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Xanthine
From Wikipedia, the free encyclopedia
| Xanthine | |
|---|---|
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| IUPAC name | 3,7-Dihydro-purine-2,6-dione |
| Other names | 1H-Purine-2,6-diol |
| Identifiers | |
| CAS number | [] |
| PubChem | |
| SMILES | C1=NC2=C(N1)C(=O)NC(=O)N2 |
| Properties | |
| Molecular formula | C5H4N4O2 |
| Molar mass | 152.111 g/mol |
| Appearance | White solid |
| Melting point |
decomposes |
| Solubility in water | 1 g/ 14.5 L @ 16 °C 1 g/1.4 L @ 100 °C |
| Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references |
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Xanthine (IPA: [ˈzænθin]), (3,7-dihydro-purine-2,6-dione), is a purine base found in most body tissues and fluids and in other organisms. Xanthine is a product on the pathway of purine degradation and is converted to uric acid by the action of the xanthine oxidase enzyme. Some people lack sufficient xanthine oxidase, and thus xanthine cannot be converted to uric acid. This rare genetic disorder is called xanthinuria.
Derivatives of xanthine, known collectively as xanthines, are a group of alkaloids that are commonly used for their effects as mild stimulants and as bronchodilators, notably in treating the symptoms of asthma. On the contrary, they really only eliminate the actions of adenosine to some extent, adenosine causing sleepiness, thus they are by far less in effectiveness as stimulants than sympathomimetic amines. Their effects, however, are widespread and their therapeutic range is narrow, so they are not the drug of choice in asthma treatment. Theraputic level is 10-20 micrograms/mL blood. Signs of toxicity include tremor, nausea, nervousness, and tachycardia/arrhythmia.
Methylated xanthine derivatives include caffeine, paraxanthine, theophylline, and theobromine (found mainly in chocolate). These drugs inhibit phosphodiesterase and antagonise adenosine. Xanthines are also found very rarely as constituents of nucleic acids.
- ^ Merck Index, 11th Edition, 9968.
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| Anticholinergics | Ipratropium, Tiotropium |
| Short acting β2-agonists | Salbutamol, Terbutaline |
| Long acting β2-agonists (LABA) | Bambuterol, Clenbuterol, Fenoterol, Formoterol, Salmeterol |
| Corticosteroids | Beclometasone, Budesonide, Ciclesonide, Fluticasone |
| Leukotriene antagonists | Montelukast, Pranlukast, Zafirlukast |
| Xanthines | Aminophylline, Theobromine, Theophylline |
| Mast cell stabilizers | Cromoglicate, Nedocromil |
| Combination products | Budesonide/formoterol, Fluticasone/salmeterol, Ipratropium/salbutamol |