Theophylline

Base Information

• Chemical Name: Theophylline
• CAS No.: 58-55-9
• Deprecated CAS: 46157-00-0,56645-32-0,75448-53-2,111079-49-3,1024160-72-2,111079-49-3,75448-53-2
• Molecular Formula: C7H8N4O2
• Molecular Weight: 180.166
• Hs Code.: 29395900
• European Community (EC) Number: 200-385-7,807-662-7
• ICSC Number: 0678
• NSC Number: 757346,2066
• UN Number: 1544
• UNII: 0I55128JYK
• DSSTox Substance ID: DTXSID5021336
• Nikkaji Number: J492.514I,J2.333G
• Wikipedia: Theophylline
• Wikidata: Q407308
• NCI Thesaurus Code: C61968
• RXCUI: 91178
• Pharos Ligand ID: U3SDZU3L3UYH
• Metabolomics Workbench ID: 37911
• ChEMBL ID: CHEMBL190
• Mol file: 58-55-9.mol

Synonyms:1,3 Dimethylxanthine;1,3-Dimethylxanthine;3,7-Dihydro-1,3-dimethyl-1H-purine-2,6-dione;Accurbron;Aerobin;Aerolate;Afonilum Retard;Anhydrous, Theophylline;Aquaphyllin;Armophylline;Bronchoparat;Bronkodyl;Constant T;Constant-T;ConstantT;ct, theo von;Elixophyllin;Euphylong;Glycinate, Theophylline Sodium;Glycine Theophyllinate;Lodrane;Monospan;Nuelin;Nuelin S.A.;Quibron T SR;Quibron T-SR;Quibron TSR;Slo Phyllin;Slo-Phyllin;SloPhyllin;Sodium Glycinate, Theophylline;Somophyllin T;Somophyllin-T;SomophyllinT;Sustaire;Synophylate;Theo 24;Theo Dur;theo von ct;Theo-24;Theo-Dur;Theo24;Theobid;Theocin;Theoconfin Continuous;Theodur;Theolair;Theolix;Theon;Theonite;Theopek;Theophyllinate, Glycine;Theophylline;Theophylline Anhydrous;Theophylline Sodium Glycinate;Theospan;Theostat;Theovent;Uniphyl;Uniphyllin;Uniphylline;von ct, theo

Chemical Property of Theophylline

Chemical Property:

• Appearance/Colour: white to light yellow crystal powder
• Vapor Pressure: 2.72E-06mmHg at 25°C
• Melting Point: 271-273 °C
• Refractive Index: 1.737
• Boiling Point: 454.091 °C at 760 mmHg
• PKA: 8.77(at 25℃)
• Flash Point: 228.426 °C
• PSA: 72.68000
• Density: 1.466 g/cm³
• LogP: -1.03970
• Storage Temp.: 2-8°C
• Solubility.: 0.1 M HCl: soluble
• Water Solubility.: 8.3 g/L (20 ºC)
• XLogP3: 0
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 180.06472551
• Heavy Atom Count: 13
• Complexity: 267

Purity/Quality:

99% ^*data from raw suppliers

Theophylline ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn, T, F, Xi
• Hazard Codes: Xn,T,F,Xi
• Statements: 22-39/23/24/25-23/24/25-11-36/37/38
• Safety Statements: 7-16-36/37-45-36-26-24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Drug Classes: Antiasthmatic Agents
• Canonical SMILES: CN1C2=C(C(=O)N(C1=O)C)NC=N2
• Recent ClinicalTrials: Theophylline Effects in the Fontan Circulation
• Recent EU Clinical Trials: A randomised, double-blind placebo controlled trial of the effectiveness of low dose oral theophylline as an adjunct to inhaled corticosteroids in preventing exacerbations of chronic obstructive pulmonary disease
• Recent NIPH Clinical Trials: Influence of habitual exercise training on sweat gland function
• Inhalation Risk: A nuisance-causing concentration of airborne particles can be reached quickly when dispersed.
• Effects of Short Term Exposure: The substance may cause effects on the heart and central nervous system. This may result in cardiac dysrhythmia and convulsions. The effects may be delayed.
• General Description: Theophylline, a methylxanthine derivative, is a bronchodilator used to treat asthma and COPD by relaxing smooth muscles in the airways. This study explores chemically modified theophylline prodrugs, particularly 7-acyl- and 7,7'-acylditheophylline derivatives, designed to enhance controlled release by reducing water solubility and increasing lipophilicity. Among these, 7,7'-succinylditheophylline shows promise due to its slow dissolution and rapid hydrolysis, suggesting potential for sustained therapeutic effects in respiratory conditions.

Technology Process of Theophylline

There total 95 articles about Theophylline 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: 97.7%

1,3-dimethyl-4-amino-5-(formylamino)uracil (7597-60-6) → theophylline (58-55-9,75448-53-2)

Guidance literature:

With triethylamine; 1,3-bis[2,6-diisopropylphenyl]imidazolium chloride; In water; at 75 ℃; for 0.916667h; under 4500.45 Torr; Pressure; Temperature; Autoclave;

Reference yield: 97.5%

Methyl formate (107-31-3) + 1,3-Dimethylxanthine potassium salt (57533-87-6) → theophylline (58-55-9,75448-53-2) + 3,7-dihydro-1,3,7-trimethyl-1H-purine-2,6-dione (58-08-2,138455-22-8,95789-13-2)

Guidance literature:

In methanol;

Reference yield: 95.0%

7-amino-1,3-dimethyl-3,7-dihydro-1H-purine-2,6-dione (81281-58-5) → theophylline (58-55-9,75448-53-2)

Guidance literature:

With hydrogenchloride; sodium nitrite; In water; at 5 ℃; for 1h;

upstream raw materials:

1,3,5-Triazine

4,5-Diamino-1,3-dimethyluracil

6-Amino-1,3-dimethylbarbituric acid

formamide

Downstream raw materials:

7-(2-hydroxyethyl)theophylline

1,3-dimethyl-7-(morpholinomethyl)xanthine

proxyphylline

7-[(2-hydroxy-2-phenyl)ethyl]theophylline

Refernces

Controlled delivery of theophylline: Chemistry of 7-acyl- and 7,7'-acylditheophylline derivatives

10.1002/jps.2600670806

The research focuses on the development of a slow-release form of theophylline, a widely used asthma treatment, through chemical modification. The study explores the synthesis, physical properties, stability, and bioavailability of various 7-acyl- and 7,7'-acylditheophylline derivatives. Key chemicals involved in the research include theophylline, succinic anhydride, thionyl chloride, dimethylformamide, pyridine, and succinyl chloride. These chemicals are used in different synthetic methods to create the derivatives, with the aim of reducing the water solubility and increasing the lipophilicity of theophylline to achieve a controlled-release prodrug. The research also investigates the stability and dissolution rates of these derivatives, with 7,7'-succinylditheophylline emerging as a promising candidate for further evaluation due to its slow dissolution rate and fast hydrolysis. The study provides insights into the potential of these derivatives for prolonged therapeutic effects in asthma treatment.