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Identification
- Summary
Fluoroestradiol F-18 is a radiolabeled analog of estradiol used as a contrast agent in the PET imaging of estrogen receptor-positive breast cancer lesions.
- Generic Name
- Fluoroestradiol F-18
- DrugBank Accession Number
- DB15690
- Background
Fluoroestradiol F-18 is an imaging agent used with positron emission tomography (PET) to detect estrogen receptor-positive breast cancer lesions.4 The ability to image ER-positive tumors in vivo is advantageous in that, while helping to visualize tumor progression/regression, it may also be used to assess for heterogeneity in ER expression across metastases (i.e. to identify sites that no longer express ER) without the need for multiple biopsies.2
Fluoroestradiol F-18 was first granted FDA approval in May 2020, and will be developed by PETNET Solutions, Inc. and Zionexa USA under the brand name Cerianna.5 It is expected to be available in late 2020/early 2021.5
- Type
- Small Molecule
- Groups
- Approved
- Structure
Structure for Fluoroestradiol F-18 (DB15690)
- Weight
- Average: 289.381
Monoisotopic: 289.170742648 - Chemical Formula
- C18H23FO2
- Synonyms
- (18F)FES
- 16-alpha-(18-Fluoro)-17betaestradiol
- 16-alpha-(18F)Fluoro-17beta-estradiol
- 16alpha-(18F)Fluoro-17beta-estradiol
- F-18 16 alpha-Fluoroestradiol
- F-18 Fes
- Fes F-18
Pharmacology
- Indication
Fluoroestradiol F-18 is a radioactive diagnostic agent indicated for use with positron emission tomography (PET) imaging for the detection of estrogen receptor-positive lesions as an adjunct to biopsy in patients with recurrent or metastatic breast cancer.4
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Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Diagnostic agent Metastatic estrogen receptor positive breast cancer •••••••••••• •••••••••• •••••••• Diagnostic agent Recurrent estrogen receptor positive breast cancer •••••••••••• •••••••••• •••••••• - Contraindications & Blackbox Warnings
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Fluoroestradiol F-18 is an analog of estradiol that emits small amounts of radioactivity, allowing it to be detected using PET. Following intravenous administration, it accumulates in cancerous tissues expressing estrogen receptors, thus allowing for visualization of these lesions.4 Fluoroestradiol has a relatively short duration of action - at 2 hours post-injection circulating levels are <5% those at peak concentration.
The uptake of fluoroestradiol F-18 is not specific to breast cancer cells and make occur in any tumor cell expressing estrogen receptors, including those arising from the uterus or ovaries.4
- Mechanism of action
Estrogen receptor (ER)-positive breast cancers are a subset of breast cancers in which the cancerous tissue expresses estrogen receptors - these receptors provide a useful target for imaging and treatment agents. Fluoroestradiol F-18 is a fluorinated analog of estradiol that binds to estrogen receptors, allowing for PET imaging of lesions.4
Following exposure in an ER-positive breast cancer cell line (MCF-7), it was found that fluoroestradiol F-18 bound with a Kd of 0.13 ± 0.02 nM, a Bmax of 1901 ± 89 fmol/mg, and a IC50 = 0.085 nM.4
Target Actions Organism UEstrogen receptor binderHumans UEstrogen receptor beta binderHumans - Absorption
Not Available
- Volume of distribution
As fluoroestradiol and its metabolites undergo enterohepatic circulation,2 it is found primarily distributed within the hepatobiliary system.4 It also distributes to the intestines, heart wall, blood, kidney, uterus, and bladder.4
- Protein binding
Following intravenous administration, approximately 95% of fluoroestradiol F-18 is protein-bound4 to both albumin and sex hormone-binding globulin.2
- Metabolism
Fluoroestradiol F-18 is highly extracted and metabolized by the liver - at 2 hours post-administration, only 10% of the total activity is attributable to unmetabolized parent drug.2 The majority of generated metabolites are products of glucuronide or sulfate conjugation.3
- Route of elimination
Elimination is primarily via urinary and biliary excretion.4 Unbound metabolites comprising mainly glucuronide and sulfate conjugates are secreted in the bile, reabsorbed via enterohepatic circulation, and then renally excreted.2
- Half-life
Not Available
- Clearance
Fluoroestradiol F-18 is rapidly cleared from the blood by the liver.2
- Adverse Effects
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.- Toxicity
Not Available
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Integrate drug-drug
interactions in your softwareBazedoxifene Bazedoxifene may decrease effectiveness of Fluoroestradiol F-18 as a diagnostic agent. Clomifene Clomifene may decrease effectiveness of Fluoroestradiol F-18 as a diagnostic agent. Fulvestrant Fulvestrant may decrease effectiveness of Fluoroestradiol F-18 as a diagnostic agent. Lasofoxifene Lasofoxifene may decrease effectiveness of Fluoroestradiol F-18 as a diagnostic agent. Ospemifene Ospemifene may decrease effectiveness of Fluoroestradiol F-18 as a diagnostic agent. - Food Interactions
- No interactions found.
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Cerianna Injection 100 mCi/1mL Intravenous GE Healthcare Inc. 2020-05-20 Not applicable US 
Categories
- Drug Categories
- Classification
- Not classified
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- T32277KB09
- CAS number
- 94153-53-4
- InChI Key
- KDLLNMRYZGUVMA-ZYMZXAKXSA-N
- 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
- IUPAC Name
- (1R,2R,3aS,3bR,9bS,11aS)-2-(¹⁸F)fluoro-11a-methyl-1H,2H,3H,3aH,3bH,4H,5H,9bH,10H,11H,11aH-cyclopenta[a]phenanthrene-1,7-diol
- SMILES
- [H][C@@]12C[C@@H]([18F])[C@H](O)[C@@]1(C)CC[C@]1([H])C3=C(CC[C@@]21[H])C=C(O)C=C3
References
- Synthesis Reference
Kiesewetter DO, Kilbourn MR, Landvatter SW, Heiman DF, Katzenellenbogen JA, Welch MJ: Preparation of four fluorine- 18-labeled estrogens and their selective uptakes in target tissues of immature rats. J Nucl Med. 1984 Nov;25(11):1212-21.
- General References
- Liu Y, Ma H, Yao J: ERalpha, A Key Target for Cancer Therapy: A Review. Onco Targets Ther. 2020 Mar 11;13:2183-2191. doi: 10.2147/OTT.S236532. eCollection 2020. [Article]
- Liao GJ, Clark AS, Schubert EK, Mankoff DA: 18F-Fluoroestradiol PET: Current Status and Potential Future Clinical Applications. J Nucl Med. 2016 Aug;57(8):1269-75. doi: 10.2967/jnumed.116.175596. Epub 2016 Jun 15. [Article]
- Mankoff DA, Tewson TJ, Eary JF: Analysis of blood clearance and labeled metabolites for the estrogen receptor tracer [F-18]-16 alpha-fluoroestradiol (FES). Nucl Med Biol. 1997 May;24(4):341-8. doi: 10.1016/s0969-8051(97)00002-4. [Article]
- FDA Approved Drug Products: Cerianna (fluoroestradiol F 18) for intravenous injection [Link]
- Applied Radiology News Release: PETNET, Zionexa Announce FDA Approval of Cerianna (Fluoroestradiol F 18) [Link]
- External Links
- ChemSpider
- 9045262
- 2372221
- ZINC
- ZINC000100657549
- Wikipedia
- Fluoroestradiol_F-18
- FDA label
- Download (169 KB)
Clinical Trials
- Clinical Trials
Clinical Trial & Rare Diseases Add-on Data Package
Explore 4,000+ rare diseases, orphan drugs & condition pairs, clinical trial why stopped data, & more. Preview package Phase Status Purpose Conditions Count Start Date Why Stopped 100+ additional columns Unlock 175K+ rows when you subscribe.View sample dataNot Available Terminated Not Available Metastatic Breast Cancer 1 somestatus stop reason just information to hide 4 Recruiting Diagnostic Metastatic Breast Cancer 1 somestatus stop reason just information to hide 3 Completed Diagnostic Carcinoma Breast Stage IV / Recurrent Breast Cancer 1 somestatus stop reason just information to hide 2 Active Not Recruiting Diagnostic Breast Neoplasms / Estrogen Receptor Positive Breast Cancer / Metastatic Breast Cancer 1 somestatus stop reason just information to hide 2 Active Not Recruiting Diagnostic Estrogen Receptor Positive / Primary or Recurrent Breast Carcinoma / Stage IV Breast Cancer AJCC v6 and v7 1 somestatus stop reason just information to hide
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Injection Intravenous 100 mCi/1mL - Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
- Not Available
- Predicted Properties
Property Value Source Water Solubility 0.0345 mg/mL ALOGPS logP 3.33 ALOGPS logP 3.56 Chemaxon logS -3.9 ALOGPS pKa (Strongest Acidic) 10.33 Chemaxon pKa (Strongest Basic) -3.5 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 2 Chemaxon Hydrogen Donor Count 2 Chemaxon Polar Surface Area 40.46 Å2 Chemaxon Rotatable Bond Count 0 Chemaxon Refractivity 79.57 m3·mol-1 Chemaxon Polarizability 32.11 Å3 Chemaxon Number of Rings 4 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
- Not Available
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-0006-0090000000-3e0e8ac05029fb51ba01 Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-00al-0950000000-048f9e58b28f2b3e6fdb Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-000i-0090000000-46f7cb9f6eac69308d56 Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-000i-0090000000-a17f09213dda5f23ad29 Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-006t-0900000000-2a7b6882945893401558 Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-0079-0090000000-c12b4e37f4e7fa6802ab Predicted 1H NMR Spectrum 1D NMR Not Applicable Predicted 13C NMR Spectrum 1D NMR Not Applicable - Chromatographic Properties
Collision Cross Sections (CCS)
Not Available
Targets
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Binder
- General Function
- Nuclear hormone receptor. The steroid hormones and their receptors are involved in the regulation of eukaryotic gene expression and affect cellular proliferation and differentiation in target tissues. Ligand-dependent nuclear transactivation involves either direct homodimer binding to a palindromic estrogen response element (ERE) sequence or association with other DNA-binding transcription factors, such as AP-1/c-Jun, c-Fos, ATF-2, Sp1 and Sp3, to mediate ERE-independent signaling. Ligand binding induces a conformational change allowing subsequent or combinatorial association with multiprotein coactivator complexes through LXXLL motifs of their respective components. Mutual transrepression occurs between the estrogen receptor (ER) and NF-kappa-B in a cell-type specific manner. Decreases NF-kappa-B DNA-binding activity and inhibits NF-kappa-B-mediated transcription from the IL6 promoter and displace RELA/p65 and associated coregulators from the promoter. Recruited to the NF-kappa-B response element of the CCL2 and IL8 promoters and can displace CREBBP. Present with NF-kappa-B components RELA/p65 and NFKB1/p50 on ERE sequences. Can also act synergistically with NF-kappa-B to activate transcription involving respective recruitment adjacent response elements; the function involves CREBBP. Can activate the transcriptional activity of TFF1. Also mediates membrane-initiated estrogen signaling involving various kinase cascades. Essential for MTA1-mediated transcriptional regulation of BRCA1 and BCAS3 (PubMed:17922032). Maintains neuronal survival in response to ischemic reperfusion injury when in the presence of circulating estradiol (17-beta-estradiol/E2) (By similarity)
- Specific Function
- 14-3-3 protein binding
- Gene Name
- ESR1
- Uniprot ID
- P03372
- Uniprot Name
- Estrogen receptor
- Molecular Weight
- 66215.45 Da
References
- FDA Approved Drug Products: Cerianna (fluoroestradiol F 18) for intravenous injection [Link]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Binder
- General Function
- Nuclear hormone receptor. Binds estrogens with an affinity similar to that of ESR1/ER-alpha, and activates expression of reporter genes containing estrogen response elements (ERE) in an estrogen-dependent manner (PubMed:20074560)
- Specific Function
- Dna binding
- Gene Name
- ESR2
- Uniprot ID
- Q92731
- Uniprot Name
- Estrogen receptor beta
- Molecular Weight
- 59215.765 Da
References
- FDA Approved Drug Products: Cerianna (fluoroestradiol F 18) for intravenous injection [Link]
Carriers
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Binder
- General Function
- Functions as an androgen transport protein, but may also be involved in receptor mediated processes. Each dimer binds one molecule of steroid. Specific for 5-alpha-dihydrotestosterone, testosterone, and 17-beta-estradiol. Regulates the plasma metabolic clearance rate of steroid hormones by controlling their plasma concentration
- Specific Function
- Androgen binding
- Gene Name
- SHBG
- Uniprot ID
- P04278
- Uniprot Name
- Sex hormone-binding globulin
- Molecular Weight
- 43778.755 Da
References
- Liao GJ, Clark AS, Schubert EK, Mankoff DA: 18F-Fluoroestradiol PET: Current Status and Potential Future Clinical Applications. J Nucl Med. 2016 Aug;57(8):1269-75. doi: 10.2967/jnumed.116.175596. Epub 2016 Jun 15. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Binder
- General Function
- Binds water, Ca(2+), Na(+), K(+), fatty acids, hormones, bilirubin and drugs (Probable). Its main function is the regulation of the colloidal osmotic pressure of blood (Probable). Major zinc transporter in plasma, typically binds about 80% of all plasma zinc (PubMed:19021548). Major calcium and magnesium transporter in plasma, binds approximately 45% of circulating calcium and magnesium in plasma (By similarity). Potentially has more than two calcium-binding sites and might additionally bind calcium in a non-specific manner (By similarity). The shared binding site between zinc and calcium at residue Asp-273 suggests a crosstalk between zinc and calcium transport in the blood (By similarity). The rank order of affinity is zinc > calcium > magnesium (By similarity). Binds to the bacterial siderophore enterobactin and inhibits enterobactin-mediated iron uptake of E.coli from ferric transferrin, and may thereby limit the utilization of iron and growth of enteric bacteria such as E.coli (PubMed:6234017). Does not prevent iron uptake by the bacterial siderophore aerobactin (PubMed:6234017)
- Specific Function
- Antioxidant activity
- Gene Name
- ALB
- Uniprot ID
- P02768
- Uniprot Name
- Albumin
- Molecular Weight
- 69365.94 Da
References
- Liao GJ, Clark AS, Schubert EK, Mankoff DA: 18F-Fluoroestradiol PET: Current Status and Potential Future Clinical Applications. J Nucl Med. 2016 Aug;57(8):1269-75. doi: 10.2967/jnumed.116.175596. Epub 2016 Jun 15. [Article]
Drug created at May 29, 2020 13:45 / Updated at October 06, 2020 17:43