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T7204

Sigma-Aldrich

Toremifene citrate salt

≥98% (HPLC)

Synonym(s):

(Z)-2-(4-(4-Chloro-1,2-diphenyl-1-butenyl)phenoxy)-N,N-dimethylethanamine, Acapodene, Fareston, GTx 006, Z-Toremifene

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About This Item

Empirical Formula (Hill Notation):
C26H28ClNO · C6H8O7
CAS Number:
89778-27-8
Molecular Weight:
598.08
MDL number:
MFCD01729016
UNSPSC Code:
51111800
PubChem Substance ID:
329826860
NACRES:
NA.77

Assay

≥98% (HPLC)

form

powder

storage condition

desiccated

color

white to off-white

solubility

DMSO: >10 mg/mL

storage temp.

2-8°C

SMILES string

OC(=O)CC(O)(CC(O)=O)C(O)=O.CN(C)CCOc1ccc(cc1)C(=C(\CCCl)c2ccccc2)\c3ccccc3

InChI

1S/C26H28ClNO.C6H8O7/c1-28(2)19-20-29-24-15-13-23(14-16-24)26(22-11-7-4-8-12-22)25(17-18-27)21-9-5-3-6-10-21;7-3(8)1-6(13,5(11)12)2-4(9)10/h3-16H,17-20H2,1-2H3;13H,1-2H2,(H,7,8)(H,9,10)(H,11,12)/b26-25-;

InChI key

IWEQQRMGNVVKQW-OQKDUQJOSA-N

Gene Information

human ... ESR1(2099) , ESR2(2100)

General description

Toremifene is a triphenylethylene derivative. It exhibits antitumor and antiestrogen effects. Toremifene has estrogen-agonist effects on blood lipids and endometrium.

Application

Toremifene citrate salt has been used:
  • in cell-based ELISA
  • as a positive control to detect its antiviral activity against Ebola virus (EBOV)
  • to treat MCF7 and T47D breast cancer cell lines

Biochem/physiol Actions

Toremifene citrate is an oral selective estrogen receptor modulator (SERM). It is used in advanced (metastatic) breast cancer and being evaluated for prevention of prostate cancer. Toremifene citrate is known to increase bone mineral density in prostate cancer patients undergoing androgen deprivation therapy†.

Features and Benefits

This compound is featured on the Nuclear Receptors (Steroids) page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

Preparation Note

Toremifene citrate salt is soluble in DMSO at a concentration that is greater than 10 mg/ml.

Signal Word

Danger

Hazard Statements

H302,H318,H410

Hazard Classifications

Acute Tox. 4 Oral - Aquatic Acute 1 - Aquatic Chronic 1 - Eye Dam. 1

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Seiji Yoshitomi et al.
Gan to kagaku ryoho. Cancer & chemotherapy, 39(12), 2074-2076 (2012-12-27)
We present a case in which a 46-year-old woman underwent mastectomy (Bt+AX) for right breast cancer (T4bN0M0, Stage IIIB) at the age of 42. A histopathological examination confirmed her cancer to be an invasive ductal carcinoma n (-),ER (+), PgR
Juhyun Kim et al.
International journal of cancer, 132(6), 1475-1485 (2012-08-24)
We investigated the in vitro metabolism and estrogenic and antiestrogenic activity of toremifene (TOR), tamoxifen (TAM) and their metabolites to better understand the potential effects of cytochrome P-450 2D6 (CYP2D6) status on the activity of these drugs in women with
Regulatory Mechanisms in Breast Cancer: Advances in Cellular and Molecular Biology of Breast Cancer (2012)
Matthew R Smith et al.
The Journal of urology, 189(1 Suppl), S45-S50 (2012-12-19)
Androgen deprivation therapy is associated with fracture risk in men with prostate cancer. We assessed the effects of toremifene, a selective estrogen receptor modulator, on fracture incidence in men receiving androgen deprivation therapy during a 2-year period. In this double-blind
Hideaki Ogata et al.
Gan to kagaku ryoho. Cancer & chemotherapy, 40(6), 749-753 (2013-07-19)
Third-generation aromatase inhibitors(AIs)are now common in adjuvant hormone therapy for breast cancer in postmenopausal women. However, a suitable treatment has yet to be established for patients who develop cancer recurrence during or after adjuvant AI therapy. This prospective study evaluated
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