Fluoroestradiol F-18 - Misplaced Pages

(Redirected from Fluoroestradiol (18F)) Chemical compound

Pharmaceutical compound

Fluoroestradiol F-18
Clinical data

Trade names	Cerianna
Other names	16α-Fluoroestradiol; 16α-Fluoroestra-1,3,5(10)-triene-3,17β-diol
License data	US DailyMed: Fluoroestradiol
Routes of administration	Intravenous injection
Drug class	Estrogen; Diagnostic radiopharmaceutical
ATC code	V09IX11 (WHO)
Legal status
Legal status	US: ℞-only
Pharmacokinetic data
Metabolism	Liver
Excretion	Gallbladder and kidney
Identifiers
IUPAC name (8R,9S,13S,14S,16R,17R)-16-(18F)fluoranyl-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopentaphenanthrene-3,17-diol
CAS Number	94153-53-4
PubChem CID	10869981
ChemSpider	9045262
UNII	T32277KB09
KEGG	D11829
CompTox Dashboard (EPA)	DTXSID101027872
Chemical and physical data
Formula	C₁₈H₂₃O₂
Molar mass	289.37
3D model (JSmol)	Interactive image
SMILES CC12CCC3C(C1CC(C2O))CCC4=C3C=CC(=C4)O
InChI InChI=1S/C18H23FO2/c1-18-7-6-13-12-5-3-11(20)8-10(12)2-4-14(13)15(18)9-16(19)17(18)21/h3,5,8,13-17,20-21H,2,4,6-7,9H2,1H3/t13-,14-,15+,16-,17+,18+/m1/s1/i19-1 Key:KDLLNMRYZGUVMA-ZYMZXAKXSA-N

Fluoroestradiol F-18, also known as 16α-fluoroestradiol and sold under the brand name Cerianna, is a radioactive diagnostic agent indicated for use with positron emission tomography (PET) imaging. It is an analog of estrogen and is used to detect estrogen receptor-positive breast cancer lesions.

Chemistry

Chemically, fluoroestradiol F-18 is 16α-fluoro-3,17β-diol-estratriene-1,3,5(10).

Fluoroestradiol F-18 was approved for medical use in the United States in May 2020.

^ "Cerianna- fluoroestradiol f 18 injection". DailyMed. 20 May 2020. Retrieved 24 September 2020.
Katzenellenbogen JA (February 2020). "The quest for improving the management of breast cancer by functional imaging: The discovery and development of 16α-[F]fluoroestradiol (FES), a PET radiotracer for the estrogen receptor, a historical review". Nucl. Med. Biol. 92: 24–37. doi:10.1016/j.nucmedbio.2020.02.007. ISSN 0969-8051. PMC 7442693. PMID 32229068.
Evangelista L, Guarneri V, Conte PF (2016). "F-Fluoroestradiol Positron Emission Tomography in Breast Cancer Patients: Systematic Review of the Literature & Meta-Analysis". Curr Radiopharm. 9 (3): 244–257. doi:10.2174/1874471009666161019144950. PMID 27774910.
Liao GJ, Clark AS, Schubert EK, Mankoff DA (August 2016). "F-Fluoroestradiol PET: Current Status and Potential Future Clinical Applications". J. Nucl. Med. 57 (8): 1269–75. doi:10.2967/jnumed.116.175596. PMID 27307345.
Sundararajan L, Linden HM, Link JM, Krohn KA, Mankoff DA (November 2007). "F-Fluoroestradiol". Semin Nucl Med. 37 (6): 470–6. doi:10.1053/j.semnuclmed.2007.08.003. PMID 17920354.
"Cerianna: FDA-Approved Drugs". U.S. Food and Drug Administration (FDA). Retrieved 22 May 2020.

Isotopes used:

ERTooltip Estrogen receptor

Agonists

Mixed
(SERMsTooltip Selective estrogen receptor modulators)

Antagonists

GPERTooltip G protein-coupled estrogen receptor

Agonists	2-Methoxyestradiol 7β-Hydroxyepiandrosterone Afimoxifene (4-hydroxytamoxifen) Aldosterone Atrazine Bisphenol A Daidzein DDT (p,p'-DDT, o',p'-DDE) Diarylpropionitrile Equol Estradiol Ethinylestradiol Fulvestrant (ICI-182780) G-1 Genistein GPER-L1 GPER-L2 Hydroxytyrosol Kepone Nicotinic acid Nicotinamide Nonylphenol Oleuropein PCBs (2,2',5'-PCB-4-OH) Propylpyrazoletriol Quercetin Raloxifene Resveratrol STX Tamoxifen Tectoridin
Antagonists	CCL18 Estriol G-15 G-36 MIBE
Unknown	Diethylstilbestrol Zearalenone

See also: Receptor/signaling modulators; Estrogens and antiestrogens; Androgen receptor modulators; Progesterone receptor modulators; List of estrogens