Fulvestrant
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MedKoo CAT#: 100390

CAS#: 129453-61-8

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.


Chemical Structure

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Fulvestrant
CAS# 129453-61-8

Theoretical Analysis

MedKoo Cat#: 100390
Name: Fulvestrant
CAS#: 129453-61-8
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

Price and Availability

Size Price Availability Quantity
25.0mg USD 90.0 Ready to ship
50.0mg USD 150.0 Ready to ship
100.0mg USD 250.0 Ready to ship
200.0mg USD 450.0 Ready to ship
500.0mg USD 1050.0 Ready to ship
1.0g USD 1750.0 Ready to ship
2.0g USD 2650.0 Ready to ship
5.0g USD 4250.0 Ready to ship
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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

Appearance: white to off-white solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO, not in water

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

Biological target: Fulvestrant (ICI-182780, ZD 9238, ZM 182780) is an estrogen receptor (ER) antagonist with IC50 of 0.94 nM in a cell-free assay.
In vitro activity: Fulvestrant (ICI 182780; ZD 9238; ZM 182780) is a potent and specific inhibitor of estrogen action and demonstrates excellent growth-inhibitory effects in both cell and animal models of human breast cancer. Fulvestrant inhibits MCF-7 human breast cancer cells growth with IC50 of 290 nM. The relative binding affinities of Fulvestrant is 0.89. Fulvestrant has significantly increased antiestrogenic potency and retains pure estrogen antagonist activity. Reference: Br J Cancer. 2004 Mar;90 Suppl 1(Suppl 1):S2-6. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2750773/
In vivo activity: When administered alone, parenterally (s.c.), to immature female rats Fulvestrant (ICI 182,780) is devoid of uterotropic activity. Complete antagonism of Estrogen action is achieved with a dose of 0.5 mg Fulvestrant/kg/day s.c. The effects of Fulvestrant administered p.o. are qualitatively similar but potency is reduced by an order of magnitude compare with s.c. dosing (ED50 0.46 and complete antagonism at 5 mg/kg/day p.o.) Reference: Br J Cancer. 2004 Mar;90 Suppl 1(Suppl 1):S2-6. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2750773/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
Soluble in DMSO, not in water 100.0 164.81
Ethanol 100.0 164.81

Preparing Stock Solutions

The following data is based on the product molecular weight 606.77 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol: 1. Wakeling AE, Dukes M, Bowler J. A potent specific pure antiestrogen with clinical potential. Cancer Res. 1991 Aug 1;51(15):3867-73. PMID: 1855205. 2. Huynh H, Nickerson T, Pollak M, Yang X. Regulation of insulin-like growth factor I receptor expression by the pure antiestrogen ICI 182780. Clin Cancer Res. 1996 Dec;2(12):2037-42. PMID: 9816164. 3. Wakeling AE, Dukes M, Bowler J. A potent specific pure antiestrogen with clinical potential. Cancer Res. 1991 Aug 1;51(15):3867-73. PMID: 1855205. 4. Kuhn J, Dina OA, Goswami C, Suckow V, Levine JD, Hucho T. GPR30 estrogen receptor agonists induce mechanical hyperalgesia in the rat. Eur J Neurosci. 2008 Apr;27(7):1700-9. doi: 10.1111/j.1460-9568.2008.06131.x. Epub 2008 Mar 26. PMID: 18371086.
In vitro protocol: 1. Wakeling AE, Dukes M, Bowler J. A potent specific pure antiestrogen with clinical potential. Cancer Res. 1991 Aug 1;51(15):3867-73. PMID: 1855205. 2. Huynh H, Nickerson T, Pollak M, Yang X. Regulation of insulin-like growth factor I receptor expression by the pure antiestrogen ICI 182780. Clin Cancer Res. 1996 Dec;2(12):2037-42. PMID: 9816164.
In vivo protocol: 1. Wakeling AE, Dukes M, Bowler J. A potent specific pure antiestrogen with clinical potential. Cancer Res. 1991 Aug 1;51(15):3867-73. PMID: 1855205. 2. Kuhn J, Dina OA, Goswami C, Suckow V, Levine JD, Hucho T. GPR30 estrogen receptor agonists induce mechanical hyperalgesia in the rat. Eur J Neurosci. 2008 Apr;27(7):1700-9. doi: 10.1111/j.1460-9568.2008.06131.x. Epub 2008 Mar 26. PMID: 18371086.

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1: Ciruelos E, Pascual T, Arroyo Vozmediano ML, Blanco M, Manso L, Parrilla L, Muñoz C, Vega E, Calderón 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: Estévez L, Alvarez I, Tusquets I, Seguí MA, Muñoz M, Fernández 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(®)) 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.



Additional Information

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.