Xanthinol

Xanthinol
Clinical data
ATC code	none;
Identifiers
	IUPAC name 7-[2-hydroxy-3-(2-hydroxyethyl-methylamino)propyl]-1,3-dimethylpurine-2,6-dione;
CAS Number	2530-97-4 ;
PubChem CID	9913;
DrugBank	1 ;
ChemSpider	9526 ;
UNII	TN1B5910V2;
CompTox Dashboard (EPA)	DTXSID1048255 ;
Chemical and physical data
Formula	C13H21N5O4
Molar mass	311.342 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES O=C2N(c1ncn(c1C(=O)N2C)CC(O)CN(CCO)C)C;
	InChI InChI=1S/C13H21N5O4/c1-15(4-5-19)6-9(20)7-18-8-14-11-10(18)12(21)17(3)13(22)16(11)2/h8-9,19-20H,4-7H2,1-3H3 ; Key:DSFGXPJYDCSWTA-UHFFFAOYSA-N ;
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Xanthinol is a drug prepared from theophylline used as a vasodilator.^[1]^[2] It is most often used as the salt with niacin (nicotinic acid), known as xanthinol nicotinate.^[3] It is a derivative of vitamin B3 (niacin), and can be found in a wide array dietary supplements. It has been marketed to increase the brain metabolism of glucose and ability to obtain ATP. Xanthinol is also used as an agent to reduced cholesterol as it is a vasodilator. It was approved as a medication in Canada in 1998, but it has since had its classification as a medication withdrawn. Xanthinol is indicated to improve cerebrovascular and peripheral vascular disorders as well as hyperlipidemias.^[4]

Mechanism of action

Xanthinol, as a positively charged ion, may increase the transportation of nicotinic acid into the cell since the later cannot freely diffuse through the cell membrane. The mechanism of action may be related to the mechanisms of the nucleotides NAD and NADP influence in the cell metabolism. Nicotinic acid is a coenzyme for multiple proteins involved in tissue respiration (Embden-Meyerhof and citrate cycle). The effect of xanthinol nicotinate causes an increase in glucose metabolism and energy gain.^[5]

References

↑ JA 38020588, Yokoyama M, Kawano S, "3-(Theophyllyl-7)-1-(N-methyl-N-hydroxyethyl)amino-2-propanol.", published 1963
↑ Morton IK, Hall JM (1999). Concise dictionary of pharmacological agents : properties and synonyms. Boston: Kluwer Academic. p. 294. ISBN 978-0-7514-0499-9.
↑ "Xanthinol niacinate". cancerweb.ncl.ac.uk.
↑ "Xanthinol". DrugBank.
↑ Loriaux SM, Deijen JB, Orlebeke JF, De Swart JH (1985). "The effects of nicotinic acid and xanthinol nicotinate on human memory in different categories of age. A double blind study". Psychopharmacology. 87 (4): 390–395. doi:10.1007/BF00432500. PMID 3936095.

[1] JA 38020588, Yokoyama M, Kawano S, "3-(Theophyllyl-7)-1-(N-methyl-N-hydroxyethyl)amino-2-propanol.", published 1963

[2] Morton IK, Hall JM (1999). Concise dictionary of pharmacological agents : properties and synonyms. Boston: Kluwer Academic. p. 294. ISBN 978-0-7514-0499-9.

[3] "Xanthinol niacinate". cancerweb.ncl.ac.uk.

[4] "Xanthinol". DrugBank.

[5] Loriaux SM, Deijen JB, Orlebeke JF, De Swart JH (1985). "The effects of nicotinic acid and xanthinol nicotinate on human memory in different categories of age. A double blind study". Psychopharmacology. 87 (4): 390–395. doi:10.1007/BF00432500. PMID 3936095.

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