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National Center for Biotechnology Information
5 Related Records Expand this section
16 Classification Expand this section
Computed by Lexichem TK 2.7.0 (PubChem release 2021.05.07)
Computed by InChI 1.0.6 (PubChem release 2021.05.07)
Computed by InChI 1.0.6 (PubChem release 2021.05.07)
Computed by OEChem 2.3.0 (PubChem release 2021.05.07)
Computed by OEChem 2.3.0 (PubChem release 2021.05.07)
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CAS Common Chemistry; ChemIDplus; DrugBank; EPA DSSTox; European Chemicals Agency (ECHA); FDA Global Substance Registration System (GSRS); Human Metabolome Database (HMDB)
FDA Global Substance Registration System (GSRS)
Japan Chemical Substance Dictionary (Nikkaji)
Japan Chemical Substance Dictionary (Nikkaji)
NIPH Clinical Trials Search of Japan
Selective Estrogen Receptor Modulators
Toremifene is an Estrogen Agonist/Antagonist. The mechanism of action of toremifene is as a Selective Estrogen Receptor Modulator.
WHO Anatomical Therapeutic Chemical (ATC) Classification
S73 | METXBIODB | Metabolite Reaction Database from BioTransformer | DOI:10.5281/zenodo.4056560
S72 | NTUPHTW | Pharmaceutically Active Substances from National Taiwan University | DOI:10.5281/zenodo.3955664
Drug Induced Liver Injury Rank (DILIrank) Dataset
Volume 66 : (1996) Some Pharmaceutical Drugs
International Agency for Research on Cancer (IARC)
Price N, Sartor O, Hutson T, Mariani S: Role of 5a-reductase inhibitors and selective estrogen receptor modulators as potential chemopreventive agents for prostate cancer. Clin Prostate Cancer. 2005 Mar;3(4):211-4. [ PMID:15882476 ] Taneja SS, Smith MR, Dalton JT, Raghow S, Barnette G, Steiner M, Veverka KA: Toremifene--a promising therapy for the prevention of prostate cancer and complications of androgen deprivation therapy. Expert Opin Investig Drugs. 2006 Mar;15(3):293-305. [ PMID:16503765 ] Thompson IM: Chemoprevention of prostate cancer: agents and study designs. J Urol. 2007 Sep;178(3 Pt 2):S9-S13. Epub 2007 Jul 20. [ PMID:17644117 ] Ariazi EA, Ariazi JL, Cordera F, Jordan VC: Estrogen receptors as therapeutic targets in breast cancer. Curr Top Med Chem. 2006;6(3):181-202. [ PMID:16515478 ] Musa MA, Khan MO, Cooperwood JS: Medicinal chemistry and emerging strategies applied to the development of selective estrogen receptor modulators (SERMs). Curr Med Chem. 2007;14(11):1249-61. [ PMID:17504144 ]
BindingDB; Drug Gene Interaction database (DGIdb); DrugBank; Therapeutic Target Database (TTD)
Avoid grapefruit products. Grapefruit inhibits CYP3A4 and therefore, may elevate toremifene serum levels. Take with or without food.
WHO Anatomical Therapeutic Chemical (ATC) Classification
International Agency for Research on Cancer (IARC)
All data curated by BindingDB staff are provided under the Creative Commons Attribution 3.0 License (https://creativecommons.org/licenses/by/3.0/us/).
2-[4-[(Z)-4-chloranyl-1,2-diphenyl-but-1-enyl]phenoxy]-N,N-dimethyl-ethanamine;2-oxidanylpropane-1,2,3-tricarboxylic acid
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ChemIDplus Chemical Information Classification
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Ethanamine, 2-[4-[(1Z)-4-chloro-1,2-diphenyl-1-buten-1-yl]phenoxy]-N,N-dimethyl
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Selective Estrogen Receptor Modulators
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Guide to Pharmacology Target Classification
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Toremifene is a nonsteroidal antiestrogen that is used in the treatment of estrogen receptor positive breast cancer. Long term toremifene therapy has been associated with development of fatty liver, steatohepatitis, cirrhosis, and rare instances of clinically apparent acute liver injury.
Toremifene is a nonsteroidal triphenylethylene antiestrogen. Chemically related to tamoxifen , toremifene is a selective estrogen receptor modulator (SERM). This agent binds competitively to estrogen receptors, thereby interfering with estrogen activity. Toremifene also has intrinsic estrogenic properties, which are manifested according to tissue type or species. (NCI04)
Toremifene is a tertiary amine, an organochlorine compound and an aromatic ether. It has a role as an antineoplastic agent, an estrogen antagonist, an estrogen receptor modulator and a bone density conservation agent. It derives from a hydride of a stilbene .
2-[4-[( Z )-4-chloro-1,2-diphenylbut-1-enyl]phenoxy]- N , N -dimethylethanamine
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-
CN(C)CCOC1=CC=C(C=C1)C(=C(CCCl)C2=CC=CC=C2)C3=CC=CC=C3
CN(C)CCOC1=CC=C(C=C1)/C(=C(/CCCl)\C2=CC=CC=C2)/C3=CC=CC=C3
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.
Toremifene is a nonsteroidal antiestrogen that is used in the treatment of estrogen receptor positive breast cancer. Long term toremifene therapy has been associated with development of fatty liver, steatohepatitis, cirrhosis, and rare instances of clinically apparent acute liver injury.
Toremifene is an antineoplastic hormonal agent primarily used in the treatment of advanced breast cancer. Toremifene is a nonsteroidal agent that has demonstrated potent antiestrogenic properties in animal test systems. The antiestrogenic effects may be related to its ability to compete with estrogen for binding sites in target tissues such as breast. Toremifene inhibits the induction of rat mammary carcinoma induced by dimethylbenzanthracene ( DMBA ) and causes the regression of already established DMBA -induced tumors. In this rat model, Toremifene appears to exert its antitumor effects by binding the estrogen receptors. In cytosols derived from human breast adenocarcinomas, Toremifene competes with estradiol for estrogen receptor protein.
A structurally diverse group of compounds distinguished from ESTROGENS by their ability to bind and activate ESTROGEN RECEPTORS but act as either an agonist or antagonist depending on the tissue type and hormonal milieu. They are classified as either first generation because they demonstrate estrogen agonist properties in the ENDOMETRIUM or second generation based on their patterns of tissue specificity. (Horm Res 1997;48:155-63) (See all compounds classified as Selective Estrogen Receptor Modulators .)
Antineoplastic agents that are used to treat hormone-sensitive tumors. Hormone-sensitive tumors may be hormone-dependent, hormone-responsive, or both. A hormone-dependent tumor regresses on removal of the hormonal stimulus, by surgery or pharmacological block. Hormone-responsive tumors may regress when pharmacologic amounts of hormones are administered regardless of whether previous signs of hormone sensitivity were observed. The major hormone-responsive cancers include carcinomas of the breast, prostate, and endometrium; lymphomas; and certain leukemias. (From AMA Drug Evaluations Annual 1994, p2079) (See all compounds classified as Antineoplastic Agents, Hormonal .)
Agents that inhibit BONE RESORPTION and/or favor BONE MINERALIZATION and BONE REGENERATION. They are used to heal BONE FRACTURES and to treat METABOLIC BONE DISEASES such as OSTEOPOROSIS. (See all compounds classified as Bone Density Conservation Agents .)
L - Antineoplastic and immunomodulating agents
L02B - Hormone antagonists and related agents
Toremifene is extensively metabolized, principally by CYP3A4 to N-demethyltoremifene , which is also antiestrogenic but with weak in vivo antitumor potency.
Hepatic. Mainly by CYP3A4 to N-demethyltoremifene , which exhibits antiestrogenic effects but has weak antitumor potency in vivo.
Toremifene has known human metabolites that include N-desmethyltoremifene .
Toremifene is a nonsteroidal triphenylethylene derivative. Toremifene binds to estrogen receptors and may exert estrogenic, antiestrogenic, or both activities, depending upon the duration of treatment, animal species, gender, target organ, or endpoint selected. The antitumor effect of toremifene in breast cancer is believed to be mainly due to its antiestrogenic effects, in other words, its ability to compete with estrogen for binding sites in the cancer, blocking the growth-stimulating effects of estrogen in the tumor. Toremifene may also inhibit tumor growth through other mechanisms, such as induction of apoptosis, regulation of oncogene expression, and growth factors.
Toremifene has been associated with mild-to-moderate serum ALT or AST elevations in 5% to 19% of patients, but these abnormalities are usually transient and not associated with symptoms or jaundice. Elevations above 5 times the ULN are uncommon (
Likelihood score: D (possible cause of clinically apparent liver injury).
M Chen, V Vijay, Q Shi, Z Liu, H Fang, W Tong. FDA-Approved Drug Labeling for the Study of Drug-Induced Liver Injury, Drug Discovery Today, 16(15-16):697-703, 2011. PMID:21624500 DOI:10.1016/j.drudis.2011.05.007
M Chen, A Suzuki, S Thakkar, K Yu, C Hu, W Tong. DILIrank: the largest reference drug list ranked by the risk for developing drug-induced liver injury in humans. Drug Discov Today 2016, 21(4): 648-653. PMID:26948801 DOI:10.1016/j.drudis.2016.02.015
Toremifen is primarily bound to albumin (92%), 2% bound to α1-acid glycoprotein, and 6% bound to β1-globulin in the serum.
Reijo Toivola, Tuomas Huuhtanen, "Toremifene crystallization method." U.S. Patent US20070093556, issued April 26, 2007.
Patents are available for this chemical structure:
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Computed by Cactvs 3.4.8.18 (PubChem release 2021.05.07)
Computed by Cactvs 3.4.8.18 (PubChem release 2021.05.07)
Computed by Cactvs 3.4.8.18 (PubChem release 2021.05.07)
Computed by PubChem 2.1 (PubChem release 2021.05.07)
Computed by PubChem 2.1 (PubChem release 2021.05.07)
Computed by Cactvs 3.4.8.18 (PubChem release 2021.05.07)
Computed by Cactvs 3.4.8.18 (PubChem release 2021.05.07)
Computed by PubChem (release 2021.05.07)
Megan Showalter, University of California, Davis
Established Pharmacologic Class [EPC] - Estrogen Agonist/Antagonist
Mechanisms of Action [MoA] - Selective Estrogen Receptor Modulators
Group 3: Not classifiable as to its carcinogenicity to humans
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Toremifene | C26H28ClNO | CID 3005573 - structure, chemical names, physical and chemical properties, classification, patents, literature, biological activities ...
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Toremifene | C26H28ClNO | CID 3005573 - structure, chemical names, physical and chemical properties, classification, patents, literature, biological activities ...
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