Xanthinol

Identification

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Name
Xanthinol
Accession Number
DB09092
Type
Small Molecule
Groups
Approved, Withdrawn
Description

Xanthinol is a very potent water-soluble derivative of niacin that can be found in diet supplements. It is also known as xanthinol nicotinate. 6 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. 7 It was approved as a drug in 1998 in Canada and nowadays its status is cancelled post marketing.

Structure
Thumb
Synonyms
  • Xantinol
Product Ingredients
IngredientUNIICASInChI Key
Xanthinol nicotinate8G60H12X2D437-74-1GEPMAHVDJHFBJI-UHFFFAOYSA-N
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Complamin Tab 150mgTablet150 mgOralSmithkline Beecham Pharma Division Of Smithkline Beecham Inc1992-12-311998-08-31Canada
Complamin Tab 300mgTablet300 mgOralSmithkline Beecham Pharma Division Of Smithkline Beecham Inc1992-12-311999-07-12Canada
Additional Data Available
  • Application Number
    Application Number

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

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  • Product Code
    Product Code

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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Categories
UNII
TN1B5910V2
CAS number
2530-97-4
Weight
Average: 311.342
Monoisotopic: 311.159354176
Chemical Formula
C13H21N5O4
InChI Key
DSFGXPJYDCSWTA-UHFFFAOYSA-N
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
IUPAC Name
7-{2-hydroxy-3-[(2-hydroxyethyl)(methyl)amino]propyl}-1,3-dimethyl-2,3,6,7-tetrahydro-1H-purine-2,6-dione
SMILES
CN(CCO)CC(O)CN1C=NC2=C1C(=O)N(C)C(=O)N2C

Pharmacology

Indication

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.7 Its action allows having an elevated rate of blood flow in the brain which helps improve memory function, concentration and awareness.6 Thus, due to his actions, xanthinol is indicated to improve cerebrovascular and peripheral vascular disorders as well as hyperlipidaemias.8

Pharmacodynamics

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.7 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.1

Mechanism of action

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.1

TargetActionsOrganism
N60S ribosomal protein L3
binder
Humans
ANAD(P) transhydrogenase, mitochondrial
cofactor
Humans
AGlyceraldehyde-3-phosphate dehydrogenase
cofactor
Humans
AIsocitrate dehydrogenase [NAD] subunit alpha, mitochondrial
cofactor
Humans
A2-oxoglutarate dehydrogenase, mitochondrial
cofactor
Humans
AMalate dehydrogenase, mitochondrial
cofactor
Humans
Absorption

Xanthinol is readily absorbed in the body with an absorption half life of 0.4 h.4 After absorption, xanthinol nicotinate rapidly degardes into the negatively charged nicotinic acid and the positively charged xanthinol ion.1

Volume of distribution

The volume of distribution of xanthinol is 0.93 L/kg.

Protein binding

From the administered dose of xanthinol between 90.9 and 100% can be retreived in the plasma.2

Metabolism

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.3

Route of elimination

In urine, the two stereoisomeric forms of the xanthinol metabolites represents about 7-8% of the eliminated xanthinol.3

Half life

The reported elimination half-life of xanthinol is 1.67h.

Clearance

The total body clearance rate for xanthinol is 0.63 L h/kg.

Toxicity

It is thought to cause flushing, hypotension and abdominal pain.5

Affected organisms
  • Humans and other mammals
  • Human Immunodeficiency Virus
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
Patent BlueThe therapeutic efficacy of Xanthinol can be decreased when used in combination with Patent Blue.
Additional Data Available
  • Extended Description
    Extended Description

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  • Severity
    Severity

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  • Evidence Level
    Evidence Level

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  • Action
    Action

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Food Interactions
Not Available

References

General References
  1. Loriaux SM, Deijen JB, Orlebeke JF, De Swart JH: The effects of nicotinic acid and xanthinol nicotinate on human memory in different categories of age. A double blind study. Psychopharmacology (Berl). 1985;87(4):390-5. [PubMed:3936095]
  2. Liu HQ, Su MX, Di B, Hang TJ, Hu Y, Tian XQ, Zhang YD, Shen JP: Development and validation of a liquid chromatography-tandem mass spectrometry method for the determination of xanthinol in human plasma and its application in a bioequivalence study of xanthinol nicotinate tablets. J Chromatogr B Analyt Technol Biomed Life Sci. 2008 Sep 15;873(1):20-6. doi: 10.1016/j.jchromb.2008.07.045. Epub 2008 Aug 7. [PubMed:18718822]
  3. Tauscher M, Eckhardt G, Geisel B, Credner K: [Isolation and structure determination of metabolites of xantinol from rat urine (author's transl)]. Arzneimittelforschung. 1976;26(7):1342-4. [PubMed:1036921]
  4. Seyffart G. (1992). Drug dosage in renal insufficiency (2nd ed.). Springer Science+Business Media Dordrecht.
  5. Turner P. and Volans G. (1986). The drugs handbook 1985-86. Macmillan Reference Books.
  6. Exercise [Link]
  7. Smart publications [Link]
  8. Xanthinol [Link]
External Links
PubChem Compound
9913
PubChem Substance
310265019
ChemSpider
9526
ChEBI
94314
ChEMBL
CHEMBL1624126
Wikipedia
Xanthinol
ATC Codes
C04AD02 — Xantinol nicotinate
MSDS
Download (17.1 KB)

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
FormRouteStrength
TabletOral150 mg
TabletOral300 mg
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)179-180 ºC'MSDS'
boiling point (°C)589.3 ºC at 760 mmHg'MSDS'
water solubility<1 mg/mL 'MSDS'
Predicted Properties
PropertyValueSource
Water Solubility17.3 mg/mLALOGPS
logP-1ALOGPS
logP-1.8ChemAxon
logS-1.2ALOGPS
pKa (Strongest Acidic)14.38ChemAxon
pKa (Strongest Basic)8.86ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area102.14 Å2ChemAxon
Rotatable Bond Count6ChemAxon
Refractivity80.11 m3·mol-1ChemAxon
Polarizability31.95 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

Description
This compound belongs to the class of organic compounds known as xanthines. These are purine derivatives with a ketone group conjugated at carbons 2 and 6 of the purine moiety.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Imidazopyrimidines
Sub Class
Purines and purine derivatives
Direct Parent
Xanthines
Alternative Parents
6-oxopurines / Alkaloids and derivatives / Pyrimidones / N-substituted imidazoles / Vinylogous amides / Heteroaromatic compounds / 1,2-aminoalcohols / Ureas / Trialkylamines / Secondary alcohols
show 6 more
Substituents
Xanthine / 6-oxopurine / Purinone / Alkaloid or derivatives / Pyrimidone / N-substituted imidazole / Pyrimidine / Heteroaromatic compound / Azole / Imidazole
show 20 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available

Targets

Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Binder
General Function
Structural constituent of ribosome
Specific Function
The L3 protein is a component of the large subunit of cytoplasmic ribosomes.
Gene Name
RPL3
Uniprot ID
P39023
Uniprot Name
60S ribosomal protein L3
Molecular Weight
46108.72 Da
References
  1. Petropoulos AD, Kouvela EC, Dinos GP, Kalpaxis DL: Stepwise binding of tylosin and erythromycin to Escherichia coli ribosomes, characterized by kinetic and footprinting analysis. J Biol Chem. 2008 Feb 22;283(8):4756-65. doi: 10.1074/jbc.M708371200. Epub 2007 Dec 13. [PubMed:18079110]
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Cofactor
General Function
Nadp binding
Specific Function
The transhydrogenation between NADH and NADP is coupled to respiration and ATP hydrolysis and functions as a proton pump across the membrane. May play a role in reactive oxygen species (ROS) detoxi...
Gene Name
NNT
Uniprot ID
Q13423
Uniprot Name
NAD(P) transhydrogenase, mitochondrial
Molecular Weight
113894.595 Da
References
  1. Loriaux SM, Deijen JB, Orlebeke JF, De Swart JH: The effects of nicotinic acid and xanthinol nicotinate on human memory in different categories of age. A double blind study. Psychopharmacology (Berl). 1985;87(4):390-5. [PubMed:3936095]
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Cofactor
General Function
Peptidyl-cysteine s-nitrosylase activity
Specific Function
Has both glyceraldehyde-3-phosphate dehydrogenase and nitrosylase activities, thereby playing a role in glycolysis and nuclear functions, respectively. Participates in nuclear events including tran...
Gene Name
GAPDH
Uniprot ID
P04406
Uniprot Name
Glyceraldehyde-3-phosphate dehydrogenase
Molecular Weight
36053.0 Da
References
  1. Loriaux SM, Deijen JB, Orlebeke JF, De Swart JH: The effects of nicotinic acid and xanthinol nicotinate on human memory in different categories of age. A double blind study. Psychopharmacology (Berl). 1985;87(4):390-5. [PubMed:3936095]
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Cofactor
General Function
Nad binding
Specific Function
Not Available
Gene Name
IDH3A
Uniprot ID
P50213
Uniprot Name
Isocitrate dehydrogenase [NAD] subunit alpha, mitochondrial
Molecular Weight
39591.365 Da
References
  1. Loriaux SM, Deijen JB, Orlebeke JF, De Swart JH: The effects of nicotinic acid and xanthinol nicotinate on human memory in different categories of age. A double blind study. Psychopharmacology (Berl). 1985;87(4):390-5. [PubMed:3936095]
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Cofactor
General Function
Thiamine pyrophosphate binding
Specific Function
The 2-oxoglutarate dehydrogenase complex catalyzes the overall conversion of 2-oxoglutarate to succinyl-CoA and CO(2). It contains multiple copies of three enzymatic components: 2-oxoglutarate dehy...
Gene Name
OGDH
Uniprot ID
Q02218
Uniprot Name
2-oxoglutarate dehydrogenase, mitochondrial
Molecular Weight
115934.37 Da
References
  1. Loriaux SM, Deijen JB, Orlebeke JF, De Swart JH: The effects of nicotinic acid and xanthinol nicotinate on human memory in different categories of age. A double blind study. Psychopharmacology (Berl). 1985;87(4):390-5. [PubMed:3936095]
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Cofactor
General Function
Poly(a) rna binding
Specific Function
Not Available
Gene Name
MDH2
Uniprot ID
P40926
Uniprot Name
Malate dehydrogenase, mitochondrial
Molecular Weight
35502.935 Da
References
  1. Loriaux SM, Deijen JB, Orlebeke JF, De Swart JH: The effects of nicotinic acid and xanthinol nicotinate on human memory in different categories of age. A double blind study. Psychopharmacology (Berl). 1985;87(4):390-5. [PubMed:3936095]

Drug created on September 16, 2015 10:10 / Updated on June 04, 2019 07:07