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| Other Sizes |
| Targets |
Fluorenone has been shown to interact with multiple biological targets. It acts as a receptor activator for group P2 purinergic receptors in rat brain tissue. Additionally, Fluorenone can inhibit the activity of xanthine oxidase, an enzyme involved in purine metabolism. It has also been found to increase the activity of α7 nicotinic acetylcholine receptors in rat brain tissue. As a metabolite of modafinil, it possesses relatively weak dopamine reuptake inhibitory activity, suggesting some interaction with the dopaminergic system. These diverse targets indicate that Fluorenone may have multiple pharmacological effects.
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| ln Vitro |
Utilized as organic synthesis intermediates.
In vitro studies have demonstrated that Fluorenone exhibits receptor-activating properties. It has been shown to activate group P2 purinergic receptors in rat brain tissue, suggesting a role in purinergic signaling. Fluorenone also inhibits xanthine oxidase activity, an enzyme that generates reactive oxygen species during purine metabolism. This inhibition may have implications for oxidative stress and uric acid production. Additionally, Fluorenone increases the activity of α7 nicotinic acetylcholine receptors, which are involved in cognitive function and neuroprotection. Its weak dopamine reuptake inhibitory activity, as a modafinil metabolite, suggests potential effects on the central nervous system. |
| ln Vivo |
In vivo studies have evaluated the effects of Fluorenone in animal models. It has been shown to reduce infarct size in rats with myocardial infarction, indicating potential cardioprotective effects. As a metabolite of fluorene, Fluorenone has been detected in the mosquitofish (Gambusia) in model ecosystem studies, demonstrating its formation through biological transformation. Its presence as a metabolite of modafinil suggests that it may contribute to the pharmacological effects of the parent drug, although its weak dopamine reuptake inhibitory activity indicates that it is not the primary mediator of modafinil's wake-promoting effects. Further in vivo studies are needed to fully characterize its pharmacological profile.
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| Enzyme Assay |
The non-cellular biochemical activity of Fluorenone can be assessed using enzyme inhibition and receptor binding assays. For xanthine oxidase inhibition, the enzyme is incubated with xanthine substrate and varying concentrations of Fluorenone in a cell-free system. The production of uric acid is monitored spectrophotometrically at 295 nm, and the IC50 is calculated from the inhibition curve. For receptor binding studies, membrane preparations from rat brain tissue are incubated with radiolabeled ligands specific for P2 purinergic receptors or α7 nicotinic acetylcholine receptors in the presence of Fluorenone. The displacement of the labeled ligand is measured to determine binding affinity. These assays provide insights into Fluorenone's interaction with its molecular targets.
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| Cell Assay |
Cellular assays for Fluorenone typically employ neuronal cell lines or primary neuronal cultures to evaluate its effects on receptor activity and cell viability. In a typical protocol, cells are treated with varying concentrations of Fluorenone (typically 1-100 μM) for 24-48 hours. Cell viability is assessed using MTT or LDH release assays. Receptor activity is measured using calcium imaging or electrophysiological recordings for P2 purinergic receptors and α7 nicotinic acetylcholine receptors. For dopamine reuptake inhibition studies, cells expressing dopamine transporters are incubated with radiolabeled dopamine in the presence of Fluorenone, and the uptake is measured. These assays help characterize the compound's cellular effects.
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| Animal Protocol |
In vivo animal experiments with Fluorenone typically involve rodent models to assess its pharmacological effects. In a study evaluating its cardioprotective effects, rats with induced myocardial infarction are administered Fluorenone, and infarct size is measured to assess reduction. For studies related to its role as a modafinil metabolite, animals may be administered Fluorenone or modafinil, and behavioral parameters such as locomotor activity and wakefulness are monitored. Tissue samples are collected for analysis of Fluorenone levels and its metabolites. These experiments help determine the compound's bioavailability, tissue distribution, and pharmacodynamic effects in vivo.
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| ADME/Pharmacokinetics |
Metabolism / Metabolites
Fluorenone is generated from 9-hydroxyfluorene. In model ecosystem studies, fluorenone is a metabolite of fluorene in the mosquitofish (Gambusia). This study investigated the metabolism of tricyclic aromatic fluorene in Cunninghamella elegans ATCC 36112. Approximately 69% of the 9-(14)C-fluorene added to the culture was metabolized within 120 hours. The main ethyl acetate-soluble metabolites were 9-fluorenone (62%), 9-fluorenol, and 2-hydroxy-9-fluorenone (total 7.0%). Similar to bacteria, Cunninghamella elegans oxidizes fluorene at the C-9 position of the five-membered ring, producing alcohols and corresponding ketones. Furthermore, Cunninghamella elegans also produces a novel metabolite, 2-hydroxy-9-fluorenone. The pharmacokinetic properties of Fluorenone are not extensively characterized, but its role as a metabolite provides some insights. As a metabolite of modafinil, Fluorenone is formed through hepatic metabolism of the parent drug. Its molecular weight of 180.21 g/mol and lipophilic nature suggest that it can cross the blood-brain barrier and distribute to the central nervous system. The compound is likely metabolized further and excreted via renal and biliary routes. Its presence in biological systems as a metabolite indicates that it has some degree of systemic exposure following administration of its parent compounds. However, its pharmacokinetic profile is not as well-studied as that of modafinil. |
| Toxicity/Toxicokinetics |
The toxicological profile of Fluorenone has not been extensively studied, but available data suggest that it has moderate toxicity. As an aromatic ketone, it may cause skin and eye irritation upon direct contact. Its use as an intermediate in pharmaceutical and chemical synthesis requires appropriate safety precautions. Inhalation or ingestion of Fluorenone may cause respiratory and gastrointestinal irritation. Long-term exposure effects are not well-documented, but it is not classified as a carcinogen or mutagen based on available data. Standard safety measures, including the use of personal protective equipment, are recommended when handling this compound in laboratory and industrial settings.
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| Additional Infomation |
Fluorene-9-one is the simplest member of the fluorene-9-one class of compounds; it is 9H-fluorene with an oxygen substituent at the 9-position. It is a fungal xenobiotic metabolite. 9-fluorene has been reported to exist in grapes (Vitis vinifera), and relevant data are available.
Fluorenone is an important organic compound with diverse applications in the chemical and pharmaceutical industries. It is primarily used as an intermediate in the synthesis of pharmaceuticals, including antimalarial drugs, and in the production of dyes, pesticides, and functional polymers. As a metabolite of the wake-promoting drug modafinil, Fluorenone has attracted attention in biochemical research. Its ability to interact with P2 purinergic receptors, xanthine oxidase, and α7 nicotinic acetylcholine receptors suggests potential pharmacological activities that warrant further investigation. However, it is primarily used as a research tool and chemical intermediate rather than as a therapeutic agent. |
| Molecular Formula |
C13H8O
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|---|---|
| Molecular Weight |
180.21
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| Exact Mass |
180.057
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| CAS # |
486-25-9
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| Related CAS # |
Fluorenone-d8;137219-34-2
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| PubChem CID |
10241
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| Appearance |
YELLOW RHOMBIC BIPYRAMIDAL CRYSTALS FROM ALCOHOL, BENZENE-PETROLEUM ETHER
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| Density |
1.2±0.1 g/cm3
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| Boiling Point |
341.5±0.0 °C at 760 mmHg
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| Melting Point |
80-83 °C(lit.)
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| Flash Point |
144.1±13.7 °C
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| Vapour Pressure |
0.0±0.7 mmHg at 25°C
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| Index of Refraction |
1.667
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| LogP |
3.58
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| Hydrogen Bond Donor Count |
0
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| Hydrogen Bond Acceptor Count |
1
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| Rotatable Bond Count |
0
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| Heavy Atom Count |
14
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| Complexity |
222
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| Defined Atom Stereocenter Count |
0
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| SMILES |
O=C1C2=C([H])C([H])=C([H])C([H])=C2C2=C([H])C([H])=C([H])C([H])=C21
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| InChi Key |
YLQWCDOCJODRMT-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C13H8O/c14-13-11-7-3-1-5-9(11)10-6-2-4-8-12(10)13/h1-8H
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| Chemical Name |
fluoren-9-one
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| Synonyms |
AI3 00858; AI3-00858; Fluorenone
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| HS Tariff Code |
2934.99.9001
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| 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)
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| 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
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| 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
Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline)(e.g. IP/IV/IM/SC) *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). View More
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)] 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). View More
Oral Formulation 3: Dissolved in PEG400 (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 5.5491 mL | 27.7454 mL | 55.4908 mL | |
| 5 mM | 1.1098 mL | 5.5491 mL | 11.0982 mL | |
| 10 mM | 0.5549 mL | 2.7745 mL | 5.5491 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
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