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Xanthine information


Xanthine[1]
Names
Preferred IUPAC name
3,7-Dihydro-1H-purine-2,6-dione
Other names
1H-Purine-2,6-dione
Identifiers
CAS Number
  • 69-89-6 checkY
3D model (JSmol)
  • Interactive image
ChEBI
  • CHEBI:17712 ☒N
ChEMBL
  • ChEMBL1424 checkY
ChemSpider
  • 1151 checkY
DrugBank
  • DB02134 ☒N
ECHA InfoCard 100.000.653 Edit this at Wikidata
IUPHAR/BPS
  • 4557
KEGG
  • C00385 ☒N
PubChem CID
  • 1188
UNII
  • 1AVZ07U9S7 ☒N
CompTox Dashboard (EPA)
  • DTXSID4035120 Edit this at Wikidata
InChI
  • InChI=1S/C5H4N4O2/c10-4-2-3(7-1-6-2)8-5(11)9-4/h1H,(H3,6,7,8,9,10,11) checkY
    Key: LRFVTYWOQMYALW-UHFFFAOYSA-N ☒N
  • InChI=1S/C5H4N4O2/c10-4-2-3(7-1-6-2)8-5(11)9-4/h1H,(H3,6,7,8,9,10,11)
  • InChI=1S/C5H4N4O2/c10-4-2-3(7-1-6-2)8-5(11)9-4/h1H,(H3,6,7,8,9,10,11)
    Key: LRFVTYWOQMYALW-UHFFFAOYSA-N
SMILES
  • c1[nH]c2c(n1)nc(nc2O)O
Properties
Chemical formula
C5H4N4O2
Molar mass 152.11 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
Hazards
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroformFlammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
2
1
0
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)
Infobox references

Xanthine (/ˈzænθn/ or /ˈzænθn/, from Ancient Greek ξανθός xanthós "yellow" due to its yellowish-white appearance; archaically xanthic acid; systematic name 3,7-dihydropurine-2,6-dione) is a purine base found in most human body tissues and fluids, as well as in other organisms.[2] Several stimulants are derived from xanthine, including caffeine, theophylline, and theobromine.[3][4]

Xanthine is a product on the pathway of purine degradation.[2]

  • It is created from guanine by guanine deaminase.
  • It is created from hypoxanthine by xanthine oxidoreductase.
  • It is also created from xanthosine by purine nucleoside phosphorylase.

Xanthine is subsequently converted to uric acid by the action of the xanthine oxidase enzyme.[2]

  1. ^ Merck Index, 11th Edition, 9968.
  2. ^ a b c "Xanthine, CID 1188". PubChem, National Library of Medicine, US National Institutes of Health. 2019. Retrieved 28 September 2019.
  3. ^ Spiller, Gene A. (1998). Caffeine. Boca Raton: CRC Press. ISBN 0-8493-2647-8.
  4. ^ Katzung, Bertram G. (1995). Basic & Clinical Pharmacology. East Norwalk, Connecticut: Paramount Publishing. pp. 310, 311. ISBN 0-8385-0619-4.

and 27 Related for: Xanthine information

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Xanthine

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Xanthine (/ˈzænθiːn/ or /ˈzænθaɪn/, from Ancient Greek ξανθός xanthós "yellow" due to its yellowish-white appearance; archaically xanthic acid; systematic...

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Xanthine oxidase

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Xanthine oxidase (XO, sometimes 'XAO') is a form of xanthine oxidoreductase, a type of enzyme that generates reactive oxygen species. These enzymes catalyze...

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Xanthine dehydrogenase

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Xanthine dehydrogenase, also known as XDH, is a protein that, in humans, is encoded by the XDH gene. Xanthine dehydrogenase belongs to the group of...

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Xanthinuria

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as xanthine oxidase deficiency, is a rare genetic disorder causing the accumulation of xanthine. It is caused by a deficiency of the enzyme xanthine oxidase...

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Xanthine oxidase inhibitor

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A xanthine oxidase inhibitor is any substance that inhibits the activity of xanthine oxidase, an enzyme involved in purine metabolism. In humans, inhibition...

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Kidney disease

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function of xanthine oxidase in the purine degradation pathway. Xanthine oxidase will degrade hypoxanthine to xanthine and then to uric acid. Xanthine is not...

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Uric acid

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substance in the said solvent. The enzyme xanthine oxidase (XO) catalyzes the formation of uric acid from xanthine and hypoxanthine. XO, which is found in...

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Xanthine phosphoribosyltransferase

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In enzymology, a xanthine phosphoribosyltransferase (EC 2.4.2.22) is an enzyme that catalyzes the chemical reaction XMP + diphosphate ⇌{\displaystyle \rightleftharpoons...

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Purine metabolism

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Guanase converts guanine to xanthine Xanthine oxidase (a form of xanthine oxidoreductase) catalyzes the oxidation of xanthine to uric acid A nuclease frees...

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Allopurinol

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result in harm, this use has not been well studied. Allopurinol is in the xanthine oxidase inhibitor family of medications. Allopurinol was approved for medical...

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Nucleobase

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groups on the complementary bases. Nucleobases such as adenine, guanine, xanthine, hypoxanthine, purine, 2,6-diaminopurine, and 6,8-diaminopurine may have...

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Hypoxanthine

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action of xanthine oxidase on xanthine. However, more frequently in purine degradation, xanthine is formed from oxidation of hypoxanthine by xanthine oxidoreductase...

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Hyperuricemia

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of hypoxanthine and xanthine via the acceleration of adenine nucleotide degradation, and is a possible weak inhibitor of xanthine dehydrogenase. As a...

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Pentoxifylline

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Pentoxifylline, also known as oxpentifylline, is a xanthine derivative used as a drug to treat muscle pain in people with peripheral artery disease. It...

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Theobromine poisoning

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chocolate poisoning or cocoa poisoning, is an overdosage reaction to the xanthine alkaloid theobromine, found in chocolate, tea, cola beverages, and some...

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DMPX

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XOTooltip Xanthine oxidase Allopurinol Amflutizole Benzbromarone Caffeic acid Cinnamaldehyde Cinnamomum osmophloeum Febuxostat Myo-inositol Kaempferol...

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Diprophylline

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Diprophylline (INN) or dyphylline (USAN) (trade names Dilor, Lufyllin) is a xanthine derivative with bronchodilator and vasodilator effects. It is used in the...

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XO

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of the sex chromosomes is absent Xanthine oxidase, an enzyme that catalyzes the oxidation of hypoxanthine to xanthine Xylenol orange, a chemical indicator...

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Superoxide

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Complex I and Complex III), as well as several other enzymes, for example xanthine oxidase, which can catalyze the transfer of electrons directly to molecular...

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Febuxostat

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Use is not recommended during pregnancy or breastfeeding. It inhibits xanthine oxidase, thus reducing production of uric acid in the body. Febuxostat...

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C8H10N4O2

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The molecular formula C8H10N4O2 may refer to: Enprofylline, a xanthine derivative used in the treatment of asthma. Caffeine, the world's most widely consumed...

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Deamination

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C-to-T mutations. Deamination of guanine results in the formation of xanthine. Xanthine, however, still pairs with cytosine. Deamination of adenine results...

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Theobromine

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molecule, a derivative of purine. It is also classified as a dimethyl xanthine. Related compounds include theophylline, caffeine, paraxanthine, and 7-methylxanthine...

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Guarana

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caffeine. Natural sources of caffeine contain widely varying mixtures of xanthine alkaloids other than caffeine, including the cardiac stimulants theophylline...

Word Count : 1352

Xanthosine

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Xanthosine is a nucleoside derived from xanthine and ribose. It is the biosynthetic precursor to 7-methylxanthosine by the action of 7-methylxanthosine...

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Nucleotide

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GMP is split into the base guanine and ribose. Guanine is deaminated to xanthine which in turn is oxidized to uric acid. This last reaction is irreversible...

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Effect of caffeine on memory

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Caffeine is a bitter, white crystalline xanthine alkaloid that acts as a psychoactive stimulant drug. It can have both positive and negative effects on...

Word Count : 2863

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