Doxofylline

Base Information

• Chemical Name: Doxofylline
• CAS No.: 69975-86-6
• Molecular Formula: C11H14N4O4
• Molecular Weight: 266.257
• Hs Code.: 29399990
• European Community (EC) Number: 274-239-6
• NSC Number: 759645
• UNII: MPM23GMO7Z
• DSSTox Substance ID: DTXSID7022968
• Nikkaji Number: J23.295E
• Wikipedia: Doxofylline
• Wikidata: Q425887
• NCI Thesaurus Code: C76317
• Metabolomics Workbench ID: 152297
• ChEMBL ID: CHEMBL1527608
• Mol file: 69975-86-6.mol

Synonyms:2-(7'-theophyllinemethyl)1,3-dioxolane;doxofylline;doxophylline;TMDO

Chemical Property of Doxofylline

Chemical Property:

• Vapor Pressure: 2.49E-10mmHg at 25°C
• Melting Point: 144-146 °C
• Refractive Index: 1.7
• Boiling Point: 505.2 °C at 760 mmHg
• PKA: 0.42±0.70(Predicted)
• Flash Point: 259.3 °C
• PSA: 80.28000
• Density: 1.59 g/cm³
• LogP: -1.19340
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• Water Solubility.: Soluble
• XLogP3: -0.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 2
• Exact Mass: 266.10150494
• Heavy Atom Count: 19
• Complexity: 398

Purity/Quality:

99% ^*data from raw suppliers

Doxofylline ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36/37

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN1C2=C(C(=O)N(C1=O)C)N(C=N2)CC3OCCO3
• Recent ClinicalTrials: Effect of add-on Doxofylline on Lung Function in Stable COPD
• Description: Doxofylline, a xanthine bronchodilator related to theophylline, is useful in the treatment of asthma and similar bronchospastic disorders. It has minimal activity on intestinal smooth muscle and the cardiovascular system, and is reportedly devoid of the behavioral effects of theophylline. Doxofylline is a methylxanthine bronchodilator that has been examined in clinical trials involving patients with either bronchial asthma or chronic obstructive pulmonary disease. Its mechanism of action is related to its ability to inhibit phosphodiesterase activity and, thus, increase cAMP. Compared to other xanthine derivatives, which have direct arrhythmogenic effects, doxofylline demonstrates decreased affinity towards adenosine A1 and A2 receptors, does not interfere with calcium influx into cells, and does not antagonize the action of calcium-channel blockers.
• Uses: Doxofylline is a xanthine molecule that appears to be both bronchodilator and anti-inflammatory with an improved therapeutic window over conventional xanthines such as Theophylline and the evidence supporting the effects of Doxofylline in the treatment of lung diseases. H1 antihistamine Doxofylline is a xanthine molecule that appears to be both bronchodilator and anti-inflammatory with an improved therapeutic window over conventional xanthines such as Theophylline and the evidence su pporting the effects of Doxofylline in the treatment of lung diseases.

Technology Process of Doxofylline

There total 5 articles about Doxofylline which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 93.0%

7-(2,2-dimethyloxyethyl)theophylline + ethylene glycol (107-21-1) → doxofylline (69975-86-6)

Guidance literature:

With toluene-4-sulfonic acid; In toluene; at 105 ℃; for 5h; Temperature; Reagent/catalyst;

Reference yield: 92.1%

2,4,6-tris(chloromethyl)-1,3,5-trioxane (1129-52-8) + theophylline (58-55-9,75448-53-2) + ethylene glycol (107-21-1) → doxofylline (69975-86-6)

Guidance literature:

With sodium carbonate; at 180 - 190 ℃; for 4h; Temperature; Reagent/catalyst; Large scale;

Reference yield: 90.0%

2-bromomethyl-1,3-dioxolane (4360-63-8) + theophylline (58-55-9,75448-53-2) → doxofylline (69975-86-6)

Guidance literature:

With tetrabutylammomium bromide; sodium hydroxide; In acetone; for 6.3h; Reagent/catalyst; Solvent; Reflux; Large scale;

upstream raw materials:

2-bromomethyl-1,3-dioxolane

theophylline

ethylene glycol

2-chloromethyl-1,3-dioxolane

Refernces

• 1、 -. "Novel method for simple, convenient, green and industrial production of doxofylline". Paragraph 0070-0071. . Retrieved 2020/06/20.
• 2、 -. "Preparation method of doxofylline". Paragraph 0049; 0068. . Retrieved 2020/01/25.