Toremifene Citrate

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Cat Number

API89778278

CAS Number

89778-27-8

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Product Detail Description Scientific Support Advanced Innovations Customer Q&A

CAS Number

89778-27-8

EINECS

663-344-6

Storage

2-8℃

Synonyms

(z)-4-chloro-1,2-diphenyl-1-(4-(2-(n,n-dimethylamino)ethoxy)phenyl)-1-butene;2-(4-(4-chloro-1,2-diphenyl-1-butenyl)phenoxy)-n,n-dimethyl-ethanamin(z)-ethanamin;2-hydroxy-1,2,3-propanetricarboxylate

Molecular Formula

C32H36ClNO8

Molecular Weight

598.1

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

Appearance

White to off-white solid

Melting Point

160-162℃

Relative Density

1.05

General Description

Toremifene Citrate is a triphenylethylene selective estrogen receptor modulator structurally related to tamoxifen but distinguished by a chlorinated side chain conferring different tissue-selective properties.

Mechanism of Action

Toremifene competitively binds estrogen receptors on breast tumor cells, blocking estrogen-stimulated transcription of genes required for proliferation. It also exhibits partial agonist activity at estrogen receptors in bone and endometrium.

Application

Used in the treatment of hormone-responsive breast cancer. Toremifene Citrate is indicated for metastatic breast cancer in postmenopausal women with estrogen receptor-positive tumors.

Toremifene citrate is a selective estrogen receptor modulator (SERM) developed as an alternative to tamoxifen for treating estrogen receptor-positive breast cancer. Toremifene differs from tamoxifen by one chlorine atom and does not require CYP2D6-mediated metabolic activation, potentially offering advantages in patients with CYP2D6 polymorphisms or those taking CYP2D6-inhibiting drugs.
Three pivotal trials in postmenopausal women with metastatic breast cancer demonstrated comparable efficacy between toremifene 60 mg daily and tamoxifen (20–40 mg daily) in response rates, time to progression, and overall survival. Adjuvant trials (IBCSG, FBCG, NAFTA) and a meta-analysis confirmed similar disease-free and overall survival between the two agents. Toremifene showed comparable safety profiles, with similar rates of thromboembolic events, endometrial changes, and hot flashes.

Fig. 1 Toremifene for metastatic breast cancer. (Vogel C L.; et al. 2014)

References

Vogel C L, et al. Toremifene for breast cancer: a review of 20 years of data. Clinical breast cancer, 2014, 14(1): 1-9.

PLGA-PEG nanoparticles encapsulating toremifene were synthesized, and a subset were conjugated with anti-PSMA antibody for targeted prostate tumor delivery. In a PC3M orthotopic mouse model, treatment with free toremifene resulted in significant reduction of prostate tumor growth. Nano-encapsulated toremifene conjugated with anti-PSMA showed approximately 15-fold greater tumor uptake compared to free toremifene and enhanced tumor necrosis. Blocking estrogen receptor-α by toremifene and targeting prostate cancer tissues with anti-PSMA antibody on the nanoparticle surface repressed the tumorigenicity of prostate cancer cells.

Fig. 2 Nanoparticle size distribution determination and nanoparticle size and morphology examination. (Hariri W.; et al. 2015)

References

Hariri W, et al. Nano-Targeted Delivery of Toremifene, an Estrogen Receptor-α Blocker in Prostate Cancer. Pharmaceutical research, 2015, 32(8): 2764-2774.

What distinguishes Toremifene Citrate from tamoxifen?

Toremifene demonstrates comparable efficacy but produces fewer DNA adducts due to its chlorinated structure, potentially offering a lower risk of endometrial carcinoma.

What storage conditions are required?

Store at room temperature in a tightly sealed container, protected from light and moisture.

What purity grade is available?

It is supplied as a high-purity grade suitable for R&D and pharmaceutical manufacturing.

Can packaging and order quantities be customized?

Yes, both packaging formats and order quantities can be tailored to meet specific R&D and production needs.