4835 Theophylline A methylxanthine derivative from tea with diuretic, smooth muscle relaxant, bronchial dilation, cardiac and central nervous system stimulant activities. Mechanistically, theophylline acts as a phosphodiesterase inhibitor, adenosine receptor blocker, and histone deacetylase activator. Theophylline is marketed under several brand names such as Uniphyl and Theochron, and it is indicated mainly for asthma, bronchospasm, and COPD. 58-55-9 2153 C7H8N4O2 White powder. 273°C 7360 mg/L (at 25°C) Theophylline is rapidly and completely absorbed after oral administration in solution or immediate-release solid oral dosage form. Theophylline relaxes the smooth muscle of the bronchial airways and pulmonary blood vessels and reduces airway responsiveness to histamine, methacholine, adenosine, and allergen. Theophylline competitively inhibits type III and type IV phosphodiesterase (PDE), the enzyme responsible for breaking down cyclic AMP in smooth muscle cells, possibly resulting in bronchodilation. Theophylline also binds to the adenosine A2B receptor and blocks adenosine mediated bronchoconstriction. In inflammatory states, theophylline activates histone deacetylase to prevent transcription of inflammatory genes that require the acetylation of histones for transcription to begin. Hepatic. Biotransformation takes place through demethylation to 1-methylxanthine and 3-methylxanthine and hydroxylation to 1,3-dimethyluric acid. 1-methylxanthine is further hydroxylated, by xanthine oxidase, to 1-methyluric acid. About 6% of a theophylline dose is N-methylated to caffeine. Caffeine and 3-methylxanthine are the only theophylline metabolites with pharmacologic activity. Route of Elimination: Theophylline does not undergo any appreciable pre-systemic elimination, distributes freely into fat-free tissues and is extensively metabolized in the liver. Renal excretion of unchanged theophylline in neonates amounts to about 50% of the dose, compared to about 10% in children older than three months and in adults. Half Life: 8 hours 3, not classifiable as to its carcinogenicity to humans. (L135) For the treatment of the symptoms and reversible airflow obstruction associated with chronic asthma and other chronic lung diseases, such as emphysema and chronic bronchitis. Symptoms of overdose include seizures, arrhythmias, and GI effects. 2014-09-11T05:16:16Z 2014-12-24T20:26:57Z Theophylline C07130 28177 THF-GLU-N DB00277 TEP true CN1C2=C(N=CN2)C(=O)N(C)C1=O C7H8N4O2 InChI=1S/C7H8N4O2/c1-10-5-4(8-3-9-5)6(12)11(2)7(10)13/h3H,1-2H3,(H,8,9) InChIKey=ZFXYFBGIUFBOJW-UHFFFAOYSA-N 180.164 180.06472552 Exogenous Solid -0.02 HMDB01889 CHEMBL190 2068 <p>Nicolae S. Bodor, Kenneth B. Sloan, Yu-Neng Kuo, &#8220;Method for synthesizing certain selected pro-drug forms of theophylline.&#8221; U.S. Patent US4000132, issued January, 1956.</p>