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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 of CHLOROTRIANISENE

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
Molecular Formula C23H21ClO3
Molecular Weight 380.864
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description
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

Wm. S. Merrell
13
Curator's Comment: Shelton, R.S. and Van Campen, M.G. Jr.; U S . Patent 2,430,891; November 18,1947; assigned to the Wm. S. Merrell Company.

Approval Year

1951
104
Targets

Targets

Primary TargetPharmacologyConditionPotency
Modulator
828
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
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.
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.
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.
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

Doses

DosePopulationAdverse 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

Sourcing

Vendor/AggregatorIDURL
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

PubMed

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

Patents

JP2005519871A
28
US2430891
1

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.
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:01:15 GMT 2023
Edited
by admin
on Fri Dec 15 15:01:15 GMT 2023
Record UNII
6V5034L121
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
CHLOROTRIANISENE
HSDB   INN   MART.   MI   ORANGE BOOK   VANDF   WHO-DD  
INN  
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
Created by admin on Fri Dec 15 15:01:15 GMT 2023 , Edited by admin on Fri Dec 15 15:01:15 GMT 2023
WHO-ATC G03CA06
Created by admin on Fri Dec 15 15:01:15 GMT 2023 , Edited by admin on Fri Dec 15 15:01:15 GMT 2023
NCI_THESAURUS C2182
Created by admin on Fri Dec 15 15:01:15 GMT 2023 , Edited by admin on Fri Dec 15 15:01:15 GMT 2023
Code System Code Type Description
FDA UNII
6V5034L121
Created by admin on Fri Dec 15 15:01:15 GMT 2023 , Edited by admin on Fri Dec 15 15:01:15 GMT 2023
PRIMARY
WIKIPEDIA
CHLOROTRIANISENE
Created by admin on Fri Dec 15 15:01:15 GMT 2023 , Edited by admin on Fri Dec 15 15:01:15 GMT 2023
PRIMARY
SMS_ID
100000081870
Created by admin on Fri Dec 15 15:01:15 GMT 2023 , Edited by admin on Fri Dec 15 15:01:15 GMT 2023
PRIMARY
RXCUI
2397
Created by admin on Fri Dec 15 15:01:15 GMT 2023 , Edited by admin on Fri Dec 15 15:01:15 GMT 2023
PRIMARY RxNorm
DRUG BANK
DB00269
Created by admin on Fri Dec 15 15:01:15 GMT 2023 , Edited by admin on Fri Dec 15 15:01:15 GMT 2023
PRIMARY
INN
595
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PRIMARY
IUPHAR
7146
Created by admin on Fri Dec 15 15:01:15 GMT 2023 , Edited by admin on Fri Dec 15 15:01:15 GMT 2023
PRIMARY
PUBCHEM
11289
Created by admin on Fri Dec 15 15:01:15 GMT 2023 , Edited by admin on Fri Dec 15 15:01:15 GMT 2023
PRIMARY
CAS
569-57-3
Created by admin on Fri Dec 15 15:01:15 GMT 2023 , Edited by admin on Fri Dec 15 15:01:15 GMT 2023
PRIMARY
MERCK INDEX
m3448
Created by admin on Fri Dec 15 15:01:15 GMT 2023 , Edited by admin on Fri Dec 15 15:01:15 GMT 2023
PRIMARY Merck Index
ECHA (EC/EINECS)
209-318-6
Created by admin on Fri Dec 15 15:01:15 GMT 2023 , Edited by admin on Fri Dec 15 15:01:15 GMT 2023
PRIMARY
EPA CompTox
DTXSID1021299
Created by admin on Fri Dec 15 15:01:15 GMT 2023 , Edited by admin on Fri Dec 15 15:01:15 GMT 2023
PRIMARY
CHEBI
3641
Created by admin on Fri Dec 15 15:01:15 GMT 2023 , Edited by admin on Fri Dec 15 15:01:15 GMT 2023
PRIMARY
ChEMBL
CHEMBL1200761
Created by admin on Fri Dec 15 15:01:15 GMT 2023 , Edited by admin on Fri Dec 15 15:01:15 GMT 2023
PRIMARY
DRUG CENTRAL
610
Created by admin on Fri Dec 15 15:01:15 GMT 2023 , Edited by admin on Fri Dec 15 15:01:15 GMT 2023
PRIMARY
NCI_THESAURUS
C65320
Created by admin on Fri Dec 15 15:01:15 GMT 2023 , Edited by admin on Fri Dec 15 15:01:15 GMT 2023
PRIMARY
EVMPD
SUB06199MIG
Created by admin on Fri Dec 15 15:01:15 GMT 2023 , Edited by admin on Fri Dec 15 15:01:15 GMT 2023
PRIMARY
MESH
D002741
Created by admin on Fri Dec 15 15:01:15 GMT 2023 , Edited by admin on Fri Dec 15 15:01:15 GMT 2023
PRIMARY
NSC
10108
Created by admin on Fri Dec 15 15:01:15 GMT 2023 , Edited by admin on Fri Dec 15 15:01:15 GMT 2023
PRIMARY
HSDB
3302
Created by admin on Fri Dec 15 15:01:15 GMT 2023 , Edited by admin on Fri Dec 15 15:01:15 GMT 2023
PRIMARY
Related Record Type Details
Structure of CHLOROTRIANISENE
ACTIVE MOIETY
NIH
NCATS
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DISCLAIMER
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