Xanthine
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| 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 | O=C1NC(=O)c2[nH]cnc2N1 |
| 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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Overview
Xanthine (3,7-dihydro-purine-2,6-dione), is a purine base found in most body tissues and fluids and in other organisms.
Reactions
Xanthine is a product on the pathway of purine degradation.
- It is created from guanine by guanine deaminase.
- It is created from hypoxanthine by xanthine oxidoreductase.
Xanthine is subsequently converted to uric acid by the action of the xanthine oxidase enzyme.
Pathology
People with the rare genetic disorder xanthinuria lack sufficient xanthine oxidase and cannot convert xanthine to uric acid.
Clinical significance of xanthine derivatives
Derivatives of xanthine, known collectively as xanthines, are a group of alkaloids 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. Therapeutic 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.
References
Psychoanaleptics: psychostimulants, agents used for ADHD and nootropics (N06B) | |
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| Centrally acting sympathomimetics | Amphetamine - Amphetaminil - Atomoxetine - Dextroamphetamine - Dextromethamphetamine - Fencamfamin - Fenozolone - Fenetylline - Methylphenidate - Mesocarb - Pemoline - Pipradrol - Prolintane |
| Xanthine derivatives | Caffeine - Propentofylline |
| Racetams | Aniracetam - Oxiracetam - Phenylpiracetam - Piracetam - Pramiracetam |
| Ampakines | CX-516 - CX-546 - CX-614 - CX-691 - CX-717 - IDRA-21 - LY-503,430 - PEPA |
| Eugeroics | Adrafinil - Armodafinil - Modafinil |
| Other psychostimulants and nootropics | Acetylcarnitine - Citicoline - Cyprodenate - Idebenone - Deanol - Dimebon - Fipexide - Linopirdine - Meclofenoxate - Nizofenone - Pirisudanol - Pyritinol - Sulbutiamine - Vinpocetine |
Drugs for obstructive airway diseases: asthma/COPD (R03) | |
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| Adrenergics, inhalants | Short acting β2-agonists: Salbutamol/Levosalbutamol • Fenoterol • Terbutaline Long acting β2-agonists (LABA): Bambuterol • Clenbuterol • Formoterol • Salmeterol other: Epinephrine • Isoproterenol • Orciprenaline |
| Glucocorticoids | Beclometasone • Budesonide • Ciclesonide • Fluticasone • Mometasone |
| Anticholinergics | Ipratropium • Tiotropium |
| Mast cell stabilizers | Cromoglicate • Nedocromil |
| Xanthines | Aminophylline • Theobromine • Theophylline |
| Leukotriene antagonists | Montelukast • Pranlukast • Zafirlukast |
| Combination products | Budesonide/formoterol • Fluticasone/salmeterol • Ipratropium/salbutamol |
da:Xanthin de:Xanthinfr:Xanthine gl:Metilxantinas nl:Xanthine ja:キサンチン
Acknowledgement and Attribution Regarding Sources of Content
Some of the initial content on this page may be incorporated in part from copyleft sources in the public domain including wikis such as Wikipedia and AskDrWiki. Drug information for patients came from the The National Library of Medicine. Infectious disease information may have come from the Centers for Disease Control (CDC). Differential Diagnoses are drawn from clinicians as well as an amalgamation of 3 sources: 1.The Disease Database; 2. Kahan, Scott, Smith, Ellen G. In A Page: Signs and Symptoms. Malden, Massachusetts: Blackwell Publishing, 2004:3; 3. Sailer, Christian, Wasner, Susanne. Differential Diagnosis Pocket. Hermosa Beach, CA: Borm Bruckmeir Publishing LLC, 2002:7 .
