Toremifene

Names

[ Name ]:
Toremifene

[Synonym ]:
Ethanamine, 2-(4-(4-chloro-1,2-diphenyl-1-butenyl)phenoxy)-N,N-dimethyl-, (Z)-
(Z)-Toremifene
2-{4-[(1Z)-4-chloro-1,2-diphenylbut-1-en-1-yl]phenoxy}-N,N-dimethylethanamine
MFCD00801070
2-{4-[(1Z)-4-Chloro-1,2-diphenyl-1-buten-1-yl]phenoxy}-N,N-dimethylethanamine
ethanamine, 2-[4-[(1Z)-4-chloro-1,2-diphenyl-1-butenyl]phenoxy]-N,N-dimethyl-
2-({4-[(1Z)-4-chloro-1,2-diphenylbut-1-en-1-yl]phenyl}oxy)-N,N-dimethylethanamine
Toremifene Base
2-(4-(4-Chloro-1,2-diphenylbut-1-en-1-yl)phenoxy)-N,N-dimethylethanamine
Toremifene
2-[4-[(Z)-4-chloro-1,2-diphenylbut-1-enyl]phenoxy]-N,N-dimethylethanamine
(Z)-4-Chloro-1,2-diphenyl-1-[4-[2-(N,N-dimethylamino)ethoxy]phenyl]-1-butene
Ethanamine, 2-[4-[(1Z)-4-chloro-1,2-diphenyl-1-buten-1-yl]phenoxy]-N,N-dimethyl-
(Z)-2-[4-(4-Chloro-1,2-diphenyl-1-butenyl)phenoxy]-N,N-dimethylethanamine

Biological Activity

[Description]:

Toremifene (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]:
1.1±0.1 g/cm3

[ Boiling Point ]:
535.1±50.0 °C at 760 mmHg

[ Melting Point ]:
108-110°C

[ Molecular Formula ]:
C₂₆H₂₈ClNO

[ Molecular Weight ]:
405.960

[ Flash Point ]:
277.4±30.1 °C

[ Exact Mass ]:
405.185944

[ PSA ]:
12.47000

[ LogP ]:
7.82

[ Vapour Pressure ]:
0.0±1.4 mmHg at 25°C

[ Index of Refraction ]:
1.588

[ Storage condition ]:
2-8℃

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: KH2156700

CHEMICAL NAME :: Ethanamine, 2-(4-(4-chloro-1,2-diphenyl-1-butenyl)phenoxy)-N,N-di methyl-, (Z)-

CAS REGISTRY NUMBER :: 89778-26-7

LAST UPDATED :: 199801

DATA ITEMS CITED :: 11

MOLECULAR FORMULA :: C26-H28-Cl-N-O

MOLECULAR WEIGHT :: 406.00

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 :: 1700 mg/kg

TOXIC EFFECTS :: Gastrointestinal - other changes Tumorigenic - active as anti-cancer agent

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 360 mg/kg/30D-I

TOXIC EFFECTS :: Blood - changes in serum composition (e.g. TP, bilirubin, cholesterol) Biochemical - Enzyme inhibition, induction, or change in blood or tissue levels - transaminases Biochemical - Metabolism (Intermediary) - other proteins

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 1092 mg/kg/13W-I

TOXIC EFFECTS :: Blood - changes in serum composition (e.g. TP, bilirubin, cholesterol) Biochemical - Enzyme inhibition, induction, or change in blood or tissue levels - transaminases Biochemical - Metabolism (Intermediary) - other proteins

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 90 mg/kg

SEX/DURATION :: female 30 day(s) pre-mating

TOXIC EFFECTS :: Reproductive - Maternal Effects - other effects

MUTATION DATA

TEST SYSTEM :: Rodent - rat

DOSE/DURATION :: 36300 ug/kg

REFERENCE :: CRNGDP Carcinogenesis (London). (Oxford Univ. Press, Pinkhill House, Southfield Road, Eynsham, Oxford OX8 1JJ, UK) V.1- 1980- Volume(issue)/page/year: 18,303,1997 *** 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

[ Hazard Codes ]:
Xi

[ Risk Phrases ]:
R37:Irritating to the respiratory system. R43:May cause sensitization by skin contact.

[ Safety Phrases ]:
S8-S24/25-S46

[ RIDADR ]:
UN 2210

[ RTECS ]:
ZB3200000

[ Packaging Group ]:
III

[ Hazard Class ]:
9

[ HS Code ]:
2922299090

Synthetic Route

Click to get detail synthetic route

Customs

[ HS Code ]: 2922299090

[ Summary ]:
2922299090. other amino-naphthols and other amino-phenols, other than those containing more than one kind of oxygen function, their ethers and esters; salts thereof. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:30.0%

Related Compounds

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