ICI 182,780

Cat. No. 1047

ICI 182,780 C32H47F5O3S [129453-61-8]

Price and Availability

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Special Conditions

No more than 1 g per customer per year to be sold.

Chemical Name: 7α,17β-[9-[(4,4,5,5,5-Pentafluoropentyl)sulfinyl]nonyl]estra-1,3,5(10)-triene-3,17-diol

Biological Activity

A high affinity estrogen receptor antagonist (IC50 = 0.29 nM), devoid of any partial agonism both in vitro and in vivo. Also high affinity agonist at the membrane estrogen receptor GPER.

Licensing Information

Sold with the permission of AstraZeneca UK Ltd.

Technical Data

Soluble to 50 mM in ethanol and to 100 mM in DMSO
>99 %
Store at RT

The technical data provided above is for guidance only. For batch specific data refer to the Certificate of Analysis.
All Tocris products are intended for laboratory research use only.

Certificate of Analysis / Safety Data Sheet

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Thomas et al (2005) Identity of an estrogen membrane receptor coupled to a G protein in human breast cancer cells. Endocrinology. 146 624. PMID: 15539556.

Howell et al (2000) ICI 182,780 (FaslodexTM): Development of a novel, "pure" antiestrogen. Cancer 89 817. PMID: 10951345.

de Cupis et al (1995) Comparison between novel steroid-like and conventional nonsteroidal antioestrogens in inhibiting oestradiol and IGF-I induced proliferation of human breast cancer-derived cells. Br.J.Pharmacol. 116 2391. PMID: 8581274.

Wakeling et al (1991) A potent specific pure antiestrogen with clinical potential. Cancer Res. 51 3867. PMID: 1855205.

If you know of a relevant reference for this product please let us know.

Citations are publications that use Tocris products. Selected citations for ICI 182,780 include:

Albanito et al (2015) Effects of Atrazine on Estrogen Receptor α- and G Protein-Coupled Receptor 30-Mediated Signaling and Proliferation in Cancer Cells and Cancer-Associated Fibroblasts. Environ Health Perspect 123 493. PMID: 25616260.

Castro et al (2015) Differential expression of upstream stimulatory factor (USF) 2 variants in eutopic endometria from women with endometriosis: estradiol regulation. Biol Res 48 56. PMID: 26453052.

Harvey et al (2015) Methoxychlor and its metabolite HPTE inhibit cAMP production and expression of estrogen receptors α and β in the rat granulosa cell in vitro. Reprod Toxicol 51 72. PMID: 25549949.

Kastrati et al (2015) PHLDA1 expression is controlled by an estrogen receptor-NFκB-miR-181 regulatory loop and is essential for formation of ER+ mammospheres. Oncogene 34 2309. PMID: 24954507.

Kim et al (2015) Estrogen promotes luteolysis by redistributing prostaglandin F2α receptors within primate luteal cells. Reproduction 149 453. PMID: 25687410.

Tomita et al (2015) A cluster of noncoding RNAs activates the ESR1 locus during breast cancer adaptation. Nat Commun 6 6966. PMID: 25923108.

Tozzi et al (2015) Endogenous 17β-estradiol is required for activity-dependent long-term potentiation in the striatum: interaction with the dopaminergic system. Front Cell Neurosci 9 192. PMID: 26074768.

Xu et al (2015) A short report: PAMM, a novel antioxidant protein, induced by oxidative stress. Redox Biol 6 446. PMID: 26402163.

Adomas et al (2014) Breast tumor specific mutation in GATA3 affects physiological mechanisms regulating transcription factor turnover. BMC Cancer 14 278. PMID: 24758297.

Alao et al (2014) Selective inhibition of RET mediated cell proliferation in vitro by the kinase inhibitor SPP86. BMC Cancer 14 853. PMID: 25409876.

Colciago et al (2014) In vitro chronic administration of ERbeta selective ligands and prostate cancer cell growth: hypotheses on the selective role of 3beta-adiol in AR-positive RV1 cells. Biomed Res Int 2014 801473. PMID: 24877132.

Fan et al (2014) Inhibition of c-Src blocks oestrogen-induced apoptosis and restores oestrogen-stimulated growth in long-term oestrogen-deprived breast cancer cells. Eur J Cancer 50 457. PMID: 24183378.

Fan et al (2014) A molecular model for the mechanism of acquired tamoxifen resistance in breast cancer. Eur J Cancer 50 2866. PMID: 25204804.

Giretti et al (2014) Effects of Estetrol on Migration and Invasion in T47-D Breast Cancer Cells through the Actin Cytoskeleton. Front Endocrinol (Lausanne) 5 80. PMID: 24904530.

Gottardo et al (2014) Antiapoptotic factor humanin is expressed in normal and tumoral pituitary cells and protects them from TNF-α-induced apoptosis. PLoS One 9 e111548. PMID: 25360890.

Haagenson et al (2014) Functional analysis of MKP-1 and MKP-2 in breast cancer tamoxifen sensitivity. Oncotarget 5 1101. PMID: 24658355.

Hill and Muldrew (2014) Oestrogen upregulates the sarcoplasmic reticulum Ca(2+) ATPase pump in coronary arteries. Clin Exp Pharmacol Physiol 41 430. PMID: 24684418.

Liang et al (2014) Egr1 protein acts downstream of estrogen-leukemia inhibitory factor (LIF)-STAT3 pathway and plays a role during implantation through targeting Wnt4. J Biol Chem 289 23534. PMID: 25012664.

Oróstica et al (2014) Estradiol increases cAMP in the oviductal secretory cells through a nongenomic mechanism. Reproduction 148 285. PMID: 25038866.

Yi et al (2014) Anti-tumor efficacy of fulvestrant in estrogen receptor positive gastric cancer. Sci Rep 4 7592. PMID: 25534230.

Greaves et al (2013) ERβ-dependent effects on uterine endothelial cells are cell specific and mediated via Sp1. Hum Reprod 28 2490. PMID: 23756706.

Johansson et al (2013) Retinoic acid receptor alpha is associated with tamoxifen resistance in breast cancer. Nat Commun 4 2175. PMID: 23868472.

Morandi et al (2013) GDNF-RET signaling in ER-positive breast cancers is a key determinant of response and resistance to aromatase inhibitors. Cancer Res 73 3783. PMID: 23650283.

Teng et al (2013) Endocrine disruptors fludioxonil and fenhexamid stimulate miR-21 expression in breast cancer cells. Toxicol Sci 131 71. PMID: 23052036.

Antoon et al (2012) Inhibition of p38-MAPK alters SRC coactivation and estrogen receptor phosphorylation. Cancer Biol Ther 13 1026. PMID: 22825349.

Babu et al (2012) Genistein prevents hyperglycemia-induced monocyte adhesion to human aortic endothelial cells through preservation of the cAMP signaling pathway and ameliorates vascular inflammation in obese diabetic mice. J Nutr 142 724. PMID: 22399524.

Bobustuc et al (2012) MGMT inhibition restores ERα functional sensitivity to antiestrogen therapy. Mol Med 18 913. PMID: 22549111.

Cao et al (2012) Estrogen receptor β activation is antinociceptive in a model of visceral pain in the rat. J Pain 13 685. PMID: 22698981.

Collins-Burow et al (2012) Antiestrogenic activity of flavonoid phytochemicals mediated via the c-Jun N-terminal protein kinase pathway. Cell-type specific regulation of estrogen receptor alpha. J Steroid Biochem Mol Biol 132 186. PMID: 22634477.

González-Arenas et al (2012) Estradiol increases cell growth in human astrocytoma cell lines through ERα activation and its interaction with SRC-1 and SRC-3 coactivators. Biochim Biophys Acta 1823 379. PMID: 22142990.

Leal et al (2012) p130Cas over-expression impairs mammary branching morphogenesis in response to estrogen and EGF. PLoS One 7 e49817. PMID: 23239970.

Mahmoodzadeh et al (2012) 17β-Estradiol-induced interaction of ERα with NPPA regulates gene expression in cardiomyocytes. Cardiovasc Res 96 411. PMID: 22962310.

Peretz et al (2012) Bisphenol A inhibits follicle growth and induces atresia in cultured mouse antral follicles independently of the genomic estrogenic pathway. Biol Reprod 87 63. PMID: 22743301.

Rodriguez-Ubreva et al (2012) Pre-B cell to macrophage transdifferentiation without significant promoter DNA methylation changes. Nucleic Acids Res 40 1954. PMID: 22086955.

Ropero et al (2012) Insulinotropic effect of the non-steroidal compound STX in pancreatic β-cells. PLoS One 7 e34650. PMID: 22506040.

Shim and Lee (2012) Estrogen receptor is activated by korean red ginseng in vitro but not in vivo. J Ginseng Res 36 169. PMID: 23717117.

Wang and Kuehl-Kovarik (2012) Estradiol directly attenuates sodium currents and depolarizing afterpotentials in isolated gonadotropin-releasing hormone neurons. Brain Res 1436 81. PMID: 22209345.

Wen et al (2012) Modulation of ovine SBD-1 expression by 17beta-estradiol in ovine oviduct epithelial cells. BMC Vet Res 8 143. PMID: 22920556.

Youn et al (2012) Inhibition of XO or NOX attenuates diethylstilbestrol-induced endothelial nitric oxide deficiency without affecting its effects on LNCaP cell invasion and apoptosis. Clin Sci (Lond) 123 509. PMID: 22568671.

Burns et al (2011) Selective mutations in estrogen receptor alpha D-domain alters nuclear translocation and non-estrogen response element gene regulatory mechanisms. J Biol Chem 286 12640. PMID: 21285458.

He et al (2011) Complete estrogen receptor blocker ICI182,780 promotes the proliferation of vascular smooth muscle cells. Acta Biochim Biophys Sin (Shanghai) 43 118. PMID: 21193431.

Ivanova et al (2011) Tamoxifen increases nuclear respiratory factor 1 transcription by activating estrogen receptor beta and AP-1 recruitment to adjacent promoter binding sites. FASEB J 25 1402. PMID: 21233487.

Tyagi et al (2011) Daidzein prevents the increase in CD4+CD28null T cells and B lymphopoesis in ovariectomized mice: a key mechanism for anti-osteoclastogenic effect. PLoS One 6 e21216. PMID: 21731677.

Yu et al (2011) mTOR controls ovarian follicle growth by regulating granulosa cell proliferation. PLoS One 6 e21415. PMID: 21750711.

Zheng et al (2011) 17β-Estradiol enhances breast cancer cell motility and invasion via extra-nuclear activation of actin-binding protein ezrin. PLoS One 6 e22439. PMID: 21818323.

Allard and Colaiácovo (2010) Bisphenol A impairs the double-strand break repair machinery in the germline and causes chromosome abnormalities. Proc Natl Acad Sci U S A 107 20405. PMID: 21059909.

Bender et al (2010) Roles of 17β-estradiol involve regulation of reelin expression and synaptogenesis in the dentate gyrus. Cereb Cortex 20 2985. PMID: 20421250.

Dalvai and Bystricky (2010) Cell cycle and anti-estrogen effects synergize to regulate cell proliferation and ER target gene expression. PLoS One 5 e11011. PMID: 20543978.

Harte et al (2010) BRD7, a subunit of SWI/SNF complexes, binds directly to BRCA1 and regulates BRCA1-dependent transcription. Cancer Res 70 2538. PMID: 20215511.

Lin et al (2010) B7-H1-dependent sex-related differences in tumor immunity and immunotherapy responses. J Immunol 185 2747. PMID: 20686128.

Madeo et al (2010) c-Jun activation is required for 4-hydroxytamoxifen-induced cell death in breast cancer cells. Oncogene 29 978. PMID: 19935718.

Mahmoodzadeh et al (2010) 17beta-Estradiol inhibits matrix metalloproteinase-2 transcription via MAP kinase in fibroblasts. Cardiovasc Res 85 719. PMID: 19861308.

Mao et al (2010) Progesterone increases systemic and local uterine proportions of CD4+CD25+ Treg cells during midterm pregnancy in mice. Endocrinology 151 5477. PMID: 20844003.

Murphy et al (2010) Estradiol suppresses NF-kappa B activation through coordinated regulation of let-7a and miR-125b in primary human macrophages. J Immunol 184 5029. PMID: 20351193.

Peng et al (2010) Unexpected hormonal activity of a catechol equine estrogen metabolite reveals reversible glutathione conjugation. Chem Res Toxicol 23 1374. PMID: 20540524.

Pradhan et al (2010) Proinflammatory cytokines enhance estrogen-dependent expression of the multidrug transporter gene ABCG2 through estrogen receptor and NF{kappa}B cooperativity at adjacent response elements. J Biol Chem 285 31100. PMID: 20705611.

Rangasamy et al (2010) Estrogen suppresses MLK3-mediated apoptosis sensitivity in ER+ breast cancer cells. Cancer Res 70 1731. PMID: 20145118.

Rasmussen et al (2010) Prolactin and oestrogen synergistically regulate gene expression and proliferation of breast cancer cells. Endocr Relat Cancer 17 809. PMID: 20601496.

Sanchez et al (2010) Estrogen receptor-alpha promotes breast cancer cell motility and invasion via focal adhesion kinase and N-WASP. Mol Endocrinol 24 2114. PMID: 20880986.

Sherrill et al (2010) Developmental exposures of male rats to soy isoflavones impact Leydig cell differentiation. Biol Reprod 83 488. PMID: 20554919.

Son et al (2010) Androgen receptor-dependent transactivation of growth arrest-specific gene 6 mediates inhibitory effects of testosterone on vascular calcification. J Biol Chem 285 7537. PMID: 20048160.

Sunters et al (2010) Mechano-transduction in osteoblastic cells involves strain-regulated estrogen receptor alpha-mediated control of insulin-like growth factor (IGF) I receptor sensitivity to Ambient IGF, leading to phosphatidylinositol 3-kinase/AKT-dependent Wnt/LRP5 receptor-independent activation of beta-catenin signaling. J Biol Chem 285 8743. PMID: 20042609.

Suzuki et al (2010) Down-regulation of PROS1 gene expression by 17beta-estradiol via estrogen receptor alpha (ERalpha)-Sp1 interaction recruiting receptor-interacting protein 140 and the corepressor-HDAC3 complex. J Biol Chem 285 13444. PMID: 20200160.

Thuillier et al (2010) Interdependence of platelet-derived growth factor and estrogen-signaling pathways in inducing neonatal rat testicular gonocytes proliferation. Biol Reprod 82 825. PMID: 20089883.

Bolanz et al (2009) Tamoxifen inhibits TRPV6 activity via estrogen receptor-independent pathways in TRPV6-expressing MCF-7 breast cancer cells. Mol Cancer Res 7 2000. PMID: 19996302.

Boue et al (2009) Identification of the potent phytoestrogen glycinol in elicited soybean (Glycine max). Endocrinology 150 2446. PMID: 19116342.

Chisamore et al (2009) Characterization of a novel small molecule subtype specific estrogen-related receptor alpha antagonist in MCF-7 breast cancer cells. PLoS One 4 e5624. PMID: 19462000.

Comitato et al (2009) A novel mechanism of natural vitamin E tocotrienol activity: involvement of ERbeta signal transduction. Am J Physiol Endocrinol Metab 297 E427. PMID: 19491296.

Flamini et al (2009) Differential actions of estrogen and SERMs in regulation of the actin cytoskeleton of endometrial cells. Mol Hum Reprod 15 675. PMID: 19541800.

Han et al (2009) The estrogen receptor alpha pathway induces oncogenic Wip1 phosphatase gene expression. Mol Cancer Res 7 713. PMID: 19435816.

Hsieh et al (2009) Mechanism of the salutary effects of estrogen on kupffer cell phagocytic capacity following trauma-hemorrhage: pivotal role of Akt activation. J Immunol 182 4406. PMID: 19299741.

Iorns et al (2009) CRK7 modifies the MAPK pathway and influences the response to endocrine therapy. Carcinogenesis 30 1696. PMID: 19651820.

Lee et al (2009) K+-dependent Na+/Ca2+ exchanger 3 is involved in renal active calcium transport and is differentially expressed in the mouse kidney. Am J Physiol Renal Physiol 297 F371. PMID: 19474185.

Park et al (2009) 17Beta-estradiol at low concentrations acts through distinct pathways in normal versus benign prostatic hyperplasia-derived prostate stromal cells. Endocrinology 150 4594. PMID: 19608654.

Quiles et al (2009) Mutational analysis of progesterone receptor functional domains in stable cell lines delineates sets of genes regulated by different mechanisms. Mol Endocrinol 23 809. PMID: 19299443.

Schaub and Wood (2009) Blockade of estrogen action upregulates estrogen receptor-alpha mRNA in the fetal brain. Neonatology 96 115. PMID: 19279395.

Tan et al (2009) Autocrine regulation of cell proliferation by estrogen receptor-alpha in estrogen receptor-alpha-positive breast cancer cell lines. BMC Cancer 9 31. PMID: 19171042.

Albanito et al (2008) G-protein-coupled receptor 30 and estrogen receptor-alpha are involved in the proliferative effects induced by atrazine in ovarian cancer cells. Environ Health Perspect 116 1648. PMID: 19079715.

Galluzzo et al (2008) The nutritional flavanone naringenin triggers antiestrogenic effects by regulating estrogen receptor alpha-palmitoylation. Endocrinology 149 2567. PMID: 18239068.

Iorns et al (2008) Identification of CDK10 as an important determinant of resistance to endocrine therapy for breast cancer. Cancer Cell 13 91. PMID: 18242510.

Liu et al (2008) Estrogen-enhanced gene expression of lipoprotein lipase in heart is antagonized by progesterone. Endocrinology 149 711. PMID: 17974624.

Oh et al (2008) Tyrosine phosphorylation of the nuclear receptor coactivator AIB1/SRC-3 is enhanced by Abl kinase and is required for its activity in cancer cells. Mol Cell Biol 28 6580. PMID: 18765637.

Subtil-Rodríguez et al (2008) Progesterone induction of the 11beta-hydroxysteroid dehydrogenase type 2 promoter in breast cancer cells involves coordinated recruitment of STAT5A and progesterone receptor to a distal enhancer and polymerase tracking. Mol Cell Biol 28 3830. PMID: 18378698.

Teng et al (2008) Roles of estrogen receptor alpha and beta in modulating urothelial cell proliferation. Endocr Relat Cancer 15 351. PMID: 18310301.

Wang et al (2008) Hormonal regulation of BCRP expression in human placental BeWo cells. Pharm Res 25 444. PMID: 17823853.

Yuan et al (2008) Effects of estradiol and progesterone on the proinflammatory cytokine production by mononuclear cells from patients with chronic hepatitis C. World J Gastroenterol 14 2200. PMID: 18407594.

Akingbemi et al (2007) Exposure to phytoestrogens in the perinatal period affects androgen secretion by testicular Leydig cells in the adult rat. Endocrinology 148 4475. PMID: 17569756.

Albanito et al (2007) G protein-coupled receptor 30 (GPR30) mediates gene expression changes and growth response to 17beta-estradiol and selective GPR30 ligand G-1 in ovarian cancer cells. Cancer Res 67 1859. PMID: 17308128.

Chang et al (2007) Activation of estrogen receptor-mediated gene transcription by the equine estrogen metabolite, 4-methoxyequilenin, in human breast cancer cells. Endocrinology 148 4793. PMID: 17584965.

Cullen et al (2007) Resveratrol inhibits expression and binding activity of the monocyte chemotactic protein-1 receptor, CCR2, on THP-1 monocytes. Atherosclerosis 195 e125. PMID: 17499741.

Peterson et al (2007) The silencing mediator of retinoic acid and thyroid hormone receptor (SMRT) corepressor is required for full estrogen receptor alpha transcriptional activity. Mol Cell Biol 27 5933. PMID: 17591692.

Velarde et al (2007) Kruppel-like factor 9 is a negative regulator of ligand-dependent estrogen receptor alpha signaling in Ishikawa endometrial adenocarcinoma cells. Mol Endocrinol 21 2988. PMID: 17717078.

Wittmann et al (2007) Definition of functionally important mechanistic differences among selective estrogen receptor down-regulators. Cancer Res 67 9549. PMID: 17909066.

Zhu and Pollard (2007) Estradiol-17beta regulates mouse uterine epithelial cell proliferation through insulin-like growth factor 1 signaling. Proc Natl Acad Sci U S A 104 15847. PMID: 17895382.

Buterin et al (2006) Convergent transcriptional profiles induced by endogenous estrogen and distinct xenoestrogens in breast cancer cells. Carcinogenesis 27 1567. PMID: 16474171.

Chen et al (2006) Activation of insulin-like growth factor I receptor-mediated pathway by ginsenoside Rg1. Br J Pharmacol 147 542. PMID: 16415910.

Dahm et al (2006) Estrogens, selective estrogen receptor modulators, and a selective estrogen receptor down-regulator inhibit endothelial production of tissue factor pathway inhibitor 1. BMC Cardiovasc Disord 6 40. PMID: 17029634.

Dalenc et al (2006) Farnesyl-transferase inhibitor R115,777 enhances tamoxifen inhibition of MCF-7 cell growth through estrogen receptor dependent and independent pathways. Breast Cancer Res 7 R1159. PMID: 16457696.

Vivacqua et al (2006) 17beta-estradiol, genistein, and 4-hydroxytamoxifen induce the proliferation of thyroid cancer cells through the g protein-coupled receptor GPR30. Mol Pharmacol 70 1414. PMID: 16835357.

Abe and Terasawa (2005) Firing pattern and rapid modulation of activity by estrogen in primate luteinizing hormone releasing hormone-1 neurons. Endocrinology 146 4312. PMID: 15976055.

Acconcia et al (2005) Palmitoylation-dependent estrogen receptor alpha membrane localization: regulation by 17beta-estradiol. Mol Biol Cell 16 231. PMID: 15496458.

Gingerich and Krukoff (2005) Estrogen modulates endothelial and neuronal nitric oxide synthase expression via an estrogen receptor beta-dependent mechanism in hypothalamic slice cultures. Endocrinology 146 2933. PMID: 15790731.

Labhart et al (2005) Identification of target genes in breast cancer cells directly regulated by the SRC-3/AIB1 coactivator. Proc Natl Acad Sci U S A 102 1339. PMID: 15677324.

Lee et al (2005) Estrogen receptor alpha pathway is involved in the regulation of Calbindin-D9k in the uterus of immature rats. Toxicol Sci 84 270. PMID: 15635152.

Park et al (2005) Formation of an IKKalpha-dependent transcription complex is required for estrogen receptor-mediated gene activation. Mol Cell 18 71. PMID: 15808510.

Stirone et al (2005) Estrogen increases mitochondrial efficiency and reduces oxidative stress in cerebral blood vessels. Mol Pharmacol 68 959. PMID: 15994367.

Zivadinovic and Watson (2005) Membrane estrogen receptor-alpha levels predict estrogen-induced ERK1/2 activation in MCF-7 cells. Breast Cancer Res 7 R130. PMID: 15642162.

Bulayeva and Watson (2004) Xenoestrogen-induced ERK-1 and ERK-2 activation via multiple membrane-initiated signaling pathways. Environ Health Perspect 112 1481. PMID: 15531431.

Maggiolini et al (2004) The G protein-coupled receptor GPR30 mediates c-fos up-regulation by 17beta-estradiol and phytoestrogens in breast cancer cells. J Biol Chem 279 27008. PMID: 15090535.

Morelli et al (2004) Nuclear insulin receptor substrate 1 interacts with estrogen receptor alpha at ERE promoters. Oncogene 23 7517. PMID: 15318176.

Ramsey et al (2004) Estrogen receptor beta isoforms exhibit differences in ligand-activated transcriptional activity in an estrogen response element sequence-dependent manner. Endocrinology 145 149. PMID: 14500565.

Wynne et al (2004) Age-related reduction in estrogen receptor-mediated mechanisms of vascular relaxation in female spontaneously hypertensive rats. Hypertension 43 405. PMID: 14699001.

Finlay et al (2003) Regulation of PDGF production and ERK activation by estrogen is associated with TSC2 gene expression. Am J Physiol Cell Physiol 285 C409. PMID: 12700139.

Kimmins et al (2003) The effects of estrogen, its antagonist ICI 182, 780, and interferon-tau on the expression of estrogen receptors and integrin alphaV beta 3 on cycle day 16 in bovine endometrium. Reprod Biol Endocrinol 1 38. PMID: 12756058.

Grimaldi et al (2002) Estrogen alters thresholds for B cell apoptosis and activation. J Clin Invest 109 1625. PMID: 12070310.

Alonso-Magdalena et al Pancreatic insulin content regulation by the estrogen receptor ER alpha. PLoS One 3 e2069. PMID: 18446233.

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Keywords: ICI 182,780, supplier, High, affinity, GPR30, agonist, Estrogen, receptors, antagonists, ER, ERR, ICI182780, AstraZeneca, GPER, Tocris Bioscience, Estrogen and Related Receptor Antagonist products

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