Synonym
EPI-002; EPI 002; EPI002; Ralaniten;
IUPAC/Chemical Name
(2R)-3-[4-[1-[4-[(2S)-3-Chloro-2-hydroxypropoxy]phenyl]-1-methylethyl]phenoxy]-1,2-propanediol
InChi Key
HDTYUHNZRYZEEB-QZTJIDSGSA-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/t17-,18-/m1/s1
SMILES Code
OC[C@@H](O)COC1=CC=C(C(C)(C2=CC=C(OC[C@H](O)CCl)C=C2)C)C=C1
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
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.
| 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 |
1: Sadar MD. Drugging the Undruggable: Targeting the N-Terminal Domain of Nuclear Hormone Receptors. Adv Exp Med Biol. 2022;1390:311-326. doi: 10.1007/978-3-031-11836-4_18. PMID: 36107327.
2: Obst JK, Mawji NR, Teskey SJL, Wang J, Sadar MD. Differential Gene Expression Profiles between N-Terminal Domain and Ligand-Binding Domain Inhibitors of Androgen Receptor Reveal Ralaniten Induction of Metallothionein by a Mechanism Dependent on MTF1. Cancers (Basel). 2022 Jan 13;14(2):386. doi: 10.3390/cancers14020386. PMID: 35053548; PMCID: PMC8773799.
3: Tien AH, Sadar MD. Cyclin-dependent Kinase 4/6 Inhibitor Palbociclib in Combination with Ralaniten Analogs for the Treatment of Androgen Receptor- positive Prostate and Breast Cancers. Mol Cancer Ther. 2022 Feb;21(2):294-309. doi: 10.1158/1535-7163.MCT-21-0411. Epub 2021 Nov 23. PMID: 34815359; PMCID: PMC8828702.
4: Leung JK, Imamura Y, Kato M, Wang J, Mawji NR, Sadar MD. Pin1 inhibition improves the efficacy of ralaniten compounds that bind to the N-terminal domain of androgen receptor. Commun Biol. 2021 Mar 22;4(1):381. doi: 10.1038/s42003-021-01927-3. PMID: 33753863; PMCID: PMC7985297.
5: Leung JK, Tam T, Wang J, Sadar MD. Isolation and characterization of castration-resistant prostate cancer LNCaP95 clones. Hum Cell. 2021 Jan;34(1):211-218. doi: 10.1007/s13577-020-00435-6. Epub 2020 Sep 20. PMID: 32954481; PMCID: PMC8693726.
6: Hirayama Y, Tam T, Jian K, Andersen RJ, Sadar MD. Combination therapy with androgen receptor N-terminal domain antagonist EPI-7170 and enzalutamide yields synergistic activity in AR-V7-positive prostate cancer. Mol Oncol. 2020 Oct;14(10):2455-2470. doi: 10.1002/1878-0261.12770. Epub 2020 Aug 9. PMID: 32734688; PMCID: PMC7530779.
7: Banuelos CA, Ito Y, Obst JK, Mawji NR, Wang J, Hirayama Y, Leung JK, Tam T, Tien AH, Andersen RJ, Sadar MD. Ralaniten Sensitizes Enzalutamide-Resistant Prostate Cancer to Ionizing Radiation in Prostate Cancer Cells that Express Androgen Receptor Splice Variants. Cancers (Basel). 2020 Jul 21;12(7):1991. doi: 10.3390/cancers12071991. PMID: 32708219; PMCID: PMC7409302.
8: Obst JK, Wang J, Jian K, Williams DE, Tien AH, Mawji N, Tam T, Yang YC, Andersen RJ, Chi KN, Montgomery B, Sadar MD. Revealing Metabolic Liabilities of Ralaniten To Enhance Novel Androgen Receptor Targeted Therapies. ACS Pharmacol Transl Sci. 2019 Sep 26;2(6):453-467. doi: 10.1021/acsptsci.9b00065. PMID: 32259077; PMCID: PMC7088963.
9: Sadar MD. Discovery of drugs that directly target the intrinsically disordered region of the androgen receptor. Expert Opin Drug Discov. 2020 May;15(5):551-560. doi: 10.1080/17460441.2020.1732920. Epub 2020 Feb 26. PMID: 32100577; PMCID: PMC8693730.
10: Ito Y, Sadar MD. Enzalutamide and blocking androgen receptor in advanced prostate cancer: lessons learnt from the history of drug development of antiandrogens. Res Rep Urol. 2018 Feb 16;10:23-32. doi: 10.2147/RRU.S157116. PMID: 29497605; PMCID: PMC5818862.
11: Andersen RJ. Sponging off nature for new drug leads. Biochem Pharmacol. 2017 Sep 1;139:3-14. doi: 10.1016/j.bcp.2017.04.012. Epub 2017 Apr 12. PMID: 28411115.
