Fulvestrantのソースを表示

{{Short description|Hormonal antineoplastic drug}}
{{Use dmy dates|date=May 2024}}
{{cs1 config |name-list-style=vanc |display-authors=6}}
{{Infobox drug
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 410130476
| image = Fulvestrant.svg
| width = 250
| alt = 

<!-- Clinical data -->
| pronounce = {{IPAc-en|f|ʊ|l|ˈ|v|ɛ|s|t|ɹ|ə|n|t}}<br />{{respell|fuul|VES|trənt}}
| tradename = Faslodex, others
| Drugs.com = {{drugs.com|monograph|fulvestrant}}
| MedlinePlus = a607031
| DailyMedID = Fulvestrant
| pregnancy_AU = D
| pregnancy_AU_comment = 
| pregnancy_category = 
| routes_of_administration = [[Intramuscular injection]]
| class = [[Antiestrogen]]
| ATC_prefix = L02
| ATC_suffix = BA03
| ATC_supplemental = 

<!-- Legal status -->
| legal_AU = S4
| legal_AU_comment = 
| legal_BR = <!-- OTC, A1, A2, A3, B1, B2, C1, C2, C3, C4, C5, D1, D2, E, F -->
| legal_BR_comment = 
| legal_CA = <!-- OTC, Rx-only, Schedule I, II, III, IV, V, VI, VII, VIII -->
| legal_CA_comment = 
| legal_DE = <!-- Anlage I, II, III or Unscheduled -->
| legal_DE_comment = 
| legal_NZ = <!-- Class A, B, C -->
| legal_NZ_comment = 
| legal_UK = POM
| legal_UK_comment = <ref name=UKlabel2016 />
| legal_US = Rx-only
| legal_US_comment = <ref name="Faslodex FDA label">{{cite web | title=Faslodex- fulvestrant injection | website=DailyMed | date=25 September 2020 | url=https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=83d7a440-e904-4e36-afb5-cb02b1c919f7 | access-date=24 May 2024 | archive-date=11 December 2023 | archive-url=https://web.archive.org/web/20231211231649/https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=83d7a440-e904-4e36-afb5-cb02b1c919f7 | url-status=live }}</ref>
| legal_EU = Rx-only
| legal_EU_comment = <ref>{{cite web | title=Faslodex | website=[[European Medicines Agency]] (EMA) | date=10 March 2004 | url=https://www.ema.europa.eu/en/medicines/human/EPAR/faslodex | access-date=24 May 2024 | archive-date=19 October 2021 | archive-url=https://web.archive.org/web/20211019022354/https://www.ema.europa.eu/en/medicines/human/EPAR/faslodex | url-status=live }}</ref>
| legal_UN = <!-- N I, II, III, IV / P I, II, III, IV -->
| legal_UN_comment = 
| legal_status = Rx-only

<!-- Pharmacokinetic data -->
| bioavailability = Low<ref name="Dörwald2013" />
| protein_bound = 99%<ref name="Dörwald2013" />
| metabolism = [[Hydroxylation]], [[conjugation (biochemistry)|conjugation]] ([[glucuronidation]], [[sulfation]])<ref name="Dörwald2013" />
| metabolites = 
| onset = 
| elimination_half-life = {{abbrlink|IM|Intramuscular injection}}: 40–50 days<ref name="Dörwald2013">{{cite book |first=Florencio Zaragoza |last=Dörwald |title=Lead Optimization for Medicinal Chemists: Pharmacokinetic Properties of Functional Groups and Organic Compounds |url=https://books.google.com/books?id=YTeY9ZEfNccC&pg=PA486 |date=4 February 2013 |publisher=John Wiley & Sons |isbn=978-3-527-64565-7 |pages=486– |access-date=20 May 2018 |archive-date=12 January 2023 |archive-url=https://web.archive.org/web/20230112174738/https://books.google.com/books?id=YTeY9ZEfNccC&pg=PA486 |url-status=live }}</ref>
| duration_of_action = 
| excretion =

<!-- Identifiers -->
| CAS_number_Ref = {{cascite|correct|??}}
| CAS_number = 129453-61-8
| CAS_supplemental = 
| PubChem = 104741
| IUPHAR_ligand = 1015
| DrugBank_Ref = {{drugbankcite|changed|drugbank}}
| DrugBank = DB00947
| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
| ChemSpiderID = 94553
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 22X328QOC4
| KEGG_Ref = {{keggcite|changed|kegg}}
| KEGG = D01161
| ChEBI_Ref = {{ebicite|changed|EBI}}
| ChEBI = 31638
| ChEMBL_Ref = {{ebicite|changed|EBI}}
| ChEMBL = 1358
| NIAID_ChemDB = 
| PDB_ligand = 
| synonyms = 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

<!-- Chemical and physical data -->
| IUPAC_name = (7''R'',8''R'',9''S'',13''S'',14''S'',17''S'')-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
| C=32 | H=47 | F=5 | O=3 | S=1
| 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
| StdInChI = 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
| StdInChI_comment = 
| StdInChIKey = VWUXBMIQPBEWFH-WCCTWKNTSA-N
| density = 
| density_notes = 
| melting_point = 
| melting_high = 
| melting_notes = 
| boiling_point = 
| boiling_notes = 
| solubility = 
| sol_units = 
| specific_rotation = 
}}

'''Fulvestrant''', sold under the brand name '''Faslodex''' among others, is an [[Antiestrogen|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.<ref name="Faslodex FDA label" /> It is given by [[intramuscular injection|injection into a muscle]].<ref name="Cochrane2016">{{cite journal | vauthors = Lee CI, Goodwin A, Wilcken N | title = Fulvestrant for hormone-sensitive metastatic breast cancer | journal = The Cochrane Database of Systematic Reviews | volume = 1 | pages = CD011093 | date = January 2017 | issue = 1 | pmid = 28043088 | pmc = 6464820 | doi = 10.1002/14651858.CD011093.pub2 }}</ref>

Fulvestrant is a [[selective estrogen receptor degrader]] (SERD) and was first-in-class to be approved.<ref name=NRDD2016>{{cite journal | vauthors = Lai AC, Crews CM | title = Induced protein degradation: an emerging drug discovery paradigm | journal = Nature Reviews. Drug Discovery | volume = 16 | issue = 2 | pages = 101–114 | date = February 2017 | pmid = 27885283 | pmc = 5684876 | doi = 10.1038/nrd.2016.211 }}</ref> It works by binding to the [[estrogen receptor]] and destabilizing it, causing the cell's normal [[protein degradation]] processes to destroy it.<ref name=NRDD2016/>

Fulvestrant was approved for medical use in the United States in 2002.<ref name=AHFS2017>{{cite web|title=Fulvestrant|url=https://www.drugs.com/monograph/fulvestrant.html|publisher=The American Society of Health-System Pharmacists|access-date=8 January 2017|archive-date=2 February 2017|archive-url=https://web.archive.org/web/20170202013913/https://www.drugs.com/monograph/fulvestrant.html|url-status=live}}</ref>