Chloroprednisone

Last updated
Chloroprednisone
Chloroprednisone.svg
Clinical data
Other names6α-Chloro-1,4-pregnadiene-17a,21-diol-3,11,20-trione
ATC code
Identifiers
  • (6α)-6-Chloro-17,21-dihydroxypregna-1,4-diene-3,11,20-trione
CAS Number
PubChem CID
ChemSpider
UNII
ECHA InfoCard 100.052.387 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula C21H25ClO5
Molar mass 392.88 g·mol−1
3D model (JSmol)
  • 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=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 11β-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.