Chloroprednisone

{{Short description|Topical glucocorticoid drug}}

{{Drugbox

| IUPAC_name = (6α)-6-Chloro-17,21-dihydroxypregna-1,4-diene-3,11,20-trione

| synonyms = 6α-Chloro-1,4-pregnadiene-17a,21-diol-3,11,20-trione

| image = Chloroprednisone.svg

| CAS_number = 52080-57-6

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = 564IBO56IP

| ATC_prefix = S01

| ATC_suffix = CA09

| ATC_supplemental = (combination with antiinfectives)

| PubChem = 3034026

| DrugBank =

| ChemSpiderID = 2298578

| C=21 | H=25 | Cl=1 | O=5

| 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

| StdInChI = 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

| StdInChIKey = NPSLCOWKFFNQKK-ZPSUVKRCSA-N

| bioavailability =

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Chloroprednisone is a topical glucocorticoid first reported in 1960.{{cite patent | country = DE | number = 1079042 | inventor = Batres E, Bowers A, Djerassi C, Kincl FA, Mancera O, Ringold HJ, Rosenkranz J, Zaffaroni A | title = 6α-Chloro- or 6α-fluoro-1,4-pregnadiene-3,20-diones. | gdate = 1960 | postscript = . }} 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.{{cite book | chapter = 2157: Chloroprednisone | veditors = Budavari S |title=The Merck Index: An Encyclopedia of Chemicals, Drugs, and Biologicals |date=1989 |publisher=Merck |location=Rahway, N.J., U.S.A. |isbn=978-0-911910-28-5 |edition=11th, centennial}}{{cite book | title = Dictionary of Steroids: Chemical Data, Structures, and Bibliographies | volume = 1 | vauthors = Roberts AD | page = 108 | publisher = CRC Press | year = 1991 }}

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.