Chloroprednisone

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
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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

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]

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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