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Description: Toremifene Citrate (NSC 613680; NK 622; FC 1157a) is an orally bioavailable SERM (selective estrogen receptor modulator) used in the treatment of advanced breast cancer. Toremifene citrate acts by antagonizing the actions of estrogen in the body. Toremifene (7.5 mM) causes approximately 60% of the cells to exhibit morphologic characteristics typical of cells undergoing programmed death, or apoptosis in human breast cancer cells. Toremifene (5-10 mM) results in elevated levels of TRPM-2 and TGF beta 1 mRNAs in in vitro or in vivo grown tumor cells.
References: J Natl Cancer Inst. 1993 Sep 1;85(17):1412-8; Carcinogenesis. 1995 Nov;16(11):2733-41.
Related CAS #: 89778-27-8 (citrate) 89778-26-7 (free base)
Chemical Name: (Z)-2-(4-(4-chloro-1,2-diphenylbut-1-en-1-yl)phenoxy)-N,N-dimethylethan-1-amine 2-hydroxypropane-1,2,3-tricarboxylate
InChi Key: IWEQQRMGNVVKQW-OQKDUQJOSA-N
InChi Code: 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-;
SMILES Code: ClCC/C(C1=CC=CC=C1)=C(C2=CC=C(OCCN(C)C)C=C2)\C3=CC=CC=C3.O=C(CC(C(O)=O)(O)CC(O)=O)O
Mass (g) = Concentration (mol/L) × Volume (L) × Molecular Weight (g/mol)
Concentration (start) × Volume (start) = Concentration (final) × Volume (final)
This equation is commonly abbreviated as: C1V1 = C2V2
In vitro activity: Toremifene (7.5 mM) causes approximately 60% of the cells to exhibit morphologic characteristics typical of cells undergoing programmed death, or apoptosis in human breast cancer cells. Toremifene (5-10 mM) results in elevated levels of TRPM-2 and TGF beta 1 mRNAs in in vitro or in vivo grown tumor cells. Toremifene causes growth inhibition of estrogen-sensitive breast cancer cells by inducing some cells to undergo apoptosis and by inhibiting other cells from entering mitosis. Toremifene induces a dose-dependent level of adducts that is lower than that observed for TAM. Toremifene significantly enhances endogenous DNA adduct formation. Toremifene affects the cell turnover by inhibiting mitotic activity and modifying abundant spontaneous apoptosis in DMBA-induced rat mammary carcinoma.
J Natl Cancer Inst. 1993 Sep 1;85(17):1412-8; Carcinogenesis. 1995 Nov;16(11):2733-41.
Purity ≥98%
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