Ligand id: 9649

Name: fosdagrocorat

Structure and Physico-chemical Properties

2D Structure
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Calculated Physico-chemical Properties
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

Molecular properties generated using the CDK

Compound class Synthetic organic
Is prodrug? Yes
Active form dagrocorat
[(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
INN number INN
9929 fosdagrocorat
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].
Database Links
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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