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'''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''', 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 |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 ] for the treatment of ] of the ].<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 ] ] for ],<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 ] ] 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;nM, 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> 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 |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 ] of the ]s (ERRs) ] and ].<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 == == See also ==

Latest revision as of 15:19, 19 January 2025

Chemical compound Pharmaceutical compound
Afimoxifene
Clinical data
Trade namesTamoGel
Other names4-Hydroxytamoxifen; 4-OHT; 4-HT; OHTAM; TamoGel
Routes of
administration		Topical (gel)
Identifiers
IUPAC name
  • (Z)-4-(1-(4-(2-(dimethylamino)ethoxy)phenyl)-2-phenylbut-1-enyl)phenol
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.163.120 Edit this at Wikidata
Chemical and physical data
FormulaC26H29NO2
Molar mass387.523 g·mol
3D model (JSmol)
SMILES
  • CC\C(c1ccccc1)=C(c2ccc(OCCN(C)C)cc2)/c3ccc(O)cc3
InChI
  • InChI=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-
  • Key:TXUZVZSFRXZGTL-QPLCGJKRSA-N
  (verify)

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. The drug is under development under the tentative brand name TamoGel as a topical gel for the treatment of hyperplasia of the breast. It has completed a phase II clinical trial for cyclical mastalgia, but further studies are required before afimoxifene can be approved for this indication and marketed.

Afimoxifene is a SERM and hence acts as a tissue-selective agonist–antagonist of the estrogen receptors ERα and ERβ with mixed estrogenic and antiestrogenic activity depending on the tissue. It is also an agonist of the G protein-coupled estrogen receptor (GPER) with relatively low affinity (100–1,000 nM, relative to 3–6 nM for estradiol). In addition to its estrogenic and antiestrogenic activity, afimoxifene has been found to act as an antagonist of the estrogen-related receptors (ERRs) ERRβ and ERRγ.

See also

References

  1. ^ "Afimoxifene - BHR Pharma". AdisInsight. Springer Nature Switzerland AG.
  2. Desta Z, Ward BA, Soukhova NV, Flockhart DA (September 2004). "Comprehensive evaluation of tamoxifen sequential biotransformation by the human cytochrome P450 system in vitro: prominent roles for CYP3A and CYP2D6". The Journal of Pharmacology and Experimental Therapeutics. 310 (3): 1062–1075. doi:10.1124/jpet.104.065607. PMID 15159443. S2CID 21413981.
  3. "Statement on a nonproprietary name adopted by the USAN council: Afimoxifene" (PDF). American Medical Association. Retrieved 2008-03-26.
  4. ^ Goyal A, Mansel RE (16 November 2016). "Mastalgia". In Jatoi I, Rody A (eds.). Management of Breast Diseases. Springer. pp. 77–. ISBN 978-3-319-46356-8.
  5. Mansel R, Goyal A, Nestour EL, Masini-Etévé V, O'Connell K (December 2007). "A phase II trial of Afimoxifene (4-hydroxytamoxifen gel) for cyclical mastalgia in premenopausal women". Breast Cancer Research and Treatment. 106 (3): 389–397. doi:10.1007/s10549-007-9507-x. PMID 17351746. S2CID 22382077.
  6. Prossnitz ER, Arterburn JB (July 2015). "International Union of Basic and Clinical Pharmacology. XCVII. G Protein-Coupled Estrogen Receptor and Its Pharmacologic Modulators". Pharmacological Reviews. 67 (3): 505–540. doi:10.1124/pr.114.009712. PMC 4485017. PMID 26023144.
  7. Levine AC (3 October 2011). Hormones and Cancer: Breast and Prostate, An Issue of Endocrinology and Metabolism Clinics of North America. Elsevier Health Sciences. pp. 271–. ISBN 978-1-4557-1239-7.
  8. Khetan SK (23 May 2014). "Anti-Androgenic Chemicals". Endocrine Disruptors in the Environment. Wiley. pp. 104–. ISBN 978-1-118-89115-5.
  9. Ariazi EA, Jordan VC (2006). "Estrogen-related receptors as emerging targets in cancer and metabolic disorders". Current Topics in Medicinal Chemistry. 6 (3): 203–215. doi:10.2174/1568026610606030203. PMID 16515477.

External links

Estrogen receptor modulators
ERTooltip Estrogen receptor
Agonists
Mixed
(SERMsTooltip Selective estrogen receptor modulators)
Antagonists
  • Coregulator-binding modulators: ERX-11
GPERTooltip G protein-coupled estrogen receptor
Agonists
Antagonists
Unknown
See also
Receptor/signaling modulators
Estrogens and antiestrogens
Androgen receptor modulators
Progesterone receptor modulators
List of estrogens
Estrogen-related receptor modulators
ERRαTooltip Estrogen-related receptor alpha
ERRβTooltip Estrogen-related receptor beta
ERRγTooltip Estrogen-related receptor gamma
See also
Receptor/signaling modulators
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