fosdagrocorat   Click here for help

GtoPdb Ligand ID: 9649

Synonyms: PF-04171327
Immunopharmacology Ligand
Compound class: Synthetic organic
Comment: Fosdagrocorat (PF-04171327) is a glucocorticoid (GC) receptor partial agonist with anti-inflammatory potential. It is an example of a new class of GC substances termed dissociated agonists of the GC receptors (DAGR), that are being developed to improve the risk-benefit profile of GC drugs. DAGRs are designed to favour interaction of the GC receptor with protein partners rather than DNA, such that the transrepressive actions are enhanced over the transactivation effects. The hypothesis is that dissociating transrepression from transactivation will cause less undesirable effects on bone and glucose metabolism compared to current GC agonists such as prednisone (reviewed in [1]). Fosdagrocorat is example 2 in Pfizer's patent US8901310 [3]. It is a phosphate ester prodrug of dagrocorat (example 1 in US8901310).
Synthesis and structure-activity relationship (SAR) of another series of DAGRs (by Boehringer Ingelheim Pharmaceuticals) are reported in [2].
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 7
Hydrogen bond donors 3
Rotatable bonds 8
Topological polar surface area 118.56
Molecular weight 574.18
XLogP 5.29
No. Lipinski's rules broken 1
SMILES / InChI / InChIKey
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Canonical SMILES O=C(c1ccc2c(c1)CCC1C2(CCC(C1)(OP(=O)(O)O)C(F)(F)F)Cc1ccccc1)Nc1cccnc1C
Isomeric SMILES O=C(c1ccc2c(c1)CC[C@H]1[C@]2(CC[C@](C1)(OP(=O)(O)O)C(F)(F)F)Cc1ccccc1)Nc1cccnc1C
InChI 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
InChI Key BVXLAHSJXXSWFF-KEKPKEOLSA-N
Classification Click here for help
Compound class Synthetic organic
Is prodrug? Yes
Active form dagrocorat
IUPAC Name Click here for help
[(2R,4aS,10aR)-4a-benzyl-7-[(2-methylpyridin-3-yl)carbamoyl]-2-(trifluoromethyl)-1,3,4,9,10,10a-hexahydrophenanthren-2-yl] dihydrogen phosphate
International Nonproprietary Names Click here for help
INN number INN
9929 fosdagrocorat
Synonyms Click here for help
PF-04171327
Database Links Click here for help
BindingDB Ligand 140010
CAS Registry No. 1044535-58-1 (source: WHO INN record)
ChEMBL Ligand CHEMBL3137316
GtoPdb PubChem SID 340590279
PubChem CID 24872952
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