Theophylline-ethylenediamine

Base Information

• Chemical Name: Theophylline-ethylenediamine
• CAS No.: 317-34-0
• Molecular Formula: 2(C7H8N4O2)^.C2H8N2
• Molecular Weight: 420.431
• Hs Code.: DERIVATION
• NSC Number: 7919
• Mol file: 317-34-0.mol

Synonyms:Afonilum;Aminodur;Aminophyllin;Aminophylline;Aminophylline DF;Cardophyllin;Carine;Clonofilin;Corophyllin;Diaphyllin;Drafilyn;Duraphyllin;Ethylenediamine, Theophylline;Eufilina;Eufilina Venosa;Euphyllin;Euphyllin Retard;Euphylline;Godafilin;Mini-Lix;Mundiphyllin;Mundiphyllin Retard;Novophyllin;Phyllocontin;Phyllotemp;Somophyllin;Tari-Dog;Theophyllamin Jenapharm;Theophyllamine;Theophyllin EDA ratiopharm;Theophyllin EDA-ratiopharm;Theophyllin EDAratiopharm;Theophylline Ethylenediamine;Truphylline

Chemical Property of Theophylline-ethylenediamine

Chemical Property:

• Appearance/Colour: white to slightly yellowish powder
• Vapor Pressure: 2.62E-32mmHg at 25°C
• Melting Point: 269-270 °C
• Boiling Point: 454.1 °C at 760 mmHg
• PKA: pKa 5.0 (Uncertain)
• Flash Point: 228.4 °C
• PSA: 197.40000
• LogP: -1.77500
• Storage Temp.: −20°C
• Solubility.: H2O: 3.7 mg/mL solutions should be freshly prepared.
• Water Solubility.: soluble
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 1
• Exact Mass: 240.13347377
• Heavy Atom Count: 17
• Complexity: 273

Purity/Quality:

85%, ^*data from raw suppliers

Aminophylline ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn, C
• Hazard Codes: Xn,C
• Statements: 22-42/43-34-36/37/38-20/21/22
• Safety Statements: 45-36/37/39-26-23-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN1C2=C(C(=O)N(C1=O)C)NC=N2.C(CN)N
• Description: Aminophylline is a drug combination consisting of bronchodilator theophylline and ethylenediamine in 2: 1 ratio. It is a kind of non-selective adenosine receptor blocker, histone deacetylase activator and phosphodiesterase inhibition. It is mainly indicated for the treatment of various kinds of lung diseases including asthma, COPD, chronic bronchitis and emphysema. Aminophylline exerts its effect through the component of theophylline in vivo. Theophylline can relax the smooth muscle of the bronchial airways and pulmonary blood vessels. It can competitively inhibits type III and type IV phosphodiesterase (PDE), which breaks down cyclic AMP in smooth muscle cells, possibly leading to bronchodilation. Theophylline also binds to the adenosine A2B receptor to block the adenosine mediated bronchoconstriction. Furthermore, during the inflammatory states, theophylline can activate the histone deacetylase to prevent transcription of inflammatory genes that require the acetylation of histones to initiate the transcription. Aminophylline is a 2/1 mixture of theophylline and ethylenediamine. It caused contact dermatitis in industrial plants, in pharmacists, and in nurses. Ethylenediamine is the sensitizer, and patch testing is generally positive to both ethylenediamine and aminophylline, but negative to theophylline.
• Uses: Aminophylline exhibits vasodilatory and anti-inflammatory activity and is occasionally clinically used to treat chronic obstructive pulmonary disorder (COPD). In animal models of allergen-induced lung inflammation, aminophylline decreases levels of IL-5, IL-8, and eosinophils. It is mostly used to prepare solutions for intravenous injections. Bronchodilatator;Mastocytes degranulation inhibitor Aminophylline is a bronchodilator and a non-selective phosphodiesterase (PDE) inhibitor.
• Therapeutic Function: Diuretic, Cardiac stimulant, Smooth muscle relaxant, Vasodilator
• Clinical Use: Reversible airways obstruction Acute severe asthma
• Drug interactions: Potentially hazardous interactions with other drugs Antibacterials: increased concentration with azithromycin, clarithromycin, erythromycin, ciprofloxacin, norfloxacin and isoniazid; decreased erythromycin levels if erythromycin is given orally; increased risk of convulsions if given with quinolones; rifampicin accelerates metabolism of aminophylline. Antidepressants: concentration increased by fluvoxamine - avoid or halve theophylline dose and monitor levels; concentration reduced by St John’s wort - avoid. Antiepileptics: metabolism increased by carbamazepine, phenobarbital and primidone; concentration of both drugs increased with fosphenytoin and phenytoin. Antifungals: concentration increased by fluconazole and ketoconazole. Antivirals: metabolism of aminophylline increased by ritonavir; concentration possibly increased by aciclovir. Calcium-channel blockers: concentration increased by diltiazem and verapamil and possibly other calcium-channel blockers. Deferasirox: concentration of aminophylline increased. Feboxostat: use with caution. Interferons: reduced metabolism of aminophylline. Tacrolimus: may increase tacrolimus levels. Ulcer-healing drugs: metabolism inhibited by cimetidine; absorption possibly reduced by sucralfate.

Technology Process of Theophylline-ethylenediamine

There total 3 articles about Theophylline-ethylenediamine 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: 91.8%

theophylline (58-55-9,75448-53-2) + ethylenediamine (107-15-3,85404-18-8) → theophylline ethylenediamine (317-34-0)

Guidance literature:

In methanol; ethyl acetate; at 5 - 80 ℃; for 2.5h; Temperature;

Reference yield:

→ theophylline ethylenediamine (317-34-0)

Guidance literature:

Reference yield:

ethylenediamine (107-15-3,85404-18-8) + Theophylline (58-55-9) → aminophylline (317-34-0,2963-72-6,5768-49-0)

Guidance literature:

In ethanol; chloroform; water; at 20 ℃; agitation at 300-700 rpm; after 10-30 min agglomeration of crystals into spherical form;

DOI:10.1248/cpb.30.1900

upstream raw materials:

ethylenediamine

Theophylline

theophylline

Downstream raw materials:

ethylenediamine

Theophylline

Refernces

• 1、 -. "LIQUID PHARMACEUTICAL FOR ORAL DELIVERY". . . Retrieved 2008/06/13.