Fluoroestradiol F-18

Fluoroestradiol F-18
Clinical data
Trade names	Cerianna
Other names	[18F]16α-Fluoroestradiol; [18F]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-decahydrocyclopenta[a]phenanthrene-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	C18H23[18F]O2
Molar mass	289.37
3D model (JSmol)	Interactive image;
	SMILES CC12CCC3C(C1CC(C2O)[18F])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 [¹⁸F]16α-fluoroestradiol and sold under the brand name Cerianna, is a radioactive diagnostic agent indicated for use with positron emission tomography (PET) imaging.^[1]^[2]^[3]^[4]^[5] It is an analog of estrogen and is used to detect estrogen receptor-positive breast cancer lesions.^[1]

Chemistry

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

Fluoroestradiol F-18 was approved for medical use in the United States in May 2020.^[6]

^ ^a ^b ^c ^d ^e ^f ^g "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-[¹⁸F]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). "¹⁸F-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). "¹⁸F-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). "¹⁸F-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.