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MedKoo Cat#: 555572 | Name: EPI-001
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

EPI-001 is an androgen receptor antagonist with an IC50 value of approximately 6 μM for inhibition of transactivation of the androgen receptor N-terminal domain (NTD). It inhibits androgen-, FSK-, and IL-6-induced, as well as ligand-independent, prostate-specific antigen (PSA) reporter gene expression in LNCaP cells expressing either the full length androgen receptor or a constitutively active mutant that lacks the ligand binding domain in a dose-dependent manner.

Chemical Structure

EPI-001
EPI-001
CAS#227947-06-0

Theoretical Analysis

MedKoo Cat#: 555572

Name: EPI-001

CAS#: 227947-06-0

Chemical Formula: C21H27ClO5

Exact Mass: 394.1547

Molecular Weight: 394.89

Elemental Analysis: C, 63.87; H, 6.89; Cl, 8.98; O, 20.26

Price and Availability

Size Price Availability Quantity
100mg USD 450.00 2 Weeks
250mg USD 850.00 2 Weeks
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Synonym
EPI-001; EPI 001; EPI001;
IUPAC/Chemical Name
3-[4-[1-[4-(3-chloro-2-hydroxypropoxy)phenyl]-1-methylethyl]phenoxy]-1,2-propanediol
InChi Key
HDTYUHNZRYZEEB-UHFFFAOYSA-N
InChi Code
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
SMILES Code
OCC(O)COC1=CC=C(C(C)(C2=CC=C(OCC(O)CCl)C=C2)C)C=C1
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>3 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info
Product Data
Product Data
Instruction
View handling instruction
Biological target:
EPI-001, a selective inhibitor of Androgen Receptor (AR), targets transactivation unit 5 (Tau-5) of the AR.
In vitro activity:
EPI-001 inhibited ligand-dependent ARGal4 transcriptional activity in LNCaP cells (Figures 1C and 1D), as well as aberrant, ligand-independent ARGal4 transcriptional activity in the CRPC C4-2 cell line (Figure 1D). Reference: Oncotarget. 2015 Feb; 6(6): 3811–3824. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4414155/
In vivo activity:
TBD
Solvent mg/mL mM
Solubility
DMSO 44.1 111.70
DMF 20.0 50.65
Ethanol 49.5 125.35
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 394.89 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
1. De Mol E, Fenwick RB, Phang CT, Buzón V, Szulc E, de la Fuente A, Escobedo A, García J, Bertoncini CW, Estébanez-Perpiñá E, McEwan IJ, Riera A, Salvatella X. EPI-001, A Compound Active against Castration-Resistant Prostate Cancer, Targets Transactivation Unit 5 of the Androgen Receptor. ACS Chem Biol. 2016 Sep 16;11(9):2499-505. doi: 10.1021/acschembio.6b00182. Epub 2016 Jul 14. PMID: 27356095; PMCID: PMC5027137. 2. Brand LJ, Olson ME, Ravindranathan P, Guo H, Kempema AM, Andrews TE, Chen X, Raj GV, Harki DA, Dehm SM. EPI-001 is a selective peroxisome proliferator-activated receptor-gamma modulator with inhibitory effects on androgen receptor expression and activity in prostate cancer. Oncotarget. 2015 Feb 28;6(6):3811-24. doi: 10.18632/oncotarget.2924. PMID: 25669987; PMCID: PMC4414155.
In vitro protocol:
1. De Mol E, Fenwick RB, Phang CT, Buzón V, Szulc E, de la Fuente A, Escobedo A, García J, Bertoncini CW, Estébanez-Perpiñá E, McEwan IJ, Riera A, Salvatella X. EPI-001, A Compound Active against Castration-Resistant Prostate Cancer, Targets Transactivation Unit 5 of the Androgen Receptor. ACS Chem Biol. 2016 Sep 16;11(9):2499-505. doi: 10.1021/acschembio.6b00182. Epub 2016 Jul 14. PMID: 27356095; PMCID: PMC5027137. 2. Brand LJ, Olson ME, Ravindranathan P, Guo H, Kempema AM, Andrews TE, Chen X, Raj GV, Harki DA, Dehm SM. EPI-001 is a selective peroxisome proliferator-activated receptor-gamma modulator with inhibitory effects on androgen receptor expression and activity in prostate cancer. Oncotarget. 2015 Feb 28;6(6):3811-24. doi: 10.18632/oncotarget.2924. PMID: 25669987; PMCID: PMC4414155.
In vivo protocol:
TBD
1: Kranzbühler B, Salemi S, Mortezavi A, Sulser T, Eberli D. Combined N-terminal androgen receptor and autophagy inhibition increases the antitumor effect in enzalutamide sensitive and enzalutamide resistant prostate cancer cells. Prostate. 2019 Feb;79(2):206-214. doi: 10.1002/pros.23725. Epub 2018 Oct 21. PubMed PMID: 30345525. 2: Cha S, Shin DH, Seok JR, Myung JK. Differential proteome expression analysis of androgen-dependent and -independent pathways in LNCaP prostate cancer cells. Exp Cell Res. 2017 Oct 1;359(1):215-225. doi: 10.1016/j.yexcr.2017.07.026. Epub 2017 Jul 20. PubMed PMID: 28736082. 3: Crona DJ, Whang YE. Androgen Receptor-Dependent and -Independent Mechanisms Involved in Prostate Cancer Therapy Resistance. Cancers (Basel). 2017 Jun 12;9(6). pii: E67. doi: 10.3390/cancers9060067. Review. PubMed PMID: 28604629; PubMed Central PMCID: PMC5483886. 4: Guo C, Yeh S, Niu Y, Li G, Zheng J, Li L, Chang C. Targeting androgen receptor versus targeting androgens to suppress castration resistant prostate cancer. Cancer Lett. 2017 Jul 1;397:133-143. doi: 10.1016/j.canlet.2017.03.022. Epub 2017 Mar 18. PubMed PMID: 28323036. 5: De Mol E, Fenwick RB, Phang CT, Buzón V, Szulc E, de la Fuente A, Escobedo A, García J, Bertoncini CW, Estébanez-Perpiñá E, McEwan IJ, Riera A, Salvatella X. EPI-001, A Compound Active against Castration-Resistant Prostate Cancer, Targets Transactivation Unit 5 of the Androgen Receptor. ACS Chem Biol. 2016 Sep 16;11(9):2499-505. doi: 10.1021/acschembio.6b00182. Epub 2016 Jul 14. PubMed PMID: 27356095; PubMed Central PMCID: PMC5027137. 6: Monaghan AE, McEwan IJ. A sting in the tail: the N-terminal domain of the androgen receptor as a drug target. Asian J Androl. 2016 Sep-Oct;18(5):687-94. doi: 10.4103/1008-682X.181081. Review. PubMed PMID: 27212126; PubMed Central PMCID: PMC5000789. 7: Crona DJ, Milowsky MI, Whang YE. Androgen receptor targeting drugs in castration-resistant prostate cancer and mechanisms of resistance. Clin Pharmacol Ther. 2015 Dec;98(6):582-9. doi: 10.1002/cpt.256. Epub 2015 Oct 1. Review. PubMed PMID: 26331358; PubMed Central PMCID: PMC4715745. 8: De Maeseneer DJ, Van Praet C, Lumen N, Rottey S. Battling resistance mechanisms in antihormonal prostate cancer treatment: Novel agents and combinations. Urol Oncol. 2015 Jul;33(7):310-21. doi: 10.1016/j.urolonc.2015.01.008. Epub 2015 Feb 21. Review. PubMed PMID: 25708954. 9: Brand LJ, Olson ME, Ravindranathan P, Guo H, Kempema AM, Andrews TE, Chen X, Raj GV, Harki DA, Dehm SM. EPI-001 is a selective peroxisome proliferator-activated receptor-gamma modulator with inhibitory effects on androgen receptor expression and activity in prostate cancer. Oncotarget. 2015 Feb 28;6(6):3811-24. PubMed PMID: 25669987; PubMed Central PMCID: PMC4414155. 10: McCarty MF, Hejazi J, Rastmanesh R. Beyond androgen deprivation: ancillary integrative strategies for targeting the androgen receptor addiction of prostate cancer. Integr Cancer Ther. 2014 Sep;13(5):386-95. doi: 10.1177/1534735414534728. Epub 2014 May 26. PubMed PMID: 24867960. 11: Agarwal N, Di Lorenzo G, Sonpavde G, Bellmunt J. New agents for prostate cancer. Ann Oncol. 2014 Sep;25(9):1700-9. doi: 10.1093/annonc/mdu038. Epub 2014 Mar 20. Review. PubMed PMID: 24658665. 12: Mostaghel EA, Plymate SR, Montgomery B. Molecular pathways: targeting resistance in the androgen receptor for therapeutic benefit. Clin Cancer Res. 2014 Feb 15;20(4):791-8. doi: 10.1158/1078-0432.CCR-12-3601. Epub 2013 Dec 4. PubMed PMID: 24305618; PubMed Central PMCID: PMC3944407. 13: Myung JK, Banuelos CA, Fernandez JG, Mawji NR, Wang J, Tien AH, Yang YC, Tavakoli I, Haile S, Watt K, McEwan IJ, Plymate S, Andersen RJ, Sadar MD. An androgen receptor N-terminal domain antagonist for treating prostate cancer. J Clin Invest. 2013 Jul;123(7):2948-60. doi: 10.1172/JCI66398. Epub 2013 Jun 3. PubMed PMID: 23722902; PubMed Central PMCID: PMC3696543. 14: Andres E, Molinari J, Remoué N, Sá-Rocha VM, Barrichello C, Hurtado SP. Successful micronucleus testing with the EPI/001 3D reconstructed epidermis model: preliminary findings. Mutat Res. 2012 Mar 18;743(1-2):36-41. doi: 10.1016/j.mrgentox.2011.12.026. Epub 2012 Jan 14. PubMed PMID: 22266475. 15: Avery JL, McEwen A, Flinders B, Francese S, Clench MR. Matrix-assisted laser desorption mass spectrometry imaging for the examination of imipramine absorption by Straticell-RHE-EPI/001 an artificial model of the human epidermis. Xenobiotica. 2011 Aug;41(8):735-42. doi: 10.3109/00498254.2011.573015. Epub 2011 Apr 11. PubMed PMID: 21480772. 16: Sadar MD. Small molecule inhibitors targeting the "achilles' heel" of androgen receptor activity. Cancer Res. 2011 Feb 15;71(4):1208-13. doi: 10.1158/0008-5472.CAN_10-3398. Epub 2011 Feb 1. Review. PubMed PMID: 21285252; PubMed Central PMCID: PMC3132148. 17: Andersen RJ, Mawji NR, Wang J, Wang G, Haile S, Myung JK, Watt K, Tam T, Yang YC, Bañuelos CA, Williams DE, McEwan IJ, Wang Y, Sadar MD. Regression of castrate-recurrent prostate cancer by a small-molecule inhibitor of the amino-terminus domain of the androgen receptor. Cancer Cell. 2010 Jun 15;17(6):535-46. doi: 10.1016/j.ccr.2010.04.027. PubMed PMID: 20541699.