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HomeProduct name listDiprophylline

Diprophylline

Synonym(s):Dyphylline;Diprophylline;7-(2,3-Dihydroxypropyl)theophylline;9-(1,3-Benzodioxol-5-yl)-4-hydroxy-6,7-dimethoxy-naphtho[2,3-c]furan-1(3H)-one;7-(2,3-Dihydroxypropyl)-3,7-dihydro-1,3-dimethyl-1H-purine-2,6-dione

  • CAS NO.:479-18-5
  • Empirical Formula: C10H14N4O4
  • Molecular Weight: 254.24
  • MDL number: MFCD00005759
  • EINECS: 207-526-1
  • SAFETY DATA SHEET (SDS)
  • Update Date: 2024-11-04 20:04:50
Diprophylline Structural

What is Diprophylline?

Toxicity

LD50=1954 mg/kg (orally in mice)

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

The Uses of Diprophylline

PDE inhibitor, bronchodilator, vasodilator

The Uses of Diprophylline

An adenosine receptor antagonist, phosphodiesterase inhibitor and vasodilator

Indications

For relief of acute bronchial asthma and for reversible bronchospasm associated with chronic bronchitis and emphysema.

Background

Dyphylline is a theophylline derivative with broncho- and vasodilator properties. It is typically used in the management of asthma, cardiac dyspnea, and bronchitis.

What are the applications of Application

Diphylline is an inhibitor of phosphodiesterase

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.

Pharmacokinetics

Dyphylline, a xanthine derivative, is a bronchodilator used for relief of acute bronchial asthma and for reversible bronchospasm associated with chronic bronchitis and emphysema. Dyphylline is a xanthine derivative with pharmacologic actions similar to theophylline and other members of this class of drugs. Its primary action is that of bronchodilation, but it also exhibits peripheral vasodilatory and other smooth muscle relaxant activity to a lesser degree.

Metabolism

Hepatic

Properties of Diprophylline

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).
form  Powder
pka 13.74±0.20(Predicted)
color  White
Water Solubility  33 g/100 mL (25 ºC)
Merck  14,3479
BRN  284563
Stability: Hygroscopic
CAS DataBase Reference 479-18-5(CAS DataBase Reference)
NIST Chemistry Reference Dyphylline(479-18-5)
EPA Substance Registry System Dyphylline (479-18-5)

Safety information for Diprophylline

Signal word Warning
Pictogram(s)
ghs
Exclamation Mark
Irritant
GHS07
GHS Hazard Statements H302:Acute toxicity,oral

Computed Descriptors for Diprophylline

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