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Details

Stereochemistry RACEMIC
Molecular Formula C13H21N5O4.C6H5NO2
Molecular Weight 434.4463
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of XANTHINOL NIACINATE

SMILES

OC(=O)C1=CN=CC=C1.CN(CCO)CC(O)CN2C=NC3=C2C(=O)N(C)C(=O)N3C

InChI

InChIKey=GEPMAHVDJHFBJI-UHFFFAOYSA-N
InChI=1S/C13H21N5O4.C6H5NO2/c1-15(4-5-19)6-9(20)7-18-8-14-11-10(18)12(21)17(3)13(22)16(11)2;8-6(9)5-2-1-3-7-4-5/h8-9,19-20H,4-7H2,1-3H3;1-4H,(H,8,9)

HIDE SMILES / InChI

Molecular Formula C6H5NO2
Molecular Weight 123.1094
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula C13H21N5O4
Molecular Weight 311.3369
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )

Description

Xanthinol (xanthinol nicotinate) is a xanthine derivative, peripheral vasodilator agent. It exerts it`s pharmacological action by acting as a vasodilator and improves blood flow to brain, arteries, and to the periphery. It increases brain glucose metabolism and thus improves brain ATP levels. It stimulates memory and concentration elevates brain energy levels. Indications for Xanthinol Nicotinate: 1. Peripheral vascular sclerosis 2. Cerebral circulatory disorders 3. Arteriosclerosis 4. Endarteritis obliterans 5. Short term memory disorders 6. Mental flagging 7. Anti ageing memory support 8. Diabetic angiopathy 9. Diabetic gangrene 10. Hyperlipidaemia 11. Intermittent claudication Side Effects of Xanthinol Nicotinate: 1. Flushing 2. Feeling of warmth 3. Nausea 4. Heart burn 5. Vomiting 6. Itching of skin For 30 years, Xanthinol nicotinate has been on the market for the treatment of impaired brain function, i.e., organic brain syndromes of various etiologies. Controlled double-blind phase-III clinical trials have shown that xantinol nicotinate is also an effective drug in the treatment of dementia. Xanthinol nicotinate is also helpful in the management of leg ulcers associated with haemoglobinopathies. Xanthinol was approved as a drug in 1998 in Canada and nowadays its status is cancelled post marketing. 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.

Originator

Approval Year

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Complamin
Primary
Complamin

PubMed

Sample Use Guides

In Vivo Use Guide
Typical Dosage for Xanthinol Nicotinate Oral: 300mg 8th hourly. Increases the dosage up to 600mg 8th hourly if required. Maximum dose: 1800mg/day. I.V. or I.M.: 300mg. Maximum dose: 900mg.
Route of Administration: Other
In Vitro Use Guide
HUASMCs were treated with different concentrations of Xanthinol (xanthinol nicotinate) (0, 2.76, 27.6 or 276 uM), and a 3-(4,5-dimethylthiazol-2yl)-2, 5-diphenyltetrazolium bromide (MTT) assay was used to detect the inhibition of HUASMC proliferation.
Substance Class Chemical
Record UNII
8G60H12X2D
Record Status Validated (UNII)
Record Version