Toremifene Citrate

Names

[ Name ]:
Toremifene Citrate

[Synonym ]:
2-[4-[(Z)-4-chloro-1,2-diphenylbut-1-enyl]phenoxy]-N,N-dimethylethanamine,2-hydroxypropane-1,2,3-tricarboxylic acid
2-{4-[(1Z)-4-Chloro-1,2-diphenyl-1-buten-1-yl]phenoxy}-N,N-dimethylethanamine 2-hydroxy-1,2,3-propanetricarboxylate (salt)
2-{4-[(1Z)-4-Chloro-1,2-diphenylbut-1-en-1-yl]phenoxy}-N,N-dimethylethanamine 2-hydroxypropane-1,2,3-tricarboxylate (1:1)
2-{4-[(1Z)-4-Chloro-1,2-diphenyl-1-buten-1-yl]phenoxy}-N,N-dimethylethanamine 2-hydroxy-1,2,3-propanetricarboxylate (1:1)
Toremifene Citrate
2-{4-[(1Z)-4-chloro-1,2-diphenylbut-1-en-1-yl]phenoxy}-N,N-dimethylethanamine 2-hydroxypropane-1,2,3-tricarboxylate (salt)
ethanamine, 2-[4-[(1Z)-4-chloro-1,2-diphenyl-1-butenyl]phenoxy]-N,N-dimethyl-, 2-hydroxy-1,2,3-propanetricarboxylate (1:1) (salt)
2-Hydroxypropan-1,2,3-tricarbonsäure--2-{4-[(1Z)-4-chlor-1,2-diphenylbut-1-en-1-yl]phenoxy}-N,N-dimethylethanamin(1:1)
acide 2-hydroxypropane-1,2,3-tricarboxylique - 2-{4-[(1Z)-4-chloro-1,2-diphénylbut-1-én-1-yl]phénoxy}-N,N-diméthyléthanamine (1:1)
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) (salt)
Toremifene (Citrate)

Biological Activity

[Description]:

Toremifene 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 μMTarget: Estrogen receptorToremifene 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].

[Related Catalog]:

Signaling Pathways >> Others >> Estrogen Receptor/ERR

Research Areas >> Cancer

[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.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.045g/cm3

[ Boiling Point ]:
535.1ºC at 760 mmHg

[ Melting Point ]:
158-164ºC

[ Molecular Formula ]:
C₃₂H₃₆ClNO₈

[ Molecular Weight ]:
598.083

[ Flash Point ]:
277.4ºC

[ Exact Mass ]:
597.212952

[ PSA ]:
144.60000

[ LogP ]:
4.96650

[ Index of Refraction ]:
1.416-1.418

[ Storage condition ]:
-20°C Freezer

[ Water Solubility ]:
DMSO: >10mg/mL

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: KH2156800

CAS REGISTRY NUMBER :: 89778-27-8

LAST UPDATED :: 199706

DATA ITEMS CITED :: 10

MOLECULAR FORMULA :: C26-H28-Cl-N-O.C6-H8-O7

MOLECULAR WEIGHT :: 598.14

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 3 gm/kg

TOXIC EFFECTS :: Sense Organs and Special Senses (Eye) - effect, not otherwise specified Kidney, Ureter, Bladder - incontinence Skin and Appendages - hair

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 520 mg/kg

TOXIC EFFECTS :: Behavioral - somnolence (general depressed activity) Kidney, Ureter, Bladder - incontinence Skin and Appendages - hair

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Primate - monkey

DOSE/DURATION :: >2 gm/kg

TOXIC EFFECTS :: Gastrointestinal - hypermotility, diarrhea

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 364 mg/kg/52W-C

TOXIC EFFECTS :: Brain and Coverings - changes in brain weight Blood - changes in erythrocyte (RBC) count Related to Chronic Data - changes in uterine weight

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 87360 ug/kg/2Y-C

TOXIC EFFECTS :: Nutritional and Gross Metabolic - weight loss or decreased weight gain

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Primate - monkey

DOSE/DURATION :: 3640 mg/kg/52W-C

TOXIC EFFECTS :: Liver - changes in liver weight Blood - pigmented or nucleated red blood cells Related to Chronic Data - changes in ovarian weight

MUTATION DATA

TEST SYSTEM :: Rodent - rat

DOSE/DURATION :: 35 mg/kg

REFERENCE :: CRNGDP Carcinogenesis (London). (Oxford Univ. Press, Pinkhill House, Southfield Road, Eynsham, Oxford OX8 1JJ, UK) V.1- 1980- Volume(issue)/page/year: 17,1051,1996 *** REVIEWS *** IARC Cancer Review:Human Inadequate Evidence IMEMDT IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man. (WHO Publications Centre USA, 49 Sheridan Ave., Albany, NY 12210) V.1- 1972- Volume(issue)/page/year: 66,367,1996 IARC Cancer Review:Animal Inadequate Evidence IMEMDT IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man. (WHO Publications Centre USA, 49 Sheridan Ave., Albany, NY 12210) V.1- 1972- Volume(issue)/page/year: 66,367,1996 IARC Cancer Review:Group 3 IMEMDT IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man. (WHO Publications Centre USA, 49 Sheridan Ave., Albany, NY 12210) V.1- 1972- Volume(issue)/page/year: 66,367,1996

Safety Information

[ Symbol ]:

GHS05, GHS07, GHS09

[ Signal Word ]:
Danger

[ Hazard Statements ]:
H302-H318-H410

[ Precautionary Statements ]:
P280-P301 + P312 + P330-P305 + P351 + P338 + P310

[ Hazard Codes ]:
Xi: Irritant;

[ Risk Phrases ]:
R36/37/38

[ Safety Phrases ]:
26-37/39

[ RIDADR ]:
UN 3077 9 / PGIII

[ RTECS ]:
KH2156700

[ HS Code ]:
2942000000

Customs

[ HS Code ]: 2942000000

Articles

Use of SERMs for treatment in postmenopausal women

J. Steroid Biochem. Mol. Biol. 142 , 142-54, (2014)

• FDA approved selective estrogen receptor modulators (SERMs) prevent and treat breast cancer, osteoporosis and dyspareunia. • SERMs have varying agonist and antagonist activities at the level of the ...

Novel off-target effect of tamoxifen--inhibition of acid ceramidase activity in cancer cells.

Biochim. Biophys. Acta 1831(12) , 1657-64, (2013)

Acid ceramidase (AC), EC 3.5.1.23, a lysosomal enzyme, catalyzes the hydrolysis of ceramide to constituent sphingoid base, sphingosine, and fatty acid. Because AC regulates the levels of pro-apoptotic...

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. 31(5) , 523-9, (2013)

Prostate cancer (PCa) prevention remains an appealing strategy for the reduction of overtreatment and secondary adverse effects. We evaluated the efficacy of toremifene citrate 20 mg in PCa prevention...

Related Compounds

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