Toremifene Citrate

CAS# 89778-27-8

Toremifene Citrate

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Chemical structure

Toremifene Citrate

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Chemical Properties of Toremifene Citrate

Cas No. 89778-27-8 SDF Download SDF
PubChem ID 3005572 Appearance Powder
Formula C32H36ClNO8 M.Wt 598.08
Type of Compound N/A Storage Desiccate at -20°C
Synonyms FC 1157a; NK 622
Solubility DMSO : ≥ 100 mg/mL (167.20 mM)
H2O : < 0.1 mg/mL (insoluble)
*"≥" means soluble, but saturation unknown.
Chemical Name 2-[4-[(Z)-4-chloro-1,2-diphenylbut-1-enyl]phenoxy]-N,N-dimethylethanamine;2-hydroxypropane-1,2,3-tricarboxylic acid
SMILES CN(C)CCOC1=CC=C(C=C1)C(=C(CCCl)C2=CC=CC=C2)C3=CC=CC=C3.C(C(=O)O)C(CC(=O)O)(C(=O)O)O
Standard InChIKey IWEQQRMGNVVKQW-OQKDUQJOSA-N
Standard InChI 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-;
General tips For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.
We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months.
Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it.
About Packaging 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial.
2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial.
3. Try to avoid loss or contamination during the experiment.
Shipping Condition Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request.

Biological Activity of Toremifene Citrate

DescriptionToremifene Citrate(NK 622; FC 1157a) is a second-generation selective estrogen-receptor modulator (SERM) in development for the prevention of osteoporosis. IC50 Value: 1±0.3 μM Target: Estrogen receptor Toremifene is a second-generation selective estrogen-receptor modulator (SERM) in development for the prevention of osteoporosis and other adverse effects resulting from ADT in men with prostate cancer [1]. in vitro: The growth of Ac-1 cells was inhibited by tamoxifen, toremifene and atamestane in vitro with IC50values of 1.8±1.3μM, 1±0.3μM and 60.4±17.2μM, respectively. The combination of toremifene plusatamestane was found to be better than toremifene or atamestane alone in vitro[2]. in vivo: The effect of this combination was then studied in vivo using Ac-1 xenografts grown in ovariectomized female SCID mice. The mice were injected with toremifene (1000μg/day), atamestane (1000μg/day), tamoxifen (100μg/day), or the combination of toremifene plus atamestane. In this study, our results indicate that the combination of toremifene plus atamestane was as effective as toremifene or tamoxifen alone but may not provide any additional benefit over toremifene alone or tamoxifen alone[2]. Clinical trail: Prostate cancer diagnosis among men with isolated high-grade intraepithelial neoplasia enrolled onto a 3-year prospective phase III clinical trial of oral toremifene[3].

References:
[1]. Matthew R Smith, Selective Estrogen Receptor Modulators to Prevent Treatment-Related Osteoporosis.Rev Urol. 2005; 7(Suppl 3): S30-S35. [2]. Gauri J Sabnis, Luciana Macedo, Olga Goloubeva, Toremifene - Atamestane; Alone or In Combination: Predictions from the Preclinical Intratumoral Aromatase Model. J Steroid Biochem Mol Biol. 2008 January; 108(1-2): 1-7. [3]. Taneja SS, Morton R, Barnette G, Prostate cancer diagnosis among men with isolated high-grade intraepithelial neoplasia enrolled onto a 3-year prospective phase III clinical trial of oral toremifene. J Clin Oncol. 2013 Feb 10;31(5):523-9.

Toremifene Citrate Dilution Calculator

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Toremifene Citrate Molarity Calculator

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Preparing Stock Solutions of Toremifene Citrate

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 1.672 mL 8.3601 mL 16.7202 mL 33.4403 mL 41.8004 mL
5 mM 0.3344 mL 1.672 mL 3.344 mL 6.6881 mL 8.3601 mL
10 mM 0.1672 mL 0.836 mL 1.672 mL 3.344 mL 4.18 mL
50 mM 0.0334 mL 0.1672 mL 0.3344 mL 0.6688 mL 0.836 mL
100 mM 0.0167 mL 0.0836 mL 0.1672 mL 0.3344 mL 0.418 mL
* Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations.

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Background on Toremifene Citrate

Toremifene Citrate is an oral selective estrogen receptor modulator (SERM) which helps oppose the actions of estrogen in the body.

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References on Toremifene Citrate

Efficacy and tolerability of weekly paclitaxel in combination with high-dose toremifene citrate in patients with metastatic breast cancer.[Pubmed:19727203]

Acta Med Okayama. 2009 Aug;63(4):187-94.

Toremifene Citrate is expected to prevent drug resistance in cancer patients by inhibiting p-glycoprotein activity. The safety and efficacy of combination therapy with high-dose Toremifene Citrate and paclitaxel were investigated. Between December 2003 and June 2004, 15 women with a mean age of 53 years old with metastatic breast cancer were enrolled. The administration schedule was 80 mg/m2 of paclitaxel given on Days 1, 8, and 15, and 120 mg/day of Toremifene Citrate orally administered starting on Day 18. On Days 32 and 39, paclitaxel was concurrently administered again. Toxicities, response rate, and time to treatment failure were assessed. All patients had been treated with endocrine or chemotherapy. Grade 3 leukopenia occurred in 2 patients on the administration of paclitaxel alone, and grade 3 febrile neutropenia occurred in 1 patient given the combination therapy. There was no grade 3 or greater non-hematological toxicity. There was no complete response and 1 partial response, producing a response rate of 6.7%. Median time to treatment failure was 2.7 months. Combination therapy of paclitaxel and toremifene was safe and well tolerated with minimal toxicity. Further clinical trials targeting patients with functional p-glycoprotein are warranted.

[Antiangiogenic and antimetastatic effects of toremifene citrate].[Pubmed:11525025]

Gan To Kagaku Ryoho. 2001 Aug;28(8):1099-104.

In this study, we demonstrated that Toremifene Citrate (TOR) inhibited the tube formation and migration of human umbilical vein endothelial cells (HUVEC) in vitro. Moreover, TOR suppressed angiogenesis in rabbit cornea and lung metastasis of human fibrosarcoma HT-1080 cells in nude mice. The antiangiogenic activity in vitro was apparent at the concentration of 5 microM which is clinically achievable by oral administration of 120 mg/kg of TOR. These results suggest that clinical treatment with 120 mg/day of TOR might be expected to exhibit antiangiogenesis and antimetastasis effects, in addition to inhibition of estrogen-dependent tumor cell growth.

Description

Toremifene Citrate(NK 622; FC 1157a) is a second-generation selective estrogen-receptor modulator (SERM) in development for the prevention of osteoporosis.

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