|
| | Diprophylline Basic information |
| Product Name: | Diprophylline | | Synonyms: | 7-(2,3-Dihydroxypropyl)-1,3-dimethylxanthine;1H-Purine-2,6-dione, 7-(2,3-dihydroxypropyl)-3,7-dihydro-1,3-dimethyl-;1h-purine-2,6-dione,7-(2,3-dihydroxypropyl)-3,7-dihydro-1,3-dimethyl;7-(2,3-Dihydroxypropyl)-1,3-dimethyl-3,7-dihydro-1H-purine-2,6-dione;Circain;circair;component of Dilor g;component of Neothylline-gg | | CAS: | 479-18-5 | | MF: | C10H14N4O4 | | MW: | 254.24 | | EINECS: | 207-526-1 | | Product Categories: | API;LUFYLLIN;Alkaloids;Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals;479-18-5 | | Mol File: | 479-18-5.mol |  |
| | Diprophylline Chemical Properties |
| Melting point | 161-162 °C(lit.) | | Boiling point | 397.46°C (rough estimate) | | density | 1.3036 (rough estimate) | | refractive index | 1.6200 (estimate) | | storage temp. | Keep in dark place,Inert atmosphere,Room temperature | | solubility | Freely soluble in water, slightly soluble in ethanol (96 per cent). | | pka | 13.74±0.20(Predicted) | | form | Powder | | color | White | | Water Solubility | 33 g/100 mL (25 ºC) | | Merck | 14,3479 | | BRN | 284563 | | Stability: | Hygroscopic | | LogP | -1.100 (est) | | CAS DataBase Reference | 479-18-5(CAS DataBase Reference) | | NIST Chemistry Reference | Dyphylline(479-18-5) | | EPA Substance Registry System | Dyphylline (479-18-5) |
| | Diprophylline Usage And Synthesis |
| Description | Dyphylline is the N-7 dihydroxypropyl derivative of theophylline and is not a theophylline salt.
Dyphylline does not get metabolized to theophylline in vivo, and even though it contains 70%
theophylline by molecular weight ratio, the equivalent amount to theophylline is not known.
Dosing must be accomplished independently by monitoring dyphylline blood levels. Dyphylline
has a diminished bronchodilator effect compared to theophylline, but it may have lower and less
serious side effects. Dosage forms available are an elixir and tablets. | | Description | Dyphylline is a xanthine derivative that acts as an A1 and A2 adenosine receptor antagonist and phosphodiesterase inhibitor and exhibits bronchodilator and vasodilator effects. It also moderately inhibits microsomal prostaglandin E synthase-1 with an IC50 value of 200 μM and downregulates ABCG2 drug transporter expression in multidrug resistant tumor cells. | | Chemical Properties | white to light yellow crystal powder | | Originator | Neothylline,Lemmon,US,1948 | | Uses | PDE inhibitor, bronchodilator, vasodilator | | Uses | An adenosine receptor antagonist, phosphodiesterase inhibitor and vasodilator | | Definition | ChEBI: An oxopurine that is theophylline bearing a 2,3-dihydroxypropyl group at the 7 position. It has broncho- and vasodilator properties, and is used in the treatment of asthma, cardiac dyspnea, and bronchitis. It is also an ingredient in preparations that have
been promoted for coughs. | | Manufacturing Process | 180 grams of theophylline is dissolved in 500 cc of boiling water. To this
solution is added 40 grams of sodium hydroxide or 56 grams of potassium
hydroxide slowly and with constant stirring.
When solution is complete, 120 grams of 1-chloro-2,3-dihydroxypropane is
slowly added. The thus provided mixture is brought to boiling and heating is
continued until a temperature of 110°C is reached.
The resultant liquid is evaporated under reduced pressure to remove all traces
of water. The resulting syrupy liquid is allowed to stand with occasional
stirring until crystallization takes place. The compound is purified by
recrystallization from alcohol. The product melts at 155°-157°C. | | Brand name | Dilor (Savage); Lufyllin (Medpointe); Neothylline (Teva). | | Therapeutic Function | Smooth muscle relaxant | | Biochem/physiol Actions | 7-(2,3-Dihydroxypropyl)theophylline is also called as dyphylline. Dyphylline serves as a bronchodilator and aids in better air flow through the lungs. It reduces the symptoms of chronic lung disorder such as asthma and bronchitis. |
| | Diprophylline Preparation Products And Raw materials |
| Raw materials | Propylene glycol-->Sodium Theophylline(1,3-Dimethyl-2,6-dione-purine-Na)-->1-CHLORO-2,5-DIMETHYL-4-NITROBENZENE2-CHLORO-5-NITRO-P-XYLENE-->Sodium hydroxide-->Theophylline-->1,3-DIMETHYL-7-(OXIRAN-2-YLMETHYL)-2,3,6,7-TETRAHYDRO-1H-PURINE-2,6-DIONE-->1,3-dimethyl-7-prop-2-enyl-purine-2,6-dione-->3-BROMO-1,2-PROPANEDIOL | | Preparation Products | Theophylline Impurity 1 |
|
