| Stereochemistry | ACHIRAL |
| Molecular Formula | C23H21ClO3 |
| Molecular Weight | 380.864 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
COC1=CC=C(C=C1)C(Cl)=C(C2=CC=C(OC)C=C2)C3=CC=C(OC)C=C3
InChI
InChIKey=BFPSDSIWYFKGBC-UHFFFAOYSA-N
InChI=1S/C23H21ClO3/c1-25-19-10-4-16(5-11-19)22(17-6-12-20(26-2)13-7-17)23(24)18-8-14-21(27-3)15-9-18/h4-15H,1-3H3
Chlorotrianisene (TACE®) is a powerful synthetic, non-steroidal estrogen used to treat symptoms of menopause, deficiencies in ovary function (including underdevelopment of female sexual characteristics and some types of infertility), and in rare cases, prostate cancer. It may also be used to prevent breast engorgement following childbirth. Chlorotrianisene (TACE®) binds to the estrogen receptor on various estrogen receptor bearing cells. Target cells include cells in the female reproductive tract, the mammary gland, the hypothalamus, and the pituitary. Estrogens increase the hepatic synthesis of sex hormone binding globulin (SHBG), thyroid-binding globulin (TBG), and other serum proteins and suppress follicle-stimulating hormone (FSH) from the anterior pituitary.
Originator
Approval Year
Doses
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PubMed
Patents
Sample Use Guides
Rat pituitary gland cells (2 x 10^5/dish) were cultured for 8 days with medium containing chlorotrianisene (TACE) or its demethylated derivative,
1,1,2-tri(4-hydroxyphenyl)chloroethylene (TCE), alone or with E2 (0.1 or 1 nM). TCE was a partial estrogen with antiestrogenic properties against E2 (0.1 nM). The antiestrogenic effect could also be reversed by increasing the concentration of E2 10-fold. TACE was less estrogenic and a less potent E2 antagonist.
ACTIVE MOIETY
