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Revision as of 20:13, 16 February 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{chembox}} taken from revid 462277817 of page Afimoxifene for the Chem/Drugbox validation project (updated: 'CASNo').  Latest revision as of 18:54, 24 November 2024 edit Teaktl17 (talk | contribs)Extended confirmed users17,934 editsm →top: +wl 
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{{Short description|Chemical compound}}
{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid of page ] with values updated to verified values.}}
{{chembox {{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

<!--Clinical data-->
| tradename = TamoGel
| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X -->
| pregnancy_US = <!-- A / B / C / D / X -->
| pregnancy_category =
| legal_AU = <!-- Unscheduled / S2 / S3 / S4 / S5 / S6 / S7 / S8 / S9 -->
| legal_CA =
| legal_UK =
| legal_US =
| legal_status =
| routes_of_administration = ] (])

<!--Pharmacokinetic data-->
| bioavailability =
| protein_bound =
| metabolism =
| elimination_half-life =
| excretion =

<!-- Identifiers -->
| 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_Ref = {{fdacite|correct|FDA}}
| UNII = 17197F0KYM | UNII = 17197F0KYM
| KEGG_Ref = {{keggcite|correct|kegg}}
| verifiedrevid = 437134207
| KEGG = D06551
|ImageFile= Afimoxifene.png
| ChEBI = 44616
|ImageSize=
|IUPACName=(''Z'')-4-(1-(4-(2-(dimethylamino)ethoxy)phenyl)-2-phenylbut-1-enyl)phenol
|OtherNames=4-hydroxytamoxifen
|Section1= {{Chembox Identifiers
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 395987
| InChI = 1/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-
| InChIKey = TXUZVZSFRXZGTL-QPLCGJKRBX
| SMILES1 = O(c1ccc(cc1)/C(c2ccc(O)cc2)=C(\c3ccccc3)CC)CCN(C)C
| ChEMBL_Ref = {{ebicite|correct|EBI}} | ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 489 | ChEMBL = 489
| synonyms = 4-Hydroxytamoxifen; 4-OHT; 4-HT; OHTAM; TamoGel

<!--Chemical data-->
| 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_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- | 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_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = TXUZVZSFRXZGTL-QPLCGJKRSA-N | StdInChIKey = TXUZVZSFRXZGTL-QPLCGJKRSA-N
| CASNo_Ref = {{cascite|correct|??}}
| CASNo = <!-- blanked - oldvalue: 68392-35-8 -->
| PubChem=449459
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = D06551
| SMILES=CC\C(c1ccccc1)=C(c2ccc(OCCN(C)C)cc2)/c3ccc(O)cc3
}}
|Section2= {{Chembox Properties
| Formula=C<sub>26</sub>H<sub>29</sub>NO<sub>2</sub>
| MolarMass=387.51396
| Appearance=
| Density=
| MeltingPt=
| BoilingPt=
| Solubility=
}}
|Section3= {{Chembox Hazards
| MainHazards=
| FlashPt=
| Autoignition=
}}
}} }}
<!-- Definition and medical uses -->
'''Afimoxifene''', also known as '''4-hydroxytamoxifen''' ('''4-OHT''') and by its tentative brand name '''TamoGel''', is a ] (SERM) of the ] group and an ] of ].<ref name="AdisInsight">{{Cite web|url=http://adisinsight.springer.com/drugs/800019175|title = Afimoxifene - BHR Pharma | work = AdisInsight | publisher = Springer Nature Switzerland AG }}</ref><ref name="Desta_2004">{{cite journal | vauthors = Desta Z, Ward BA, Soukhova NV, Flockhart DA | 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 | date = September 2004 | pmid = 15159443 | doi = 10.1124/jpet.104.065607 | s2cid = 21413981 }}</ref><ref name="AMA_USAN">{{cite web | url = http://www.ama-assn.org/ama1/pub/upload/mm/365/afimoxifene.pdf | title = Statement on a nonproprietary name adopted by the USAN council: Afimoxifene | access-date = 2008-03-26 | publisher = American Medical Association }}</ref> The drug is under development under the tentative brand name '''TamoGel''' as a ] for the treatment of ] of the ].<ref name="AdisInsight" /><ref name="JatoiRody2016">{{cite book| vauthors = Goyal A, Mansel RE | chapter = Mastalgia| veditors = Jatoi I, Rody A |title=Management of Breast Diseases| chapter-url =https://books.google.com/books?id=f9iCDQAAQBAJ&pg=PA77|date=16 November 2016|publisher=Springer|isbn=978-3-319-46356-8|pages=77–}}</ref> It has completed a ] ] for ],<ref name="pmid17351746">{{cite journal | vauthors = Mansel R, Goyal A, Nestour EL, Masini-Etévé V, O'Connell K | 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 | date = December 2007 | pmid = 17351746 | doi = 10.1007/s10549-007-9507-x | 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 ] ] of the ]s ] and ] with mixed ]ic and ]ic activity depending on the ]. It is also an ] of the ] (GPER) with relatively low ] (100–1,000&nbsp;], relative to 3–6&nbsp;nM for ]).<ref name="pmid26023144">{{cite journal | vauthors = Prossnitz ER, Arterburn JB | 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 | date = July 2015 | pmid = 26023144 | pmc = 4485017 | doi = 10.1124/pr.114.009712 }}</ref> In addition to its estrogenic and antiestrogenic activity, afimoxifene has been found to act as an ] of the ]s (ERRs) ] and ].<ref name="Levine2011">{{cite book| vauthors = Levine AC |title=Hormones and Cancer: Breast and Prostate, An Issue of Endocrinology and Metabolism Clinics of North America|url=https://books.google.com/books?id=ZabQAQAAQBAJ&pg=PT271|date=3 October 2011|publisher=Elsevier Health Sciences|isbn=978-1-4557-1239-7|pages=271–}}</ref><ref name="Khetan2014">{{cite book| vauthors = Khetan SK | chapter = Anti-Androgenic Chemicals |title=Endocrine Disruptors in the Environment|chapter-url=https://books.google.com/books?id=s2ajAwAAQBAJ&pg=PT104|date=23 May 2014|publisher=Wiley|isbn=978-1-118-89115-5|pages=104–}}</ref><ref name="pmid16515477">{{cite journal | vauthors = Ariazi EA, Jordan VC | 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 | date = 2006 | pmid = 16515477 | doi = 10.2174/1568026610606030203 }}</ref>

== See also ==
* ]
* ]

== References ==
{{Reflist}}

== External links ==
* {{MeshName|4-hydroxytamoxifen}}
*

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

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{{Genito-urinary-drug-stub}}