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Toremifene
Identification
- Name
- Toremifene
- Accession Number
- DB00539
- Description
A first generation nonsteroidal selective estrogen receptor modulator (SERM) that is structurally related to tamoxifen. Like tamoxifen, it is an estrogen agonist for bone tissue and cholesterol metabolism but is antagonistic on mammary and uterine tissue.
- Type
- Small Molecule
- Groups
- Approved, Investigational
- Structure
Structure for Toremifene (DB00539)
- Weight
- Average: 405.96
Monoisotopic: 405.18594223 - Chemical Formula
- C26H28ClNO
- Synonyms
- Toremifene
- Toremifeno
- Toremifenum
- External IDs
- GTX-006
- J33.157K
Pharmacology
- 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.
- Associated Conditions
- Contraindications & Blackbox Warnings
Learn about our commercial Contraindications & Blackbox Warnings data.
Learn More- Pharmacodynamics
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.
- Mechanism of action
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.
Target Actions Organism AEstrogen receptor alpha modulatorHumans USex hormone-binding globulin Not Available Humans - Absorption
Well absorbed
- Volume of distribution
- 580 L
- Protein binding
Toremifen is primarily bound to albumin (92%), 2% bound to α1-acid glycoprotein, and 6% bound to β1-globulin in the serum.
- Metabolism
Hepatic. Mainly by CYP3A4 to N-demethyltoremifene, which exhibits antiestrogenic effects but has weak antitumor potency in vivo.
Hover over products below to view reaction partners
- Route of elimination
Toremifene is extensively metabolized, principally by CYP3A4 to N-demethyltoremifene, which is also antiestrogenic but with weak in vivo antitumor potency.
- Half-life
5 days
- Clearance
- 5 L/h
- Adverse Effects
Learn about our commercial Adverse Effects data.
Learn More- Toxicity
- Not Available
- Affected organisms
- Humans and other mammals
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Unlock Additional DataAbametapir The serum concentration of Toremifene can be increased when it is combined with Abametapir. Abciximab The risk or severity of bleeding can be increased when Toremifene is combined with Abciximab. Acebutolol The risk or severity of QTc prolongation can be increased when Acebutolol is combined with Toremifene. Acenocoumarol The risk or severity of bleeding can be increased when Toremifene is combined with Acenocoumarol. Acetylsalicylic acid The risk or severity of bleeding can be increased when Toremifene is combined with Acetylsalicylic acid. Acrivastine The risk or severity of QTc prolongation can be increased when Acrivastine is combined with Toremifene. Adenosine The risk or severity of QTc prolongation can be increased when Adenosine is combined with Toremifene. Afatinib The serum concentration of Afatinib can be increased when it is combined with Toremifene. Ajmaline The risk or severity of QTc prolongation can be increased when Ajmaline is combined with Toremifene. Alfuzosin The risk or severity of QTc prolongation can be increased when Alfuzosin is combined with Toremifene. Additional Data Available- Extended DescriptionExtended Description
Extended description of the mechanism of action and particular properties of each drug interaction.
Learn more - Severity
- Evidence Level
- ActionAction
An effect category for each drug interaction. Know how this interaction affects the subject drug.
Learn more
- Food Interactions
- Avoid grapefruit products. Grapefruit inhibits CYP3A4 and therefore, may elevate toremifene serum levels.
- Take with or without food.
Products
- Product Ingredients
Ingredient UNII CAS InChI Key Toremifene citrate 2498Y783QT 89778-27-8 IWEQQRMGNVVKQW-OQKDUQJOSA-N - International/Other Brands
- Acapodene
- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Unlock Additional DataFareston Tablet 60 mg/1 Oral KYOWA KIRIN, INC, 1997-06-30 Not applicable US 
Fareston Tablet 60 mg Oral Orion Corporation 1996-02-14 Not applicable EU 
Fareston Tablet 60 mg/1 Oral G Tx 1997-06-30 2016-04-30 US Fareston Tablet 60 mg Oral Orion Corporation 1996-02-14 Not applicable EU Additional Data Available- Application NumberApplication Number
A unique ID assigned by the FDA when a product is submitted for approval by the labeller.
Learn more - Product CodeProduct Code
A governmentally-recognized ID which uniquely identifies the product within its regulatory market.
Learn more
- Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Unlock Additional DataToremifene Citrate Tablet 60 mg/1 Oral Rising Pharmaceuticals, Inc. 2019-01-18 Not applicable US Toremifene Citrate Tablet 60 mg/1 Oral Novadoz Pharmaceuticals Llc 2020-09-02 Not applicable US Toremifene Citrate Tablet 60 mg/1 Oral Msn Laboratories Private Limited 2020-08-20 Not applicable US Additional Data Available- Application NumberApplication Number
A unique ID assigned by the FDA when a product is submitted for approval by the labeller.
Learn more - Product CodeProduct Code
A governmentally-recognized ID which uniquely identifies the product within its regulatory market.
Learn more
Categories
- ATC Codes
- L02BA02 — Toremifene
- Drug 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
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as stilbenes. These are organic compounds containing a 1,2-diphenylethylene moiety. Stilbenes (C6-C2-C6 ) are derived from the common phenylpropene (C6-C3) skeleton building block. The introduction of one or more hydroxyl groups to a phenyl ring lead to stilbenoids.
- Kingdom
- Organic compounds
- Super Class
- Phenylpropanoids and polyketides
- Class
- Stilbenes
- Sub Class
- Not Available
- Direct Parent
- Stilbenes
- Alternative Parents
- Diphenylmethanes / Phenoxy compounds / Phenol ethers / Alkyl aryl ethers / Trialkylamines / Organopnictogen compounds / Organochlorides / Hydrocarbon derivatives / Alkyl chlorides
- Substituents
- Alkyl aryl ether / Alkyl chloride / Alkyl halide / Amine / Aromatic homomonocyclic compound / Benzenoid / Diphenylmethane / Ether / Hydrocarbon derivative / Monocyclic benzene moiety
- Molecular Framework
- Aromatic homomonocyclic compounds
- External Descriptors
- aromatic ether, tertiary amine, organochlorine compound (CHEBI:9635)
Chemical Identifiers
- UNII
- 7NFE54O27T
- CAS number
- 89778-26-7
- InChI Key
- XFCLJVABOIYOMF-QPLCGJKRSA-N
- 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-
- IUPAC Name
- (2-{4-[(1Z)-4-chloro-1,2-diphenylbut-1-en-1-yl]phenoxy}ethyl)dimethylamine
- SMILES
- CN(C)CCOC1=CC=C(C=C1)C(=C(\CCCl)C1=CC=CC=C1)\C1=CC=CC=C1
References
- Synthesis Reference
Reijo Toivola, Tuomas Huuhtanen, "Toremifene crystallization method." U.S. Patent US20070093556, issued April 26, 2007.
US20070093556- General References
- 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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed:17504144]
- External Links
- Human Metabolome Database
- HMDB0014679
- KEGG Compound
- C08166
- PubChem Compound
- 3005573
- PubChem Substance
- 46506087
- ChemSpider
- 2275722
- BindingDB
- 58492
- 38409
- ChEBI
- 9635
- ChEMBL
- CHEMBL1655
- ZINC
- ZINC000012404516
- Therapeutic Targets Database
- DAP000793
- PharmGKB
- PA451731
- PDBe Ligand
- T0R
- RxList
- RxList Drug Page
- Drugs.com
- Drugs.com Drug Page
- Wikipedia
- Toremifene
- PDB Entries
- 5jq7
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count 4 Completed Treatment Breast Cancer 1 4 Recruiting Treatment Female Breast Cancer 1 4 Withdrawn Treatment HER2/Neu Negative / Invasive Breast Carcinoma / One to five years postmenopausal / Stage 0 Breast Cancer / Stage IA Breast Cancer 1 3 Completed Diagnostic Circulatory; Change 1 3 Completed Prevention Fracture Bone / Osteoporosis / Prostate Cancer 1 3 Completed Prevention Preneoplastic Conditions / Prostatic Intraepithelial Neoplasia 1 3 Completed Treatment Breast Cancer 1 3 Completed Treatment Breast Pain 1 3 Completed Treatment Neoplasms, Breast / Neoplasms, Hormone-Dependent 1 3 Not Yet Recruiting Treatment Breast Cancer / Chemotherapy Induced Amenorrhea / Ovarian Function Suppression 1
Pharmacoeconomics
- Manufacturers
- Gtx inc
- Packagers
- GTx Inc.
- Dosage Forms
Form Route Strength Tablet Oral 60 mg/1 Tablet Oral 60 mg Suspension Conjunctival; Ophthalmic 3.5 mg - Prices
Unit description Cost Unit Fareston 60 mg tablet 11.84USD tablet DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.- Patents
Patent Number Pediatric Extension Approved Expires (estimated) Region Unlock Additional DataUS4696949 No 1987-09-29 2009-09-29 US Additional Data Available- Filed On
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 108-110 °C Not Available logP 6.8 Not Available - Predicted Properties
Property Value Source Water Solubility 0.000409 mg/mL ALOGPS logP 5.65 ALOGPS logP 6.27 ChemAxon logS -6 ALOGPS pKa (Strongest Basic) 8.76 ChemAxon Physiological Charge 1 ChemAxon Hydrogen Acceptor Count 2 ChemAxon Hydrogen Donor Count 0 ChemAxon Polar Surface Area 12.47 Å2 ChemAxon Rotatable Bond Count 9 ChemAxon Refractivity 133.41 m3·mol-1 ChemAxon Polarizability 46.49 Å3 ChemAxon Number of Rings 3 ChemAxon Bioavailability 1 ChemAxon Rule of Five No ChemAxon Ghose Filter No ChemAxon Veber's Rule Yes ChemAxon MDDR-like Rule Yes ChemAxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 1.0 Blood Brain Barrier + 0.7488 Caco-2 permeable + 0.8266 P-glycoprotein substrate Substrate 0.7067 P-glycoprotein inhibitor I Inhibitor 0.79 P-glycoprotein inhibitor II Non-inhibitor 0.5917 Renal organic cation transporter Inhibitor 0.7552 CYP450 2C9 substrate Non-substrate 0.7502 CYP450 2D6 substrate Non-substrate 0.759 CYP450 3A4 substrate Substrate 0.7574 CYP450 1A2 substrate Inhibitor 0.8683 CYP450 2C9 inhibitor Non-inhibitor 0.882 CYP450 2D6 inhibitor Inhibitor 0.7217 CYP450 2C19 inhibitor Non-inhibitor 0.7443 CYP450 3A4 inhibitor Non-inhibitor 0.8824 CYP450 inhibitory promiscuity High CYP Inhibitory Promiscuity 0.5128 Ames test Non AMES toxic 0.7545 Carcinogenicity Non-carcinogens 0.616 Biodegradation Not ready biodegradable 0.9601 Rat acute toxicity 2.3467 LD50, mol/kg Not applicable hERG inhibition (predictor I) Strong inhibitor 0.7708 hERG inhibition (predictor II) Inhibitor 0.5086
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS Not Available Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not Available MS/MS Spectrum - , positive LC-MS/MS splash10-0a4i-0010900000-f55f03796d8b627e24e1
Targets
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Modulator
- General Function
- Zinc ion binding
- Specific Function
- Nuclear hormone receptor. The steroid hormones and their receptors are involved in the regulation of eukaryotic gene expression and affect cellular proliferation and differentiation in target tissu...
- Gene Name
- ESR1
- Uniprot ID
- P03372
- Uniprot Name
- Estrogen receptor
- Molecular Weight
- 66215.45 Da
References
- Locci P, Bellocchio S, Lilli C, Marinucci L, Cagini L, Baroni T, Giustozzi G, Balducci C, Becchetti E: Synthesis and secretion of transforming growth factor-beta1 by human desmoid fibroblast cell line and its modulation by toremifene. J Interferon Cytokine Res. 2001 Nov;21(11):961-70. [PubMed:11747628]
- Liu X, Pisha E, Tonetti DA, Yao D, Li Y, Yao J, Burdette JE, Bolton JL: Antiestrogenic and DNA damaging effects induced by tamoxifen and toremifene metabolites. Chem Res Toxicol. 2003 Jul;16(7):832-7. [PubMed:12870885]
- Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]
- Jones KL, Buzdar AU: A review of adjuvant hormonal therapy in breast cancer. Endocr Relat Cancer. 2004 Sep;11(3):391-406. [PubMed:15369444]
- Shelly W, Draper MW, Krishnan V, Wong M, Jaffe RB: Selective estrogen receptor modulators: an update on recent clinical findings. Obstet Gynecol Surv. 2008 Mar;63(3):163-81. doi: 10.1097/OGX.0b013e31816400d7. [PubMed:18279543]
- Gennari L, Merlotti D, Valleggi F, Martini G, Nuti R: Selective estrogen receptor modulators for postmenopausal osteoporosis: current state of development. Drugs Aging. 2007;24(5):361-79. [PubMed:17503894]
- Lewis-Wambi JS, Jordan VC: Treatment of Postmenopausal Breast Cancer with Selective Estrogen Receptor Modulators (SERMs). Breast Dis. 2005-2006;24:93-105. [PubMed:16917142]
- 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. [PubMed:16515478]
- 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. [PubMed:16503765]
- Goldstein LJ: Controversies in adjuvant endocrine treatment of premenopausal women. Clin Breast Cancer. 2006 Feb;6 Suppl 2:S36-40. [PubMed:16595024]
- Smith MR: Treatment-related osteoporosis in men with prostate cancer. Clin Cancer Res. 2006 Oct 15;12(20 Pt 2):6315s-6319s. [PubMed:17062721]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Androgen binding
- Specific Function
- Functions as an androgen transport protein, but may also be involved in receptor mediated processes. Each dimer binds one molecule of steroid. Specific for 5-alpha-dihydrotestosterone, testosterone...
- Gene Name
- SHBG
- Uniprot ID
- P04278
- Uniprot Name
- Sex hormone-binding globulin
- Molecular Weight
- 43778.755 Da
References
- Hong H, Branham WS, Ng HW, Moland CL, Dial SL, Fang H, Perkins R, Sheehan D, Tong W: Human sex hormone-binding globulin binding affinities of 125 structurally diverse chemicals and comparison with their binding to androgen receptor, estrogen receptor, and alpha-fetoprotein. Toxicol Sci. 2015 Feb;143(2):333-48. doi: 10.1093/toxsci/kfu231. Epub 2014 Oct 27. [PubMed:25349334]
Enzymes
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- SubstrateInhibitor
- General Function
- Vitamin d3 25-hydroxylase activity
- Specific Function
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
- Gene Name
- CYP3A4
- Uniprot ID
- P08684
- Uniprot Name
- Cytochrome P450 3A4
- Molecular Weight
- 57342.67 Da
References
- 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. [PubMed:16503765]
- Kivisto KT, Villikka K, Nyman L, Anttila M, Neuvonen PJ: Tamoxifen and toremifene concentrations in plasma are greatly decreased by rifampin. Clin Pharmacol Ther. 1998 Dec;64(6):648-54. [PubMed:9871429]
- Berthou F, Dreano Y, Belloc C, Kangas L, Gautier JC, Beaune P: Involvement of cytochrome P450 3A enzyme family in the major metabolic pathways of toremifene in human liver microsomes. Biochem Pharmacol. 1994 May 18;47(10):1883-95. [PubMed:8204106]
- Kim J, Peraire C, Sola J, Johanning KM, Dalton JT, Veverka KA: Drug interaction potential of toremifene and N-desmethyltoremifene with multiple cytochrome P450 isoforms. Xenobiotica. 2011 Oct;41(10):851-62. doi: 10.3109/00498254.2011.590546. Epub 2011 Jul 5. [PubMed:21726172]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Vitamin d 24-hydroxylase activity
- Specific Function
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
- Gene Name
- CYP1A1
- Uniprot ID
- P04798
- Uniprot Name
- Cytochrome P450 1A1
- Molecular Weight
- 58164.815 Da
References
- Berthou F, Dreano Y, Belloc C, Kangas L, Gautier JC, Beaune P: Involvement of cytochrome P450 3A enzyme family in the major metabolic pathways of toremifene in human liver microsomes. Biochem Pharmacol. 1994 May 18;47(10):1883-95. [PubMed:8204106]
Transporters
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Xenobiotic-transporting atpase activity
- Specific Function
- Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells.
- Gene Name
- ABCB1
- Uniprot ID
- P08183
- Uniprot Name
- Multidrug resistance protein 1
- Molecular Weight
- 141477.255 Da
References
- Rao US, Fine RL, Scarborough GA: Antiestrogens and steroid hormones: substrates of the human P-glycoprotein. Biochem Pharmacol. 1994 Jul 19;48(2):287-92. [PubMed:7914405]
Drug created on June 13, 2005 07:24 / Updated on June 12, 2020 10:51
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