Fulvestrant

Fulvestrant
Clinical data
Pronunciation	/fʊlˈvɛstrənt/; fuul-VES-trənt
Trade names	Faslodex, others
Other names	ICI-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.com	Monograph
MedlinePlus	a607031
License data	US DailyMed: Fulvestrant;
Pregnancy; category	AU: D;
Routes of; administration	Intramuscular injection
Drug class	Antiestrogen
ATC code	L02BA03 (WHO) ;
Legal status
Legal status	AU: S4 (Prescription only); UK: POM (Prescription only); US: ℞-only; EU: Rx-only; In general: ℞ (Prescription only);
Pharmacokinetic data
Bioavailability	Low
Protein binding	99%
Metabolism	Hydroxylation, conjugation (glucuronidation, sulfation)
Elimination half-life	IMTooltip Intramuscular injection: 40–50 days
Identifiers
	IUPAC name (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	129453-61-8 ;
PubChem CID	104741;
IUPHAR/BPS	1015;
DrugBank	DB00947 ;
ChemSpider	94553 ;
UNII	22X328QOC4;
KEGG	D01161 ;
ChEBI	CHEBI:31638 ;
ChEMBL	ChEMBL1358 ;
CompTox Dashboard (EPA)	DTXSID4022369 ;
ECHA InfoCard	100.170.955
Chemical and physical data
Formula	C32H47F5O3S
Molar mass	606.78 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES 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 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;
	(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]

^ Cite error: The named reference UKlabel2016 was invoked but never defined (see the help page).
^ ^a ^b "Faslodex- fulvestrant injection". DailyMed. 25 September 2020. Archived from the original on 11 December 2023. Retrieved 24 May 2024.
^ "Faslodex". European Medicines Agency (EMA). 10 March 2004. Archived from the original on 19 October 2021. Retrieved 24 May 2024.
^ ^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.
^ 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.
^ ^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.
^ "Fulvestrant". The American Society of Health-System Pharmacists. Archived from the original on 2 February 2017. Retrieved 8 January 2017.

[UKlabel2016-1] Cite error: The named reference UKlabel2016 was invoked but never defined (see the help page).

[Faslodex_FDA_label-2] "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.

[Dörwald2013-4] 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.

[Cochrane2016-5] 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.

[NRDD2016-6] 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.

[AHFS2017-7] "Fulvestrant". The American Society of Health-System Pharmacists. Archived from the original on 2 February 2017. Retrieved 8 January 2017.

[1]

[2]

[3]

[4]

[5]

[6]

[7]