fosdagrocorat

Ligand id: 9649

Name: fosdagrocorat

Structure and Physico-chemical Properties

2D Structure
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 9.33
No. Lipinski's rules broken 1

Molecular properties generated using the CDK

Classification
Compound class Synthetic organic
Is prodrug? Yes
Active form dagrocorat
IUPAC Name
[(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
Synonyms
PF-04171327
Database Links
BindingDB Ligand 140010
CAS Registry No. 1044535-58-1 (source: WHO INN record)
ChEMBL Ligand CHEMBL3137316
PubChem CID 24872952
Search Google for chemical match using the InChIKey BVXLAHSJXXSWFF-KEKPKEOLSA-N
Search Google for chemicals with the same backbone BVXLAHSJXXSWFF
Search PubMed clinical trials fosdagrocorat
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Search UniChem for chemical match using the InChIKey BVXLAHSJXXSWFF-KEKPKEOLSA-N
Search UniChem for chemicals with the same backbone BVXLAHSJXXSWFF
Comments
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].