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| 5mg |
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| 10mg |
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| Targets |
Furafylline targets CYP1A2, a cytochrome P450 enzyme involved in the metabolism of many drugs and xenobiotics. It acts as a mechanism-based inhibitor, leading to irreversible inactivation of the enzyme. This process involves a time-dependent loss of enzyme activity that does not reverse upon dialysis. It also inhibits phosphodiesterase (PDE), which is the mechanism of action of theophylline, explaining its potential as an anti-asthmatic agent.
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| ln Vitro |
In vitro, Furafylline is a potent, non-competitive inhibitor of CYP1A2 with an IC50 of 0.07 μM. It inhibits high-affinity phenacetin O-deethylase activity in human liver microsomes. Its mechanism of inhibition is irreversible and time-dependent. It also inhibits phosphodiesterase (PDE). These in vitro activities demonstrate its dual mechanism of action.
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| ln Vivo |
Furafylline, with an IC50 of 0.07 μM in kinase tests, is a strong and specific inhibitor of human cytochrome P450IA2. A methylxanthine derivative called furafylline is used to treat asthma in place of theophylline, providing a longer-acting option. When furafylline is administered, the inhibition of caffeine oxidation—a process that is performed by P450 isoenzymes and is caused by one or more hydrocarbons—may lead to an increase in plasma caffeine levels. When human monooxygenase is catalyzed by different P450 isoenzymes, such as P4501ID1, P4501IC, and P450IIIA, furafylline has little to no effect on its activity [1].
In vivo, Furafylline was developed as a potential long-acting bronchodilator for the treatment of asthma, based on its PDE inhibitory activity. However, its development as a therapeutic agent may have been limited due to its potent CYP1A2 inhibitory activity, which could lead to drug-drug interactions. Its in vivo pharmacokinetic and pharmacodynamic properties are not detailed in the available sources. |
| Enzyme Assay |
For in vitro cell-free assays, the inhibitory activity of Furafylline against CYP1A2 is measured using standard cytochrome P450 activity assays. Human liver microsomes or recombinant CYP1A2 are incubated with a specific substrate, such as phenacetin, and varying concentrations of Furafylline. The formation of the metabolite, acetaminophen (from phenacetin O-deethylation), is measured by HPLC or LC-MS. The IC50 value is calculated from a dose-response curve. Its mechanism-based inhibition can be confirmed by pre-incubating the enzyme with the compound and NADPH before adding the substrate.
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| Cell Assay |
Furafylline is not typically used in standard cell-based pharmacological assays as a test compound. Its primary application is as a selective inhibitor of CYP1A2 in drug metabolism studies.
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| Animal Protocol |
Furafylline could be used in vivo to inhibit CYP1A2 activity in animal models to study the role of this enzyme in drug metabolism. It could be administered orally or intraperitoneally. Its effect on the metabolism of a probe substrate, such as caffeine or theophylline, would be measured.
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| ADME/Pharmacokinetics |
Metabolism / Metabolites
The known metabolites of furacilin include 3-[(furan-2-yl)methyl]-8-hydroxy-1-methyl-2,3,6,7-tetrahydro-1H-purine-2,6-dione. Furafylline has a molecular weight of 260.25 g/mol. Its CAS number is 80288-49-9. It is a methylxanthine derivative and is typically supplied as a powder. It is soluble in DMSO. For in vitro studies, stock solutions are prepared in DMSO. Storage is recommended at -20°C, protected from light. Its purity is typically >95% for research use. |
| Toxicity/Toxicokinetics |
No detailed toxicity data is publicly available. As a potent inhibitor of CYP1A2, its use could lead to significant drug-drug interactions by altering the metabolism of other drugs. Its safety profile would need to be established through standard toxicological studies.
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| References | |
| Additional Infomation |
Furafylline is an oxypurine drug. It is a derivative of methylxanthine. It was developed in the context of asthma treatment as a long-acting alternative to theophylline.
Furafylline is a research-grade compound and is not approved for any therapeutic use. It serves primarily as a valuable pharmacological tool for studying CYP1A2 function and drug metabolism. Its mechanism of action involves the selective and irreversible inhibition of CYP1A2. Its potent inhibitory activity makes it a key compound for investigating the role of CYP1A2 in the metabolism of various drugs and endogenous compounds. No clinical trials have been reported. |
| Molecular Formula |
C12H12N4O3
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|---|---|
| Molecular Weight |
260.24900
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| Exact Mass |
260.09
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| CAS # |
80288-49-9
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| PubChem CID |
3433
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| Appearance |
White to light yellow solid powder
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| Density |
1.4±0.1 g/cm3
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| Boiling Point |
543.6±60.0 °C at 760 mmHg
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| Flash Point |
282.6±32.9 °C
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| Vapour Pressure |
0.0±1.5 mmHg at 25°C
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| Index of Refraction |
1.637
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| LogP |
-0.24
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| Hydrogen Bond Donor Count |
1
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| Hydrogen Bond Acceptor Count |
4
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| Rotatable Bond Count |
2
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| Heavy Atom Count |
19
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| Complexity |
402
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| Defined Atom Stereocenter Count |
0
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| InChi Key |
KGQZGCIVHYLPBH-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C12H12N4O3/c1-7-13-9-10(14-7)16(6-8-4-3-5-19-8)12(18)15(2)11(9)17/h3-5H,6H2,1-2H3,(H,13,14)
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| Chemical Name |
3-(furan-2-ylmethyl)-1,8-dimethyl-7H-purine-2,6-dione
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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) |
DMSO : ~12.5 mg/mL (~48.03 mM)
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| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.17 mg/mL (8.34 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 21.7 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 2.17 mg/mL (8.34 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 21.7 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly. (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 3.8425 mL | 19.2123 mL | 38.4246 mL | |
| 5 mM | 0.7685 mL | 3.8425 mL | 7.6849 mL | |
| 10 mM | 0.3842 mL | 1.9212 mL | 3.8425 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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