EPI-001

EPI-001

Legal status
Legal status	Investigational
Identifiers
IUPAC name 3-(4-{2-[4-(3-Chloro-2-hydroxypropoxy)phenyl]-2-propanyl}phenoxy)-1,2-propanediol
PubChem (CID)	4166922
ChemSpider	3378517
Chemical and physical data
Formula	C21H27ClO5
Molar mass	394.89 g/mol
3D model (Jmol)	Interactive image
SMILES ClCC(O)COc1ccc(cc1)C(c2ccc(OCC(O)CO)cc2)(C)C
InChI InChI=1S/C21H27ClO5/c1-21(2,15-3-7-19(8-4-15)26-13-17(24)11-22)16-5-9-20(10-6-16)27-14-18(25)12-23/h3-10,17-18,23-25H,11-14H2,1-2H3 Key:HDTYUHNZRYZEEB-UHFFFAOYSA-N

EPI-001 is a novel experimental non-steroidal antiandrogen that is under investigation for the treatment of prostate cancer. The drug is being developed by the pharmaceutical company ESSA Pharma Inc (Vancouver, Canada) for the treatment of castration-resistant prostate cancer (CRPC) and is currently in pre-clinical development.

EPI-001 is an antagonist of the androgen receptor (AR) that acts by binding covalently to the N-terminal domain (NTD) of the AR and blocking protein-protein interactions required for transcriptional activity of the AR and its splice variants (IC₅₀ for inhibition of AR NTD transactivation ≈ 6 µM). This is different from all currently-used antiandrogens, which, conversely, bind to the C-terminal ligand-binding domain (LBD) of the AR and competitively block binding and activation of the receptor by androgens. Due to its unique mechanism of action, EPI-001 may prove to be effective in the treatment of advanced prostate cancer resistant to conventional antiandrogens such as enzalutamide.

As of 2016, EPI-001's successor, EPI-506, is under clinical investigation in a phase I/II study.

EPI-001 was discovered by Marianne Sadar at the British Columbia Cancer Agency and Raymond Andersen at the University of British Columbia. It was derived from bisphenol A diglycidyl ether (BADGE), a known antiandrogenic endocrine disruptor of the bisphenol family.