Dagrocorat

Dagrocorat (developmental code names PF-00251802, PF-251802) 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 described as a partial agonist and "dissociable" agonist of the glucocorticoid receptor.[5][6] The drug reached phase I clinical trials prior to the discontinuation of its development.[1][3][4] The C2α dihydrogen phosphate ester of dagrocorat, fosdagrocorat, was also under investigation, but its development was terminated as well.[7]

Dagrocorat
Clinical data
Other namesPF-00251802; PF-251802
Drug classSelective glucocorticoid receptor modulator
Identifiers
IUPAC name
  • (4bS,7R,8aR)-4b-Benzyl-7-hydroxy-N-(2-methylpyridin-3-yl)-7-(trifluoromethyl)-5,6,8,8a,9,10-hexahydrophenanthrene-2-carboxamide
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC29H29F3N2O2
Molar mass494.558 g·mol−1
3D model (JSmol)
SMILES
  • CC1=C(C=CC=N1)NC(=O)C2=CC3=C(C=C2)[C@@]4(CC[C@@](C[C@H]4CC3)(C(F)(F)F)O)CC5=CC=CC=C5
InChI
  • InChI=1S/C29H29F3N2O2/c1-19-25(8-5-15-33-19)34-26(35)22-10-12-24-21(16-22)9-11-23-18-28(36,29(30,31)32)14-13-27(23,24)17-20-6-3-2-4-7-20/h2-8,10,12,15-16,23,36H,9,11,13-14,17-18H2,1H3,(H,34,35)/t23-,27+,28-/m1/s1
  • Key:QJJBNCHSWFGXML-KEKPKEOLSA-N

See also

References
  1. "Dagrocorat - AdisInsight".
  2. https://www.who.int/medicines/publications/druginformation/innlists/PL111.pdf
  3. 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. 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.
  7. "Fosdagrocorat - AdisInsight".


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