阿非昔芬

阿非昔芬
临床资料
商品名（英语：Drug nomenclature）	TamoGel
其他名称	4-羟基他莫昔芬、4-OHT、4-HT、OHTAM
给药途径	外用（凝胶）
识别信息
	IUPAC命名法 (Z)-4-(1-(4-(2-(dimethylamino)ethoxy)phenyl)-2-phenylbut-1-enyl)phenol; ;
CAS号	68392-35-8
PubChem CID	449459;
ChemSpider	395987 ;
UNII	17197F0KYM;
KEGG	D06551 ;
ChEBI	CHEBI:44616;
ChEMBL	ChEMBL489 ;
CompTox Dashboard（英语：CompTox Chemicals Dashboard） (EPA)	DTXSID7022384 ;
ECHA InfoCard	100.163.120
化学信息
化学式	C26H29NO2
摩尔质量	387.52 g·mol−1
3D模型（JSmol（英语：JSmol））	交互式图像;
	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 ;

阿非昔芬（INN：afimoxifene），也叫4-羟基他莫昔芬（简称4-OHT）,是三苯乙烯基的选择性雌激素受体调节剂（SERM），也是他莫昔芬的活性代谢物。^[1]^[2]^[3]该药物正在开发中，暂定品牌为TamoGel，作为治疗乳腺增生的外用凝胶（英语：Topical gels）。^[1]^[4]它已经完成了针对周期性乳腺痛的II期临床试验，^[5]但阿非昔芬获批用于该适应症并上市之前还需要进一步研究。^[4]

阿非昔芬是一种SERM，因此可作为雌激素受体 ERα和ERβ的组织选择性（英语：Tissue selectivity）激动剂或拮抗剂（英语：Agonist-antagonist），根据组织的不同，具有混合的雌激素（英语：Estrogen (medication)）和抗雌激素（英语：Antiestrogen）活性。它也是G蛋白偶联雌激素受体（英语：GPER）（GPER）的激动剂，具有相对较低的亲和力（100-1,000 nM，对比雌二醇的3-6 nM）。^[6]除了其雌激素和抗雌激素活性外，阿非昔芬还被发现可作为雌激素相关受体（英语：Estrogen-related receptor）ERRβ和ERRγ的拮抗剂。^[7]^[8]^[9]

参考资料

^ ^1.0 ^1.1 Afimoxifene - BHR Pharma. AdisInsight. Springer Nature Switzerland AG.
^ Desta Z, Ward BA, Soukhova NV, Flockhart DA. 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. September 2004, 310 (3): 1062–1075. PMID 15159443. S2CID 21413981. doi:10.1124/jpet.104.065607.
^ Statement on a nonproprietary name adopted by the USAN council: Afimoxifene (PDF). American Medical Association. [2008-03-26].
^ ^4.0 ^4.1 Goyal A, Mansel RE. Mastalgia. Jatoi I, Rody A (编). Management of Breast Diseases. Springer. 16 November 2016: 77–. ISBN 978-3-319-46356-8.
^ Mansel R, Goyal A, Nestour EL, Masini-Etévé V, O'Connell K. A phase II trial of Afimoxifene (4-hydroxytamoxifen gel) for cyclical mastalgia in premenopausal women. Breast Cancer Research and Treatment. December 2007, 106 (3): 389–397. PMID 17351746. S2CID 22382077. doi:10.1007/s10549-007-9507-x.
^ Prossnitz ER, Arterburn JB. International Union of Basic and Clinical Pharmacology. XCVII. G Protein-Coupled Estrogen Receptor and Its Pharmacologic Modulators. Pharmacological Reviews. July 2015, 67 (3): 505–540. PMC 4485017  . PMID 26023144. doi:10.1124/pr.114.009712.
^ Levine AC. Hormones and Cancer: Breast and Prostate, An Issue of Endocrinology and Metabolism Clinics of North America. Elsevier Health Sciences. 3 October 2011: 271–. ISBN 978-1-4557-1239-7.
^ Khetan SK. Anti-Androgenic Chemicals. Endocrine Disruptors in the Environment. Wiley. 23 May 2014: 104–. ISBN 978-1-118-89115-5.
^ Ariazi EA, Jordan VC. Estrogen-related receptors as emerging targets in cancer and metabolic disorders. Current Topics in Medicinal Chemistry. 2006, 6 (3): 203–215. PMID 16515477. doi:10.2174/1568026610606030203.

外部链接

[AdisInsight-1] 1.0 ^1.1 Afimoxifene - BHR Pharma. AdisInsight. Springer Nature Switzerland AG.

[Desta_2004-2] Desta Z, Ward BA, Soukhova NV, Flockhart DA. 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. September 2004, 310 (3): 1062–1075. PMID 15159443. S2CID 21413981. doi:10.1124/jpet.104.065607.

[AMA_USAN-3] Statement on a nonproprietary name adopted by the USAN council: Afimoxifene (PDF). American Medical Association. [2008-03-26].

[JatoiRody2016-4] 4.0 ^4.1 Goyal A, Mansel RE. Mastalgia. Jatoi I, Rody A (编). Management of Breast Diseases. Springer. 16 November 2016: 77–. ISBN 978-3-319-46356-8.

[pmid17351746-5] Mansel R, Goyal A, Nestour EL, Masini-Etévé V, O'Connell K. A phase II trial of Afimoxifene (4-hydroxytamoxifen gel) for cyclical mastalgia in premenopausal women. Breast Cancer Research and Treatment. December 2007, 106 (3): 389–397. PMID 17351746. S2CID 22382077. doi:10.1007/s10549-007-9507-x.

[pmid26023144-6] Prossnitz ER, Arterburn JB. International Union of Basic and Clinical Pharmacology. XCVII. G Protein-Coupled Estrogen Receptor and Its Pharmacologic Modulators. Pharmacological Reviews. July 2015, 67 (3): 505–540. PMC 4485017  . PMID 26023144. doi:10.1124/pr.114.009712.

[Levine2011-7] Levine AC. Hormones and Cancer: Breast and Prostate, An Issue of Endocrinology and Metabolism Clinics of North America. Elsevier Health Sciences. 3 October 2011: 271–. ISBN 978-1-4557-1239-7.

[Khetan2014-8] Khetan SK. Anti-Androgenic Chemicals. Endocrine Disruptors in the Environment. Wiley. 23 May 2014: 104–. ISBN 978-1-118-89115-5.

[pmid16515477-9] Ariazi EA, Jordan VC. Estrogen-related receptors as emerging targets in cancer and metabolic disorders. Current Topics in Medicinal Chemistry. 2006, 6 (3): 203–215. PMID 16515477. doi:10.2174/1568026610606030203.

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