Chlorotrianisene

    WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 317512

CAS#: 569-57-3

Description: Chlorotrianisene is a non-steroidal synthetic estrogen that was used for the treatment of menopause, deficiencies in ovary function, and prostate cancer.


Chemical Structure

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Chlorotrianisene
CAS# 569-57-3

Theoretical Analysis

MedKoo Cat#: 317512
Name: Chlorotrianisene
CAS#: 569-57-3
Chemical Formula: C23H21ClO3
Exact Mass: 380.11792
Molecular Weight: 380.86
Elemental Analysis: C, 72.53; H, 5.56; Cl, 9.31; O, 12.60

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Synonym: Chlorotrianisene; Chlortrianisestrol; Chlortrianizen; Chlorotrianisine; Chlorestrolo; Chlorotrianizen; Khlortrianizen; Clorestrolo; Clorotrisin; Hormonisene; Anisene; Metace; Rianil; Tace;

IUPAC/Chemical Name: 1-[1-chloro-2,2-bis(4-methoxyphenyl)ethenyl]-4-methoxybenzene

InChi Key: BFPSDSIWYFKGBC-UHFFFAOYSA-N

InChi Code: 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

SMILES Code: COC1=CC=C(C=C1)C(=C(C2=CC=C(C=C2)OC)Cl)C3=CC=C(C=C3)OC

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO, not in water

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

Preparing Stock Solutions

The following data is based on the product molecular weight 380.86 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL

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1: Zhang J, Yang W, Shen Z. [Prevention of bone loss by chlorotrianisene in
oophorectomized rats]. Zhonghua Fu Chan Ke Za Zhi. 1997 Sep;32(9):535-7. Chinese.
PubMed PMID: 9639753.

2: Kupfer D, Bulger WH. Inactivation of the uterine estrogen receptor binding of
estradiol during P-450 catalyzed metabolism of chlorotrianisene (TACE).
Speculation that TACE antiestrogenic activity involves covalent binding to the
estrogen receptor. FEBS Lett. 1990 Feb 12;261(1):59-62. PubMed PMID: 2307235.

3: Juedes MJ, Bulger WH, Kupfer D. Monooxygenase-mediated activation of
chlorotrianisene (TACE) in covalent binding to rat hepatic microsomal proteins.
Drug Metab Dispos. 1987 Nov-Dec;15(6):786-93. PubMed PMID: 2893703.

4: Barrabes A, Thanh Haï Duong, Combescot C, Lacroix R. [The influence of
synthetic oestrogens on experimental Schistosoma mansoni parasitosis in hamster:
studies of the effects of hexestrol and chlorotrianisene (author's transl)]. Ann
Pharm Fr. 1981 Jun;39(2):141-6. French. PubMed PMID: 6266329.

5: Niebyl JR, Bell WR, Schaaf ME, Blake DA, Dubin NH, King TM. The effect of
chlorotrianisene as postpartum lactation suppression on blood coagulation
factors. Am J Obstet Gynecol. 1979 Jul 1;134(5):518-22. PubMed PMID: 453287.

6: Ruenitz PC. Rabbit hepatic microsomal O-demethylation of chlorotrianisene.
Drug Metab Dispos. 1978 Nov-Dec;6(6):631-6. PubMed PMID: 33024.

7: Phillips WP. Prevention of postpartum breast engorgement: double-blind
comparison of chlorotrianisene 72 mg. and placebo. J Ark Med Soc. 1975
Sep;72(4):163-7. PubMed PMID: 127773.

8: Dexeus Trias de Bes J. [Prevention of postpartum lactation using a new ergot
derivative: 2-Br-alpha-ergocryptine or CB-154. Comparison with chlorotrianisene].
Gynakol Rundsch. 1975;15(1):91-6. French. PubMed PMID: 1243823.

9: Kheifets SN, Rep'eva KA. [Chlorotrianisene therapy of menstrual function
disorders and of female sterility of endocrine origin]. Akush Ginekol (Mosk).
1973 Jan;49(1):36-40. Russian. PubMed PMID: 4695992.

10: Schunk J. [On a sensitizing effect of chlorotrianisene on nitrogen mustard].
Strahlentherapie. 1968 Nov;136(5):639-40. German. PubMed PMID: 5708891.

11: Alfieri G. [Chlorotrianisene, a synthetic estrogen with prolonged action in
the treatment of senile genital dystrophic states]. Ann Ostet Ginecol Med
Perinat. 1967 Mar;89(3):200-9. Italian. PubMed PMID: 5606696.

12: Pagnini P. [The use of chlorotrianisene (Tace) in the pre- and
post-menopausal period]. Minerva Ginecol. 1966 Feb 28;18(4):168-74. Italian.
PubMed PMID: 5934707.

13: KOUNTZ WB, KHEIM T, TORO J, ACKERMANN PG, TORO G. The action of
chlorotrianisene (TACE) with androgen on nitrogen retention in elderly people. J
Am Geriatr Soc. 1959 Oct;7:757-68. PubMed PMID: 14411339.

14: DARNIS F. [Clinical applications of chlorotrianisene (TACE)]. Sem Med Prof
Med Soc. 1958 Dec 14;34(42-43):1254-5. French. PubMed PMID: 13615381.

15: RAVINA A, RAVINA J. [Clinical applications of chlorotrianisene]. Presse Med.
1958 Apr 30;66(34):761-3. French. PubMed PMID: 13554199.

16: BRUMBAUGH JJ. Chlorotrianisene (TACE), a physiologic treatment for the
climacteric. Antibiotic Med Clin Ther (New York). 1957 Mar;4(3):179-82. PubMed
PMID: 13412073.

17: RAVINA A. [New advances in hormonal treatment of prostate cancer; the use of
chlorotrianisene]. Presse Med. 1955 Sep 14;63(59):1198. French. PubMed PMID:
13266742.

18: WELSH AL. Use of synthetic estrogenic substance chlorotrianisene (TACE) in
treatment of acne. AMA Arch Derm Syphilol. 1954 Apr;69(4):418-27. PubMed PMID:
13147544.

19: HENDRICKS CH. Use of chlorotrianisene (TACE) for suppression of postpartum
lactation. J Clin Endocrinol Metab. 1954 Mar;14(3):339-41. PubMed PMID: 13143070.

20: NEW and nonofficial remedies: chlorotrianisene. J Am Med Assoc. 1953 Jan
3;151(1):43. PubMed PMID: 12999506.