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Volumn 22, Issue 3, 1999, Pages 279-287

A novel approach to the discovery of non-systemic anti-inflammatory steroids; antedrug

Author keywords

Antedrug; Croton oil ear edema; Prednisolone derivative; Receptor binding

Indexed keywords

ANTIINFLAMMATORY AGENT; CARBOXYLIC ACID; CORTICOSTERONE; CROTON OIL; ISOXAZOLE DERIVATIVE; PREDNISOLONE; PRODRUG;

EID: 0033144772     PISSN: 02536269     EISSN: None     Source Type: Journal    
DOI: 10.1007/BF02976363     Document Type: Article
Times cited : (14)

References (47)
  • 1
    • 0001199533 scopus 로고
    • Chemical aspects of selective toxicity
    • Albert, A., Chemical aspects of selective toxicity. Nature, 182, 421-423 (1958).
    • (1958) Nature , vol.182 , pp. 421-423
    • Albert, A.1
  • 2
    • 0025188612 scopus 로고
    • In vitro hydrolysis of steroid acid ester derivatives of prednisolone in plasma of different species
    • Al-Habet, S. M. H. and Lee, H. J., In vitro hydrolysis of steroid acid ester derivatives of prednisolone in plasma of different species. J. Pharm. Sci., 79, 916-918 (1990).
    • (1990) J. Pharm. Sci. , vol.79 , pp. 916-918
    • Al-Habet, S.M.H.1    Lee, H.J.2
  • 3
    • 0000136353 scopus 로고    scopus 로고
    • Antiinflammatory steroids
    • Wolfe, M. E. (Ed). John Wiley & Sons, Inc.
    • Avery, M. A. and Woolfrey, J. R., Antiinflammatory steroids: Wolfe, M. E. (Ed). Medicinal Chemistry and Drug Discovery, John Wiley & Sons, Inc., pp. 281-376 (1997).
    • (1997) Medicinal Chemistry and Drug Discovery , pp. 281-376
    • Avery, M.A.1    Woolfrey, J.R.2
  • 4
    • 0022454697 scopus 로고
    • The effects of new local anti-inflammatory steroids on leucocyte migration and prostanoid liberation in rats
    • Bird, J., Lay, J. C. and Lee, H. J., The effects of new local anti-inflammatory steroids on leucocyte migration and prostanoid liberation in rats. J. Pharm. Pharmacol., 38, 589-594 (1986a).
    • (1986) J. Pharm. Pharmacol. , vol.38 , pp. 589-594
    • Bird, J.1    Lay, J.C.2    Lee, H.J.3
  • 5
    • 0023027129 scopus 로고
    • Topical anti-inflammatory activity of esters of steroid-21-oic acids
    • Bird, J., Kim, H. P. and Lee, H. J., Topical anti-inflammatory activity of esters of steroid-21-oic acids. Steroids, 47, 35-45 (1986).
    • (1986) Steroids , vol.47 , pp. 35-45
    • Bird, J.1    Kim, H.P.2    Lee, H.J.3
  • 6
    • 0020510098 scopus 로고
    • Specificity and inhibition of glucocorticoid-induced macrocortin secretion from rat peritoneal macrophages
    • Blackwell, G. J., Specificity and inhibition of glucocorticoid-induced macrocortin secretion from rat peritoneal macrophages. Br. J. Pharmacol., 79, 587-594 (1983).
    • (1983) Br. J. Pharmacol. , vol.79 , pp. 587-594
    • Blackwell, G.J.1
  • 7
    • 0020673689 scopus 로고
    • Structure-activity relationships in the antiinflammatory steroids: A pattern-recognition approach
    • Bodor, N., Harget, A. J. and Philip, E. W., Structure-activity relationships in the antiinflammatory steroids: A pattern-recognition approach. J. Med. Chem., 26, 318-328 (1983).
    • (1983) J. Med. Chem. , vol.26 , pp. 318-328
    • Bodor, N.1    Harget, A.J.2    Philip, E.W.3
  • 8
    • 0000445323 scopus 로고
    • Chemical and biological factors in the activity of adrenocortical steroids
    • Bush, I. E., Chemical and biological factors in the activity of adrenocortical steroids. Pharmacol. Rev., 14, 374-392 (1962).
    • (1962) Pharmacol. Rev. , vol.14 , pp. 374-392
    • Bush, I.E.1
  • 9
    • 0018844783 scopus 로고
    • Effects of a new glucocorticoid, deflazacort on pituitary-adrenal function in man: A comparison with prednisolone
    • Criscuolo, D., Fraioli, F. and Bonifacio, V., Effects of a new glucocorticoid, deflazacort on pituitary-adrenal function in man: a comparison with prednisolone. Int. J. Clin. Pharmacol. Ther. Toxicol., 18, 37-41 (1980).
    • (1980) Int. J. Clin. Pharmacol. Ther. Toxicol. , vol.18 , pp. 37-41
    • Criscuolo, D.1    Fraioli, F.2    Bonifacio, V.3
  • 10
    • 0016931550 scopus 로고
    • Steroid structure and steroid activity
    • Elks, J., Steroid structure and steroid activity. Br. J. Dermatol., 94, 2-13 (1976).
    • (1976) Br. J. Dermatol. , vol.94 , pp. 2-13
    • Elks, J.1
  • 11
    • 0018755280 scopus 로고
    • 2 inhibitor which prevents prostaglandin generation
    • 2 inhibitor which prevents prostaglandin generation. Nature, 278, 456-459 (1979).
    • (1979) Nature , vol.278 , pp. 456-459
    • Flower, R.J.1    Blackwell, G.J.2
  • 14
    • 0025329249 scopus 로고
    • New potent topical anti-inflammatory steroids with reduced side effects: Derivatives of steroid-16-carboxy esters
    • Heiman, A. S., Taraporewala, I. B., McLean, H. M., Hong, D. and Lee, H. J., New potent topical anti-inflammatory steroids with reduced side effects: derivatives of steroid-16-carboxy esters. J. Pharm. Sci., 79, 617-621 (1990).
    • (1990) J. Pharm. Sci. , vol.79 , pp. 617-621
    • Heiman, A.S.1    Taraporewala, I.B.2    McLean, H.M.3    Hong, D.4    Lee, H.J.5
  • 15
    • 0031009643 scopus 로고    scopus 로고
    • New steroidal anti-inflammatory antedrug
    • Heiman, A. S., Ko, D.-H., Chen, M. and Lee, H. J., New steroidal anti-inflammatory antedrug, Steroids, 62, 491-499 (1997).
    • (1997) Steroids , vol.62 , pp. 491-499
    • Heiman, A.S.1    Ko, D.-H.2    Chen, M.3    Lee, H.J.4
  • 16
    • 0032443703 scopus 로고    scopus 로고
    • New steroidal anti-inflammatory antedrugs bind to macrophage glucocorticoid receptors and inhibit nitric oxide generation
    • Heiman, A. S., Hickman, F., Ko, D.-H. and Lee, H. J., New steroidal anti-inflammatory antedrugs bind to macrophage glucocorticoid receptors and inhibit nitric oxide generation. Steroids, 63, 644-649 (1998).
    • (1998) Steroids , vol.63 , pp. 644-649
    • Heiman, A.S.1    Hickman, F.2    Ko, D.-H.3    Lee, H.J.4
  • 18
    • 0021989421 scopus 로고
    • Synthesis of a new anti-inflammatory steroidal acid ester: Methyl 11β-hydroxy-3,20-dioxo-1,4-pregnadien-21-oate
    • Khalil, M. A., Lay, J. C. and Lee, H. J., Synthesis of a new anti-inflammatory steroidal acid ester: methyl 11β-hydroxy-3,20-dioxo-1,4-pregnadien-21-oate. J. Pharm. Sci., 74, 180-183 (1985).
    • (1985) J. Pharm. Sci. , vol.74 , pp. 180-183
    • Khalil, M.A.1    Lay, J.C.2    Lee, H.J.3
  • 19
    • 0002104784 scopus 로고    scopus 로고
    • New antiinflammatory steroids: [17α,16α-d]-isoxazoline derivatives of prednisolone and 9α-fluoroprednisolone
    • Khalil, M. A., Maponya, M. F., Ko, D.-H., You, Z. and Lee, H. J., New antiinflammatory steroids: [17α,16α-d]-isoxazoline derivatives of prednisolone and 9α-fluoroprednisolone. J. Med. Chem. Res. 6, 52-60 (1996).
    • (1996) J. Med. Chem. Res. , vol.6 , pp. 52-60
    • Khalil, M.A.1    Maponya, M.F.2    Ko, D.-H.3    You, Z.4    Lee, H.J.5
  • 20
    • 0028225668 scopus 로고
    • Colonic mucosa-specific pro-antedrugs for oral treatment of ulcerative colitis: Design, synthesis and fate of methyl 20-glucopyranosyloxyprednisolonates
    • Kimura, T, Yamaguchi, T., Usuki, K., Kurosaki, Y., Nakayama, T., Fujiwara, Y., Matsuda, Y., Unno, K. and Suzuki, T., Colonic mucosa-specific pro-antedrugs for oral treatment of ulcerative colitis: design, synthesis and fate of methyl 20-glucopyranosyloxyprednisolonates. J. Control. Release, 30, 125-135 (1994).
    • (1994) J. Control. Release , vol.30 , pp. 125-135
    • Kimura, T.1    Yamaguchi, T.2    Usuki, K.3    Kurosaki, Y.4    Nakayama, T.5    Fujiwara, Y.6    Matsuda, Y.7    Unno, K.8    Suzuki, T.9
  • 21
    • 0000506441 scopus 로고    scopus 로고
    • New anti-inflammatory steroids: [17α,16α-d]-3′-hydroxy-iminoformylisoxazoline derivatives of prednisolone and 9α-fluoroprednisolone
    • Ko, D.-H., Maponya, M. F., Khalil, M.A., You, Z. and Lee, H. J., New anti-inflammatory steroids: [17α,16α-d]-3′-hydroxy-iminoformylisoxazoline derivatives of prednisolone and 9α-fluoroprednisolone. J. Med. Chem. Res. 7, 313-323 (1997).
    • (1997) J. Med. Chem. Res. , vol.7 , pp. 313-323
    • Ko, D.-H.1    Maponya, M.F.2    Khalil, M.A.3    You, Z.4    Lee, H.J.5
  • 22
    • 0022341856 scopus 로고
    • Hydrolysis of methyl steroid 21-oates and acetyl steroid 21-ols by rat liver microsomes
    • Kumari, D. and Lee, H. J., Hydrolysis of methyl steroid 21-oates and acetyl steroid 21-ols by rat liver microsomes. Drug Metab. Desp., 13, 627-629 (1985).
    • (1985) Drug Metab. Desp. , vol.13 , pp. 627-629
    • Kumari, D.1    Lee, H.J.2
  • 23
    • 0028970008 scopus 로고
    • New steroidal antiinflammatory antedrugs: Steroidal [17α,16α-d]-3′-carethoxyisoxazolines
    • Kwon, T., Heiman, A. S., Oriaku, E. T., Yoon, K. and Lee, H. J., New steroidal antiinflammatory antedrugs: steroidal [17α,16α-d]-3′-carethoxyisoxazolines. J. Med. Chem., 38, 1048-1051 (1995).
    • (1995) J. Med. Chem. , vol.38 , pp. 1048-1051
    • Kwon, T.1    Heiman, A.S.2    Oriaku, E.T.3    Yoon, K.4    Lee, H.J.5
  • 25
    • 0020037486 scopus 로고
    • Anti-inflammatory steroids without pituitary adrenal suppression
    • Lee, H. J. and Soliman, M. R. I., Anti-inflammatory steroids without pituitary adrenal suppression. Science, 215, 989-991 (1982).
    • (1982) Science , vol.215 , pp. 989-991
    • Lee, H.J.1    Soliman, M.R.I.2
  • 26
    • 0021706638 scopus 로고
    • Antedrug: A conceptual basis for safer antiinflammatory steroids
    • Lee, H. J., Khalil, M. A. and Lee, J. W., Antedrug: A conceptual basis for safer antiinflammatory steroids. Drugs Expl. Clin. Res., 10, 835-844 (1984).
    • (1984) Drugs Expl. Clin. Res. , vol.10 , pp. 835-844
    • Lee, H.J.1    Khalil, M.A.2    Lee, J.W.3
  • 27
    • 0022297908 scopus 로고
    • Binding of ester and amide epimers of 20-dihydro-prednisolonic acid to cytosol receptors and their acute pharmacological activities in rats
    • Lee, J. W. and Lee, H. J., Binding of ester and amide epimers of 20-dihydro-prednisolonic acid to cytosol receptors and their acute pharmacological activities in rats. J. Steroid. Biochem., 23, 943-948 (1985).
    • (1985) J. Steroid. Biochem. , vol.23 , pp. 943-948
    • Lee, J.W.1    Lee, H.J.2
  • 28
  • 30
    • 0031725758 scopus 로고    scopus 로고
    • New steroidal antiinflammatory agents: Prednisolone derivatives with a isoxazoline fusion at the 16- and 17-carbons and an alkyl carbonylate at the 16α-position
    • Lee, H. J., You, Z., Ko, D.-H. and Yoon, K. J., New steroidal antiinflammatory agents: prednisolone derivatives with a isoxazoline fusion at the 16- and 17-carbons and an alkyl carbonylate at the 16α-position. Drug Exptl. Clin. Res., 24 (2), 57-66 (1998b).
    • (1998) Drug Exptl. Clin. Res. , vol.24 , Issue.2 , pp. 57-66
    • Lee, H.J.1    You, Z.2    Ko, D.-H.3    Yoon, K.J.4
  • 31
    • 0008590343 scopus 로고
    • Conversion of steroid-17-yl glyoxals to epimeric glycolic esters
    • Lewbart, M. L. and Mattox, V. R., Conversion of steroid-17-yl glyoxals to epimeric glycolic esters. J. Org. Chem., 28, 1779-1786 (1963).
    • (1963) J. Org. Chem. , vol.28 , pp. 1779-1786
    • Lewbart, M.L.1    Mattox, V.R.2
  • 33
    • 0015102877 scopus 로고
    • Synthesis of steroids containing the α-keto acid sidechain
    • Monder, C., Synthesis of steroids containing the α-keto acid sidechain. Steroids, 18, 187-194 (1971).
    • (1971) Steroids , vol.18 , pp. 187-194
    • Monder, C.1
  • 34
    • 0017181158 scopus 로고
    • Partial purification of rabbit aorta contracting substance-releasing factor and inhibition of its activity by anti-inflammatory steroids
    • Nijkamp, F. P., Flower, R. J., Moncado, S. and Vane, J. R., Partial purification of rabbit aorta contracting substance-releasing factor and inhibition of its activity by anti-inflammatory steroids, Nature, 263, 479-482 (1976).
    • (1976) Nature , vol.263 , pp. 479-482
    • Nijkamp, F.P.1    Flower, R.J.2    Moncado, S.3    Vane, J.R.4
  • 35
    • 0021743881 scopus 로고
    • Systemic effects of chronically administered methyl prednisolonate and methyl 17-deoxyprednisolonate
    • Olejniczak, E. and Lee, H. J., Systemic effects of chronically administered methyl prednisolonate and methyl 17-deoxyprednisolonate. Steroids, 43, 657-662, (1984).
    • (1984) Steroids , vol.43 , pp. 657-662
    • Olejniczak, E.1    Lee, H.J.2
  • 36
    • 0002469339 scopus 로고
    • Locally active corticoids: Structure activity relationships
    • Wilson, L. and Marks, R. (Eds.) Livingstone, Edingburgh, U.K.
    • Phillips, G. H., Locally active corticoids: structure activity relationships. In Wilson, L. and Marks, R. (Eds.). Mechanism of topical coticoid activity. Livingstone, Edingburgh, U.K., pp. 1-18, 1976.
    • (1976) Mechanism of Topical Coticoid Activity , pp. 1-18
    • Phillips, G.H.1
  • 37
    • 0002469339 scopus 로고
    • Mechanism of topical corticosteroid activity
    • London
    • Phillips, G. H., Mechanism of topical corticosteroid activity. Glaxo symposium, London, 1976.
    • (1976) Glaxo Symposium
    • Phillips, G.H.1
  • 38
    • 0019423008 scopus 로고
    • Corticoids and cultured human epidermal keratinocytes: Specific intracellular binding and clinical efficacy
    • Ponec, M., Kempenaar, J. A. and Kloet, E. R., Corticoids and cultured human epidermal keratinocytes: specific intracellular binding and clinical efficacy. J. Invest. Dermatol., 76, 211-214 (1981).
    • (1981) J. Invest. Dermatol. , vol.76 , pp. 211-214
    • Ponec, M.1    Kempenaar, J.A.2    Kloet, E.R.3
  • 40
    • 0345284792 scopus 로고
    • Comparative efficacy of topical anti-inflammatory corticosteroids
    • Schlagel, C.A., Comparative efficacy of topical anti-inflammatory corticosteroids. J. Pharm. Sci., 54, 335-354 (1965).
    • (1965) J. Pharm. Sci. , vol.54 , pp. 335-354
    • Schlagel, C.A.1
  • 41
    • 0019907613 scopus 로고
    • Glucocorticoid-specific binding: Structure-activity relationship
    • Shroot, B., Caron, J. C. and Ponec, M., Glucocorticoid-specific binding: Structure-activity relationship. Br. J. Dermatol., 107 (suppl 23), 30-34 (1982).
    • (1982) Br. J. Dermatol. , vol.107 , Issue.23 SUPPL. , pp. 30-34
    • Shroot, B.1    Caron, J.C.2    Ponec, M.3
  • 42
    • 0019465972 scopus 로고
    • Local antiinflammatory activity of acid ester derivatives of prednisolone
    • Soliman, M. R. I. and Lee, H. J., Local antiinflammatory activity of acid ester derivatives of prednisolone. Res. Commun. Pathol. Pharmacol., 33, 357-360 (1981).
    • (1981) Res. Commun. Pathol. Pharmacol. , vol.33 , pp. 357-360
    • Soliman, M.R.I.1    Lee, H.J.2
  • 44
    • 0018695570 scopus 로고
    • Synthesis and anti-inflammatory properties of Budesonide, a new non-halogenated glucocorticoid with high local activity
    • Thalen, A. and Brattsand, E., Synthesis and anti-inflammatory properties of Budesonide, a new non-halogenated glucocorticoid with high local activity. Arzneim-Forsch Drug Res., 29 (II), 687-690 (1979).
    • (1979) Arzneim-Forsch Drug Res. , vol.29 , Issue.2 , pp. 687-690
    • Thalen, A.1    Brattsand, E.2
  • 45
    • 0013806318 scopus 로고
    • A bioassay for the concomitant assessment of the antiphlogistic and thymolytic activities of topically applied corticosteroid
    • Tonneli, G., Thiabault, L. and Ringler, J., A bioassay for the concomitant assessment of the antiphlogistic and thymolytic activities of topically applied corticosteroid. Endocrinol., 77, 625-634 (1965).
    • (1965) Endocrinol. , vol.77 , pp. 625-634
    • Tonneli, G.1    Thiabault, L.2    Ringler, J.3
  • 46
    • 0028970020 scopus 로고
    • Suppression of the Mattox rearrangement of 16α-cyanoprednisolones in acid: Synthesis of methyl 16α-prednisolonecarboxylates
    • You, Z., Khalil, M. A., Ko, D.-H. and Lee, H. J., Suppression of the Mattox rearrangement of 16α-cyanoprednisolones in acid: synthesis of methyl 16α-prednisolonecarboxylates. Tetrahedron Lett., 36(19), 3303-3306 (1995).
    • (1995) Tetrahedron Lett. , vol.36 , Issue.19 , pp. 3303-3306
    • You, Z.1    Khalil, M.A.2    Ko, D.-H.3    Lee, H.J.4
  • 47
    • 0030056342 scopus 로고    scopus 로고
    • One step conversion of highly dipolarophilic olefins to α-hydroxy-β-cyanoadducts with metal fulminate
    • You, Z. and Lee, H. J., One step conversion of highly dipolarophilic olefins to α-hydroxy-β-cyanoadducts with metal fulminate. Tetrahedron Lett., 37(8), 1165-1168 (1996).
    • (1996) Tetrahedron Lett. , vol.37 , Issue.8 , pp. 1165-1168
    • You, Z.1    Lee, H.J.2


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