Home Endocrinology & Hormones Estrogen/progestogen Receptor modulator - CRISPR/Cas9 activator 4-Hydroxytamoxifen (Afimoxifene) For research use only.

4-Hydroxytamoxifen (Afimoxifene)

Synonyms: Afimoxifene

4-Hydroxytamoxifen (Afimoxifene) is the active metabolite of tamoxifen and a selective estrogen receptor (ER) modulator that is widely used in the therapeutic and chemopreventive treatment of breast cancer. It activates on-target modification frequency for intein-Cas9 variants.

4-Hydroxytamoxifen (Afimoxifene) Chemical Structure

4-Hydroxytamoxifen (Afimoxifene) Chemical Structure

CAS No. 68392-35-8

Purity & Quality Control

4-Hydroxytamoxifen (Afimoxifene) Related Products

Signaling Pathway

Estrogen/progestogen Receptor Signaling Pathways

Estrogen/progestogen Receptor Signaling Pathway

Cell Data

Cell Lines Assay Type Concentration Incubation Time Formulation Activity Description PMID
MCF7 cells Proliferation assay Inhibition of estrogen-stimulated MCF-7 cell proliferation, IC50=0.5 nM 9548817
MCF7 Function assay Effective dose for [3H]- estradiol against proliferation of MCF-7 cells, EC50 = 0.00003 μM. 2769681
MCF7 Function assay 4 hrs Induction of ERalpha degradation in human MCF7 cells in phenol red free RPMI medium containing 5% charcoal dextran-treated FBS incubated for 4 hrs by SP1 and anti-ER rabbit monocolnal antibody based in-cell Western assay, Activity = 0.0001 μM. 30086626
MCF7 Function assay Effective concentration against MCF-7 breast tumor cells using MCF-7 assay, EC50 = 0.00012 μM. 12825935
MCF7 Antiproliferative assay Antiproliferative activity against human MCF7 cells, IC50 = 0.0005 μM. 22405286
MCF7 Antiproliferative assay Antiproliferative activity against human MCF7 cells, IC50 = 0.000537 μM. 26407012
MCF Function assay Antagonist activity at progesterone receptor in human MCF cells assessed as estradiol-induced receptor response, IC50 = 0.0007943 μM. 26407012
Ishikawa endometrial cells Function assay Agonist activity as alkaline phosphatase induction in Ishikawa endometrial cells compared to E2, EC50 = 0.0008 μM. 15380208
MCF7 Function assay Inhibition of estrogen-induced proliferation in human MCF-7 breast cancer cells, IC50 = 0.00117 μM. 9154963
MCF7 Function assay 24 hrs Antagonist activity at ERalpha in human MCF7 cells assessed as inhibition of estrogen-induced transcription preincubated overnight followed by estrogen addition measured after 24 hrs by dual luciferase reporter gene assay, IC50 = 0.003 μM. 28296398
Rosetta 2 DE3 Function assay 1 hr Displacement of [3H]-estradiol from recombinant human N-terminal His-tagged ERalpha LBD harboring C381S/C417S/C530S mutant expressed in Rosetta 2 DE3 competent cells after 1 hr by SPA binding assay, IC50 = 0.004 μM. 28296398
insect cells Function assay Inhibition of fluormone ES2 green binding to recombinant full length human ERalpha expressed in insect cells by fluorescence polarization assay, IC50 = 0.00629 μM. 28735214
MCF-7-2a Function assay Inhibition of estradiol induced estrogen receptor transcriptional activation in MCF-7-2a cells, IC50 = 0.007 μM. 12672249
MCF7 Antiproliferative assay 24 hrs Antiproliferative activity against human MCF7 cells after 24 hrs by MTS assay, IC50 = 0.0085 μM. 18272256
MCF7 Function assay Inhibitory concentration against MCF-7 breast tumor cells using MCF-7 assay, IC50 = 0.0085 μM. 12825935
Ishikawa cells Function assay 72 hrs Antagonist activity at estrogen receptor alpha/beta in human Ishikawa cells after 72 hrs by alkaline phosphatase assay, IC50 = 0.01 μM. 28426931
insect cells Function assay Displacement of fluorescein labeled estradiol from human recombinant ERbeta expressed in baculovirus infected insect cells by fluorescence polarization assay, IC50 = 0.02 μM. 18835176
MCF7 Cytotoxicity assay 5 days Cytotoxicity against human MCF7 cells after 5 days, IC50 = 0.0291 μM. 23864928
GT1-7 Function assay 20 to 24 hrs Antagonist activity at estrogen receptor in mouse GT1-7 cells harboring beta-galactosidase reporter gene assessed as reduction in 17beta-estradiol induced response measured after 20 to 24 hrs by luciferase reporter gene assay, IC50 = 0.0332 μM. 28400239
insect cells Function assay Displacement of fluorescein labeled estradiol from human recombinant ERalpha expressed in baculovirus infected insect cells by fluorescence polarization assay, IC50 = 0.04 μM. 18835176
HEK293 Function assay 30 mins Inhibition of GFP-tagged human PLD2 expressed in human HEK293 cells assessed as decrease in phosphatidylbutanol-[d9] production after 30 mins by mass spectrometric analysis, IC50 = 0.044 μM. 19136975
HEK293 Function assay 1 hr Antagonist activity at recombinant human ERalpha expressed in HEK293 cells assessed as inhibition of estradiol-induced YFP-fused SRC1 coactivator recruitment measured after 1 hr in presence of Coelenterazine H by BRET assay, IC50 = 0.07 μM. 30078609
MCF7 Antiproliferative assay 72 hrs Antiproliferative activity against estrogen receptor dependent human MCF7 cells after 72 hrs by MTT assay, IC50 = 0.107 μM. 18835176
MCF7 Antiproliferative assay 72 hrs Antiproliferative activity against human MCF7 cells after 72 hrs by trypan blue assay, GI50 = 0.107 μM. 23735829
MCF7 Antiproliferative assay 72 hrs Antiproliferative activity against ER-dependent human MCF7 cells after 72 hrs by MTT assay, IC50 = 0.11 μM. 28426931
T47D Cytotoxicity assay 5 days Cytotoxicity against human T47D cells after 5 days, IC50 = 0.21 μM. 23864928
Ishikawa endometrial cells Function assay Antagonist activity as inhibition of 1 nM 17-beta-estradiol stimulated alkaline phosphatase induction in Ishikawa endometrial cells, IC50 = 0.51 μM. 15380208
CV1 Function assay 45 hrs Inverse agonist activity at GAL4-DNA binding domain-fused mouse ERRgamma ligand binding domain expressed in African green monkey CV1 cells assessed as decrease in receptor transcriptional activity after 45 hrs by luciferase reporter gene assay, IC50 = 0.6 μM. 28189393
CV1 Function assay 45 hrs Inverse agonist activity at GAL4-DNA binding domain-fused human ERRbeta ligand binding domain expressed in African green monkey CV1 cells assessed as decrease in receptor transcriptional activity after 45 hrs by luciferase reporter gene assay, IC50 = 0.65 μM. 28189393
HEK293 Function assay Agonist activity at human estrogen related receptor gamma expressed in HEK293 cells by luciferase reporter gene assay, IC50 = 1.35 μM. 25305688
MCF7 Antiproliferative assay 48 hrs Antiproliferative activity against human MCF7 cells expressing estrogen receptor incubated with 0.003 nM of estradiol and 0.01 nM of testosterone after 48 hrs by sulforhodamine B assay in presence of 5% fetal bovine serum, GI50 = 1.41254 μM. 21513275
MCF7 Antiproliferative assay 48 hrs Antiproliferative activity against human MCF7 cells expressing estrogen receptor incubated with 0.06 nM of estradiol and 0.07 nM of testosterone after 48 hrs by sulforhodamine B assay in presence of fetal bovine serum and NuSerum, GI50 = 1.90546 μM. 21513275
HeLa Function assay 4.5 hrs Inhibition of Ebolavirus glycoprotein/matrix protein VP40 entry in human HeLa cells after 4.5 hrs beta-lactamase reporter assay, IC50 = 1.96 μM. 29624387
MDA-MB-231 Cytotoxicity assay 4 days Cytotoxicity against ER negative human MDA-MB-231 cells treated every 2 days for 4 days measured after 7 days by CellTiter-Glo luminescence assay, IC50 = 2.5 μM. 30078609
MCF7 Antiproliferative assay Antiproliferative activity against human MCF7 cells assessed as incorporation of [methyl-3H]thymidine into cellular DNA in serum free medium in in absence of 6.2 ug/mL RNase 1, IC50 = 2.7 μM. 22611478
MCF7 Antiproliferative assay 72 hrs Antiproliferative activity against human MCF7 cells after 72 hrs by MTT assay, IC50 = 2.79 μM. 26896706
MCF12A Antiproliferative assay 48 hrs Antiproliferative activity against estrogen receptor-deficient human MCF12A cells incubated with 100 nM of estradiol and 0.07 nM of testosterone after 48 hrs by sulforhodamine B assay in presence of fetal bovine serum and NuSerum, GI50 = 3.23594 μM. 21513275
MCF7 Cytotoxicity assay 4 days Cytotoxicity against ER positive human MCF7 cells treated every 2 days for 4 days measured after 7 days by CellTiter-Glo luminescence assay, IC50 = 3.3 μM. 30078609
MCF12A Antiproliferative assay 48 hrs Antiproliferative activity against estrogen receptor-deficient human MCF12A cells incubated with 0.003 nM of estradiol and 0.01 nM of testosterone after 48 hrs by sulforhodamine B assay in presence of 5% fetal bovine serum, GI50 = 3.31131 μM. 21513275
MCF7 Antiproliferative assay 48 hrs Antiproliferative activity against human MCF7 cells expressing estrogen receptor incubated with 100 nM of estradiol and 0.07 nM of testosterone after 48 hrs by sulforhodamine B assay in presence of fetal bovine serum and NuSerum, GI50 = 3.46737 μM. 21513275
MDA-MB-231 Cytotoxicity assay 4 days Cytotoxicity against ER negative human MDA-MB-231 cells treated every 2 days for 4 days measured post last dose by CellTiter-Glo luminescence assay, IC50 = 3.5 μM. 30078609
MCF12A Antiproliferative assay 48 hrs Antiproliferative activity against estrogen receptor-deficient human MCF12A cells incubated with 0.06 nM of estradiol and 0.07 nM of testosterone after 48 hrs by sulforhodamine B assay in presence of fetal bovine serum and NuSerum, GI50 = 3.89045 μM. 21513275
MCF7 Cytotoxicity assay 4 days Cytotoxicity against ER positive human MCF7 cells treated every 2 days for 4 days measured post last dose by CellTiter-Glo luminescence assay, IC50 = 3.9 μM. 30078609
MCF7 Function assay Inhibitory activity against proliferation of MCF-7 cells in presence of 10e-6 M concentration of [3H]- estradiol (E2), IC30 = 4 μM. 2769681
MCF10A Cytotoxicity assay 4 days Cytotoxicity against ER negative human MCF10A cells treated every 2 days for 4 days measured post last dose by CellTiter-Glo luminescence assay, IC50 = 4 μM. 30078609
MCF10A Cytotoxicity assay 4 days Cytotoxicity against ER negative human MCF10A cells treated every 2 days for 4 days measured after 7 days by CellTiter-Glo luminescence assay, IC50 = 4 μM. 30078609
yeast cells Antiestrogenic assay Antiestrogenic activity at estrogen receptor alpha expressed in yeast cells assessed as inhibition of 17-beta-estradiol-induced beta-galactosidase activity by two hybrid assay, IC50 = 4.4 μM. 16441086
NCI-ADR-RES Antiproliferative assay 48 hrs Antiproliferative activity against estrogen receptor-deficient human NCI-ADR-RES cells incubated with 0.003 nM of estradiol and 0.01 nM of testosterone after 48 hrs by sulforhodamine B assay in presence of 5% fetal bovine serum, GI50 = 4.46684 μM. 21513275
BT-20 Function assay 10 μM Inhibitory activity against proliferation of BT-20 cells in presence of TPE at 10e-5 M concentration, IC30 = 4.8 μM. 2769681
Calu-1 Function assay 30 mins Inhibition of PLD1 in human Calu-1 cells assessed as decrease in phosphatidylbutanol-[d9] production after 30 mins by mass spectrometric analysis, IC50 = 4.8 μM. 19136975
MCF7 Function assay Antagonist activity at ERalpha receptor in human MCF7 cells, IC50 = 4.89779 μM. 26407012
MDA-MB-231 Anticancer assay 48 hrs Anticancer against human ER-positive MDA-MB-231 cells assessed as cell viability after 48 hrs by SRB assay, IC50 = 5.4 μM. 24946145
MCF-7 Cytotoxicity assay Cytotoxicity against MCF-7 cells in the absence of 1 uM E2 (estradiol), Cytotoxicity = 6 μM. 9089332
NCI-ADR-RES Antiproliferative assay 48 hrs Antiproliferative activity against estrogen receptor-deficient human NCI-ADR-RES cells incubated with 0.06 nM of estradiol and 0.07 nM of testosterone after 48 hrs by sulforhodamine B assay in presence of fetal bovine serum and NuSerum, GI50 = 6.16595 μM. 21513275
AU565 Anticancer assay 48 hrs Anticancer against human ER-negative AU565 cells assessed as cell viability after 48 hrs by SRB assay, IC50 = 6.2 μM. 24946145
MCF7L Anticancer assay 48 hrs Anticancer against human ER-positive MCF7L cells assessed as cell viability after 48 hrs by SRB assay, IC50 = 6.3 μM. 24946145
SKOV3-MDR1-M6/6 Anticancer assay 48 hrs Anticancer against human SKOV3-MDR1-M6/6 cells assessed as cell viability after 48 hrs by SRB assay, IC50 = 6.49 μM. 24946145
MCF7 Antiproliferative assay 24 hrs Antiproliferative activity against human MCF7 cells after 24 hrs by MTT assay, IC50 = 7.2 μM. 24189055
SKOV3 Anticancer assay 48 hrs Anticancer against human SKOV3 cells overexpressing P-gp assessed as cell viability after 48 hrs by SRB assay, IC50 = 7.46 μM. 24946145
PC3 Antiproliferative assay 48 hrs Antiproliferative activity against androgen receptor-deficient human PC3 cells incubated with 0.6 nM of estradiol and 0.7 nM of testosterone after 48 hrs by sulforhodamine B assay, GI50 = 7.58578 μM. 21513275
NCI-ADR-RES Antiproliferative assay 48 hrs Antiproliferative activity against estrogen receptor-deficient human NCI-ADR-RES cells incubated with 100 nM of estradiol and 0.07 nM of testosterone after 48 hrs by sulforhodamine B assay in presence of fetal bovine serum and NuSerum, GI50 = 7.76247 μM. 21513275
MCF-7 Cytotoxicity assay Cytostaticity against MCF-7 cells in the presence of 1 uMolar E2 (estradiol), IC50 = 8 μM. 9089332
LNCAP Antiproliferative assay 48 hrs Antiproliferative activity against human LNCAP cells expressing androgen receptor incubated with 0.6 nM of estradiol and 0.7 nM of testosterone after 48 hrs by sulforhodamine B assay, GI50 = 8.31764 μM. 21513275
MCF7 Antiproliferative assay 5 days Antiproliferative activity against human MCF7 cells after 5 days by WST-8 assay, IC50 = 8.9 μM. 25614118
MCF7 Anticancer assay 48 hrs Anticancer against human ER-positive MCF7 cells assessed as cell viability after 48 hrs by SRB assay, IC50 = 9.2 μM. 24946145
MCF-7 Cytotoxicity assay Cytotoxicity against MCF-7 cells in presence of 1 uM E2 (estradiol), Cytotoxicity = 9.4 μM. 9089332
MDA-MB-231 Antiproliferative assay 24 hrs Antiproliferative activity against human MDA-MB-231 cells after 24 hrs by MTT assay, IC50 = 10.4 μM. 24189055
MDA-MB-453 Antiproliferative assay 72 hrs Antiproliferative activity against human MDA-MB-453 cells after 72 hrs by MTT assay, IC50 = 10.4 μM. 28506582
DU145 Antiproliferative assay 48 hrs Antiproliferative activity against androgen receptor-deficient human DU145 cells incubated with 0.6 nM of estradiol and 0.7 nM of testosterone after 48 hrs by sulforhodamine B assay, GI50 = 10.7152 μM. 21513275
MCF7 Cytotoxicity assay 48 hrs Cytotoxicity against human MCF7 cells after 48 hrs by MTT assay, IC50 = 13.6 μM. 25618595
Vero Antiproliferative assay 72 hrs Antiproliferative activity against african green monkey Vero cells assessed as inhibition of cell viability after 72 hrs by MTT assay, IC50 = 15.1 μM. 25993269
DU145 Antiproliferative assay 72 hrs Antiproliferative activity against human DU145 cells assessed as inhibition of cell viability after 72 hrs by MTT assay, IC50 = 15.3 μM. 25993269
MCF7 Antiproliferative assay 72 hrs Antiproliferative activity against human MCF7 cells after 72 hrs by MTT assay, IC50 = 15.6 μM. 28506582
MCF7 Antiproliferative assay 72 hrs Antiproliferative activity against human MCF7 cells assessed as inhibition of cell viability after 72 hrs by MTT assay, IC50 = 15.6 μM. 25993269
MDA-MB-231 Antiproliferative assay 72 hrs Antiproliferative activity against human MDA-MB-231 cells after 72 hrs by MTT assay, IC50 = 20.1 μM. 28506582
MCF7 Antiproliferative assay 0.625 nM 24 hrs Antiproliferative activity against human MCF7 cells at 0.625 nM after 24 hrs by MTS assay 18272256
MCF7 Antiproliferative assay 0.625 to 10 nM 24 hrs Antiproliferative activity against human MCF7 cells at >0.625 to 10 nM after 24 hrs by MTS assay 18272256
MCF7:WS8 Function assay Activation of human ER in human MCF7:WS8 cells expressing estrogen responsive element by luciferase reporter gene assay 20334368
MCF7:WS8 Antiestrogenic assay 1 uM 7 days Antiestrogenic activity in human ERalpha expressing MCF7:WS8 cells assessed as inhibition of estradiol-induced proliferation at 1 uM after 7 days 20334368
MCF7 Antiestrogenic assay Antiestrogenic activity in human MCF7 cells assessed as inhibition of estradiol-stimulated prolactin gene expression 20334368
MCF7 Antiestrogenic assay Antiestrogenic activity in human MCF7 cells assessed as inhibition of estradiol-stimulated proliferation 20334368
T47D:C:4:2 Function assay Estrogenic activity at wild type ER alpha expressed in T47D:C:4:2 cells coexpressing estrogen response element by duel luciferase reporter gene assay 20334368
MDA-MB-231 Cytotoxicity assay 3 days Cytostatic activity against human MDA-MB-231 cells after 3 days by microtiter assay 20598555
T47D:C:4:2 Function assay Estrogenic activity at wild type ER alpha D351G mutant expressed in T47D:C:4:2 cells coexpressing estrogen response element by duel luciferase reporter gene assay 20334368
MCF7 Function assay 1 μM 6 days Drug uptake in human MCF7 cells at 10'-6 M after 6 days by HPLC-MS/MS analysis 23864928
MCF7 Function assay 10 uM 6 hrs Upregulation of ERalpha protein levels in human MCF7 cells at 10 uM after 6 hrs by Western blot method 24332630
MCF7:WS8 Function assay 1 μM 48 hrs Agonist activity at ER in human MCF7:WS8 cells assessed as pS2 gene expression at 10'-6 M after 48 hrs by RT-PCR analysis 24805199
MCF7:WS8 Function assay 1 μM 48 hrs Agonist activity at ER in human MCF7:WS8 cells assessed as GREB1 gene expression at 10'-6 M after 48 hrs by RT-PCR analysis 24805199
GH3 Function assay 1 μM 48 hrs Antagonist activity at ER in rat GH3 cells assessed as inhibition of estradiol-induced prolactin gene expression at 10'-6 M after 48 hrs by RT-PCR analysis 24805199
GH3 Function assay 0.1 nM to 1 μM 48 hrs Antagonist activity at ER in rat GH3 cells assessed as inhibition of estradiol-induced prolactin gene expression at 10'-10 to 10'-6 M after 48 hrs by RT-PCR analysis 24805199
MCF7 Anticancer assay 250 to 500 nM 5 days Anticancer against human ER-positive MCF7 cells assessed as inhibition of estradiol-induced cell proliferation at 250 to 500 nM after 5 days 24946145
MCF7 Function assay 5 uM 24 hrs Antagonist activity at ERalpha in human MCF7 cells assessed as suppression of MYC mRNA expression at 5 uM after 24 hrs by QIAzol reagent based RT-qPCR analysis 30078609
MCF7 Function assay 5 uM 24 hrs Antagonist activity at ERalpha in human MCF7 cells assessed as suppression of TFF1 mRNA expression at 5 uM after 24 hrs by QIAzol reagent based RT-qPCR analysis 30078609
MCF7 Function assay 5 uM 24 hrs Antagonist activity at ERalpha in human MCF7 cells assessed as suppression of GREB1 mRNA expression at 5 uM after 24 hrs by QIAzol reagent based RT-qPCR analysis 30078609
MCF7 Function assay 5 uM 24 hrs Antagonist activity at ERalpha in human MCF7 cells assessed as suppression of MYBL2 mRNA expression at 5 uM after 24 hrs by QIAzol reagent based RT-qPCR analysis 30078609
MCF7 Function assay 5 uM 24 hrs Antagonist activity at ERalpha in human MCF7 cells assessed as suppression of CCND1 mRNA expression at 5 uM after 24 hrs by QIAzol reagent based RT-qPCR analysis 30078609
MCF7 Function assay 5 uM 24 hrs Antagonist activity at ERalpha in human MCF7 cells assessed as suppression of CDC6 mRNA expression at 5 uM after 24 hrs by QIAzol reagent based RT-qPCR analysis 30078609
MCF7 Function assay 5 uM 24 hrs Antagonist activity at ERalpha in human MCF7 cells assessed as suppression of E2F1 mRNA expression at 5 uM after 24 hrs by QIAzol reagent based RT-qPCR analysis 30078609
MCF7 Function assay 5 uM 24 hrs Antagonist activity at ERalpha in human MCF7 cells assessed as suppression of MKI67 mRNA expression at 5 uM after 24 hrs by QIAzol reagent based RT-qPCR analysis 30078609
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Biological Activity

Description 4-Hydroxytamoxifen (Afimoxifene) is the active metabolite of tamoxifen and a selective estrogen receptor (ER) modulator that is widely used in the therapeutic and chemopreventive treatment of breast cancer. It activates on-target modification frequency for intein-Cas9 variants.
In vitro
In vitro

4-OHT is a potent activator of ER and has been shown to have a higher affinity for estrogen receptors. It has significant dose and time-dependent direct effects to alter the contractile function of isolated adult rat cardiac myocytes[1]. 4-HT activates on-target modification frequency for intein-Cas9 variants [3].
Cell Research Cell lines Adult Rat and Mouse Cardiac Myocytes
Concentrations 0, 0.5, 1, 3, 5, and 10 µM
Incubation Time 15-45 min
Method

For sarcomere length measurements, cells are covered in Tyrode’s containing 4OHT, allowed to reach 36 ± 1°C, and then stimulated at 0.2 Hz.
Experimental Result Images Methods Biomarkers Images PMID
Western blot p-ERK / ERK / p-MEK / MEK1 / MEK2 / p21 / Cyclin D1 26163823
Growth inhibition assay Cell viability 26014809
NCT Number Recruitment Conditions Sponsor/Collaborators Start Date Phases
NCT05133674 Unknown status
Breast Cancer|Breast Carcinoma|Breast Tumors|Cancer of Breast|Malignant Neoplasm of Breast
Karolinska University Hospital
 April 4 2022 Phase 2

Chemical Information & Solubility

Molecular Weight 387.51 Formula

C26H29NO2
CAS No. 68392-35-8 SDF Download 4-Hydroxytamoxifen (Afimoxifene) SDF
Smiles CCC(=C(C1=CC=C(C=C1)O)C2=CC=C(C=C2)OCCN(C)C)C3=CC=CC=C3
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DMSO : 77 mg/mL ( (198.7 mM) Moisture-absorbing DMSO reduces solubility. Please use fresh DMSO.)

Water : Insoluble

Ethanol : Insoluble


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Frequently Asked Questions

Question 1:
4-Hydroxytamoxifen (Afimoxifene) has two configurations, E and Z, which one does selleck provide?

Answer:
According to the literature, the configuration of 4-Hydroxytamoxifen (Afimoxifene) does not affect its biological activity. S7827 is a mixture of E configuration and Z configuration, of which Z configuration accounts for more than 70%.

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