Differences in endogenous esterification and retention in the rat trachea between budesonide and ciclesonide active metabolite

Drug Metabolism and Disposition

Volumn 35, Issue 10, 2007, Pages 1788-1796

  Lexmüller, Kristina ^a   Gullstrand, Helena ^a   Axelsson, Bengt Olof ^a   Sjölin, Petter ^a   Korn, Solange H ^a   Silberstein, David S ^a   Miller Larsson, Anna ^a  

^a ASTRAZENECA R AND D   (Sweden)

Author keywords

[No Author keywords available]

Indexed keywords

CICLESONIDE; CYCLANDELATE; DRUG METABOLITE; DRUG VEHICLE; FLUTICASONE PROPIONATE; MOMETASONE FUROATE;

ANIMAL EXPERIMENT; ANIMAL TISSUE; ARTICLE; BROWN NORWAY RAT; CONTROLLED STUDY; DRUG HYDROLYSIS; DRUG RETENTION; DRUG SOLUBILITY; DRUG UPTAKE; ESTERIFICATION; LIPOPHILICITY; MALE; NONHUMAN; PRIORITY JOURNAL; RADIOCHROMATOGRAPHY; RAT; STATISTICAL ANALYSIS; TRACHEA;

ANIMALS; BUDESONIDE; CYCLANDELATE; ESTERIFICATION; GLUCOCORTICOIDS; MALE; PREGNENEDIONES; RATS; RATS, INBRED BN; SOLUBILITY; TRACHEA;

RATTUS;

EID: 34748870397     PISSN: 00909556     EISSN: 1521009X     Source Type: Journal    
DOI: 10.1124/dmd.107.015297     Document Type: Article

References (47)

1. Banov CH, Howland WC 3rd, and Lumry WR (2001) Once-daily budesonide via Turbohaler improves symptoms in adults with persistent asthma. Ann Allergy Asthma Immunol 86:627-632.
2. Brattsand R (1997) What factors determine anti-inflammatory activity and selectivity of inhaled steroids. Eur Respir Rev 7:356-361.
3. Brattsand R (1999) The ideal steroid. Pulm Pharmacol 12:119-122.
4. Campbell LM, Watson DG, Venables TL, Taylor MD, and Richardson PDL (1991) Once daily budesonide Turbohaler compared with placebo as initial prophylactic therapy for asthma. Br J Clin Res 2:111-122.
5. Chapman KR, Patel P, D'Urzo AD, Alexander M, Mehra S, Oedekoven C, Engelstatter R, and Boulet LP (2005) Maintenance of asthma control by once-daily inhaled ciclesonide in adults with persistent asthma. Allergy 60:330-337.
6. Cooray HC, Shahi S, Cahn AP, van Veen HW, Hladky SB, and Barrand MA (2006) Modulation of p-glycoprotein and breast cancer resistance protein by some prescribed corticosteroids. Eur J Pharmacol 531:25-33.
7. Dilger K, Schwab M, and Fromm MF (2004) Identification of budesonide and prednisone as substrates of the intestinal drug efflux pump P-glycoprotein. Inflamm Bowel Dis 10:578-583.
8. Edsbäcker S (2002) Uptake, retention, and biotransformation of corticosteroids in the lung and airways, in Inhaled Steroids in Asthma: Optimizing the Effects in the Airways (Schleimer RP, O'Byrne PM, Szefler SJ, and Bratssand R eds) pp 213-246. Marcel Dekker, New York.
9. Edsbäcker S and Jendbro M (1998) Modes to achieve topical selectivity of inhaled glucocorticosteroids. Respir Drug Delivery 6:71-82.
10. Esmailpour N, Högger P, Rabe KF, Heitmann U, Nakashima M, and Rohdewald P (1997) Distribution of inhaled fluticasone propionate between human lung tissue and serum in vivo. Eur Respir J 10:1496-1499.
11. Gullstrand H, Falk Nilsson H, Smailagic A, Sjölin P, Silberstein D, and Miller-Larsson A (2005) Esterification and the ratio between airway and peripheral tissue concentrations are greater for budesonide than ciclesonide after intratracheal instillation into rats. Unknown metabolite of ciclesonide in lung. Proc Am Thoracic Soc 2:A354.
12. Hochberg RB, Pahuja SL, Zielinski JE, and Larner JM (1991) Steroidal fatty acid esters. J Steroid Biochem Mol Biol 40:577-585.
13. Jendbro M and Johansson C-J (2002) Reversible glucocorticoid esterification, in Inhaled Steroids in Asthma: Optimizing the Effects in the Airways (Schleimer RP, O'Byrne PM, Szefler SJ, and Brattsand R eds) pp 309-330. Marcel Dekker, New York.
14. Jendbro M, Johansson C-J, Strandberg P, Falk-Nilsson H, and Edsbäcker S (2001) Pharmacokinetics of budesonide and its major ester metabolite after inhalation and intravenous administration of budesonide in the rat. Drug Metab Dispos 29:769-776.
15. Jerre A, Sjölin P, Silberstein D, and Wieslander E (2006) Cellular uptake and fatty acid esterification of budesonide and ciclesonide in protein-rich medium. Proc Am Thoracic Society 3:A73.
16. Jones AH, Langdon CG, Lee PS, Lingham SA, Nankani JP, Follows RM, Tollemar U, and Richardson PD (1994) Pulmicort Turbohaler once daily as initial prophylactic therapy for asthma. Respir Med 88:293-299.
17. Karpel JP, Busse WW, Noonan MJ, Monahan ME, Lutsky B, and Staudinger H (2005) Effects of mometasone furoate given once daily in the evening on lung function and symptom control in persistent asthma. Ann Pharmacother 39:1977-1983.
18. Lipworth BJ and Jackson CM (2000) Safety of inhaled and intranasal corticosteroids - lessons for the new millennium. Drug Safety 23:11-33.
19. Maassen van den Brink KI, Staal-van den Brekel J, Boorsma M, Edsbäcker S, Wouters EF, and Thorsson L (2005) Evidence of in vivo esterification of budesonide in humans. Eur Respir J 26 (Suppl 49):370s (P2389).
20. Miller-Larsson A, Ivarsson R, Mattsson H, Tunek A, and Brattsand R (1999) High capacity of airway/lung tissue for budesonide esterification as compared to peripheral striated muscles. Eur Respir J 14 (Suppl 30):195s.
21. Miller-Larsson A, Jansson P, Runström A, and Brattsand R (2000) Prolonged airway activity and improved selectivity of budesonide possibly due to esterification. Am J Respir Crit Care Med 162:1455-1461.
22. Miller-Larsson A, Mattsson H, Hjertberg E, Dahlbäck M, Tunek A, and Brattsand R (1998) Reversible fatty acid conjugation of budesonide. Novel mechanism for prolonged retention of topically applied steroid in airway tissue. Drug Metab Dispos 26:623-630.
23. Nave R, Fisher R, and Zech K (2006a) In vitro metabolism of four corticosteroids in human precision-cut lung slices. Proc Am Thoracic Society 3:A74.
24. Nave R, Fisher R, and Zech K (2006b) In vitro metabolism of ciclesonide in human lung and liver precision-cut tissue slices. Biopharm Drug Dispos 27:197-207.
25. Nave R, Meyer W, Fuhst R, and Zech K (2005a) Formation of fatty acid conjugates of ciclesonide active metabolite in the rat lung after 4-week inhalation of ciclesonide. Pulm Pharmacol Ther 18:390-396.
26. Nave R, Sato H, Nonaka T, Mochiduki T, Takahama S, and Kondo S (2005b) Uptake, retention and metabolism of ciclesonide in human alveolar epithelial cells. Eur Respir J 26 (Suppl 49):255s (P1739).
27. Nave R, Sato H, Nonaka T, Mochizuki T, Takahama S, and Kondo S (2006c) Airway specific activation and metabolism of the corticosteroid ciclesonide. Proc Am Thoracic Society 3:A76.
28. Nave R, Schmidt B, Hummel R, Wohlsen A, Herzog R, and Zech K (2004) Highly lipophilic fatty acid esters of the active metabolite of ciclesonide formed in vitro in rat lung tissue. Eur Respir J 24 (Suppl 48):345s (P2170).
29. Nayak AS, Banov C, Corren J, Feinstein BK, Floreani A, Friedman BF, Goldsobel A, Gottschlich GM, Hannaway PJ, Lampl KL, et al. (2000) Once-daily mometasone furoate dry powder inhaler in the treatment of patients with persistent asthma. Ann Allergy Asthma Immunol 84:417-424.
30. Pearlman DS, Berger WE, Kerwin E, Laforce C, Kundu S, and Banerji D (2005) Once-daily ciclesonide improves lung function and is well tolerated by patients with mild-to-moderate persistent asthma. J Allergy Clin Immunol 116:1206-1212.
31. Petersen H, Kullberg A, Edsbäcker S, and Greiff L (2001) Nasal retention of budesonide and fluticasone in man: formation of airway mucosal budesonide-esters in vivo. Br J Clin Pharmacol 51:159-163.
32. Robinson NP, Kyle H, Webber SE, and Widdicombe JG (1989) Electrolyte and other chemical concentrations in tracheal airway surface liquid and mucus. J Appl Physiol 66:2129-2135.
33. Rohatagi S, Luo Y, Shen L, Guo Z, Schemm C, Huang Y, Chen K, David M, Nave R, and King SP (2005) Protein binding and its potential for eliciting minimal systemic side effects with a novel inhaled corticosteroid, ciclesonide. Am J Ther 12:201-209.
34. Rothemund S, Krause E, Ehrlich A, Bienert M, Glusa E, and Verhallen P (1994) Determination of peptide hydrophobicity parameters by reversed-phase high-performance liquid chromatography. J Chromatogr A 661:77-82.
35. Ryrfeldt A, Andersson P, Edsbäcker S, Tönnesson M, Davies D, and Pauwels R (1982) Pharmacokinetics and metabolism of budesonide, a selective glucocorticoid. Eur J Respir Dis 63 (Suppl 122):86-95.
36. Selroos O, Edsbäcker S, and Hultquist C (2004) Once-daily inhaled budesonide for the treatment of asthma: clinical evidence and pharmacokinetic explanation. J Asthma 41:771-790.
37. Thorsson L, Dahlström K, Edsbäcker S, Källén A, Paulson J, and Wirén J-E (1997) Pharmacokinetics and systemic effects of inhaled fluticasone propionate in healthy subjects. Br J Clin Pharmacol 43:155-161.
38. Thorsson L, Edsbäcker S, Källen A, and Löfdahl CG (2001) Pharmacokinetics and systemic activity of fluticasone via Diskus (R) and pMDI, and of budesonide via Turbuhaler (R). Br J Clin Pharmacol 52:529-538.
39. Thorsson L, Thunnisen FBJM, Korn S, Carlshaf A, Edsbäcker S, and Wouters EFM (1998) Formation of fatty acid conjugates of budesonide in human lung tissue in vivo. Am J Respir Crit Care Med 153:A404.
40. Tsantili-Kakoulidou A, Filippatos E, Todoulou O, and Papadaki-Valiraki A (1993) Use of reversed-phase high-performance liquid chromatography in lipophilicity studies of 9H-xanthene and 9H-thioxanthene derivatives containing an aminoalkanamide or a nitrosoureido group: comparison between capacity factors and calculated octanol-water partition coefficients. J Chromatogr A 654:43-52.
41. Tunek A, Sjödin K, and Hallström G (1997) Reversible formation of fatty acid esters of budesonide, an antiasthma glucocorticoid, in human lung and liver microsomes. Drug Metab Dispos 25:1311-1317.
42. Van den Bosch JMM, Westermann CJJ, Aumann J, Edsbäcker S, Tönnesson M, and Selroos O (1993) Relationship between lung tissue and blood plasma concentrations of inhaled budesonide. Biopharm Drug Dispos 14:455-459.
43. Watz H, Boss H, Drollmann A, Nave R, Bethke TD, Magnussen H, and Hoffman H (2006) Concentrations of ciclesonide and its metabolites in the human lung after inhalation of 1280 μg ciclesonide. Eur Respir J 28 (Suppl 50):212s.
44. Wieslander E, Delander E-L, Järkelid L, Hjertberg E, Tunek A, and Brattsand R (1998) Pharmacologic importance of the reversible fatty acid conjugation of budesonide studied in a rat cell line in vitro. Am J Respir Cell Mol Biol 19:477-484.
45. Wieslander E, Jerre A, Delander E-L, and Brattsand R (2000) The prolonged activity of a budesonide pulse depends on its reversible intracellular esterification - studied in vitro. Am J Respir Crit Care Med 161:A775.
46. Yamagami C, Kawai K, and Iwate K (2002) Hydrophobicity parameters determined by reversedphase liquid chromatography. XV: Optimal conditions for prediction of log P(oct) by using RP-HPLC procedures. Chem Pharm Bull (Tokyo) 50:1578-1583.
47. Yates CR, Chang C, Kearbey JD, Yasuda K, Schuetz EG, Miller DD, Dalton JT, and Swaan PW (2003) Structural determinants of P-glycoprotein-mediated transport of glucocorticoids. Pharmacol Res 20:1794-1803.