Fulvestrant

Fulvestrant
Clinical data
Pronunciation/fʊlˈvɛstrənt/
fuul-VES-trənt
Trade namesFaslodex, others
Other namesICI-182780; ZD-182780; ZD-9238; 7α-[9-[(4,4,5,5,5-Pentafluoropentyl)-sulfinyl]nonyl]estra-1,3,5(10)-triene-3,17β-diol
AHFS/Drugs.comMonograph
MedlinePlusa607031
License data
Pregnancy
category
  • AU: D
Routes of
administration		Intramuscular injection
Drug classAntiestrogen
ATC code
Legal status
Legal status
  • AU: S4 (Prescription only)
  • UK: POM (Prescription only)[1]
  • US: ℞-only[2]
  • EU: Rx-only[3]
  • In general: ℞ (Prescription only)
Pharmacokinetic data
BioavailabilityLow[4]
Protein binding99%[4]
MetabolismHydroxylation, conjugation (glucuronidation, sulfation)[4]
Elimination half-lifeIMTooltip Intramuscular injection: 40–50 days[4]
Identifiers
  • (7R,8R,9S,13S,14S,17S)-13-methyl-7-[9-(4,4,5,5,5-pentafluoropentylsulfinyl)nonyl]-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthrene-3,17-diol
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.170.955 Edit this at Wikidata
Chemical and physical data
FormulaC32H47F5O3S
Molar mass606.78 g·mol−1
3D model (JSmol)
  • C[C@]12CC[C@@H]3c4ccc(O)cc4CC(CCCCCCCCCS(=O)CCCC(F)(F)C(F)(F)F)[C@H]3[C@@H]1CC[C@@H]2O
  • 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
  • Key:VWUXBMIQPBEWFH-WCCTWKNTSA-N
 ☒NcheckY (what is this?)  (verify)

Fulvestrant, sold under the brand name Faslodex among others, is an antiestrogenic medication used to treat hormone receptor (HR)-positive metastatic breast cancer in postmenopausal women with disease progression as well as HR-positive, HER2-negative advanced breast cancer in combination with abemaciclib or palbociclib in women with disease progression after endocrine therapy.[2] It is given by injection into a muscle.[5]

Fulvestrant is a selective estrogen receptor degrader (SERD) and was first-in-class to be approved.[6] It works by binding to the estrogen receptor and destabilizing it, causing the cell's normal protein degradation processes to destroy it.[6]

Fulvestrant was approved for medical use in the United States in 2002.[7]

  1. ^ Cite error: The named reference UKlabel2016 was invoked but never defined (see the help page).
  2. ^ a b "Faslodex- fulvestrant injection". DailyMed. 25 September 2020. Archived from the original on 11 December 2023. Retrieved 24 May 2024.
  3. ^ "Faslodex". European Medicines Agency (EMA). 10 March 2004. Archived from the original on 19 October 2021. Retrieved 24 May 2024.
  4. ^ a b c d Dörwald FZ (4 February 2013). Lead Optimization for Medicinal Chemists: Pharmacokinetic Properties of Functional Groups and Organic Compounds. John Wiley & Sons. pp. 486–. ISBN 978-3-527-64565-7. Archived from the original on 12 January 2023. Retrieved 20 May 2018.
  5. ^ Lee CI, Goodwin A, Wilcken N (January 2017). "Fulvestrant for hormone-sensitive metastatic breast cancer". The Cochrane Database of Systematic Reviews. 1 (1): CD011093. doi:10.1002/14651858.CD011093.pub2. PMC 6464820. PMID 28043088.
  6. ^ a b Lai AC, Crews CM (February 2017). "Induced protein degradation: an emerging drug discovery paradigm". Nature Reviews. Drug Discovery. 16 (2): 101–114. doi:10.1038/nrd.2016.211. PMC 5684876. PMID 27885283.
  7. ^ "Fulvestrant". The American Society of Health-System Pharmacists. Archived from the original on 2 February 2017. Retrieved 8 January 2017.