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SML1844

Sigma-Aldrich

EPI-001

≥98% (HPLC)

Synonym(s):

3-[4-[1-[4-(3-Chloro-2-hydroxypropoxy)phenyl]-1-methylethyl]phenoxy]-1,2-propanediol, EPI 001

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About This Item

Empirical Formula (Hill Notation):
C21H27ClO5
CAS Number:
227947-06-0
Molecular Weight:
394.89
MDL number:
MFCD02683414
UNSPSC Code:
12352200
NACRES:
NA.77

Quality Level

100

Assay

≥98% (HPLC)

form

powder

color

white to beige

solubility

DMSO: 15 mg/mL, clear

storage temp.

−20°C

SMILES string

ClCC(O)COc1ccc(cc1)C(C)(C)c2ccc(cc2)OCC(O)CO

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

InChI key

HDTYUHNZRYZEEB-UHFFFAOYSA-N

Biochem/physiol Actions

EPI-001 is a specific inhibitor of the AR (androgen receptor) without inhibiting PR or GR transcriptional activities. EPI-001 selectively interacts with transactivation unit 5 (Tau-5) of the androgen receptor, which is essential for prostate cells to proliferate in the absence of androgens. EPI-001 is active against castration-resistant prostate cancer (CRPC) in xenografts.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
027M4740V

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Eva De Mol et al.
ACS chemical biology, 11(9), 2499-2505 (2016-06-30)
Castration-resistant prostate cancer is the lethal condition suffered by prostate cancer patients that become refractory to androgen deprivation therapy. EPI-001 is a recently identified compound active against this condition that modulates the activity of the androgen receptor, a nuclear receptor
Raymond J Andersen et al.
Cancer cell, 17(6), 535-546 (2010-06-15)
Castration-recurrent prostate cancer (CRPC) is suspected to depend on androgen receptor (AR). The AF-1 region in the amino-terminal domain (NTD) of AR contains most, if not all, of the transcriptional activity. Here we identify EPI-001, a small molecule that blocked
Lucas J Brand et al.
Oncotarget, 6(6), 3811-3824 (2015-02-12)
The androgen receptor (AR) is a driver of prostate cancer (PCa) cell growth and disease progression. Therapies for advanced PCa exploit AR dependence by blocking the production or action of androgens, but these interventions inevitably fail via multiple mechanisms including

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