Fosdagrocorat

Last updated
Fosdagrocorat
Fosdagrocorat.svg
Clinical data
Other namesPF-04171327; PF-4171327; Dagrocorat 2-(dihydrogen phosphate); Dagrocorat dihydrogen phosphate
Drug class Selective glucocorticoid receptor modulator
Identifiers
  • [(2R,4aS,10aR)-4a-Benzyl-7-[(2-methylpyridin-3-yl)carbamoyl]-2-(trifluoromethyl)-1,3,4,9,10,10a-hexahydrophenanthren-2-yl] dihydrogen phosphate
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
Formula C29H30F3N2O5P
Molar mass 574.537 g·mol−1
3D model (JSmol)
  • CC1=C(C=CC=N1)NC(=O)C2=CC3=C(C=C2)[C@@]4(CC[C@@](C[C@H]4CC3)(C(F)(F)F)OP(=O)(O)O)CC5=CC=CC=C5
  • InChI=1S/C29H30F3N2O5P/c1-19-25(8-5-15-33-19)34-26(35)22-10-12-24-21(16-22)9-11-23-18-28(29(30,31)32,39-40(36,37)38)14-13-27(23,24)17-20-6-3-2-4-7-20/h2-8,10,12,15-16,23H,9,11,13-14,17-18H2,1H3,(H,34,35)(H2,36,37,38)/t23-,27+,28-/m1/s1
  • Key:BVXLAHSJXXSWFF-KEKPKEOLSA-N

Fosdagrocorat (developmental code names PF-04171327 and PF-4171327; also known as dagrocorat 2-(dihydrogen phosphate)) is a nonsteroidal but steroid-like selective glucocorticoid receptor modulator (SGRM) which was under development for the treatment of rheumatoid arthritis but was never marketed. [1] [2] [3] [4] It is the C2 dihydrogen phosphate ester of dagrocorat, and acts as a prodrug of dagrocorat with improved pharmacokinetics. [5] [6] The drug reached phase II clinical trials prior to the discontinuation of its development. [1] [3] [4]

Contents

See also

References

  1. 1 2 "Fosdagrocorat - AdisInsight". adisinsight.springer.com.
  2. ↑ International Nonproprietary Names for Pharmaceutical Substances (INN)
  3. 1 2 Yoshioka H, Yamada A, Nishiyama Y, Kagechika H, Hashimoto Y, Fujii S (2017). "Development of nonsteroidal glucocorticoid receptor modulators based on N-benzyl-N-(4-phenoxyphenyl)benzenesulfonamide scaffold". Bioorg. Med. Chem. 25 (13): 3461–3470. doi:10.1016/j.bmc.2017.04.032. PMID   28506584.
  4. 1 2 Strehl C, van der Goes MC, Bijlsma JW, Jacobs JW, Buttgereit F (2017). "Glucocorticoid-targeted therapies for the treatment of rheumatoid arthritis". Expert Opin Investig Drugs. 26 (2): 187–195. doi:10.1080/13543784.2017.1276562. PMID   28043173. S2CID   2306241.
  5. ↑ Miyoshi S, Hey-Hadavi J, Nagaoka M, Tammara B (2016). "Pharmacokinetics and food-effect of fosdagrocorat (PF-04171327), a dissociated agonist of the glucocorticoid receptor, in healthy adult Caucasian and Japanese subjects". Int J Clin Pharmacol Ther. 54 (12): 966–976. doi:10.5414/CP202659. PMID   27781421.
  6. ↑ Stock T, Fleishaker D, Wang X, Mukherjee A, Mebus C (2017). "Improved disease activity with fosdagrocorat (PF-04171327), a partial agonist of the glucocorticoid receptor, in patients with rheumatoid arthritis: a Phase 2 randomized study". Int J Rheum Dis. 20 (8): 960–970. doi:10.1111/1756-185X.13053. PMC   6084298 . PMID   28328159.



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