Toremifene citrate

Product Name: Toremifene citrate
CAS No.: 89778-27-8
Chemical Name: Toremifene citrate
Synonyms: fareston;nk622;fc1157a;Ccris 6719;Nsc 613680;Toremifine;Toremifene citrat;Oremifene Citrate;TOREMIFENE CITRATE;Toremefene Citrate
CBNumber: CB3287855
Molecular Formula: C26H28ClNO.C6H8O7
Formula Weight: 598.08
MOL File: 89778-27-8.mol

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Toremifene citrate Property

Melting point:: 160-162°C
Boiling point:: 146-148C
Density: 1,045g/cm
refractive index: 1,416-1,418
storage temp.: 2-8°C
solubility: DMSO: >10mg/mL
form: powder
color: white to off-white
Merck: 14,9550
Stability:: Light Sensitive

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Safety

Hazard Codes: Xi,N,Xn
Risk Statements: 36/37/38-50/53-41-22
Safety Statements: 26-37/39-61-60-39
RIDADR: UN 3077 9 / PGIII
WGK Germany: 3
RTECS: KH2156700

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Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Danger

Hazard statements

H302Harmful if swallowed

H318Causes serious eye damage

H410Very toxic to aquatic life with long lasting effects

Precautionary statements

P273Avoid release to the environment.

P280Wear protective gloves/protective clothing/eye protection/face protection.

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N-Bromosuccinimide Price

Sigma-Aldrich

Product number: T7204
Product name: Toremifene citrate salt
Purity: ≥98% (HPLC)
Packaging: 5mg
Price: $65.2
Updated: 2024/03/01

Sigma-Aldrich

Product number: T7204
Product name: Toremifene citrate salt
Purity: ≥98% (HPLC)
Packaging: 25mg
Price: $263
Updated: 2024/03/01

Cayman Chemical

Product number: 20854
Product name: Toremifene (citrate)
Purity: ≥98%
Packaging: 50mg
Price: $32
Updated: 2024/03/01

Cayman Chemical

Product number: 20854
Product name: Toremifene (citrate)
Purity: ≥98%
Packaging: 100mg
Price: $57
Updated: 2024/03/01

Cayman Chemical

Product number: 20854
Product name: Toremifene (citrate)
Purity: ≥98%
Packaging: 250mg
Price: $131
Updated: 2024/03/01

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Toremifene citrate Chemical Properties,Usage,Production

Description

Toremifene (citrate) is an orally bioavailable selective estrogen receptor modulator (SERM) that evokes tissue-dependent effects similar to that of tamoxifen . It has been shown to block estrogen-stimulated growth of MCF-7 breast cancer cells grown in tissue culture, to inhibit ovariectomy-induced bone loss in rats, and to stimulate endometrial growth similar to that of tamoxifen.

Chemical Properties

White-to-Off-White Solid

Originator

Fareston,Orion Corporation,Finland

Uses

An antiestrogen and antineoplastic. Nonsteroidal antiestrogen structurally similar to Tamoxifen.

Uses

anesthetic

Uses

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

Definition

ChEBI: Toremifene citrate is a stilbenoid. It has a role as an anticoronaviral agent.

Manufacturing Process

The reaction is performed under dry conditions. 2.1 g of lithium aluminum hydride and 50 ml of dry tetrahydrofuran are placed in a flask. Then 13.2 g of cinnamaldehyde in 50 ml of dry tetrahydrofuran are added while stirring and keeping the temperature at 25°-35°C. The stirring is continued for another 30 min at room temperature. Then 26.9 g of 4-[2-(N,N-dimethylamino)- ethoxy]benzophenone in 70 ml of dry tetrahydrofuran are added while stirring. The temperature is kept at 35°-45°C during the addition. After stirring for 2 h at 40°C the reaction mixture is poured into 150 ml of 25% ammonium chloride solution, and aluminium hydroxide is precipitated and filtered off. The filtrate is transferred to a separating funnel and the organic layer is separated. The aqueous layer is once again extracted with 60 ml of ethyl acetate. The organic layers are combined and dried over sodium sulfate. The solvent is evaporated. The residue is recrystallized from toluene. The yield is 27.5 g (68%) of 1,2-diphenyl-1-[4-[2-(N,N-dimethylamino)ethoxy]phenyl]- butane-1,4-diol.
The reaction is performed under dry conditions. 40.5 g 1,2-diphenyl-1-[4-[2- (N,N-dimethylamino)ethoxy]phenyl]butane-1,4-diol and 150 ml of acetic acid anhydride are placed in a flask. The temperature is raised to 90°C, where it is kept until the primary OH-group is completely acetylated. [4-Acetoxy-1,2-diphenyl-1-[4-[2-(N,N-dimethylamino)ethoxy]phenyl]butan-1-ol is obtained as intermediate; melting point of the (RR, SS)-isomer pair is 97°-99°C. While stirring the reaction mixture, 30 ml of acetyl chloride in 50 ml of acetic acid anhydride are added at 90°C. The stirring is continued at this temperature for 2 h. The solvent is evaporated. Then 1 M sodium carbonate solution is added in excess, after which the product is extracted in toluene. The solution is dried over sodium sulfate, and the solvent is evaporated. The yield of the pure isomer mixture (Z:E 2:1) of 4-acetoxy-1,2-diphenyl-1-[4-[2-(N,N_x0002_dimethylamino)ethoxy]-phenyl]-1-butene is quantitative. The4-acetoxy-1,2-diphenyl-1-[4-[2-(N,N-dimethylamino)ethoxy]-phenyl]-1- butene are dissolved in 94% ethanol, after which water and 20% sodium hydroxide solution are added. The mixture is refluxed for 1 h. The solution is neutralized with 2 M hydrochloric acid, after wich the ethanol is evaporated. Water is added into the residue. The product is extracted in ethyl acetate, the ethyl acetate solution is dried and the solvent is avaporated. The product is recrystallized from a mixture of water and methanol. The yield of the pure mixture of the isomers (Z:E 2:1) of 1,2-diphenyl-1-[4-[2-(N,Ndimethylamino)ethoxy]phenyl]-1-buten-4-ol, melting point 93°-100°C, is quantitative.
Isolation of the (Z)-isomer as a free base: the mixture of the isomers (Z:E 2:1) of 1,2-diphenyl-1-[4-[2-(N,N-dimethylamino)ethoxy]phenyl]-1-buten-4-ol is recrystallized from toluene, and 15.9 g (41%) of the (Z)-isomer is obtained, melting point 110°-112°C.
The reaction is performed under dry conditions. 42.4 g of (Z)-1,2-diphenyl-1- [4-[2-(N,N-dimethylamino)ethoxy]phenyl]-1-buten-4-ol are dissolved in 250 ml of chloroform. Then 23.8 g of thionyl chloride are added dropwise. The mixture is refluxed 3 h. The solvent is evaporated, after which the product is recrystallized from ethyl acetate. The yield of the hydrochloride salt of 4- chloro-1,2-diphenyl-1-[4-[2-(N,N-dimethylamino)ethoxy]-phenyl]-1-butene (Z) is 36.7 g (83%), melting point 194°-196°C.
The base can be liberated from the salt with 1 M sodium carbonate solution, after which the base is extracted in toluene. The toluene solution is dried and the solvent is evaporated. The free base, 4-chloro-1,2-diphenyl-1-[4-[2-(N,Ndimethylamino)ethoxy]-phenyl]-1-butene (Z), has melting point 108°-110°C (from acetone). In practice it is usually used as citrate salt (1:1).

brand name

Toremifene is INN and BAN.

Therapeutic Function

Antiestrogen, Antineoplastic

General Description

Toremifene, 2-[4-[(1Z)-4-chloro-1,2-diphenyl-1-butenyl]phenoxy]-N,N-dimethylethanamine(Fareston), differs structurally fromtamoxifen only by having a chloroethyl group (rather than anethyl group) attached to the triphenylethylene structure. Asmight be expected, the pharmacological actions of toremifeneand tamoxifen are quite similar. Toremifene is also a SERM,with estrogen antagonist action in breast tissue but agonist actionin the endometrium, on bone tissue, and on serum lipidprofiles. Recent clinical data indicate that the incidence ofendometrial cancer is lower with toremifene use than with tamoxifen. Toremifene is used in the treatment of metastaticbreast cancer in postmenopausal women.

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?.

Toremifene citrate Preparation Products And Raw materials

Raw materials

Preparation Products

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View Lastest Price from Toremifene citrate manufacturers

HangZhou RunYan Pharma Technology Co.,LTD.

Product: Toremifene Citrate 89778-27-8
Price: US $0.00-0.00/MG
Min. Order: 10MG
Purity: 99% HPLC
Supply Ability: 10000
Release date: 2024-09-20

WUHAN FORTUNA CHEMICAL CO., LTD

Product: Toremifene citrate 89778-27-8
Price: US $1.00/g
Min. Order: 1g
Purity: 99%
Supply Ability: 1kg/month
Release date: 2021-09-18

Wuhan Senwayer Century Chemical Co.,Ltd

Product: Toremifene citrate 89778-27-8
Price: US $0.00/g
Min. Order: 10g
Purity: 98%
Supply Ability: 50kg
Release date: 2023-02-09

89778-27-8, Toremifene citrateRelated Search:

Dimethyl sulfoxide BISMUTH POTASSIUM CITRATE 1,5-Diphenylcarbazide Zinc citrate Calcium citrate Sildenafil citrate Dimethyl phthalate 3,4'-DIAMINODIPHENYLMETHANE 2-[5-(4-Chlorophenyl)pentyl]oxirane-2-carboxylic acid ETHANE Dimethyl sulfide Dimethyldimethoxysilane Dimethyl fumarate Dimethyl ether Citric acid monohydrate N,N-Dimethylformamide Clomiphene Citrate Toremifene

(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(1:1)

fareston

fc1157a

nk622

TOREMIFENE CITRATE

(z)-2-[4-(4-chloro-1,2-diphenyl-1-butenyl)phenoxy]-n,n-dimethyl-ethanamine 2-hydroxy-1,2,3-propanetricarboxylate

TROPISETRON CITRATE

(Z)-4-Chloro-1,2-diphenyl-1-(4-(2-(N,N-dimethylamino)ethoxy)phenyl)-1-butene citrate (1:1)

Ccris 6719

Ethanamine, 2-(4-(4-chloro-1,2-diphenyl-1-butenyl)phenoxy)-N,N-dimethyl-, (Z)-, 2-hydroxy-1,2,3-propanetricarboxylate (1:1)

Nsc 613680

Toremefene Citrate

2-[4-[(1Z)-4-CHLORO-1,2-DIPHENYL-1-BUTENYL]PHENOXY]-N,N-DIMETHYLETHANAMINE

Toremifine

ToreMifene Citrate(Fareston, Acapodene)

2-[4-[(1Z)-4-Chloro-1,2-diphenyl-1-butenyl]phenoxy]-N,N-diMethylethanaMine 2-Hydroxy-1,2,3-propanetricarboxylate

(Z)-4-Chloro-1-(4-dimethylaminoethoxyphenyl)-1,2-diphenyl-1-butene Citrate (Z)-2-[4-(4-Chloro-1,2-diphenyl-1-butenyl)phenoxy]-N,N-dimethylethanamine Citrate

ToreMifene (Z-isoMer)-d6

TOREMIPHENE CITRATE

2-[4-[(1Z)-4-chloro-1,2-diphenyl-1-buten-1-yl]phenoxy]-N,N-dimethyl-ethanamine, 2-hydroxy-1,2,3-propanetricarboxylate (1:1)

Toremifene citrate (Z)-2-[4-(4-Chloro-1,2-diphenyl-1-butenyl)phenoxy]-N,N-dimethyl-ethanamine 2-hydroxy-1,2,3-propanetricarboxylate

Toremifene citrate salt

(Z)-2-[4-(4-Chloro-1,2-diphenyl-1-butenyl)phenoxy]-N,N-dimethylethanamine Citrate

(Z)-4-Chloro-1-(4-dimethylaminoethoxyphenyl)-1,2-diphenyl-1-butene Citrate

Toremifene citrate USP/EP/BP

(Z)-2-(4-(4-chloro-1,2-diphenylbut-1-en-1-yl)phenoxy)-N,N-dimethylethan-1-amine 2-hydroxypropane-1,2,3-tricarboxylate

Toremifene Citrate (FC 1157a)

Toremifene citrat

Oremifene Citrate

Toremifene Citrate (NK 622)

Ethanamine, 2-[4-[(1Z)-4-chloro-1,2-diphenyl-1-buten-1-yl]phenoxy]-N,N-dimethyl-, 2-hydroxy-1,2,3-propanetricarboxylate (1:1)

89778-27-8

89778-29-8

C32H36CINO8

XYREM

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