Hydrocortisone phosphate

Hydrocortisone phosphate
Clinical data
Drug classCorticosteroid; Glucocorticoid
Identifiers
  • Disodium [2-[(8S,9S,10R,11S,13S,14S,17R)-11,17-Dihydroxy-10,13-dimethyl-3-oxo-2,6,7,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthren-17-yl]-2-oxoethyl] phosphate
CAS Number
PubChem CID
UNII
CompTox Dashboard (EPA)
ECHA InfoCard100.025.312 Edit this at Wikidata
Chemical and physical data
FormulaC21H29Na2O8P
Molar mass486.408 g·mol−1
3D model (JSmol)
  • C[C@]12CCC(=O)C=C1CC[C@@H]3[C@@H]2[C@H](C[C@]4([C@H]3CC[C@@]4(C(=O)COP(=O)([O-])[O-])O)C)O.[Na+].[Na+]
  • InChI=1S/C21H31O8P.2Na/c1-19-7-5-13(22)9-12(19)3-4-14-15-6-8-21(25,17(24)11-29-30(26,27)28)20(15,2)10-16(23)18(14)19;;/h9,14-16,18,23,25H,3-8,10-11H2,1-2H3,(H2,26,27,28);;/q;2*+1/p-2/t14-,15-,16-,18+,19-,20-,21-;;/m0../s1
  • Key:RYJIRNNXCHOUTQ-OJJGEMKLSA-L

Hydrocortisone sodium phosphate is the 21-O-phosphate ester prodrug of the glucocorticoid hydrocortisone. The phosphate group is esterified to hydrocortisone’s C21 hydroxyl group, improving aqueous solubility. Upon hydrolysis, it releases pharmacologically active hydrocortisone, which activates the glucocorticoid receptor to regulate gene expression and suppress inflammatory and immune responses.

It is chemically unstable, but can be stored in the absence of water or by certain neutral formulations.

References

  1. ↑ Brownfield RB, Shultz W (December 1963). "A direct method for the preparation of steroid-21-phosphates". Steroids. 2 (6): 597–603. doi:10.1016/0039-128x(63)90037-0.
  2. 1 2 Stella VJ, Charman WN, Naringrekar VH (May 1985). "Prodrugs. Do they have advantages in clinical practice?". Drugs. 29 (5): 455–473. doi:10.2165/00003495-198529050-00002. PMID 3891303.
  3. ↑ Cruz-Topete D, Cidlowski JA (2015). "One hormone, two actions: anti- and pro-inflammatory effects of glucocorticoids". Neuroimmunomodulation. 22 (1–2): 20–32. doi:10.1159/000362724. PMC 4243162. PMID 25227506.
  4. ↑ Connors KA, Amidon GL, Stella VJ (1986). Chemical Stability of Pharmaceuticals: A Handbook for Pharmacists. Wiley. pp. 491, 494–495. ISBN 978-0-471-87955-8. Retrieved September 23, 2026.