Etacstil

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

MedKoo CAT#: 206770

CAS#: 155701-61-4

Description: Etacstil, also known as GW5638 and DPC974, is a estrogen receptor ligand. Similar to tamoxifen, GW5638 is considered as a prodrug of its active metabolite GW7604. GW5638 appears to function as an antagonist in these in vitro systems, although in a manner distinct from other known ER modulators. GW5638 is also classified as a pseudo-SERD, which could form the basis of a new paradigm of breast cancer hormonal therapy in its own right.

Chemical Structure

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Etacstil
CAS# 155701-61-4
Instruction

Theoretical Analysis

MedKoo Cat#: 206770
Name: Etacstil
CAS#: 155701-61-4
Chemical Formula: C25H22O2
Exact Mass: 354.16
Molecular Weight: 354.449
Elemental Analysis: C, 84.72; H, 6.26; O, 9.03

Price and Availability

This product is not in stock, which may be available by custom synthesis. For cost-effective reason, minimum order is 1g (price is usually high, lead time is 2~3 months, depending on the technical challenge). Quote less than 1g will not be provided. To request quote, please email to sales @medkoo.com or click below button.
Note: Price will be listed if it is available in the future.

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Synonym: GW5638; GW-5638; GW 5638; DPC974; DPC-974; DPC 974; Etacstil.

IUPAC/Chemical Name: (E)-3-(4-((E)-1,2-diphenylbut-1-en-1-yl)phenyl)acrylic acid

InChi Key: HJQQVNIORAQATK-LXFXVVTESA-N

InChi Code: InChI=1S/C25H22O2/c1-2-23(20-9-5-3-6-10-20)25(21-11-7-4-8-12-21)22-16-13-19(14-17-22)15-18-24(26)27/h3-18H,2H2,1H3,(H,26,27)/b18-15+,25-23+

SMILES Code: O=C(O)/C=C/C1=CC=C(/C(C2=CC=CC=C2)=C(C3=CC=CC=C3)\CC)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: >2 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:

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 354.45 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:
In vitro protocol:
In vivo protocol:

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1: Laxmi YR, Liu X, Suzuki N, Kim SY, Okamoto K, Kim HJ, Zhang G, Chen JJ, Okamoto Y, Shibutani S. Anti-breast cancer potential of SS1020, a novel antiestrogen lacking estrogenic and genotoxic actions. Int J Cancer. 2010 Oct 1;127(7):1718-26. doi: 10.1002/ijc.25167. PubMed PMID: 20073065.

2: Wittmann BM, Sherk A, McDonnell DP. Definition of functionally important mechanistic differences among selective estrogen receptor down-regulators. Cancer Res. 2007 Oct 1;67(19):9549-60. PubMed PMID: 17909066.

3: Fan M, Rickert EL, Chen L, Aftab SA, Nephew KP, Weatherman RV. Characterization of molecular and structural determinants of selective estrogen receptor downregulators. Breast Cancer Res Treat. 2007 May;103(1):37-44. PubMed PMID: 17033922.

4: Tong S, Chen Q, Shan SQ, Dewhirst MW, Yuan F. Quantitative comparison of the inhibitory effects of GW5638 and tamoxifen on angiogenesis in the cornea pocket assay. Angiogenesis. 2006;9(2):53-8. PubMed PMID: 16622786.

5: Ariazi EA, Ariazi JL, Cordera F, Jordan VC. Estrogen receptors as therapeutic targets in breast cancer. Curr Top Med Chem. 2006;6(3):181-202. Review. PubMed PMID: 16515478.

6: Wu YL, Yang X, Ren Z, McDonnell DP, Norris JD, Willson TM, Greene GL. Structural basis for an unexpected mode of SERM-mediated ER antagonism. Mol Cell. 2005 May 13;18(4):413-24. PubMed PMID: 15893725.

7: Farnell YZ, Ing NH. Myometrial effects of selective estrogen receptor modulators on estradiol-responsive gene expression are gene and cell-specific. J Steroid Biochem Mol Biol. 2003 Apr;84(5):527-36. PubMed PMID: 12767277.

8: Farnell YZ, Ing NH. Endometrial effects of selective estrogen receptor modulators (SERMs) on estradiol-responsive gene expression are gene and cell-specific. J Steroid Biochem Mol Biol. 2003 Apr;84(5):513-26. PubMed PMID: 12767276.

9: Dardes RC, O'Regan RM, Gajdos C, Robinson SP, Bentrem D, De Los Reyes A, Jordan VC. Effects of a new clinically relevant antiestrogen (GW5638) related to tamoxifen on breast and endometrial cancer growth in vivo. Clin Cancer Res. 2002 Jun;8(6):1995-2001. PubMed PMID: 12060645.

10: Gutman M, Couillard S, Roy J, Labrie F, Candas B, Labrie C. Comparison of the effects of EM-652 (SCH57068), tamoxifen, toremifene, droloxifene, idoxifene, GW-5638 and raloxifene on the growth of human ZR-75-1 breast tumors in nude mice. Int J Cancer. 2002 May 10;99(2):273-8. PubMed PMID: 11979444.

11: Howell A. Future use of selective estrogen receptor modulators and aromatase inhibitors. Clin Cancer Res. 2001 Dec;7(12 Suppl):4402s-4410s; discussion 4411s-4412s. Review. PubMed PMID: 11916232.

12: Gajdos C, Jordan VC. Selective estrogen receptor modulators as a new therapeutic drug group: concept to reality in a decade. Clin Breast Cancer. 2002 Jan;2(4):272-81. Review. PubMed PMID: 11899358.

13: Weatherman RV, Clegg NJ, Scanlan TS. Differential SERM activation of the estrogen receptors (ERalpha and ERbeta) at AP-1 sites. Chem Biol. 2001 May;8(5):427-36. PubMed PMID: 11358690.

14: Connor CE, Norris JD, Broadwater G, Willson TM, Gottardis MM, Dewhirst MW, McDonnell DP. Circumventing tamoxifen resistance in breast cancers using antiestrogens that induce unique conformational changes in the estrogen receptor. Cancer Res. 2001 Apr 1;61(7):2917-22. PubMed PMID: 11306468.

15: Bentrem D, Dardes R, Liu H, MacGregor-Schafer J, Zapf J, Jordan V. Molecular mechanism of action at estrogen receptor alpha of a new clinically relevant antiestrogen (GW7604) related to tamoxifen. Endocrinology. 2001 Feb;142(2):838-46. PubMed PMID: 11159857.

16: Seifert M, Galid A, Kubista E. The oestrogen receptor and its selective modulators in gynaecological oncology. Eur J Cancer. 2000 Sep;36 Suppl 4:S66-7. PubMed PMID: 11056325.

17: Willson TM, Norris JD, Wagner BL, Asplin I, Baer P, Brown HR, Jones SA, Henke B, Sauls H, Wolfe S, Morris DC, McDonnell DP. Dissection of the molecular mechanism of action of GW5638, a novel estrogen receptor ligand, provides insights into the role of estrogen receptor in bone. Endocrinology. 1997 Sep;138(9):3901-11. PubMed PMID: 9275080.

18: Willson TM, Henke BR, Momtahen TM, Charifson PS, Batchelor KW, Lubahn DB, Moore LB, Oliver BB, Sauls HR, Triantafillou JA, et al. 3-[4-(1,2-Diphenylbut-1-enyl)phenyl]acrylic acid: a non-steroidal estrogen with functional selectivity for bone over uterus in rats. J Med Chem. 1994 May 27;37(11):1550-2. PubMed PMID: 8201587.