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T7204

Sigma-Aldrich

Toremifene citrate salt

≥98% (HPLC)

Synonyme(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

Formule empirique (notation de Hill):
C26H28ClNO · C6H8O7
Numéro CAS:
89778-27-8
Poids moléculaire :
598.08
Numéro MDL:
MFCD01729016
Code UNSPSC :
51111800
ID de substance PubChem :
329826860
Nomenclature NACRES :
NA.77

Pureté

≥98% (HPLC)

Forme

powder

Conditions de stockage

desiccated

Couleur

white to off-white

Solubilité

DMSO: >10 mg/mL

Température de stockage

2-8°C

Chaîne SMILES 

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-;

Clé InChI

IWEQQRMGNVVKQW-OQKDUQJOSA-N

Informations sur le gène

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

Description générale

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

Actions biochimiques/physiologiques

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†.

Caractéristiques et avantages

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.

Notes préparatoires

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

Pictogrammes

CorrosionExclamation markEnvironment
GHS05,GHS07,GHS09

Mention d'avertissement

Danger

Mentions de danger

H302,H318,H410

Classification des risques

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

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Certificats d'analyse (COA)

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Consulter la Bibliothèque de documents

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
Stefan Kudlacek et al.
Wiener medizinische Wochenschrift (1946), 162(17-18), 380-385 (2012-08-10)
Osteoporosis is defined as a continuous loss of bone mineral density accompanied by an increased fracture risk in females and males. A fall of estrogen concentrations at the menopause and the consecutive rapid bone loss are an established pathogenic mechanism
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