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{{Short description|Chemical compound}}
{{Drugbox
| Verifiedfields = verified
| Watchedfields = verified
| verifiedrevid = 477243306
| IUPAC_name = (''Z'')-4-(1-(4-(2-(dimethylamino)ethoxy)phenyl)-2-phenylbut-1-enyl)phenol
| image = Afimoxifene2DACS.svg
| width = 250px


| tradename = TamoGel
| pregnancy_AU = 
| pregnancy_US = 
| pregnancy_category =
| legal_AU = 
| legal_CA =
| legal_UK =
| legal_US =
| legal_status =
| routes_of_administration = [[Topical administration|Topical]] ([[gel]])


| bioavailability =
| protein_bound =
| metabolism =
| elimination_half-life =
| excretion =


| CAS_number_Ref = {{cascite|correct|CAS}}
| CAS_number = 68392-35-8
| CAS_supplemental =
| ATC_prefix =
| ATC_suffix =
| ATC_supplemental =
| PubChem = 449459
| IUPHAR_ligand =
| DrugBank_Ref =
| DrugBank =
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 395987
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 17197F0KYM
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = D06551
| ChEBI = 44616
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 489
| synonyms = 4-Hydroxytamoxifen; 4-OHT; 4-HT; OHTAM; TamoGel


| C=26 | H=29 | N=1 | O=2
| SMILES = CC\C(c1ccccc1)=C(c2ccc(OCCN(C)C)cc2)/c3ccc(O)cc3
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C26H29NO2/c1-4-25(20-8-6-5-7-9-20)26(21-10-14-23(28)15-11-21)22-12-16-24(17-13-22)29-19-18-27(2)3/h5-17,28H,4,18-19H2,1-3H3/b26-25-
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = TXUZVZSFRXZGTL-QPLCGJKRSA-N
}}

'''Afimoxifene''', also known as '''4-hydroxytamoxifen''' ('''4-OHT''') and by its tentative brand name '''TamoGel''', is a [[selective estrogen receptor modulator]] (SERM) of the [[triphenylethylene]] group and an [[active metabolite]] of [[tamoxifen]].<ref name="AdisInsight">{{Cite web |title=Afimoxifene - BHR Pharma |url=http://adisinsight.springer.com/drugs/800019175 |website=AdisInsight |publisher=Springer Nature Switzerland AG}}</ref><ref name="Desta_2004">{{Cite journal |vauthors=Desta Z, Ward BA, Soukhova NV, Flockhart DA |date=September 2004 |title=Comprehensive evaluation of tamoxifen sequential biotransformation by the human cytochrome P450 system in vitro: prominent roles for CYP3A and CYP2D6 |journal=The Journal of Pharmacology and Experimental Therapeutics |volume=310 |issue=3 |pages=1062–1075 |doi=10.1124/jpet.104.065607 |pmid=15159443 |s2cid=21413981}}</ref><ref name="AMA_USAN">{{Cite web |title=Statement on a nonproprietary name adopted by the USAN council: Afimoxifene |url=http://www.ama-assn.org/ama1/pub/upload/mm/365/afimoxifene.pdf |access-date=2008-03-26 |publisher=American Medical Association}}</ref> The drug is under development under the tentative brand name '''TamoGel''' as a [[Topical gels|topical gel]] for the treatment of [[hyperplasia]] of the [[breast]].<ref name="AdisInsight" /><ref name="JatoiRody2016">{{Cite book |title=Management of Breast Diseases |vauthors=Goyal A, Mansel RE |date=16 November 2016 |publisher=Springer |isbn=978-3-319-46356-8 |veditors=Jatoi I, Rody A |pages=77– |chapter=Mastalgia |chapter-url=https://books.google.com/books?id=f9iCDQAAQBAJ&pg=PA77}}</ref> It has completed a [[Phases of clinical research#Phase II|phase II]] [[clinical trial]] for [[mastalgia|cyclical mastalgia]],<ref name="pmid17351746">{{Cite journal |vauthors=Mansel R, Goyal A, Nestour EL, Masini-Etévé V, O'Connell K |date=December 2007 |title=A phase II trial of Afimoxifene (4-hydroxytamoxifen gel) for cyclical mastalgia in premenopausal women |journal=Breast Cancer Research and Treatment |volume=106 |issue=3 |pages=389–397 |doi=10.1007/s10549-007-9507-x |pmid=17351746 |s2cid=22382077}}</ref> but further studies are required before afimoxifene can be approved for this indication and marketed.<ref name="JatoiRody2016" />

Afimoxifene is a SERM and hence acts as a [[tissue selectivity|tissue-selective]] [[agonist–antagonist]] of the [[estrogen receptor]]s [[ERα]] and [[ERβ]] with mixed [[estrogen (medication)|estrogen]]ic and [[antiestrogen]]ic activity depending on the [[tissue (biology)|tissue]]. It is also an [[agonist]] of the [[G protein-coupled estrogen receptor]] (GPER) with relatively low [[affinity (pharmacology)|affinity]] (100–1,000 [[Nanomolar|nM]], relative to 3–6 nM for [[estradiol (medication)|estradiol]]).<ref name="pmid26023144">{{Cite journal |vauthors=Prossnitz ER, Arterburn JB |date=July 2015 |title=International Union of Basic and Clinical Pharmacology. XCVII. G Protein-Coupled Estrogen Receptor and Its Pharmacologic Modulators |journal=Pharmacological Reviews |volume=67 |issue=3 |pages=505–540 |doi=10.1124/pr.114.009712 |pmc=4485017 |pmid=26023144}}</ref> In addition to its estrogenic and antiestrogenic activity, afimoxifene has been found to act as an [[receptor antagonist|antagonist]] of the [[estrogen-related receptor]]s (ERRs) [[ERRβ]] and [[ERRγ]].<ref name="Levine2011">{{Cite book |url=https://books.google.com/books?id=ZabQAQAAQBAJ&pg=PT271 |title=Hormones and Cancer: Breast and Prostate, An Issue of Endocrinology and Metabolism Clinics of North America |vauthors=Levine AC |date=3 October 2011 |publisher=Elsevier Health Sciences |isbn=978-1-4557-1239-7 |pages=271–}}</ref><ref name="Khetan2014">{{Cite book |title=Endocrine Disruptors in the Environment |vauthors=Khetan SK |date=23 May 2014 |publisher=Wiley |isbn=978-1-118-89115-5 |pages=104– |chapter=Anti-Androgenic Chemicals |chapter-url=https://books.google.com/books?id=s2ajAwAAQBAJ&pg=PT104}}</ref><ref name="pmid16515477">{{Cite journal |vauthors=Ariazi EA, Jordan VC |date=2006 |title=Estrogen-related receptors as emerging targets in cancer and metabolic disorders |journal=Current Topics in Medicinal Chemistry |volume=6 |issue=3 |pages=203–215 |doi=10.2174/1568026610606030203 |pmid=16515477}}</ref>

== See also ==
* [[List of investigational sex-hormonal agents#Estrogenics|List of investigational sex-hormonal agents § Estrogenics]]
* [[List of selective estrogen receptor modulators]]

== References ==
{{Reflist}}

== External links ==
* {{MeshName|4-hydroxytamoxifen}}
* [https://adisinsight.springer.com/drugs/800019175 Afimoxifene - AdisInsight]

{{Estrogen receptor modulators}}
{{Estrogen-related receptor modulators}}

[[Category:Dimethylamino compounds]]
[[Category:Experimental cancer drugs]]
[[Category:Experimental sex-hormone agents]]
[[Category:GPER agonists]]
[[Category:Human drug metabolites]]
[[Category:2-Phenoxyethanamines]]
[[Category:4-Hydroxyphenyl compounds]]
[[Category:Selective estrogen receptor modulators]]
[[Category:Triphenylethylenes]]
[[Category:Ethanolamines]]

{{Genito-urinary-drug-stub}}

Afimoxifene - 版の履歴

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