T0R

Toremifene

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Chemical Component Summary
Name	Toremifene
Identifiers	2-[4-[(~{Z})-4-chloranyl-1,2-diphenyl-but-1-enyl]phenoxy]-~{N},~{N}-dimethyl-ethanamine
Formula	C₂₆ H₂₈ Cl N O
Molecular Weight	405.96
Type	NON-POLYMER
Isomeric SMILES	CN(C)CCOc1ccc(cc1)/C(=C(/CCCl)\c2ccccc2)/c3ccccc3
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

Chemical Details
Formal Charge	0
Atom Count	57
Chiral Atom Count	0
Bond Count	59
Aromatic Bond Count	18

Drug Info: DrugBank

DrugBank ID	DB00539
Name	Toremifene
Groups	approved investigational
Description	Toremifene is a selective estrogen receptor modulator (SERM) and a nonsteroidal antiestrogen used to treat estrogen receptor positive breast cancer.[A256923] Like [tamoxifen], toremifene is part of the first-generation triphenylethylene derivative chemical class of SERMs.[A256928] Toremifene possesses tissue-specific actions: it has estrogenic (agonist) activity on the cardiovascular system and on bone tissue and it has weak estrogenic effects on uterine tissue, however, it also has antiestrogenic (estrogen-antagonist) activity on breast tissue.[A256923]
Synonyms	Toremifenum Toremifene citrate Toremifeno Toremifene
Brand Names	Toremifene Citrate Fareston
Indication	For the treatment of metastatic breast cancer in postmenopausal women with estrogen receptor-positive or receptor-unknown tumors. Toremifene is currently under investigation as a preventative agent for prostate cancer in men with high-grade prostatic intraepithelial neoplasia and no evidence of prostate cancer.
Categories	Anti-Estrogens Antineoplastic Agents Antineoplastic Agents, Hormonal Antineoplastic and Immunomodulating Agents Benzene Derivatives Benzylidene Compounds Bone Density Conservation Agents Cytochrome P-450 CYP3A Inhibitors Cytochrome P-450 CYP3A Substrates Cytochrome P-450 CYP3A4 Inhibitors Cytochrome P-450 CYP3A4 Inhibitors (strength unknown) Cytochrome P-450 CYP3A4 Substrates Cytochrome P-450 Enzyme Inhibitors Cytochrome P-450 Substrates Endocrine Therapy Estrogen Agonist/Antagonist Estrogen Receptor Modulators Highest Risk QTc-Prolonging Agents Hormone Antagonists Hormone Antagonists and Related Agents Hormones, Hormone Substitutes, and Hormone Antagonists P-glycoprotein inhibitors P-glycoprotein substrates QTc Prolonging Agents Selective Estrogen Receptor Modulators Stilbenes
ATC-Code	L02BA02
CAS number	89778-26-7

Drug Targets

Name	Target Sequence	Pharmacological Action	Actions
Estrogen receptor alpha	MTMTLHTKASGMALLHQIQGNELEPLNRPQLKIPLERPLGEVYLDSSKPA...	unknown	modulator
Sex hormone-binding globulin	MESRGPLATSRLLLLLLLLLLRHTRQGWALRPVLPTQSAHDPPAVHLSNG...	unknown
Cytochrome P450 1A1	MLFPISMSATEFLLASVIFCLVFWVIRASRPQVPKGLKNPPGPWGWPLIG...	unknown	substrate
Cytochrome P450 3A4	MALIPDLAMETWLLLAVSLVLLYLYGTHSHGLFKKLGIPGPTPLPFLGNI...	unknown	substrate,inhibitor
P-glycoprotein 1	MDLEGDRNGGAKKKNFFKLNNKSEKDKKEKKPTVSVFSMFRYSNWLDKLY...	unknown	substrate

Drug Info/Drug Targets: DrugBank 3.0: a comprehensive resource for 'omics' research on drugs. Knox C, Law V, Jewison T, Liu P, Ly S, Frolkis A, Pon A, Banco K, Mak C, Neveu V, Djoumbou Y, Eisner R, Guo AC, Wishart DS. Nucleic Acids Res. 2011 Jan; 39 (Database issue):D1035-41. | PMID:21059682