Toremifeneのソースを表示

{{Short description|Chemical compound}}
{{Drugbox
| verifiedrevid = 470611877
| IUPAC_name = 2-[4-[(1''Z'')-4-Chloro-1,2-diphenyl-but-1-en-1-yl]phenoxy]-''N'',''N''-dimethylethanamine
| image = Toremifene.svg
| width = 250px
| image2 = Toremifene molecule ball.png
| width2 = 250px

<!--Clinical data-->
| pronounce = {{IPAc-en|ˈ|t|ɔːr|ə|m|ɪ|f|iː|n}}
| tradename = Fareston, others
| Drugs.com = {{drugs.com|monograph|fareston}}
| MedlinePlus = a608003
| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X -->
| pregnancy_US = <!-- A / B / C / D / X -->
| pregnancy_category =
| licence_EU = yes
| legal_AU = <!-- Unscheduled / S2 / S4 / S8 -->
| legal_UK = <!-- GSL / P / POM / CD -->
| legal_US = <!-- OTC / Rx-only -->
| legal_status =
| routes_of_administration = [[Oral administration|By mouth]]
| class = [[Selective estrogen receptor modulator]]

<!--Pharmacokinetic data-->
| bioavailability = Good/~100%<ref name="pmid11108432" /><ref name="Jr.Lawrence2015">{{cite book| vauthors = DeVita Jr VT, Lawrence TS, Rosenberg SA |title=DeVita, Hellman, and Rosenberg's Cancer: Principles & Practice of Oncology|url=https://books.google.com/books?id=HEAYBgAAQBAJ&pg=PT1126|date=7 January 2015|publisher=Wolters Kluwer Health|isbn=978-1-4698-9455-3|pages=1126–}}</ref>
| protein_bound = 99.7%<ref name="pmid11108432" />
| metabolism = [[Liver]] ([[CYP3A4]])<ref name="RosenthalBurchum2017" /><ref name="Jr.Lawrence2015" />
| metabolites = N-Desmethyltoremifene; 4-Hydroxytoremifene; [[Ospemifene]]<ref name="ChabnerLongo2011" /><ref name="Toremifene-Label"/>
| elimination_half-life = Toremifene: 3–7 days<ref name="pmid11108432" /><br />Metabolites: 4–21 days<ref name="Jr.Lawrence2015" /><ref name="Toremifene-Label"/><ref name="pmid11108432" />
| excretion = [[Feces]]: 70% (as metabolites)<ref name="Jr.Lawrence2015" />

<!--Identifiers-->
| CAS_number_Ref = {{cascite|correct|??}}
| CAS_number = 89778-26-7
| CAS_supplemental = <br />89778-27-8 ([[citrate]])
| ATC_prefix = L02
| ATC_suffix = BA02
| ATC_supplemental =
| PubChem = 3005573
| IUPHAR_ligand = 4325
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank = DB00539
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 2275722
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 7NFE54O27T
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = D08620
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 9635
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 1655
| PDB_ligand = T0R
| synonyms = (''Z'')-Toremifene; 4-Chlorotamoxifen; 4-CT; Acapodene; CCRIS-8745; FC-1157; FC-1157a; GTx-006; NK-622; NSC-613680

<!--Chemical data-->
| C=26 | H=28 | Cl=1 | N=1 | O=1
| SMILES = ClCCC(/c1ccccc1)=C(/c2ccc(OCCN(C)C)cc2)c3ccccc3
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 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-
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = XFCLJVABOIYOMF-QPLCGJKRSA-N
}}
<!-- Definition and medical uses -->
'''Toremifene''', sold under the brand name '''Fareston''' among others, is a medication which is used in the treatment of [[metastatic breast cancer|advanced breast cancer]] in [[menopause|postmenopausal]] women.<ref name="Toremifene-Label">{{cite web | title = FARESTON (toremifene citrate) 60 mg Tablets oral administration | url = https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/020497s006lbl.pdf | work = GTx, Inc. | publisher = U.S. Food and Drug Administration | date = March 2011 }}</ref><ref name="MillerIngle2002">{{cite book| vauthors = Miller WR, Ingle JN |title=Endocrine Therapy in Breast Cancer|url=https://books.google.com/books?id=00_LBQAAQBAJ&pg=PA55|date=8 March 2002|publisher=CRC Press|isbn=978-0-203-90983-6|pages=55–57}}</ref><ref name="ChabnerLongo2011">{{cite book| vauthors = Chabner BA, Longo DL |title=Cancer Chemotherapy and Biotherapy: Principles and Practice|url=https://books.google.com/books?id=0U4aj4GZWCIC&pg=PA659|date=7 December 2011|publisher=Lippincott Williams & Wilkins|isbn=978-1-4511-4820-6|pages=659–}}</ref> It is taken [[oral administration|by mouth]].<ref name="Toremifene-Label" />

<!-- Side effects -->
[[Side effect]]s of toremifene include [[hot flash]]es, [[sweating]], [[nausea]], [[vomiting]], [[dizziness]], [[vaginal discharge]], and [[vaginal bleeding]].<ref name="RosenthalBurchum2017" /><ref name="SchiffArrillaga2017" /> It can also cause [[blood clot]]s, [[heart dysrhythmia|irregular heartbeat]], [[cataract]]s, [[visual disturbance]]s, [[elevated liver enzymes]], [[endometrial hyperplasia]], and [[endometrial cancer]].<ref name="RosenthalBurchum2017" /> [[Hypercalcemia|High blood calcium levels]] can occur in women with [[bone metastasis|bone metastases]].<ref name="RosenthalBurchum2017" />

<!-- Mechanism of action -->
The medication is a [[selective estrogen receptor modulator]] (SERM) and hence is a mixed [[agonist]]–[[receptor antagonist|antagonist]] of the [[estrogen receptor]] (ER), the [[biological target]] of [[estrogen]]s like [[estradiol]].<ref name="RosenthalBurchum2017" /><ref name="SchiffArrillaga2017" /> It has [[estrogen (medication)|estrogen]]ic effects in [[bone]], the [[liver]], and the [[uterus]] and [[antiestrogen]]ic effects in the [[breast]]s.<ref name="MillerIngle2002" /><ref name="MorrowJordan2003" /><ref name="ScholarlyEditions2013" /><ref name="RosenthalBurchum2017" /> It is a [[triphenylethylene]] [[chemical derivative|derivative]] and is closely related to [[tamoxifen]].<ref name="CanoAlsina2006" />

<!-- History, society, and culture -->
Toremifene was introduced for medical use in 1997.<ref name="SilvaZurrida2005" /><ref name="BidlackOmaye2000" /> It was the first [[antiestrogen]] to be introduced since tamoxifen in 1978.<ref name="DiSaiaCreasman2017" /> It is available as a [[generic drug|generic medication]] in the [[United States]].<ref name="Drugs.com-Generic">{{Cite news|url=https://www.drugs.com/availability/generic-fareston.html|title=Generic Fareston Availability - Drugs.com|work=Drugs.com|access-date=2019-04-19|language=en-US}}</ref>

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