fulvestrant   Click here for help

GtoPdb Ligand ID: 1015

Synonyms: Faslodex® | ICI 182,780 | ICI 182780 | ICI182780 | ZD-9238
Approved drug
fulvestrant is an approved drug (FDA (2002), EMA (2004))
Compound class: Synthetic organic
Comment: Fulvestrant is an estrogen receptor antagonist. It behaves as a selective estrogen receptor degrader (SERD). Fulvestrant binding triggers ERα's degradation by ubiquitination.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 2
Hydrogen bond donors 2
Rotatable bonds 15
Topological polar surface area 76.74
Molecular weight 606.32
XLogP 10.2
No. Lipinski's rules broken 2
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Isomeric SMILES O=S(CCCC(C(F)(F)F)(F)F)CCCCCCCCC[C@@H]1Cc2cc(O)ccc2[C@@H]2[C@@H]1[C@@H]1CC[C@@H]([C@]1(CC2)C)O
InChI 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
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Summary of Clinical Use Click here for help
Fulvestrant is used to treat hormone receptor-positive (HR +ve) metastatic breast cancer in post-menopausal women. In September 2017, fulvestrant was FDA approved as a first-line monotherapy for HR +ve, HER2 -ve advanced breast cancer in endocrine-therapy näive, post-menopausal women. Due to its poor pharmacokinetic properties in humans (low solubility and bioavailability and high metabolism) fulvestrant has to be administered as monthly intramuscular injections.
Mechanism Of Action and Pharmacodynamic Effects Click here for help
Fulvestrant binds to estrogen receptors present in cancer cells and leads to receptor desensitisation and degradation, such that estrogen-responsiveness is lost and the cancer cells die.
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