 Chemical Structure.png)
Physicochemical Properties
| Exact Mass | 289.171 |
| CAS # | 94153-53-4 |
| PubChem CID | 10869981 |
| Appearance | Typically exists as solid at room temperature |
| LogP | 3.557 |
| Hydrogen Bond Donor Count | 2 |
| Hydrogen Bond Acceptor Count | 3 |
| Rotatable Bond Count | 0 |
| Heavy Atom Count | 21 |
| Complexity | 414 |
| Defined Atom Stereocenter Count | 6 |
| SMILES | C[C@]12CC[C@H]3[C@H]([C@@H]1C[C@H]([C@@H]2O)[18F])CCC4=C3C=CC(=C4)O |
| InChi Key | KDLLNMRYZGUVMA-ZYMZXAKXSA-N |
| InChi Code | 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 |
| Chemical 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 |
| HS Tariff Code | 2934.99.9001 |
| Storage |
Powder-20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month |
| Shipping Condition | Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs) |
Biological Activity
| ADME/Pharmacokinetics |
Absorption, Distribution and Excretion Elimination is primarily via urinary and biliary excretion. Unbound metabolites comprising mainly glucuronide and sulfate conjugates are secreted in the bile, reabsorbed via enterohepatic circulation, and then renally excreted. As fluoroestradiol and its metabolites undergo enterohepatic circulation, it is found primarily distributed within the hepatobiliary system. It also distributes to the intestines, heart wall, blood, kidney, uterus, and bladder. Fluoroestradiol F-18 is rapidly cleared from the blood by the liver. Metabolism / Metabolites 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. The majority of generated metabolites are products of glucuronide or sulfate conjugation. |
| Toxicity/Toxicokinetics |
Effects During Pregnancy and Lactation ◉ Summary of Use during Lactation Information in this record refers to the use of fluoroestradiol F18 (18F-FES) as a diagnostic agent. No information is available on the clinical use of fluoroestradiol F18 during breastfeeding. The manufacturer recommends that mothers avoid breastfeeding for 4 hours after administration of fluoroestradiol F18. Nursing mothers should not work with radioactive substances used in PET scans in their workplace. ◉ Effects in Breastfed Infants Relevant published information was not found as of the revision date. ◉ Effects on Lactation and Breastmilk Relevant published information was not found as of the revision date. Protein Binding Following intravenous administration, approximately 95% of fluoroestradiol F-18 is protein-bound to both albumin and sex hormone-binding globulin. |
| Additional Infomation |
Fluoroestradiol F-18 is an imaging agent used with positron emission tomography (PET) to detect estrogen receptor-positive breast cancer lesions. 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. 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. It is expected to be available in late 2020/early 2021. Fluoroestradiol f-18 is a Radioactive Diagnostic Agent. The mechanism of action of fluoroestradiol f-18 is as a Positron Emitting Activity. F-18 16 Alpha-Fluoroestradiol is a radiopharmaceutical consisting of an estradiol analogue radiolabeled with the positron-emitting isotope fluorine F 18. F-18 16 alpha-fluoroestradiol is actively taken up in tumor cells expressing the estrogen receptor (ER), allowing visualization of ER-positive tumor cells with positron emission tomography (PET). Uptake of this agent depends upon the ER status of target tissues. Drug 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. FDA Label Detection of increased expression of oestrogen receptors in tissues and organs for diagnostic purposes Detection of pathological expression of estrogen receptors in organs and tissues 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. 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. Pharmacodynamics 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. 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. |
Solubility Data
| Solubility (In Vitro) | May dissolve in DMSO (in most cases), if not, try other solvents such as H2O, Ethanol, or DMF with a minute amount of products to avoid loss of samples |
| Solubility (In Vivo) |
Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples. Injection Formulations (e.g. IP/IV/IM/SC) Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline) *Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution. Injection Formulation 2: DMSO : PEG300 ：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO → 900 μL Corn oil) Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals). Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO → 900 μL (20% SBE-β-CD in saline)] *Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. Injection Formulation 5: 2-Hydroxypropyl-β-cyclodextrin : Saline = 50 : 50 (i.e. 500 μL 2-Hydroxypropyl-β-cyclodextrin → 500 μL Saline) Injection Formulation 6: DMSO : PEG300 : castor oil : Saline = 5 : 10 : 20 : 65 (i.e. 50 μL DMSO → 100 μLPEG300 → 200 μL castor oil → 650 μL Saline) Injection Formulation 7: Ethanol : Cremophor : Saline = 10： 10 : 80 (i.e. 100 μL Ethanol → 100 μL Cremophor → 800 μL Saline) Injection Formulation 8: Dissolve in Cremophor/Ethanol (50 : 50), then diluted by Saline Injection Formulation 9: EtOH : Corn oil = 10 : 90 (i.e. 100 μL EtOH → 900 μL Corn oil) Injection Formulation 10: EtOH : PEG300：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL EtOH → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Oral Formulations Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium) Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals). Oral Formulation 3: Dissolved in PEG400 Oral Formulation 4: Suspend in 0.2% Carboxymethyl cellulose Oral Formulation 5: Dissolve in 0.25% Tween 80 and 0.5% Carboxymethyl cellulose Oral Formulation 6: Mixing with food powders Note: Please be aware that the above formulations are for reference only. InvivoChem strongly recommends customers to read literature methods/protocols carefully before determining which formulation you should use for in vivo studies, as different compounds have different solubility properties and have to be formulated differently. (Please use freshly prepared in vivo formulations for optimal results.) |