Afimoxifene - Misplaced Pages

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Afimoxifene
Clinical data

Trade names	TamoGel
Other names	4-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	68392-35-8
PubChem CID	449459
ChemSpider	395987
UNII	17197F0KYM
KEGG	D06551
ChEBI	CHEBI:44616
ChEMBL	ChEMBL489
CompTox Dashboard (EPA)	DTXSID7022384
ECHA InfoCard	100.163.120
Chemical and physical data
Formula	C₂₆H₂₉NO₂
Molar mass	387.523 g·mol
3D model (JSmol)	Interactive image
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
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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.

References

^ "Afimoxifene - BHR Pharma". AdisInsight. Springer Nature Switzerland AG.
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.
"Statement on a nonproprietary name adopted by the USAN council: Afimoxifene" (PDF). American Medical Association. Retrieved 2008-03-26.
^ 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.
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.
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.
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.
Khetan SK (23 May 2014). "Anti-Androgenic Chemicals". Endocrine Disruptors in the Environment. Wiley. pp. 104–. ISBN 978-1-118-89115-5.
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

4-hydroxytamoxifen at the U.S. National Library of Medicine Medical Subject Headings (MeSH)
Afimoxifene - AdisInsight

Estrogen receptor modulators

ERTooltip Estrogen receptor

Agonists

Unknown/unsorted: ERB-26
ERA-45
ERB-79
ZK-283197

Xenoestrogens: Anise-related (e.g., anethole, anol, dianethole, dianol, photoanethole)
Chalconoids (e.g., isoliquiritigenin, phloretin, phlorizin (phloridzin), wedelolactone)
Coumestans (e.g., coumestrol, psoralidin)
Flavonoids (incl. 7,8-DHF, 8-prenylnaringenin, apigenin, baicalein, baicalin, biochanin A, calycosin, catechin, daidzein, daidzin, ECG, EGCG, epicatechin, equol, formononetin, glabrene, glabridin, genistein, genistin, glycitein, kaempferol, liquiritigenin, mirificin, myricetin, naringenin, penduletin, pinocembrin, prunetin, puerarin, quercetin, tectoridin, tectorigenin)
Lavender oil
Lignans (e.g., enterodiol, enterolactone, nyasol (cis-hinokiresinol))
Metalloestrogens (e.g., cadmium)
Pesticides (e.g., alternariol, dieldrin, endosulfan, fenarimol, HPTE, methiocarb, methoxychlor, triclocarban, triclosan)
Phytosteroids (e.g., digitoxin (digitalis), diosgenin, guggulsterone)
Phytosterols (e.g., β-sitosterol, campesterol, stigmasterol)
Resorcylic acid lactones (e.g., zearalanone, α-zearalenol, β-zearalenol, zearalenone, zeranol (α-zearalanol), taleranol (teranol, β-zearalanol))
Steroid-like (e.g., deoxymiroestrol, miroestrol)
Stilbenoids (e.g., resveratrol, rhaponticin)
Synthetic xenoestrogens (e.g., alkylphenols, bisphenols (e.g., BPA, BPF, BPS), DDT, parabens, PBBs, PHBA, phthalates, PCBs)
Others (e.g., agnuside, rotundifuran)

Mixed
(SERMsTooltip Selective estrogen receptor modulators)

Antagonists

Coregulator-binding modulators: ERX-11

Noncompetitive inhibitors: Trilostane

GPERTooltip G protein-coupled estrogen receptor

Agonists	2-Methoxyestradiol 7β-Hydroxyepiandrosterone Afimoxifene (4-hydroxytamoxifen) Aldosterone Atrazine Bisphenol A Daidzein DDT (p,p'-DDT, o',p'-DDE) Diarylpropionitrile Equol Estradiol Ethinylestradiol Fulvestrant (ICI-182780) G-1 Genistein GPER-L1 GPER-L2 Hydroxytyrosol Kepone Nicotinic acid Nicotinamide Nonylphenol Oleuropein PCBs (2,2',5'-PCB-4-OH) Propylpyrazoletriol Quercetin Raloxifene Resveratrol STX Tamoxifen Tectoridin
Antagonists	CCL18 Estriol G-15 G-36 MIBE
Unknown	Diethylstilbestrol Zearalenone

See also: Receptor/signaling modulators; Estrogens and antiestrogens; Androgen receptor modulators; Progesterone receptor modulators; List of estrogens

v t e Estrogen-related receptor modulators
ERRαTooltip Estrogen-related receptor alpha	Agonists: 6,3′,4′-Trihydroxyflavone Biochanin A Bisphenol AF Cholesterol Daidzein Genistein SLU-PP-332 Antagonists: Diethylstilbestrol XCT-790
ERRβTooltip Estrogen-related receptor beta	Agonists: DY-131 (GSK-9089) GSK-4716 (GW-4716) SLU-PP-332 Antagonists: 4-Hydroxytamoxifen (afimoxifene) Bisphenol AF Diethylstilbestrol
ERRγTooltip Estrogen-related receptor gamma	Agonists: Bisphenol A DY-131 (GSK-9089) GSK-4716 (GW-4716) SLU-PP-332 Antagonists: 4-Hydroxytamoxifen (afimoxifene) Diethylstilbestrol
See also Receptor/signaling modulators

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References

External links