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阿非昔芬

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阿非昔芬
臨床資料
商品名英语Drug nomenclatureTamoGel
其他名稱4-羟基他莫昔芬、4-OHT、4-HT、OHTAM
给药途径外用凝胶
识别信息
  • (Z)-4-(1-(4-(2-(dimethylamino)ethoxy)phenyl)-2-phenylbut-1-enyl)phenol
CAS号68392-35-8  checkY
PubChem CID
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard英语CompTox Chemicals Dashboard (EPA)
ECHA InfoCard100.163.120 編輯維基數據鏈接
化学信息
化学式C26H29NO2
摩尔质量387.52 g·mol−1
3D模型(JSmol英语JSmol
  • CC\C(c1ccccc1)=C(c2ccc(OCCN(C)C)cc2)/c3ccc(O)cc3
  • 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- checkY
  • Key:TXUZVZSFRXZGTL-QPLCGJKRSA-N checkY

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ERαERβ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)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 receptorERRβERRγ的拮抗剂。[7][8][9]

参考资料

  1. ^ 1.0 1.1 Afimoxifene - BHR Pharma. AdisInsight. Springer Nature Switzerland AG. 
  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. 
  3. ^ Statement on a nonproprietary name adopted by the USAN council: Afimoxifene (PDF). American Medical Association. [2008-03-26]. 
  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. 
  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. 
  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可免费查阅. PMID 26023144. doi:10.1124/pr.114.009712. 
  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. 
  8. ^ Khetan SK. Anti-Androgenic Chemicals. Endocrine Disruptors in the Environment. Wiley. 23 May 2014: 104–. ISBN 978-1-118-89115-5. 
  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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