Doxofylline CAS 69975-86-6
Doxofylline Basic information
| Product Name: | Doxofylline |
| Synonyms: | DOXOFYLLINE;DOXOPHYLLINE;2-(7’-teofillinmetil)-1,3-diossolano;Doxofyliine;7-(1,3-dioxolan-2-ylmethyl)-1,3-dimethyl-purine-2,6-dione;DOXOFYLLINE [7-(1,3-DIOXOLAN-2-YLMETHYL)-3,7-DIHYDRO-1,3-DIMETHYL-1H-PURINE-2,6-DIONE];MAXIVENT;Ansirnar |
| CAS: | 69975-86-6 |
| MF: | C11H14N4O4 |
| MW: | 266.25 |
| EINECS: | 274-239-6 |
| Product Categories: | ZYRTEC;Respiratory system;69975-86-6;API |
| Mol File: | 69975-86-6.mol |
Doxofylline Chemical Properties
| Melting point | 144-146°C |
| Boiling point | 409.46°C (rough estimate) |
| density | 1.2896 (rough estimate) |
| refractive index | 1.6000 (estimate) |
| RTECS | XH5135000 |
| storage temp. | under inert gas (nitrogen or Argon) at 2-8°C |
| solubility | DMSO (Slightly), Methanol (Slightly) |
| pka | 0.42±0.70(Predicted) |
| form | Solid |
| color | White to Off-White |
| Water Solubility | Soluble |
| Merck | 14,3438 |
| InChI | InChI=1S/C11H14N4O4/c1-13-9-8(10(16)14(2)11(13)17)15(6-12-9)5-7-18-3-4-19-7/h6-7H,3-5H2,1-2H3 |
| InChIKey | HWXIGFIVGWUZAO-UHFFFAOYSA-N |
| SMILES | N1(CC2OCCO2)C2=C(N(C)C(=O)N(C)C2=O)N=C1 |
| CAS DataBase Reference | 69975-86-6(CAS DataBase Reference) |
Safety Information
| Hazard Codes | Xi |
| Risk Statements | 36/37/38 |
| Safety Statements | 26-36/37 |
| HS Code | 29399990 |
| Toxicity | LD50 in mice (mg/kg): 841 orally; 215.6 i.v.; in rats: 1022.4 orally, 445 i.p. (Franzone) |
| Description | Doxofylline, a xanthine bronchodilator related to theophylline, is useful in thetreatment of asthma and similar bronchospastic disorders. It has minimal activityon intestinal smooth muscle and the cardiovascular system, and is reportedlydevoid of the behavioral effects of theophylline. |
| Description | 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. |
| Originator | ABC S.p.A. (Italy) |
| 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. |
| Uses | H1 antihistamine |
| Definition | ChEBI: Doxofylline is an oxopurine that is a derivative of xanthine, methylated at N-1 and N-3 and carrying a 1,3-dioxolan-2-ylmethyl group at N-7, used in the treatment of asthma. It has a role as a bronchodilator agent, an antitussive and an anti-asthmatic drug. It is functionally related to a 7H-xanthine. |
| Brand name | Maxivent (Roberts Pharmaceutical);ANSIMAR. |
| Synthesis | 4360-63-8 58-55-9 69975-86-6 The general procedure for the synthesis of 7-((1,3-dioxolan-2-yl)methyl)-1,3-dimethyl-1H-purine-2,6(3H,7H)-dione from 2-bromomethyl-1,3-dioxolane and 1,3-dimethyl-1H-purine-2,6(3H,9H)-dione was carried out as follows: to a reactor, 13 kg (72.16 mol) of 1,3- dimethyl-1H-purine-2,6(3H,9H)-dione (theophylline), 8 L of acetone, 5.77 kg (144.32 mol) of sodium hydroxide and 0.7 kg (2.16 mol) of tetrabutyl ammonium bromide. After stirring for 10 min, 14.47 kg (86.64 mmol) of 2-bromomethyl-1,3-dioxolane (bromoacetaldehyde acetal) was added. The mixture was refluxed for 6.3 h and the progress of the reaction was monitored by thin-layer chromatography (unfolding reagent ratio acetone: dichloromethane = 3:1). Upon completion of the reaction, the solvent was removed by distillation under reduced pressure, washed three times with saturated sodium chloride solution, and the residue was recrystallized from anhydrous ethanol to give 17.28 kg (64.98 mol) of 7-((1,3-dioxolan-2-yl)methyl)-1,3-dimethyl-1H-purine-2,6(3H,7H)-dione (doxophyllotoxin) in 90% yield and purity over 98.5%. |
| References | [1] Patent: CN105418612, 2016, A. Location in patent: Paragraph 0029; 0041; 0042 [2] Patent: CN105237538, 2016, A. Location in patent: Paragraph 0055; 0056; 0058 |
Doxofylline Preparation Products And Raw materials
| Raw materials | p-Toluenesulfonic acid-->Theophylline-->3-Chloro-1,2-propanediol-->Trichloroparaldehyde-->2-Chloromethyl-1,3-dioxolane-->2-Bromomethyl-1,3-dioxolane-->Ethylene glycol-->Sodium hydroxide-->TETRABUTYLAMMOMIUM BROMIDE-->Acetone |
