Metabolisation and receptor affinity of topically applied esters of glucocorticoids;Metabolisierung und rezeptoraffinitat topisch angewandter glucocorticoidester

H+G Zeitschrift fur Hautkrankheiten

Volumn 73, Issue 9, 1998, Pages 581-590

  Bonsmann, U ^a   Rohdewald, P ^a  

^a UNIVERSITY OF MÜNSTER   (Germany)

Author keywords

Glucocorticoids; Human skin; Metabolisation; Receptor affinity

Indexed keywords

BETAMETHASONE; BETAMETHASONE VALERATE; DRUG METABOLITE; ESTERASE; GLUCOCORTICOID; GLUCOCORTICOID RECEPTOR; HYDROCORTISONE; HYDROCORTISONE 17 BUTYRATE 21 PROPIONATE; HYDROCORTISONE 21 BUTYRATE; HYDROCORTISONE BUTYRATE; PREDNICARBATE; PREDNISOLONE; PREDNISOLONE 21 ETHYL CARBONATE; RECEPTOR PROTEIN; UNCLASSIFIED DRUG;

ARTICLE; DRUG ABSORPTION; DRUG METABOLISM; DRUG RECEPTOR BINDING; ESTERIFICATION; HUMAN; HUMAN TISSUE; ISOMERISM; RECEPTOR AFFINITY; SKIN; TOPICAL DRUG ADMINISTRATION; VASOCONSTRICTION;

EID: 0031655329     PISSN: 03010481     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (38)

1. Andersson, P., S. Edsbäcker, A. Ryrfeldt, C. von Bahr (1982): In vitro biotransformation of glucocorticoids in liver and skin homogenate fraction from man, rat and hairless mouse. J. Steroid. Biochemistry 16, 787-795.
2. Behrendt, H., H.C. Korting, O. Braun-Falco (1989): Zum Metabolismus von Pharmaka in der Haut. Hautarzt 40, 8-13.
3. Bodor, N., A.J. Harget, E.W. Phillips (1983): Structure-activity relationships in the antiinflammatory steroids, a pattern-recognition approach. J. Med. Chem. 26, 318-328.
4. Görmar, F.E., A. Bernd, H. Holzmann (1990): Wirkung von Hydrocortisonaceponat auf Proliferation, Gesamtprotein- und Kollagen-Synthese menschlicher Hautfibroblasten in vitro. Arzneim.-Forschung 40, 192-196.
5. Gysler, A., K. Lange, W. Schäfer-Korting (1996), Eur. J. Pharm. Sei. 7 Suppl., S97.
6. Hein, R. (1993): Effects of connective-tissue cells. In: Topical glucpcorticoids with increased benefit risk ratio. Current Problems in Dermatology 21, . Hrsg. Korting, H.C.& H.I. Maibach, pp. 73-78, Basel, Karger-Verlag.
7. Hein, R., H.C. Korting, T. Mehring (1994): Differential effect of medium potent nonhalogenated double-ester-type and conventional glucocorticoids on proliferation and chemotaxis of fibroblasts in vitro. Skin. Pharmacol. 7, 300-306.
8. Hermann, W.P. (1970): Elektrophoretische und immunologische Untersuchungen an esterspaltenden Enzymen der menschlichen Haut. Arch. Klin. Exp. Dermatol. 236, 385-394.
9. Hsia, S.L, Y.L Hao (1966): Metabolie transformation of cortisol-4-(14C) in human skin. Biochemistry 5, 1469-1474.
10. 14 in human skin. J. Invest. Derm. 45, 384-390.
11. 14 in human skin. J. Invest. Derm. 43, 407-412.
12. Kerscher, M.J., H.C. Korting (1992): Topical glucocorticoids of the non-fluorinated doubleester type. Lack of atrophogenicity in normal skin as assessed by high-frequency ultrasound. Acta Derm. Venereo. (Stockh) 72, 214-216.
13. Kimura, M., Y. Tarumoto, S. Nakane, S. Otomo (1986): Comparative toxicity study of hydrocortisone-17-butyrate (HBP) ointment and other topical corticosteroids in rats. Drugs Exptl. Clin. Res. XII, 643-652.
14. Kitano, Y. (1986): Hydrolysis of hydrocortisone17-butyrate-21-propionate by cultured human keratinocytes. Acta Derm. Venereo. (Stockh) 66, 98-102.
15. Korting, H.C., E. Hulsebus, M.J. Kerscher, R. Greber, M. Schäfer-Korting (1995): Discrimination of the toxic potential of chemically differing topical glucocorticoids using a neutral red release assay with human keratinocytes and fibroblasts. Br. J. Dermatol. 133, 416-419.
16. Korting, H.C., , D. Vieluf, M. Kerscher (1992): 0.25% Prednicarbate cream and the corresponding vehicle induce less skin atrophy than 0.1% betamethasone-17-valerate cream and 0.05% clobetasol-17-propionate cream. Eur. J. Clin. Pharmacol. 42, 159-161.
17. Lan, S.J., LmM. Scanlan, J. Mitroka, S.H. Weinstein, B.N. Lutsky, C.A. Free, R.J. Wojnar, R.C. Millonig, B.H. Migdalof (1988): Rapid metabolic inactivation of tipredane, a structurally novel topical steroid. J. Steroid. Biochem. 31, 825-834.
18. Lowry, O.H., N.J. Rosebrough, A.L Farr, R.J. Randell (1951): Protein measurement with folin phenol reagent. J. Bio. Chem. 193, 265.
19. Malkinson, F.D., M.W. Lee, I. Cutukovic (1959): In vitro studies of adrenal steroid metabolism in the skin. J. Invest. Dermatol. 32, 101-106.
20. McKenzie, A.W., R.B. Stoughton (1962). Methods for comparing percutaneous absorption of steroids. Arch. Dermatol. 86, 611-614.
21. Misaki, T., M. Yamada, R. Hirai, M. Komori, M. Washitake, Y. Ozawa, I. Koyama, H. Yoshizawa (1986): Enzymatic hydrolysis of hydrocortisone diesters in skin. Yakuzaigaku 42, 92-98.
22. Muramatsu, M., M. Tanaka, S. Otomo, H. Aihara, K. Kuriyama (1985): Characteristics of binding of a new anti-inflammatory glucocorticoid, hydrocortisone-17-butyrate-21 -propionate, to glucocorticoid receptors of rat liver. Japan J. Pharmacol. 37, 143-150.
23. Niedner, R. (1992): Glucocorticosteroide. In: Niedner, R., J. Ziegenmeyer (Hrsg.), Dermatika Wiss. Verlagsgesellschaft Stuttgart, 1. Auflage.
24. Nozu, T., K. Fukushima, H. Yoshida, M. Ohzeki: Species differences in hydrolytic reaction of hydrocortisone-17-butyrate-21-propionate (HBP) with serum esterase. Publikation in Vorbereitung.
25. Oikarinen, A., P. Autio (1991): New aspects of the mechanism of corticosteroid-induced dermal atrophy. Clin. Exp. Dermatol. 16, 416-419.
26. O'Neill, R.C., J.E. Carless (1980): Influence of the side chain on the hydrolysis of some hydrocortisone esters. J. Pharm. Pharmacol. 32, 10P.
27. Ozawa, Y., I. Koyama, S. Murayama, T. Nadai (1985): Percutaneous absorption and metabolism of hydrocortisone butyrate propionate in dog skin. Chem. Pharm. Bull. 33, 5113-5118.
28. Ponec, M., J.A. Kempenaar, E.R. De Kloet (1981): Corticoids and cultured human epidermal keratinocytes: Specific intracellular binding and clinical efficacy. J. Invest. Dermatol. 76, 211-214.
29. Ponec, M., J.A. Kempenaar, B. Shroot, J. Caron (1986): Glucocorticoids: Binding affinity and lipophilicity. J. Pharm. Sei. 75, 973-975.
30. Rawlins, M.D., V. Shaw, S. Shuster (1989): The in vitro metabolism of betamethasone-17-valerate by human skin. Br. J. Pharmacol. 66, 441 P.
31. Robertson, D.B., H.I. Maibach (1989): Topical glucocorticoids. In: Anti-inflammatory steroid action: Basis and clinical aspects. Hrsg. Schleimer, R.P., H.N. Claman, A.L Oransky. Academic Press, Inc., San Diego, USA.
32. Rodbard, D., P.L Rayford, J. Cooper, G.T. Ross (1968): Statistical quality control radioimmunoassay. J. Clin. Endocrinol. 29, 352-561.
33. Schäfer-Korting, M., H.C. Korting, M. Kerscher, S. Lenhard (1993): Prednicarbate activity and benefit/risk ratio in relation to other topical glucocorticoids. Clin. Pharmacol. Ther. 54, 448-456.
34. Schäfer-Korting, M., M.H. Schmid, H.C. Korting (1996): Topical glucocorticoids with improved risk-benefit ratio. Drug Safe 14, 375-385.
35. Schalla, W., B. Busch-Heidger, F. Hevert (1994): Ansätze zur Optimierung topischer Kortikoide: Erste Belege anhand des Zeitverlaufs der Vasokonstriktion nach epi- und intrakutaner Applikation. Z. Hautkrankh. 69, 166-170.
36. Solo, A.J., K.M. Tramposch, D.W. Szeto, M.J. Suto (1982): Relative affinity of 17 and or 21esters and 17, 21-diesters of cortisol for a glucocorticoid receptor from rat thymus. J. Med. Chem. 25, 747-749.
37. Tojo, K., C.C. Chiang, Y.W. Chien (1987): Drug permeation across the skin: effect of penetrant hydrophilicity. J. Pharm. Sei. 76, 123-126.
38. Würthwein, G., S. Rehder, P. Rohdewald (1992): Upophilicity and receptor affinity of glucocorticoids. Pharm. Ztg. Wiss. 137, 161-167.