WARNING: This product is for research use only, not for human or veterinary use.
MedKoo CAT#: 100390
Description: Fulvestrant is a synthetic estrogen receptor antagonist. Unlike tamoxifen (which has partial agonist effects) and the aromatase inhibitors (which reduce the estrogen available to tumor cells), fulvestrant binds competitively to estrogen receptors in breast cancer cells, resulting in estrogen receptor deformation and decreased estrogen binding. In vitro studies indicate that fulvestrant reversibly inhibits the growth of tamoxifen-resistant, estrogen-sensitive, human breast cancer cell lines.
MedKoo Cat#: 100390
Chemical Formula: C32H47F5O3S
Exact Mass: 606.31661
Molecular Weight: 606.77
Elemental Analysis: C, 63.34; H, 7.81; F, 15.66; O, 7.91; S, 5.28
Synonym: ZD9238; ZD-9238; ZD 9238; ICI 182780; ICI182780; ICI-182780; ZM182780; ZM 182780; ZM-182780; Fulvestrant ; Faslodex.
IUPAC/Chemical Name: (7R,8R,9S,13S,14S,17S)-13-methyl-7-(9-((4,4,5,5,5-pentafluoropentyl)sulfinyl)nonyl)-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthrene-3,17-diol
InChi Key: VWUXBMIQPBEWFH-WCCTWKNTSA-N
InChi Code: InChI=1S/C32H47F5O3S/c1-30-17-15-26-25-12-11-24(38)21-23(25)20-22(29(26)27(30)13-14-28(30)39)10-7-5-3-2-4-6-8-18-41(40)19-9-16-31(33,34)32(35,36)37/h11-12,21-22,26-29,38-39H,2-10,13-20H2,1H3/t22-,26-,27+,28+,29-,30+,41?/m1/s1
SMILES Code: OC1=CC=C2[C@@]3([H])CC[C@]4(C)[C@@H](O)CC[C@@]4([H])[C@]3([H])[C@H](CCCCCCCCCS(CCCC(F)(F)C(F)(F)F)=O)CC2=C1
Fulvestrant is a white powder with a molecular weight of 606.77. The solution for injection is a clear, colorless to yellow, viscous liquid. Each injection contains as inactive ingredients: Alcohol, USP, Benzyl Alcohol, NF, and Benzyl Benzoate, USP, as co-solvents, and Castor Oil, USP as a co-solvent and release rate modifier. FASLODEX is supplied in sterile single patient pre-filled syringes containing 50-mg/mL fulvestrant either as a single 5 mL or two concurrent 2.5 mL injections to deliver the required monthly dose. FASLODEX is administered as an intramuscular injection of 250 mg once monthly.
Many breast cancers have estrogen receptors (ER), and the growth of these tumors can be stimulated by estrogen. Fulvestrant is an estrogen receptor antagonist that binds to the estrogen receptor in a competitive manner with affinity comparable to that of estradiol. Fulvestrant downregulates the ER protein in human breast cancer cells. In a clinical study in postmenopausal women with primary breast cancer treated with single doses of FASLODEX 15-22 days prior to surgery, there was evidence of increasing down regulation of ER with increasing dose. This was associated with a dose-related decrease in the expression of the progesterone receptor, an estrogen-regulated protein. These effects on the ER pathway were also associated with a decrease in Ki67 labeling index, a marker of cell proliferation. In vitro studies demonstrated that fulvestrant is a reversible inhibitor of the growth of tamoxifen-resistant, as well as estrogen-sensitive human breast cancer (MCF-7) cell lines. In in vivo tumor studies, fulvestrant delayed the establishment of tumors from xenografts of human breast cancer MCF-7 cells in nude mice. Fulvestrant inhibited the growth of established MCF-7 xenografts and of tamoxifen-resistant breast tumor xenografts. Fulvestrant resistant breast tumor xenografts may also be cross-resistant to tamoxifen. Fulvestrant showed no agonist-type effects in in vivo uterotropic assays in immature or ovariectomized mice and rats. In in vivo studies in immature rats and ovariectomized monkeys, fulvestrant blocked the uterotrophic action of estradiol. In postmenopausal women, the absence of changes in plasma concentrations of FSH and LH in response to fulvestrant treatment (250 mg monthly) suggests no peripheral steroidal effects.
1: Ciruelos E, Pascual T, Arroyo Vozmediano ML, Blanco M, Manso L, Parrilla L, MuÃ±oz C, Vega E, CalderÃ³n MJ, Sancho B, Cortes-Funes H. The therapeutic role of fulvestrant in the management of patients with hormone receptor-positive breast cancer. Breast. 2014 Mar 1. pii: S0960-9776(14)00017-4. doi: 10.1016/j.breast.2014.01.016. [Epub ahead of print] Review. PubMed PMID: 24589524.
2: Al-Mubarak M, Sacher AG, Ocana A, Vera-Badillo F, Seruga B, Amir E. Fulvestrant for advanced breast cancer: a meta-analysis. Cancer Treat Rev. 2013 Nov;39(7):753-8. doi: 10.1016/j.ctrv.2013.03.004. Epub 2013 Jun 10. Review. PubMed PMID: 23764179.
3: EstÃ©vez L, Alvarez I, Tusquets I, SeguÃ MA, MuÃ±oz M, FernÃ¡ndez Y, Lluch A. Finding the right dose of fulvestrant in breast cancer. Cancer Treat Rev. 2013 Apr;39(2):136-41. doi: 10.1016/j.ctrv.2012.06.003. Epub 2012 Jul 15. Review. PubMed PMID: 22795960.
4: Yano S, Kamano S, Sato T, Chen L. [Pharmacological and clinical profiles of Fulvestrant (Faslodex(Â®)) in the treatment of advanced or recurrenced breast cancer]. Nihon Yakurigaku Zasshi. 2012 Feb;139(2):75-82. Review. Japanese. PubMed PMID: 22322932.
5: Krell J, Januszewski A, Yan K, Palmieri C. Role of fulvestrant in the management of postmenopausal breast cancer. Expert Rev Anticancer Ther. 2011 Nov;11(11):1641-52. doi: 10.1586/era.11.138. Review. PubMed PMID: 22050013.
6: Howell A, Sapunar F. Fulvestrant revisited: efficacy and safety of the 500-mg dose. Clin Breast Cancer. 2011 Aug;11(4):204-10. doi: 10.1016/j.clbc.2011.02.002. Epub 2011 May 4. Review. PubMed PMID: 21729658.
7: Scott SM, Brown M, Come SE. Emerging data on the efficacy and safety of fulvestrant, a unique antiestrogen therapy for advanced breast cancer. Expert Opin Drug Saf. 2011 Sep;10(5):819-26. doi: 10.1517/14740338.2011.595560. Epub 2011 Jun 24. Review. PubMed PMID: 21699443.
8: Croxtall JD, McKeage K. Fulvestrant: a review of its use in the management of hormone receptor-positive metastatic breast cancer in postmenopausal women. Drugs. 2011 Feb 12;71(3):363-80. doi: 10.2165/11204810-000000000-00000. Review. PubMed PMID: 21319872.
9: Johnston SJ, Cheung KL. Fulvestrant - a novel endocrine therapy for breast cancer. Curr Med Chem. 2010;17(10):902-14. Review. PubMed PMID: 20156170.
10: Kabos P, Borges VF. Fulvestrant: a unique antiendocrine agent for estrogen-sensitive breast cancer. Expert Opin Pharmacother. 2010 Apr;11(5):807-16. doi: 10.1517/14656561003641982. Review. PubMed PMID: 20151846.