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Information about Methylxanthine

Not to be confused with xanthene.


Xanthine
IUPAC name3,7-Dihydro-purine-2,6-dione
Other names1H-Purine-2,6-diol
Identifiers
CAS number69-89-6
PubChem1188
SMILESO=C1NC(=O)c2[nH]cnc2N1
Properties
Molecular formulaC5H4N4O2
Molar mass152.111 g/mol
AppearanceWhite solid
Melting point decomposes
Solubility in water1 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)
Xanthine (IPA: /ˈzænθiːn, ˈzænθaɪn]/), (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. 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



 •  • [ e]
Psychoanaleptics: psychostimulants, agents used for ADHD and nootropics (N06B)
Centrally acting sympathomimeticsAmphetamine - Dexamphetamine - Dextromethamphetamine - Methylphenidate - Pemoline - Fencamfamin - Modafinil - Fenozolone - Atomoxetine - Fenetylline
Xanthine derivativesCaffeine - Propentofylline
Other psychostimulants and nootropicsRacetams (Piracetam, Oxiracetam, Aniracetam, Pramiracetam) - Meclofenoxate - Pyritinol - Deanol - Fipexide - Citicoline - Pirisudanol - Linopirdine - Nizofenone - Acetylcarnitine - Idebenone - Prolintane - Pipradrol - Adrafinil - Vinpocetine
 •  • [ e]
Drugs for obstructive airway diseases: asthma/COPD (R03)
Adrenergics, inhalantsShort acting β2-agonists: Salbutamol • Fenoterol • Terbutaline
Long acting β2-agonists (LABA): Bambuterol • Clenbuterol • Formoterol • Salmeterol
other: Epinephrine • Isoproterenol • Orciprenaline
GlucocorticoidsBeclometasone • Budesonide • Ciclesonide • Fluticasone • Mometasone
AnticholinergicsIpratropium • Tiotropium
Mast cell stabilizersCromoglicate • Nedocromil
XanthinesAminophylline • Theobromine • Theophylline
Leukotriene antagonistsMontelukast • Pranlukast • Zafirlukast
Combination productsBudesonide/formoterol • Fluticasone/salmeterol • Ipratropium/salbutamol
Not to be confused with xanthine.


Xanthene (9H-xanthene, 10H-9-oxaanthracene) is a yellow organic heterocyclic compound. Its chemical formula is C13H10O. It is soluble in ether.
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IUPAC nomenclature is a system of naming chemical compounds and of describing the science of chemistry in general. It is developed and kept up to date under the auspices of the International Union of Pure and Applied Chemistry (IUPAC).
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CAS registry numbers are unique numerical identifiers for chemical compounds, polymers, biological sequences, mixtures and alloys. They are also referred to as CAS numbers, CAS RNs or CAS #s.
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PubChem is a database of chemical molecules. The system is maintained by the National Center for Biotechnology Information (NCBI), a component of the National Library of Medicine, which is part of the United States National Institutes of Health (NIH).
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smiles

File extension: .smi
Type of format: chemical file format

The simplified molecular input line entry specification or SMILES
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A chemical formula is a concise way of expressing information about the atoms that constitute a particular chemical compound. A chemical formula is also a short way of showing how a chemical reaction occurs.
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Molar mass, symbol M,[1] is the mass of one mole of a substance (chemical element or chemical compound).[2] It is a physical property which is characteristic of each pure substance.
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The melting point of a crystalline solid is the temperature range at which it changes state from solid to liquid. Although the phrase would suggest a specific temperature and is commonly and incorrectly used as such in most textbooks and literature, most crystalline compounds
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Solubility is a physical property referring to the ability for a given substance, the solute, to dissolve in a solvent.[1] It is measured in terms of the maximum amount of solute dissolved in a solvent at equilibrium. The resulting solution is called a saturated solution.
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Water is a common chemical substance that is essential to all known forms of life.[1] In typical usage, water refers only to its liquid form or state, but the substance also has a solid state, ice, and a gaseous state, water vapor.
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standard state of a material is its state at 1 bar (100 kilopascals exactly). This pressure was changed from 1 atm (101.325 kilopascals) by IUPAC in 1990.[1] The standard state of a material can be defined at any given temperature, most commonly 25 degrees Celsius,
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This chart shows concisely the most common way in which the International Phonetic Alphabet (IPA) is applied to represent the English language.

See International Phonetic Alphabet for English for a more complete version and Pronunciation respelling for English for phonetic
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Purine (1) is a heterocyclic aromatic organic compound, consisting of a pyrimidine ring fused to an imidazole ring. Purines make up one of the two groups of nitrogenous bases. Pyrimidines make up the other group.
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    In chemistry, a base is most commonly thought of as a substance that can accept protons. This refers to the Brønsted-Lowry theory of acids and bases. Alternate definitions of bases include electron pair donors (Lewis), and as sources of hydroxide anions (Arrhenius).
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    Many organisms have metabolic pathways to synthesise and break down purines.

    Synthesis

    Purines are biologically synthesized as nucleosides (bases attached to ribose). The committed step is amidophosphoribosyltransferase.
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    Guanine is one of the five main nucleobases found in the nucleic acids DNA and RNA; the others being adenine, cytosine, thymine, and uracil. With the formula C5H5N5
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    Guanine deaminase (or guanine aminohydrolase) is an enzyme which converts guanine to xanthine.

    guanine

    xanthine. Note nitrogen replaced with oxygen. (Ignore rotation.

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    Hypoxanthine is a naturally occurring purine derivative.

    It is occasionally found as a constituent of nucleic acids where it is present in the anticodon of tRNA in the form of its nucleoside inosine.
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    The enzyme xanthine oxidase, or XO, (bovine milk enzyme is PDB 1FIQ , EC 1.17.3.2 ) catalyzes the oxidation of hypoxanthine to xanthine and can further catalyze the oxidation of xanthine to uric acid

    Reaction

    • hypoxanthine + O2 + H2

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    Uric acid (or urate) is an organic compound of carbon, nitrogen, oxygen and hydrogen with the formula C5H4N4O3.

    Metabolic processes

    Xanthine oxidase oxidizes oxypurines such as xanthine and hypoxanthine to uric acid.
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    The enzyme xanthine oxidase, or XO, (bovine milk enzyme is PDB 1FIQ , EC 1.17.3.2 ) catalyzes the oxidation of hypoxanthine to xanthine and can further catalyze the oxidation of xanthine to uric acid

    Reaction

    • hypoxanthine + O2 + H2

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    A genetic disorder is a condition caused by abnormalities in genes or chromosomes. While some diseases, such as cancer, are due to genetic abnormalities acquired in a few cells during life, the term "genetic disease" most commonly refers to diseases present in all cells of the body
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    Xanthinuria
    Classification & external resources

    The structure of xanthine.
    ICD-10 E 79.8
    ICD-9 277.2

    OMIM 278300 603592
    DiseasesDB 14194 29821

    eMedicine ped/2452   Xanthinuria, also known as Xanthine oxydase deficiency
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    alkaloid is, strictly speaking, a naturally occurring amine produced by a plant, but amines produced by animals and fungi are also called alkaloids[1]. Many alkaloids have pharmacological effects on humans and other animals.
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    Stimulants are drugs that temporarily increase alertness and awareness. They usually have increased side-effects with increased effectiveness, and the more powerful variants are therefore often prescription medicines or illegal drugs.
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    A bronchodilator is a substance that dilates the bronchi and bronchioles, increasing airflow. Bronchodilators may be endogenous (originating naturally within the body), or they may be medications administered for the treatment of breathing difficulties.
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    Asthma
    Classification & external resources

    ICD-10 J 45.
    ICD-9 493

    OMIM 600807
    DiseasesDB 1006
    MedlinePlus 000141
    eMedicine med/177   emerg/43

    MeSH C08.127.
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    Adenosine is a nucleoside composed of adenine attached to a ribose (ribofuranose) moiety via a β-N9-glycosidic bond.

    Adenosine plays an important role in biochemical processes, such as energy transfer - as adenosine triphosphate (ATP) and adenosine
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    Sympathomimetic drugs are substances that mimic the effects of the hormone epinephrine (adrenaline) and the hormone/neurotransmitter norepinephrine (noradrenaline). They all raise blood pressure and are all weak bases.
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    The therapeutic index (also known as therapeutic ratio), is a comparison of the amount of a therapeutic agent that causes the therapeutic effect to the amount that causes toxic effects.
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