocchetto, D.M., Alexander, W.J., van As, A. A comparison of salmeterol with albuterol in the treatment of mild-to-moderate asthma. N. Engl. J. Med. 327:1420-1425, 1992.
47. Ramage, L., Lipworth, B.J., Ingram, C.G., Cree, I.A., Dhillon, D.P. Reduced protection against exercise induced bronchoconstriction after chronic dosing with salmeterol. Respir. Med. 88:363-368, 1994.
48. Inman, M.D., O'Byrne, P.M. The effect of regular inhaled albuterol on exercise-induced bronchoconstriction. Am. J. Respir. Crit. Care. Med. 153:65-69, 1996.
49. Taylor, D.R., Sears, M.R. Bronchodilators and bronchial hyperresponsiveness. Thorax. 49:190-191, 1994 (letter; comment).
50. Kraan, J., Koeter, G.H., Mark, ThWvd., Sluiter, H.J., de Vries, K. Changes in bronchial hyperreactivity induced by 4 weeks of treatment with antiasthmatic drugs in patients with allergic asthma: A comparison between budesonide and terbutaline. J. Allergy Clin. Immunol. 76:628-636, 1985.
51. Kerribijn, K.F., van Essen-Zandvliet, E.E.M., Niejens, H.J. Effects of long-term treatment with inhaled corticosteroids and beta-agonists on the bronchial responsiveness in children with asthma. J. Allergy Clin. Immunol. 79:653-659, 1987.
52. Vathenen, A.S., Knox, A.J., Higgins, B.G., Britton, J.R., Tattersfield, A.E. Rebound increase in bronchial responsiveness after treatment with inhaled terbutaline. Lancet. i:554-557, 1988.
53. Sears, M.R., Taylor, D.R., Print, C.G., Lake, D.C., Li, Q., Flannery, E.M., Yates, D.M., Lukas, M.K., Herbison, G.P. Regular inhaled beta-agonist treatment in bronchial asthma. Lancet 336:1391-1396, 1990.
54. Crowther, S.D. Can we relate the pharmacology to the current clinical knowledge? In Sympathomimetic Enantiomers in the Treatment of Asthma. Costello, J.F., ed. Carnforth, Lancashire: Parthenon Publishing Group, 1997:121-132.
55. Cho, Y.W., Aviado, D.M., Lish, P.M. Efficacy of a new bronchodilator, soterenol, on experimental locked-lung syndrome in dogs. J. Allergy Clin. Immunol. 42:36-48, 1968.
56. Bouhyus, A., Douglas, J.S., Lewis, A.J. Hypersensitivity to adrenoceptor agents in the guinea-pig in vitro and in vivo. Br. J. Pharmacol. 46:520-521P, 1972.
57. Williams, J.C., Strausser, H.R., Giles, R.E. Physiological consequences of beta-adrenoceptor desensitization in guinea pigs. Eur. J. Pharmacol. 88:347-356, 1983.
58. Mazzoni, L., Morley, J., Page, C.P., Sanjar, S. Prophylactic anti-asthma drugs impair the airway hyperreactivity that follows exposure to platelet activating factor (PAF). Br. J. Pharmacol. 86:571P, 1985.
59. Sanjar, S., Kristersson, A., Mazzoni, L., Morley, J., Schaeublin, E. Increased airway reactivity in the guinea pig follows exposure to intravenous isoprenaline. J. Physiol. 425:43-54, 1990.
60. 2-selective sympathomimetics. Pulm. Pharmacol. 7:367-376, 1994.
61. Buchheit, K.H., Hofmann, A., Fozard, J.R. Salbutamol-induced airway hyperreactivity in guinea-pigs is not due to receptor desensitisation. Eur. J. Pharmacol. 287:85-88, 1995.
62. Jafarian, A., Handley, D.A., Biggs, D.F. Effects of RS-albuterol on the development of antigen-mediated airway hyperreactivity in guinea-pigs. Clinical. Revs. Allergy Immunol. 14:91-100, 1996.
63. Hoshiko, K., Morley, J. Allergic bronchospasm and airway hyperreactivity in the guinea-pig. Jpn. J. Pharmacol. 63:151-157, 1993.
64. Hoshiko, K., Morley, J. Exacerbation of airway hyperreactivity by racemic salbutamol in sensitized guinea-pigs. Jpn. J. Pharmacol. 63:159-163, 1993.
65. Crowther, S.D., Chapman, I.D., Morley, J. Heterogeneity of airway hyperresponsiveness. Clinical. Exp. Allergy 27:606-616, 1997.
66. 2-adrenoceptor agonist increases the airway response to methacholine. Eur. J. Pharmacol. 241: 121-123, 1993.
67. Wang, Z-L., Bramley, A.M., McNamara, A., Pare, P.D., Bai, T.R. Chronic fenoterol exposure increases in vivo and in vitro airway responses in guinea pigs. Am. J. Respir. Crit. Care Med. 149:960-965, 1994.
68. Seidehamel, R.J., Dungan, K.W., Hickey, T.E. Specific hypotensive and antihypertensive ocular effects of d-isoproterenol in rabbits. Am. J. Ophthalmol. 79:1018-1025, 1975.
69. 2 receptor blockade. Biochem. Pharmacol. 37:3023-3033, 1988.
70. Potter, D.E., Nicholson, H.T., Rowland, J.M. Ocular hypertensive response to β-adrenoceptor agonists. Curr. Eye. Res. 2:711-719, 1982/ 1983.
71. Rowland, J.M., Potter, D.E. Steric structure activity relationships of various adrenergic agonists: Ocular and systemic effects. Curr. Eye. Res. 1:25-35, 1981.
72. Rowland, J.M., Potter, D.E. Adrenergic drugs and intraocular pressure: The hypertensive effect of epinephrine. Ophthalmol. Res 12:221-229, 1980.
73. Kass, M.A., Reid, T.W., Neufeld, A.H., Bauscher, L.P., Sears, M.L. The effects of d-isoproterenol on intraocular pressure of the rabbit, monkey, and man. Invest. Ophthalmol. Vis. Sci. 15:113-118, 1976.
74. Neufeld, A.H., Jampol, L.M., Sears, M.L. Cyclic-AMP in the aqueous humor: The effects of adrenergic agents. Exp. Eye. Res. 14:242-250, 1972.
75. Kau, S.T., Limp, G.L. On the topically effective ocular hypotensive properties of ICI 147,798, a natriuretic β-adrenoceptor antagonist, in rabbits. Pharmacol. Toxicol. 64:132-136, 1989.
76. Fedyna, J.S., Adejare, A., Miller, D.D., Feller, D.R. Pharmacological evaluation of the beta-adrenoceptor agonist and thromboxane antagonist properties of N-substituted trimetoquinol analogues. Eur. J. Pharmacol. 135:161-171, 1987.
77. Foster, A., Chapman, I.D., Mazzoni, L., Morley, J. Resolution of airway obstruction by reduction of airway hyperreactivity. Br. J. Pharmacol. 106:3P, 1992.
78. Tobert, J.A. Enhancement of uricosuric properties of indacrinone by manipulation of the enantiomer ratio. Clin. Pharmacol. Ther. 29:344-350, 1981.
79. Sanjar, S., Morley, J. Airway hyperreactivity. Lancet ii:160-161, 1988.
80. Galland, B.C., Blackman, J.G. Enhancement of airway reactivity to histamine by isoprenaline and related beta-adrenoceptor agonists in the guinea-pig. Br. J. Pharmacol. 108:1016-1023, 1993.
81. Morley, J., Hoshiko, K., Chapman, I.D., Mazzoni, L. The selective nature of airway hyperreactivity. J Physiol. 446:117P, 1992.
82. Hansel, T.T., Schwarz, F., Villiger, B., Naef, R., Richardson, B.P., Morley, J. Anomalous bronchospasm following inhalation of (+)isoprenaline by asthmatics. Agents Actions (Suppl.) 43:281-288, 1993.
83. Morley, J., Chapman, I.D., Foster, A., Hoshiko, K., Mazzoni, L. Effects of (+) and racemic salbutamol on airway responses in the guinea-pig. Br. J. Pharmacol. 104:295P, 1991.
84. Akers, I.A., Coleman, R.A., Johnson, M., Nials, A.T., Vardey, C.J. The effect of repeated inhalation of (+)-albuterol on airways reactivity in the guinea-pig. Am. J. Respir. Crit. Care. Med. 151:A274, 1995.
85. Perrin-Fayolle, M. Salbutamol in the treatment of asthma. Lancet. 346: 1101, 1995.
86. Perrin-Fayolle, M., Blum, P.S., Morley, J., Grosclaude, M., Chambe, M.-T. Differential responses of asthmatic airways to enantiomers of albuterol. Clin. Rev. Allergy Immunol. 14:139-147, 1996.
87. Tan, Y.K., Soldin, S.J. Analysis of salbutamol enantiomers in human urine by chiral high-performance liquid chromatography and preliminary studies related to the stereoselective disposition kinetics in man. J. Chromatogr. 422:187-195, 1987.
88. Boulton, D.W., Fawcett, J.P. Enantioselective disposition of albuterol in man following oral and intravenous administration. Br. J. Clin. Pharmacol. 41:35-40, 1996.
89. Walle, U.K., Pesola, G.R., Walle, T. Stereoselective sulphate conjugation of salbutamol in humans: Comparison of hepatic, intestinal and platelet activity. Br. J. Clin. Pharmacol. 35:413-418, 1993.
90. Walle, T., Walle, U.K. Stereoselective sulfate conjugation of 4-hydroxypropranolol and terbutaline by human liver phenosulfotransferases. Drug. Metab. Dispos. 20:333-336, 1992.
91. Borgstrom, L., Nyberg, L., Jonsson, S., Lindberg, C., Paulson, J. Pharmacokinetic evaluation in man of terbutaline given as separate enantiomers and as the racemate. Br. J. Clin. Pharmacol. 27:49-56, 1989.
92. Löfdahl, C.-G., Svedmyr, N. Beta-agonists: Still more friends than foes. Eur. Respir. J. 5:898-900, 1992.
93. Kaumann, A.J., Lemoine, H. Separation of catecholamine binding and relaxation in bovine tracheal muscle dependent upon cyclic AMP. J. Physiol. 348:47P, 1984.
94. Andersson, R.G.G., Aberg, G., Handley, D., Morley, J. Effects of S-salbutamol on airway smooth muscle. Eur. Respir. J. 1997 (in press).
95. Yamaguchi, H., McCullough, J.R. S-albuterol exacerbates calcium responses to carbachol in airway smooth muscle cells. Clin. Rev. Allergy Immunol. 14:47-55, 1996.