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Merck

T7204

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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R$613.00

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About This Item

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

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Product Name

Toremifene citrate salt, ≥98% (HPLC)

InChI key

IWEQQRMGNVVKQW-OQKDUQJOSA-N

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-;

assay

≥98% (HPLC)

form

powder

storage condition

desiccated

color

white to off-white

solubility

DMSO: >10 mg/mL

storage temp.

2-8°C

Quality Level

100

Gene Information

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

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Toremifene citrate salt ≥98% (HPLC)

Sigma-Aldrich

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Sigma-Aldrich

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Tamoxifen citrate salt

Ospemifene ≥98% (HPLC)

Sigma-Aldrich

SML0996

Ospemifene

(Z)-4-Hydroxytamoxifen ≥98% Z isomer

Sigma-Aldrich

H7904

(Z)-4-Hydroxytamoxifen

assay

≥98% (HPLC)

assay

≥99%

assay

≥98% (HPLC)

assay

≥98% (HPLC)

form

powder

form

-

form

powder

form

powder

Quality Level

100

Quality Level

200

Quality Level

100

Quality Level

300

storage temp.

2-8°C

storage temp.

2-8°C

storage temp.

2-8°C

storage temp.

2-8°C

solubility

DMSO: >10 mg/mL

solubility

methanol: soluble 50 mg/mL, clear, colorless

solubility

DMSO: 20 mg/mL, clear

solubility

methanol: 10 mg/mL, ethanol: 20 mg/mL (with heating)

storage condition

desiccated

storage condition

-

storage condition

-

storage condition

desiccated, protect from light

Application

Toremifene citrate salt has been used:
  • in cell-based ELISA[1]
  • as a positive control to detect its antiviral activity against Ebola virus (EBOV)[2]
  • to treat MCF7 and T47D breast cancer cell lines[3]

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.

General description

Toremifene is a triphenylethylene derivative.[4] It exhibits antitumor and antiestrogen effects.[5] Toremifene has estrogen-agonist effects on blood lipids and endometrium.[6]

Preparation Note

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

signalword

Danger

Hazard Classifications

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

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
081M4711V
0000136072
0000109529
0000109530
0000093685

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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
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
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
Lack of effect of lamivudine on Ebola virus replication
Hensley LE, et al.
Emerging Infectious Diseases, 21(3), 550-550 (2015)
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