Chloroprednisone

Chloroprednisone is a topical glucocorticoid first reported in 1960.[1] It is a chlorinated derivative of prednisone. The acetate ester prodrug, chloroprednisone 21-acetate, was sold under the brand name Topilan as an anti-inflammatory agent.[2][3]

Chloroprednisone
Clinical data
Other names6α-Chloro-1,4-pregnadiene-17a,21-diol-3,11,20-trione
ATC code
Identifiers
IUPAC name
  • (6α)-6-Chloro-17,21-dihydroxypregna-1,4-diene-3,11,20-trione
CAS Number
PubChem CID
ChemSpider
UNII
ECHA InfoCard100.052.387
Chemical and physical data
FormulaC21H25ClO5
Molar mass392.88 g·mol−1
3D model (JSmol)
SMILES
  • O=C(CO)[C@@]3(O)CC[C@H]2[C@@H]4C[C@H](Cl)\C1=C\C(=O)\C=C/[C@]1(C)[C@H]4C(=O)C[C@@]23C
InChI
  • InChI=1S/C21H25ClO5/c1-19-5-3-11(24)7-14(19)15(22)8-12-13-4-6-21(27,17(26)10-23)20(13,2)9-16(25)18(12)19/h3,5,7,12-13,15,18,23,27H,4,6,8-10H2,1-2H3/t12-,13-,15-,18+,19-,20-,21-/m0/s1
  • Key:NPSLCOWKFFNQKK-ZPSUVKRCSA-N

There is little published about chloroprednisone. This may be due to limited activity topically because the skin lacks the necessary activating enzyme 11-Beta hydroxysteroid dehydrogenase. Systemically, this agent's activity on glucocorticoid receptors may not have competed with agents like fludrocortisone or dexamethasone.

References
  1. DE 1079042, Batres E, Bowers A, Djerassi C, Kincl FA, Mancera O, Ringold HJ, Rosenkranz J, Zaffaroni A, "6α-Chloro- or 6α-fluoro-1,4-pregnadiene-3,20-diones.", issued 1960.
  2. Budavari S, ed. (1989). "2157: Chloroprednisone". The Merck Index: An Encyclopedia of Chemicals, Drugs, and Biologicals (11th, centennial ed.). Rahway, N.J., U.S.A.: Merck. ISBN 978-0-911910-28-5.
  3. Roberts AD (1991). Dictionary of Steroids: Chemical Data, Structures, and Bibliographies. Vol. 1. CRC Press. p. 108.



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