New steroidal anti-inflammatory antedrugs: Methyl 21-desoxy-21-chloro-11β,17α-dihydroxy-3,20-dioxo-1,4-pregnadiene-16α-carboxylate, methyl 21-desoxy-21-chloro-11β-hydroxy-3,20-dioxo-1,4-pregnadiene-16α-carboxylate, and their 9α-fluoro derivatives

Steroids

Volumn 65, Issue 4, 2000, Pages 210-218

  Ko, Dong Hoon ^a   Heiman, Ann S ^a   Chen, Meiqin ^a   Lee, Henry J ^a  

^a FLORIDA A AND M UNIVERSITY   (United States)

Author keywords

Antedrug; Anti inflammatory steroids; Croton oil induced ear edema

Indexed keywords

ANTIINFLAMMATORY AGENT; FLUORINATED STEROID; GLUCOCORTICOID RECEPTOR; STEROID; TYROSINE AMINOTRANSFERASE;

ANIMAL CELL; ANIMAL EXPERIMENT; ANIMAL MODEL; ANTIINFLAMMATORY ACTIVITY; ARTICLE; BINDING AFFINITY; CONTROLLED STUDY; DOSE RESPONSE; DRUG RECEPTOR BINDING; DRUG SYNTHESIS; EDEMA; ENZYME INDUCTION; INFLAMMATION; MALE; NONHUMAN; RAT;

ANIMALS; ANTI-INFLAMMATORY AGENTS; CARCINOMA, HEPATOCELLULAR; CROTON OIL; DOSE-RESPONSE RELATIONSHIP, DRUG; DRUG EVALUATION, PRECLINICAL; EAR DISEASES; EDEMA; MALE; PREDNISOLONE; PREGNADIENES; RATS; RATS, SPRAGUE-DAWLEY; RECEPTORS, GLUCOCORTICOID; TUMOR CELLS, CULTURED; TYROSINE TRANSAMINASE;

CROTON;

EID: 0034098564     PISSN: 0039128X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0039-128X(99)00103-8     Document Type: Article

References (41)

1. Hench P.S., Kendall E.C., Slocumb C.H., Polley H.F. Effect of hormone of adrenal cortex (17-hydroxy-11-dehydrocorticosterone; compound E) and of pituitary adrenocorticotropic hormone on rheumatoid arthritis; preliminary report. Proc Staff Meet Mayo Clin. 24:1949;181-197.
2. Hench P.S., Kendall E.C., Slocumb C.H., Polley H.F. Effects of cortisone acetate and pituitary ACTH on rheumatoid arthritis, rheumatic fever and certain other conditions. Arch Intern Med. 85:1950;545-666.
3. Avery MA, Woolfrey JR. Antiinflammatory steroids. In: Wolff ME, editor. Medicinal chemistry and drug discovery. New York: John Wiley & Sons, Inc. 1997. pp. 281-376.
4. Fried J., Sabo E.F. Synthesis of 17α-hydroxycorticosterone and its 9α-halo derivatives from 11-epi-17α-hydroxycorticosterone. J Am Chem Soc. 75:1953;2273.
5. Fried J., Sabo E.F. 9α-Fluoro derivatives of cortisone and hydrocortisone. J Am Chem Soc. 76:1954;1455.
6. Arth G.E., Fried J., Johnston D.B.R., Hoff D.R., Sarett L.H., Silber R.H., Stoerk H.C., Winter C.A. 16-Methylated steroids. 2. 16α-Methyl analogues of cortisone, a new group of antiinflammatory steroids, 9α-halo derivatives. J Am Chem Soc. 80:1958;3161.
7. Oliveto E.P., Rausser R., Herzog H.L., Hershberg E.B., Tolksdorf S., Eisler M., Perlman P.L., Pechet M.M. 16-Alkylated corticoids. 3. 16β-Methyl-9α-fluoroprednisolone 21-acetate. J Am Chem Soc. 80:1958;6687.
8. Toogood J.H., Lefcoe N.M., Haines D.S.M., Chuang L., Jenning B., Erington N., Baksh L., Cauchi M. Minimum dose requirements of steroid dependent asthmatic patients for aerosol beclomethasone and oral prednisolone. J Allergy Clin Immunol. 61:1978;355-364.
9. Maibach H.J. Topical corticoid therapy. Part 1. Adverse effect of topical corticoids. Systemic Cutis. 24:1979;446-448.
10. Nilsson J.E., Gip L.J. Systemic effects of local treatment with high doses of potent corticosteroids in psoriatrics. Acta Derm Venereol (Stockh). 59:1979;245-248.
11. Lee HJ, Heiman AS, Taraporewala B. New steroidal anti-inflammatory drugs. In: Rainsford KD, Velo GP, editors. New Developments in Antirheumatic Therapy. Lancaster, England: Kluwer Academic Publisher, Vol III: 1989. pp. 153-86.
12. Lee H.J., Khalil M.A., Lee J.W. Antedrug a conceptual basis for safer antiinflammatory steroids . Drugs Expl Clin Res. 10:1984;835-844.
13. Popper TL, Watnick AS. Anti-inflammatory steroid. In: Scherer RA, Whitehouse MW, editors. Anti-inflammatory Agents - Chemistry and Pharmacology. Vol. 1: 1974. pp. 245-94.
14. Lee H.J., Soliman M.R.I. Anti-inflammatory steroids without pituitary adrenal suppression. Science. 215:1982;989-991.
15. Heiman A.S., Ko D.H., Chen M., Lee H.J. New steroidal anti-inflammatory antedrugs methyl 3,20-dioxo-9α-fluoro-11β,17α,21-trihydroxy-1,4-pregnadiene- 16α-carboxylate and methyl 21-acetyloxy-3,20-dioxo-11β,17α-dihydroxy-9α-fluoro-1,4- pregnadiene-16α-carboxylate . Steroids. 62:1997;491-499.
16. Solo A.J., Tramposch K.M., Szeto D.W., Suto M.J. Relative affinity of 17α- and/or 21-esters and 17α,21-diesters of cortisol for a glucocorticoid receptor from thymocytes. J Med Chem. 25:1982;747.
17. Phillips GH. Mechanism of topical corticosteroid activity. In: Glaxo Symposium. London: Churchill Livingstone, 1976.
18. Carruthers J.A., August P.J., Staughton R.C.D. Observations on the systemic effect of topical Clobetasol Propionate (Dermovate). Br Med J. 4:1975;203.
19. Ueno H., Maruyama A., Miyake M., Nakao E., Nakao K., Umezu K., Nitta I. Synthesis and evaluation of antiinflammatory activities of a series of corticosteroid 17α-esters containing a functional group. J Med Chem. 34:1991;2468-2473.
20. Khalil M.A., Maponya M.F., Ko D.-H., You Z., Oriaku E.T., Lee H.J. New antiinflammatory steroids [16α,17α-d]-3′-hydroxyiminoformylisoxazoline derivatives of prednisolone and 9α-fluoroprednisolone . Med Chem Res. 6:1996;52-60.
21. Ko D.-H., Maponya M.F., Khalil M.A., Oriaku E.T., You Z., Lee H.J. New anti-inflammatory steroids [16α,17α-d]-isoxazoline derivatives of prednisolone and 9α-fluoroprednisolone . Med Chem Res. 7:1997;313-323.
22. You Z., Khalil M.A., Ko D.-H., Lee H.J. Suppression of the Mattox rearrangement of 16α-cyanoprednisolones in acid synthesis of methyl 16α-prednisolone carboxylates . Tetrahedron Lett 36(19). 1995;3303-3306.
23. Kwon T., Heiman A.S., Oriaku E.T., Yoon K., Lee H.J. New steroidal antiinflammatory antedrugs steroidal [16α,17α-d]-3′-carbethoxyisoxazolines . J Med Chem. 38:1995;1048-1051.
24. Hong D., Heiman A.S., Lee H.J. Synthesis of 6-methoxycarbonylprednisolone and its derivatives as new antiinflammatory steroidal antedrugs. J Pharm Sci. 83:1993;357-361.
25. nd communication pharmacological studies of methyl 11β,17α,21-trihydroxy 3,20-dioxo-pregna-1,4-diene-16α-carboxylate and 11β,21-dihydroxy-3,20-dioxo-pregna-1,4-diene-16α-carboxylate . Arzneimittelforschung. 39:1989;262-267.
26. Heiman A.S., Taraporewala I.B., McLean M., Hong D., Lee H.J. New potent topical anti-inflammatory steroids with reduced side effects derivatives of steroid-16-carboxy esters . J Pharm Sci. 79:1990;617-721.
27. Lee H.J., You Z., Ko D.-H., Yoon K.J. New steroidal antiinflammatory agents prednisolone derivatives with an isoxazoline fusion at the 16- and 17-carbons and an alkyl carboxylate at the 16a-position . Drugs Exp Clin Res. 24:(2):1998;57-66.
28. Heiman A.S., Tonner L.E. The acute effect of lead acetate on glucocorticoid regulation of tyrosine aminotransferase in hepatoma cells. Toxicol. 100:1995;57-68.
29. Simons SS, Mercier L, Miller NR, et al. Differential modulation of gene induction by glucocorticoids and antiglucocorticoids in rat hepatoma tissue culture cells. Cancer Res (suppl. X) 1989;49:2244-51.
30. Watson, CS, Gametchu B. Membrane-initiated steroid actions and the proteins that mediate them. Proc Soc Exp Biol Med 1999;220:9-19.
31. Hammond G.L., Smith C.L., Underhill C.M., Nguyen V.T. Interaction between corticosteroid binding globulin and activated leukocytes in vitro. Biochem Biophys Res Commun. 172:1991;172-177.
32. Strel'chyonok O.A., Avvakumov G.V. Interaction of human CBG with cell membranes. J Steroid Biochem Molec Biol. 40:1991;795-803.
33. Endo Y., Fugihara E. Characteristics of glucocorticoid-binding by inflammatory tissues of rats. J Steroid Biochem Molec Biol. 37:1990;103-112.
34. Drexler H., Zeiher A.M., Wollshlager H., Meinertz H., Just H., Bonzel T. Flow-dependent coronary artery dilatation in humans. Circulation. 80:1989;466-474.
35. Persson M.G., Gustaffson L.E., Wiklund N.P., Moncada S., Hedqvist P. Endogenous NO as a probable modulator of pulmonary circulation and hypoxic pressor response in vivo. Acta Physiol Scand. 140:1990;449-457.
36. Tracey WR, Xue C, Klinghofer V, et al. Immunochemical detection of inducible NO synthase in human lung. Am J Physiol 1994;266:L722-7.
37. Stuehr D.J., Marletta M.A. Synthesis of nitrite and nitrate in murine macrophage cell lines. Cancer Res. 47:1987;5590-5594.
38. Radomski M.W., Palmer R.M.J., Moncada S. Glucocorticoids inhibit the expression of an inducible, but not constitutive, nitric oxide synthase in vascular endothelial cells. Proc Natl Acad Sci USA. 87:1990;10043-10047.
39. DiRosa M., Radomski M., Carnuccio R., Moncada S. Glucocorticoids inhibit the induction of nitric oxide synthase in macrophages. Biochem Biophys Res Comm. 172:1990;1246-1252.
40. Heiman A.S., Hickman F., Ko D.-H., Lee H.J. New steroidal anti-inflammatory antedrugs bind to macrophage glucocorticoid receptors and inhibit nitric oxide generation. Steroids. 63:1998;644-649.
41. Schmid E., Schmid W., Jantzen M., Mayer D., Jastorff B., Schultz G. Transcription activation of the tyrosine aminotransferase gene by glucocorticoids and cAMP in primary hepatocytes. Eur J Biochem. 165:1987;499-506.