Formation of fatty acid conjugates of ciclesonide active metabolite in the rat lung after 4-week inhalation of ciclesonide

Pulmonary Pharmacology and Therapeutics

Volumn 18, Issue 6, 2005, Pages 390-396

  Nave, R ^a   Meyer, W ^b   Fuhst, R ^c   Zech, K ^a  

^a ALTANA PHARMA AG   (Germany)

^b MDS Pharma Services Switzerland AG   (Switzerland)

^c FRAUNHOFER INSTITUTE FOR TOXICOLOGY AND EXPERIMENTAL MEDICINE   (Germany)

Author keywords

Asthma; Ciclesonide; Inhaled corticosteroid; Lipid conjugation; Lung metabolism

Indexed keywords

ALCOHOL; CICLESONIDE; DESISOBUTYRYL CICLESONIDE; DRUG METABOLITE; FATTY ACID; FATTY ACID ESTER; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ANIMAL MODEL; ANIMAL TISSUE; ANTIINFLAMMATORY ACTIVITY; ARTICLE; CONTROLLED STUDY; DRUG ACTIVATION; DRUG ACTIVITY; DRUG CONJUGATION; DRUG METABOLISM; ESTERIFICATION; FATTY ACID SYNTHESIS; FEMALE; IN VITRO STUDY; INHALATION; LUNG; MALE; METABOLITE; NONHUMAN; PRIORITY JOURNAL; RAT; REVERSED PHASE HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; SINGLE DRUG DOSE; SOLID PHASE EXTRACTION; TANDEM MASS SPECTROMETRY;

ADMINISTRATION, INHALATION; ANIMALS; ANTI-INFLAMMATORY AGENTS; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; FATTY ACIDS; FEMALE; MALE; MASS SPECTROMETRY; PREGNENEDIONES; RATS; RATS, WISTAR;

EID: 24944496629     PISSN: 10945539     EISSN: 15229629     Source Type: Journal    
DOI: 10.1016/j.pupt.2005.02.012     Document Type: Article

References (38)

1. P.J. Barnes, S. Pedersen, and W.W. Busse Efficacy and safety of inhaled corticosteroids. New developments Am J Respir Crit Care Med 157 1998 S1 S53
2. S.G. Williams, D.K. Schmidt, S.C. Redd, and W. Storms Key clinical activities for quality asthma care. Recommendations of the National asthma education and prevention program MMWR Recomm Rep 52 2003 1 8
3. P.G. Gibson, N. Saltos, and K. Fakes Acute anti-inflammatory effects of inhaled budesonide in asthma: a randomized controlled trial Am J Respir Crit Care Med 163 2001 32 36
4. S.P. Umland, R.P. Schleimer, and S.L. Johnston Review of the molecular and cellular mechanisms of action of glucocorticoids for use in asthma Pulm Pharmacol Ther 15 2002 35 50
5. H. Booth, I. Richmond, C. Ward, P.V. Gardiner, R. Harkawat, and E.H. Walters Effect of high dose inhaled fluticasone propionate on airway inflammation in asthma Am J Respir Crit Care Med 152 1995 45 52
6. S. Suissa, T. Assimes, P. Brassard, and P. Ernst Inhaled corticosteroid use in asthma and the prevention of myocardial infarction Am J Med 115 2003 377 381
7. S. Suissa, and P. Ernst Use of anti-inflammatory therapy and asthma mortality in Japan Eur Respir J 21 2003 101 104
8. S. Suissa, P. Ernst, and A. Kezouh Regular use of inhaled corticosteroids and the long term prevention of hospitalisation for asthma Thorax 57 2002 880 884
9. S. Suissa, and P. Ernst Inhaled corticosteroids: impact on asthma morbidity and mortality J Allergy Clin Immunol 107 2001 937 944
10. D.D. Sin, and J.V. Tu Inhaled corticosteroid therapy reduces the risk of rehospitalization and all-cause mortality in elderly asthmatics Eur Respir J 17 2001 380 385
11. S. Rohatagi, S. Appajosyula, H. Derendorf, S. Szefler, R. Nave, and K. Zech Risk-benefit value of inhaled glucocorticoids: a pharmacokinetic/ pharmacodynamic perspective J Clin Pharmacol 44 2004 37 47
12. N. Esmailpour, P. Hogger, K.F. Rabe, U. Heitmann, M. Nakashima, and P. Rohdewald Distribution of inhaled fluticasone propionate between human lung tissue and serum in vivo Eur Respir J 10 1997 1496 1499
13. J.M. Van den Bosch, C.J. Westermann, J. Aumann, S. Edsbacker, M. Tonnesson, and O. Selroos Relationship between lung tissue and blood plasma concentrations of inhaled budesonide Biopharm Drug Dispos 14 1993 455 459
14. A. Miller-Larsson, H. Mattsson, E. Hjertberg, M. Dahlbäck, A. Tunek, and R. Brattsand Reversible fatty acid conjugation of budesonide. Novel mechanism for prolonged retention of topically applied steroid in airway tissue Drug Metab Dispos 26 1998 623 630
15. A. Tunek, K. Sjödin, and G. Hallström Reversible formation of fatty acid esters of budesonide, an antiasthma glucocorticoid, in human lung and liver microsomes Drug Metab Dispos 25 1997 1311 1317
16. S.L. Pahuja, and R.B. Hochberg A comparison of the fatty acid esters of estradiol and corticosterone synthesized by tissues of the rat J Biol Chem 264 1989 3216 3222
17. R.B. Hochberg, S.L. Pahuja, J.E. Zielinski, and J.M. Larner Steroidal fatty acid esters J Steroid Biochem Mol Biol 40 1991 577 585
18. E. Wieslander, E.L. Delander, L. Järkelid, E. Hjertberg, A. Tunek, and R. Brattsand Pharmacologic importance of the reversible fatty acid conjugation of budesonide studied in a rat cell line in vitro Am J Respir Cell Mol Biol 19 1998 477 484
19. S.P. Newman Deposition and effects of inhaled corticosteroids Clin Pharmacokinet 42 2003 529 544
20. J.P. Kemp Expected characteristics of an ideal, all-purpose inhaled corticosteroid for the treatment of asthma Clin Ther 25 suppl C 2003 C15 C27
21. B.J. Lipworth Systemic adverse effects of inhaled corticosteroid therapy: a systematic review and meta-analysis Arch Intern Med 159 1999 941 955
22. H. Derendorf Pharmacokinetic and pharmacodynamic properties of inhaled corticosteroids in relation to efficacy and safety Respir Med 91 suppl A 1997 22 28
23. G. Dent Ciclesonide (Byk Gulden) Curr Opin Investig Drugs 3 2002 78 83
24. F. Kanniess, K. Richter, S. Böhme, R.A. Jörres, and H. Magnussen Effect of inhaled ciclesonide on airway responsiveness to inhaled AMP, the composition of induced sputum and exhaled nitric oxide in patients with mild asthma Pulm Pharmacol Ther 14 2001 141 147
25. D.S. Postma, C. Sevette, Y. Martinat, N. Schlösser, J. Aumann, and H. Kafé Treatment of asthma by the inhaled corticosteroid ciclesonide given either in the morning or evening Eur Respir J 17 2001 1083 1088
26. B.B. Larsen, L.P. Nielsen, R. Engelstätter, V. Steinijans, and R. Dahl Effect of ciclesonide on allergen challenge in subjects with bronchial asthma Allergy 58 2003 207 212
27. D.A. Taylor, M.W. Jensen, V. Kanabar, R. Engelstätter, V.W. Steinijans, and P.J. Barnes A dose-dependent effect of the novel inhaled corticosteroid ciclesonide on airway responsiveness to adenosine-5′- monophosphate in asthmatic patients Am J Respir Crit Care Med 160 1999 237 243
28. M. Stoeck, R. Riedel, G. Hochhaus, D. Hafner, J.M. Masso, and B. Schmidt In vitro and in vivo anti-inflammatory activity of the new glucocorticoid ciclesonide J Pharmacol Exp Ther 309 2004 249 258
29. 14C]ciclesonide after oral and intravenous administration to healthy subjects Clin Pharmacokinet 43 2004 479 486
30. A. Weinbrenner, D. Hüneke, M. Zschiesche, G. Engel, W. Timmer, and V.W. Steinijans Circadian rhythm of serum cortisol after repeated inhalation of the new topical steroid ciclesonide J Clin Endocrinol Metab 87 2002 2160 2163
31. N.E. Mealy, M. Bayès, and J. Castañer Ciclesonide Drugs Fut 26 2001 1033 1039
32. K. Dietzel, R. Engelstätter, and A. Keller Ciclesonide: an on-site-activated steroid T.T. Hansel P.J. Barnes New drugs for asthma, allergy and COPD Progress in Respiratory Research vol. 31 2001 S. Karger Basel, Switzerland 91 93
33. E. Kerwin, P. Chervinsky, J. Fish, S. Kundu, J. Williams, D. Banerji, and P. Hamedani Ciclesonide has no effect on hypothalamic-pituitary-adrenal (HPA)-axis at once-daily doses of 80 μg 160 μg or 320 μg in the treatment of patients with mild-to-moderate asthma [abstract] Am J Respir Crit Care Med 2004 Abstract A90
34. R. Nave, R.-P. Hummel, A. Wohlsen, R. Herzog, and K. Zech The active metabolite of ciclesonide, des-isobutyryl ciclesonide, forms highly lipophilic fatty acid conjugates in precision-cut rat lung slices [abstract] Am J Respir Crit Care Med 169 suppl. 2004 A91
35. R. Nave, R. Fisher, and K. Zech In vitro metabolism of ciclesonide in the human lung and liver as determined by use of precision-cut tissue slices [abstract] Am J Respir Crit Care Med 167 suppl 2003 A771 Abstract A1510
36. B. Asgharian, J.T. Kelly, and E.W. Tewksbury Respiratory deposition and inhalability of monodisperse aerosols in Long-Evans rats Toxicol Sci 71 2003 104 111
37. G. Borchard, M.L. Cassará, P.E.H. Roemelé, B.I. Florea, and H.E. Junginger Transport and local metabolism of budesonide and fluticasone propionate in a human bronchial epithelial cell line (Calu-3) J Pharm Sci 91 2002 1561 1567
38. K.R. Chapman, P. Patel, A.D. D'Urzo, M. Alexander, S. Mehra, and C. Oedekoven Maintenance of asthma control by once-daily inhaled ciclesonide in adults with persistent asthma Allergy 60 2005 330 337