Xanthinol
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Xanthinol
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CAS No:
2530-97-4
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Formula:
C13H21N5O4
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Chemical Name:
Xanthinol
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Synonyms:
1H-Purine-2,6-dione,3,7-dihydro-7-[2-hydroxy-3-[(2-hydroxyethyl)methylamino]propyl]-1,3-dimethyl-;Theophylline,7-[2-hydroxy-3-[(2-hydroxyethyl)methylamino]propyl]-;3,7-Dihydro-7-[2-hydroxy-3-[(2-hydroxyethyl)methylamino]propyl]-1,3-dimethyl-1H-purine-2,6-dione;7-[2-Hydroxy-3-[(2-hydroxyethyl)methylamino]propyl]theophylline;Xanthinol;117030-05-4;59496-54-7
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CAS No:
Description
7-[2-hydroxy-3-[2-hydroxyethyl(methyl)amino]propyl]-1,3-dimethylpurine-2,6-dione is an oxopurine.|Xanthinol is a very potent water-soluble derivative of niacin that can be found in diet supplements. It is also known as xanthinol nicotinate. Xaninthol is known to be a potent vasodilator that can easily pass through the cell membrane and once inside the cell it causes an increase in glucose metabolism resulting in an increased energy. It was approved as a drug in 1998 in Canada and nowadays its status is cancelled post marketing.|A vasodilator used in peripheral vascular disorders and insufficiency. It may cause gastric discomfort and hypotension.
Toxicity
It is thought to cause flushing, hypotension and abdominal pain.
From the administered dose of xanthinol between 90.9 and 100% can be retreived in the plasma.
Drug Information
Xanthinol is primarily used in diet supplements to increase the brain metabolism of glucose and obtain ATP. Xanthinol is also used as an agent to reduced cholesterol as it is a vasodilator. Its action allows having an elevated rate of blood flow in the brain which helps improve memory function, concentration and awareness. Thus, due to his actions, xanthinol is indicated to improve cerebrovascular and peripheral vascular disorders as well as hyperlipidaemias.
Reports indicate that xanthinol increases blood flow in the vascular beds. The use of xanthinol in clinical trials have reported improvements in the performance of healthy elderly individuals in short- and long-term memory tests. The later effect is explained by the enhancing on the cell metabolism and oxygen supply in the brain by the rise of ATP in erythrocytes which allows penetration into capillaries easier and a higher oxygen pressure in the capillary blood which improves oxygenation of surrounding tissue.
Drugs used to cause dilation of the blood vessels. (See all compounds classified as Vasodilator Agents.)
Xanthinol is readily absorbed in the body with an absorption half life of 0.4 h. After absorption, xanthinol nicotinate rapidly degardes into the negatively charged nicotinic acid and the positively charged xanthinol ion.|In urine, the two stereoisomeric forms of the xanthinol metabolites represents about 7-8% of the eliminated xanthinol.|The volume of distribution of xanthinol is 0.93 L/kg.|The total body clearance rate for xanthinol is 0.63 L h/kg.
As part of the metabolism of xanthinol, there is a formation of two metabolites that correspond to stereoisomeric forms of 2-coffeinyl-N-methyl-6-hydroxy-morpholines. These metabolites can be described structurally as semiacetals of a terminal aldehyde formed from xanthinol.
The reported elimination half-life of xanthinol is 1.67h.
The positively charged xanthinol ion is thought to help the transportation of the nicotinic acid into the cell since the later cannot freely diffuse through the cell membrane. The mechanism of action is thought to be related to present influence in the cell metabolism through the nucleotides NAD and NADP. Also, the nicotinic acid is a coenzyme for a lot of proteins involved in tissue respiration (Embden-Meyerhof and citrate cycle). The effect of xanthinol nicotinate causes an increase in glucose metabolism and energy gain.
Jupal|Complamin
Computed Properties
Molecular Weight:311.34
XLogP3:-1.8
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:6
Rotatable Bond Count:6
Exact Mass:311.15935417
Monoisotopic Mass:311.15935417
Topological Polar Surface Area:102
Heavy Atom Count:22
Complexity:435
Undefined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes