CHLOROTRIANISENE

US Previously Marketed

First approved in 1951

Details

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

Structure Search

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

HIDE SMILES / InChI

Description
Sources: https://www.drugbank.ca/drugs/DB00269
Curator's Comment: description was created based on several sources, including https://www.ncbi.nlm.nih.gov/mesh/68002741

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

Targets

Primary Target	Pharmacology	Condition	Potency
Estrogen receptor 75 Target ID: CHEMBL2094114 Sources: https://www.drugbank.ca/drugs/DB00269	Modulator 828

Conditions

Condition	Modality	Highest Phase	Product
Menopause 3 Sources: https://www.drugbank.ca/drugs/DB00269	Palliative	Approved 8429	TACE Approved Use 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. Chlorotrianisene may also be used to prevent breast engorgement following childbirth.
Deficiencies in ovary function 1 Sources: https://www.drugbank.ca/drugs/DB00269	Curative	Approved 8429	TACE Approved Use 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. Chlorotrianisene may also be used to prevent breast engorgement following childbirth.
Prostate cancer 178 Sources: https://www.drugbank.ca/drugs/DB00269	Palliative	Approved 8429	TACE Approved Use 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. Chlorotrianisene may also be used to prevent breast engorgement following childbirth.
Breast engorgement 1 Sources: https://www.drugbank.ca/drugs/DB00269	Preventing	Approved 8429	TACE Approved Use 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. Chlorotrianisene may also be used to prevent breast engorgement following childbirth.

Doses

Dose	Population	Adverse events
72 mg 2 times / day multiple, oral Dose: 72 mg, 2 times / day Route: oral Route: multiple Dose: 72 mg, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/453287	healthy, 21 years n = 24 Health Status: healthy Age Group: 21 years Sex: F Population Size: 24 Sources: https://pubmed.ncbi.nlm.nih.gov/453287	Sources: https://pubmed.ncbi.nlm.nih.gov/453287

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:3641	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:3641
ChemicalBook	CB9321078	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB9321078
MolPort	MolPort-001-783-515	https://www.molport.com/shop/molecule-link/MolPort-001-783-515
ZINC	ZINC000001530598	http://zinc15.docking.org/substances/ZINC000001530598
eMolecules	536400	https://www.emolecules.com/cgi-bin/more?vid=536400

PubMed

Title	Date	PubMed
The choice of estrogen preparations in the treatment of prostatic cancer.	1975 Nov 8	1182631
Hydroxyurea in stage D carcinoma of the prostate: a pilot study.	1975 Sep	1142528
The effect of chlorotrianisene as postpartum lactation suppression on blood coagulation factors.	1979 Jul 1	453287
Tracing the origins of COX-2 inhibitors' structures.	2002 Aug	12173976
An inventory of yeast proteins associated with nucleolar and ribosomal components.	2006	17067374
Treatments for suppression of lactation.	2009 Jan 21	19160258
FDA-approved drugs and other compounds tested as inhibitors of human glutathione transferase P1-1.	2013 Sep 5	23769903

Patents

Sample Use Guides

In Vivo Use Guide

Unknown

Route of Administration: Oral

In Vitro Use Guide

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.

Name

Type

Language

CHLOROTRIANISENE

Official Name

English

CHLOROTRIS(P-METHOXYPHENYL)ETHYLENE

Common Name

English

chlorotrianisene [INN]

Common Name

English

CHLOROTRIANISENE [MART.]

Common Name

English

TACE

Brand Name

English

BENZENE, 1,1',1''-(1-CHLORO-1-ETHENYL-2-YLIDENE)TRIS(4-METHOXY)-

Common Name

English

CHLOROTRIANISENE [VANDF]

Common Name

English

Chlorotrianisene [WHO-DD]

Common Name

English

CHLOROTRIANISENE [MI]

Common Name

English

CHLOROTRIANISENE [HSDB]

Common Name

English

CHLOROTRIANISENE [ORANGE BOOK]

Common Name

English

NSC-10108

Code

English

Classification Tree Code System Code

WHO-VATC

QG03CA06