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Dexamethasone in Dermatology

Dexamethasone in Dermatology Abstract Dexamethasone is 9-α-fluoro,16-α-methylprednisolone.* It is one of a group of prednisolone analogues synthesized and studied by Arth and his co-workers1,2 in the continuing search for modifications of hydrocortisone which would afford increased anti-inflammatory and antiallergic activity but would produce minimal mineral imbalance and the other undesirable sideeffects that sometimes result from therapy with the corticosteroids. The formation of prednisone and prednisolone from cortisone and hydrocortisone by the introduction of a double bond (Δ-1) in the C1-C2 position increases the anti-inflammatory potency of hydrocortisone four or five times without enhancing its effect on sodium-potassium balance. Fluorination of hydrocortisone at the 9-α position increases its anti-inflammatory effect tenfold. However, the profound sodium-retaining and potassium-excreting effects of this modification interdicted its systemic use. Addition of a hydroxyl group in the 16-α position made it possible to utilize the enhanced anti-inflammatory and References 1. The dexamethasone used in this study was supplied as Decadron by Merck Sharp & Dohme, Westpoint, Pa. 2. Arth, G. E.; Johnston, D. B. R.; Fried, J.: Spooncer, W. W.; Hoff, D. R., and Sarett, L. H.: 16-Methylated Steroids: I. 16-Alpha Methylated Analogs of Cortisone; A New Group of Anti-Inflammatory Steroids , J. Am. Chem. Soc. 80:3160, 1958.Crossref 3. Arth, G. E.; Fried, J.; Johnston, D. B. R.; Hoff, D. R.; Sarett, L. H.; Silber, R. H.; Stoerk, H. C., and Winter, C. A.: 16-Methylated Steroids: II. 16-Alpha Methyl Analogs of Cortisone; a New Group of Anti-Inflammatory Steroids; 9-Alpha Halo Derivatives , J. Am. Chem. Soc. 80:3161, 1958.Crossref 4. Boland, E. W.: 16-Alpha Methyl Corticosteroids , Col. Med. 88:417, 1958. 5. Bunim, J. J.; Black, R. L.; Lutwak, L.; Peterson, R. E., and Whedon, G. D.: Studies on Dexamethasone: A New Synthetic Steroid in Rheumatoid Arthritis; a Preliminary Report , Arthritis & Rheumat. 1:313, 1958. http://www.deepdyve.com/assets/images/DeepDyve-Logo-lg.png A.M.A. Archives of Dermatology American Medical Association

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Publisher
American Medical Association
Copyright
Copyright © 1959 American Medical Association. All Rights Reserved.
ISSN
0096-5359
DOI
10.1001/archderm.1959.01560200066007
Publisher site
See Article on Publisher Site

Abstract

Abstract Dexamethasone is 9-α-fluoro,16-α-methylprednisolone.* It is one of a group of prednisolone analogues synthesized and studied by Arth and his co-workers1,2 in the continuing search for modifications of hydrocortisone which would afford increased anti-inflammatory and antiallergic activity but would produce minimal mineral imbalance and the other undesirable sideeffects that sometimes result from therapy with the corticosteroids. The formation of prednisone and prednisolone from cortisone and hydrocortisone by the introduction of a double bond (Δ-1) in the C1-C2 position increases the anti-inflammatory potency of hydrocortisone four or five times without enhancing its effect on sodium-potassium balance. Fluorination of hydrocortisone at the 9-α position increases its anti-inflammatory effect tenfold. However, the profound sodium-retaining and potassium-excreting effects of this modification interdicted its systemic use. Addition of a hydroxyl group in the 16-α position made it possible to utilize the enhanced anti-inflammatory and References 1. The dexamethasone used in this study was supplied as Decadron by Merck Sharp & Dohme, Westpoint, Pa. 2. Arth, G. E.; Johnston, D. B. R.; Fried, J.: Spooncer, W. W.; Hoff, D. R., and Sarett, L. H.: 16-Methylated Steroids: I. 16-Alpha Methylated Analogs of Cortisone; A New Group of Anti-Inflammatory Steroids , J. Am. Chem. Soc. 80:3160, 1958.Crossref 3. Arth, G. E.; Fried, J.; Johnston, D. B. R.; Hoff, D. R.; Sarett, L. H.; Silber, R. H.; Stoerk, H. C., and Winter, C. A.: 16-Methylated Steroids: II. 16-Alpha Methyl Analogs of Cortisone; a New Group of Anti-Inflammatory Steroids; 9-Alpha Halo Derivatives , J. Am. Chem. Soc. 80:3161, 1958.Crossref 4. Boland, E. W.: 16-Alpha Methyl Corticosteroids , Col. Med. 88:417, 1958. 5. Bunim, J. J.; Black, R. L.; Lutwak, L.; Peterson, R. E., and Whedon, G. D.: Studies on Dexamethasone: A New Synthetic Steroid in Rheumatoid Arthritis; a Preliminary Report , Arthritis & Rheumat. 1:313, 1958.

Journal

A.M.A. Archives of DermatologyAmerican Medical Association

Published: Aug 1, 1959

References