| Size | Price | Stock | Qty |
|---|---|---|---|
| 5g |
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| Other Sizes |
| Targets |
Theophylline targets phosphodiesterases (PDE3, PDE4), adenosine receptors, and histone deacetylases (HDAC). It acts as a competitive nonselective phosphodiesterase inhibitor, preventing the breakdown of cAMP and cGMP. This leads to increased intracellular levels of these cyclic nucleotides, which have various physiological effects, including bronchodilation and anti-inflammatory activity. Theophylline also acts as a nonselective adenosine receptor antagonist, blocking the effects of adenosine at its receptors. This contributes to its bronchodilator and cardiac stimulant effects. The compound is also a histone deacetylase activator, which may contribute to its anti-inflammatory activity. By inhibiting phosphodiesterase and adenosine receptors, and activating HDAC, Theophylline exerts its therapeutic effects in respiratory diseases.
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| ln Vitro |
Human bronchial and pulmonary arteries are relaxed when theophylline (1,3-dimethylxanthine) (1-1000 µM) inhibits PDE-induced cAMP hydrolysis in bronchial tissue homogenates [1]. By decreasing the anti-apoptotic protein Bcl-2, theophylline (1,3-dimethylxanthine) (10 µg/mL; 24 hours; eosinophils) promotes apoptosis [2]. In A549 cells, theophylline (1,3-dimethylxanthine) (0-500 µM; 2 hours) suppresses the activation of NF-κB, the degradation of I-κBα, and the production of IL-6[3]. Histone deacetylase activity is induced by theophylline (1,3-dimethylxanthine) (0-1000 µM; 30 min; A549 cells), which lowers the expression of inflammatory genes [4].
In vitro, Theophylline inhibits PDE3 activity and relaxes airway smooth muscle. It has anti-inflammatory activity by increasing IL-10 and inhibiting NF-κB entry into the nucleus. The compound causes apoptosis in certain cell types. It inhibits phosphodiesterase and prostaglandin production, regulates calcium flux and intracellular calcium distribution, and antagonizes adenosine. The compound's in vitro activity is well-characterized and forms the basis for its use as a pharmaceutical agent. Theophylline is a valuable tool for studying phosphodiesterase, adenosine receptor, and HDAC signaling. |
| ln Vivo |
In male Swiss mice, theophylline (1,3-dimethylxanthine) (100 mg/kg; i.p.; daily for 9 days) shows anti-inflammatory effect by raising IL-6 and IL-10 levels and suppressing NO and TNF-α [1].
In vivo, Theophylline is indicated for the treatment of acute exacerbations and reversible airflow obstruction associated with asthma, emphysema, and chronic bronchitis. It increases cAMP and cGMP levels, leading to smooth muscle relaxation. The compound's in vivo effects are attributed to its phosphodiesterase inhibition, adenosine receptor antagonism, and HDAC activation. Theophylline has been evaluated in animal models of asthma and COPD, where it has shown bronchodilator and anti-inflammatory activity. |
| Enzyme Assay |
Cell-free assays for Theophylline are performed using purified PDE3 or PDE4 enzymes. The enzyme is incubated with cAMP or cGMP substrates and varying concentrations of Theophylline. Enzyme activity is measured by colorimetric or luminescent assays to determine IC50 values. Adenosine receptor binding assays are performed using membranes from cells expressing adenosine receptors. These cell-free assays are essential for characterizing the potency and selectivity of Theophylline for its various targets.
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| Cell Assay |
Western Blot Analysis [3]
Cell Types: A549 Cell Tested Concentrations: 0, 20, 100 and 500 µM Incubation Duration: 2 hrs (hours) Experimental Results: diminished NF-κB p65 expression and I-κBα degradation in a concentration-dependent manner. Western Blot Analysis[2] Cell Types: Eosinophils Tested Concentrations: 10 µg/mL Incubation Duration: 24 hrs (hours) Experimental Results: diminished Bcl-2 expression. In cellular assays, airway smooth muscle cells or immune cells are treated with Theophylline at varying concentrations. cAMP levels are measured by ELISA. IL-10 production is assessed by ELISA or qPCR. NF-κB nuclear translocation is evaluated by immunofluorescence or Western blot. These cellular assays are crucial for understanding the functional consequences of phosphodiesterase inhibition, adenosine receptor antagonism, and HDAC activation. |
| Animal Protocol |
Animal/Disease Models: Male Swiss mice [1]
Doses: 100 mg/kg Route of Administration: intraperitoneal (ip) injection; one time/day for 9 days Experimental Results: Increased IL-6 and IL-10 levels and inhibited TNF-α and NO. Theophylline is evaluated in animal models of asthma and COPD. The compound is administered orally or intravenously. Bronchodilation is assessed by measuring airway resistance. Inflammatory cell infiltration and cytokine levels in bronchoalveolar lavage fluid are analyzed. These in vivo studies are essential for confirming the compound's efficacy in a physiologically relevant context. |
| ADME/Pharmacokinetics |
Theophylline is orally bioavailable. It is metabolized in the liver by CYP450 enzymes. Pharmacokinetic parameters including Cmax, Tmax, half-life, and bioavailability are well characterized. Therapeutic drug monitoring is used clinically due to narrow therapeutic index. The compound's pharmacokinetic profile is important for optimizing dosing and minimizing toxicity.
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| Toxicity/Toxicokinetics |
Theophylline has a narrow therapeutic index. Adverse effects include gastrointestinal disturbances, tachycardia, arrhythmias, and CNS stimulation at high doses. Toxicity is dose-dependent. Overdose can be life-threatening. Contraindicated in patients with certain cardiac conditions. The compound's safety profile is well-established, and it is available as a pharmaceutical product.
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| References | |
| Additional Infomation |
Theophylline (1,3-dimethylxanthine, CAS 58-55-9) is a methylated xanthine derivative that acts as a competitive nonselective phosphodiesterase inhibitor and a nonselective adenosine receptor antagonist. It is used clinically for asthma, bronchospasm, and COPD. The compound is marketed under several brand names such as Uniphyl and Theochron. It is available as a pharmaceutical product and as a research-grade compound. When handling Theophylline, researchers should follow standard safety protocols for handling chemical reagents, including the use of appropriate personal protective equipment and working in a well-ventilated area.
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| Molecular Formula |
C7H8N4O2
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|---|---|
| Molecular Weight |
180.1640
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| Exact Mass |
180.064
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| CAS # |
58-55-9
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| Related CAS # |
Theophylline-d6;117490-39-8;Theophylline sodium glycinate;8000-10-0;Theophylline monohydrate;5967-84-0;Theophylline sodium acetate;8002-89-9
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| PubChem CID |
2153
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| Appearance |
White to off-white solid powder
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| Density |
1.5±0.1 g/cm3
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| Boiling Point |
454.1±37.0 °C at 760 mmHg
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| Melting Point |
271-273 °C
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| Flash Point |
228.4±26.5 °C
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| Vapour Pressure |
0.0±1.1 mmHg at 25°C
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| Index of Refraction |
1.620
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| LogP |
-0.17
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| Hydrogen Bond Donor Count |
1
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| Hydrogen Bond Acceptor Count |
3
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| Heavy Atom Count |
13
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| Complexity |
267
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| Defined Atom Stereocenter Count |
0
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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) |
0.1 M NaOH : ~20 mg/mL (~111.01 mM)
DMSO : ~11.11 mg/mL (~61.67 mM) H2O : ~5 mg/mL (~27.75 mM) |
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| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 1.11 mg/mL (6.16 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 11.1 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: ≥ 1.11 mg/mL (6.16 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in 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 11.1 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. 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. View More
Solubility in Formulation 3: ≥ 1.11 mg/mL (6.16 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. Solubility in Formulation 4: 11 mg/mL (61.06 mM) in PBS (add these co-solvents sequentially from left to right, and one by one), clear solution; with ultrasonication. |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 5.5506 mL | 27.7531 mL | 55.5062 mL | |
| 5 mM | 1.1101 mL | 5.5506 mL | 11.1012 mL | |
| 10 mM | 0.5551 mL | 2.7753 mL | 5.5506 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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