toremifene (CHEBI:9635)

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ChEBI Name	toremifene

ChEBI ID	CHEBI:9635

Stars	This entity has been manually annotated by the ChEBI Team.

Supplier Information	ChemicalBook:CB0287854, ZINC000012404516

Download	Molfile XML SDF

Wikipedia	License
Toremifene, sold under the brand name Fareston among others, is a medication which is used in the treatment of advanced breast cancer in postmenopausal women. It is taken by mouth. Side effects of toremifene include hot flashes, sweating, nausea, vomiting, dizziness, vaginal discharge, and vaginal bleeding. It can also cause blood clots, irregular heartbeat, cataracts, visual disturbances, elevated liver enzymes, endometrial hyperplasia, and endometrial cancer. High blood calcium levels can occur in women with bone metastases. The medication is a selective estrogen receptor modulator (SERM) and hence is a mixed agonist–antagonist of the estrogen receptor (ER), the biological target of estrogens like estradiol. It has estrogenic effects in bone, the liver, and the uterus and antiestrogenic effects in the breasts. It is a triphenylethylene derivative and is closely related to tamoxifen. Toremifene was introduced for medical use in 1997. It was the first antiestrogen to be introduced since tamoxifen in 1978. It is available as a generic medication in the United States.
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Formula

C26H28ClNO

Net Charge

Average Mass

405.95936

Monoisotopic Mass

405.18594

InChI

InChI=1S/C26H28ClNO/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/h3-16H,17-20H2,1-2H3/b26-25-

InChIKey

XFCLJVABOIYOMF-QPLCGJKRSA-N

SMILES

CN(C)CCOc1ccc(cc1)C(\c1ccccc1)=C(\CCCl)c1ccccc1

Roles Classification
Chemical Role(s):	Bronsted base A molecular entity capable of accepting a hydron from a donor (Bronsted acid). (via organic amino compound )

Biological Role(s):	estrogen antagonist A compound which inhibits or antagonises the biosynthesis or actions of estrogens.

Application(s):	antineoplastic agent A substance that inhibits or prevents the proliferation of neoplasms. estrogen antagonist A compound which inhibits or antagonises the biosynthesis or actions of estrogens. bone density conservation agent An agent that inhibits bone resorption and/or favor bone mineralization and bone regeneration. Used to heal bone fractures and to treat bone diseases such as osteopenia and osteoporosis. estrogen receptor modulator A substance that possess antiestrogenic actions but can also produce estrogenic effects as well. It acts as complete or partial agonist or as antagonist. It can be either steroidal or nonsteroidal in structure.

ChEBI Ontology
Outgoing	toremifene (CHEBI:9635) has parent hydride stilbene (CHEBI:26775) toremifene (CHEBI:9635) has role antineoplastic agent (CHEBI:35610) toremifene (CHEBI:9635) has role bone density conservation agent (CHEBI:50646) toremifene (CHEBI:9635) has role estrogen antagonist (CHEBI:50837) toremifene (CHEBI:9635) has role estrogen receptor modulator (CHEBI:50739) toremifene (CHEBI:9635) is a aromatic ether (CHEBI:35618) toremifene (CHEBI:9635) is a organochlorine compound (CHEBI:36683) toremifene (CHEBI:9635) is a tertiary amine (CHEBI:32876)

IUPAC Name

2-{4-[(1Z)-4-chloro-1,2-diphenylbut-1-en-1-yl]phenoxy}-N,N-dimethylethanamine

Last Modified

22 February 2017