479-18-5 Usage
Description
Different sources of media describe the Description of 479-18-5 differently. You can refer to the following data:
1. 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.
2. 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
Different sources of media describe the Uses of 479-18-5 differently. You can refer to the following data:
1. PDE inhibitor, bronchodilator, vasodilator
2. 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.
Check Digit Verification of cas no
The CAS Registry Mumber 479-18-5 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 4,7 and 9 respectively; the second part has 2 digits, 1 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 479-18:
(5*4)+(4*7)+(3*9)+(2*1)+(1*8)=85
85 % 10 = 5
So 479-18-5 is a valid CAS Registry Number.
InChI:InChI=1/C10H14N4O4/c1-12-8-7(9(17)13(2)10(12)18)14(5-11-8)3-6(16)4-15/h5-6,15-16H,3-4H2,1-2H3/t6-/m1/s1
479-18-5Relevant articles and documents
Dyphylline prodrugs: Plasma hydrolysis and dyphylline release in rabbits
Huang,Ayres
, p. 104 - 109 (1988)
Ester hydrolysis of prodrugs of dyphylline [7-(2,3-dihydroxypropyl)theophylline] followed first-order kinetics in both human and rabbit plasma. Rate constants were estimated by linear regression analysis of initial conversion rates, determined at different initial prodrug concentrations. Release of dyphylline from different prodrugs was 1.3 to 13 times faster in rabbit plasma than human plasma. However, relative rates of drug release (lability order) followed the same patterns in rabbit and human plasma. Dyphylline concentrations in rabbit plasma were extended slightly following intravenous administration of dyphylline 2',3'-dipivaloate. Oral dosing of the prodrug in rabbits greatly sustained plasma dyphylline concentrations.
Synthesis method of diprophylline drug active pharmaceutical ingredient 7-(2,3-dihydroxypropyl)-theine
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Paragraph 0013-0014, (2017/03/08)
The invention relates to a synthesis method of a diprophylline drug active pharmaceutical ingredient 7-(2,3-dihydroxypropyl)-theine, which comprises the following steps: adding 300ml of potassium bisulfite solution and 0.71 mol of stannous chloride into a reaction vessel which is provided with a stirrer, a reflux condenser, a dropping funnel and a thermometer, controlling the stirring rate at 130-160 rpm, heating the solution to 60-65 DEG C, slowly adding 0.56 mol of theine, heating the solution to 80-85 DEG C, reacting for 90-120 minutes, cooling the solution to 50-55 DEG C, and dropwisely adding 1.2-1.4 mol of 3-amino-1,2-propanediol; and after finishing addition, continuing reacting for 120-160 minutes, heating the solution to 130-140 DEG C, continuing reacting for 60-70 minutes, distilling under reduced pressure to remove water, cooling, adding hexane, heating under reflux until the condensate is completely dissolved, filtering while the solution is hot, washing the filter cake with ethyl acetate, cooling the washing solution to precipitate a solid, carrying out vacuum filtration, washing with a salt solution, washing with acetonitrile, and recrystallizing in nitromethane to obtain the crystal 7-(2,3-dihydroxypropyl)-theine, wherein the mass percent of the potassium bisulfite solution is 15-20%.
Method for treating benign prostate hyperplasia
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, (2008/06/13)
A method of treating and/or preventing renal dysfunction in a patient, such as renal colic or contrast nephropathy by administering to a patient, a compound of the formula: is described herein. Administration of dyphylline in a sustained release oral dosage form is preferred.
