Identification
- Summary
Xanthinol is a vasodilatory niacin found in diet supplements.
- Generic Name
- Xanthinol
- DrugBank Accession Number
- DB09092
- Background
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.
- Type
- Small Molecule
- Groups
- Approved, Withdrawn
- Structure
Structure for Xanthinol (DB09092)
- Weight
- Average: 311.342
Monoisotopic: 311.159354176 - Chemical Formula
- C13H21N5O4
- Synonyms
- Xantinol
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
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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
Target Actions Organism ANAD(P) transhydrogenase, mitochondrial cofactorHumans AGlyceraldehyde-3-phosphate dehydrogenase cofactorHumans AIsocitrate dehydrogenase [NAD] subunit alpha, mitochondrial cofactorHumans A2-oxoglutarate dehydrogenase, mitochondrial cofactorHumans AMalate dehydrogenase, mitochondrial cofactorHumans N60S ribosomal protein L3 binderHumans - 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.
- Adverse Effects
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It is thought to cause flushing, hypotension and abdominal pain.5
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
- Not Available
Interactions
- Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Integrate drug-drug
interactions in your softwareIsosorbide mononitrate Xanthinol may increase the vasodilatory activities of Isosorbide mononitrate. Patent Blue The therapeutic efficacy of Xanthinol can be decreased when used in combination with Patent Blue. - Food Interactions
- Not Available
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- Product Ingredients
Ingredient UNII CAS InChI Key Xanthinol nicotinate 8G60H12X2D 437-74-1 GEPMAHVDJHFBJI-UHFFFAOYSA-N - Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Complamin Tab 150mg Tablet 150 mg / tab Oral Smithkline Beecham Pharma Division Of Smithkline Beecham Inc 1992-12-31 1998-08-31 Canada 
Complamin Tab 300mg Tablet 300 mg / tab Oral Smithkline Beecham Pharma Division Of Smithkline Beecham Inc 1992-12-31 1999-07-12 Canada
Categories
- ATC Codes
- C04AD02 — Xantinol nicotinate
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- 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
- 1,2-aminoalcohol / 6-oxopurine / Alcohol / Alkaloid or derivatives / Alkanolamine / Amine / Aromatic heteropolycyclic compound / Azacycle / Azole / Heteroaromatic compound show 20 more
- Molecular Framework
- Aromatic heteropolycyclic compounds
- External Descriptors
- Not Available
- Affected organisms
- Humans and other mammals
- Human Immunodeficiency Virus
Chemical Identifiers
- UNII
- TN1B5910V2
- CAS number
- 2530-97-4
- 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
References
- General References
- 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. [Article]
- 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. [Article]
- 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. [Article]
- Seyffart G. (1992). Drug dosage in renal insufficiency (2nd ed.). Springer Science+Business Media Dordrecht.
- Turner P. and Volans G. (1986). The drugs handbook 1985-86. Macmillan Reference Books.
- Exercise [Link]
- Smart publications [Link]
- Xanthinol [Link]
- External Links
- MSDS
- Download (17.1 KB)
Clinical Trials
- Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
Phase Status Purpose Conditions Count
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Injection, solution Intravenous Pill Solution / drops Oral Tablet Oral 150 mg / tab Tablet Oral 300 mg / tab Tablet Oral - Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source 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
Property Value Source Water Solubility 17.3 mg/mL ALOGPS logP -1 ALOGPS logP -1.8 Chemaxon logS -1.2 ALOGPS pKa (Strongest Acidic) 14.38 Chemaxon pKa (Strongest Basic) 8.86 Chemaxon Physiological Charge 1 Chemaxon Hydrogen Acceptor Count 6 Chemaxon Hydrogen Donor Count 2 Chemaxon Polar Surface Area 102.14 Å2 Chemaxon Rotatable Bond Count 6 Chemaxon Refractivity 80.11 m3·mol-1 Chemaxon Polarizability 31.95 Å3 Chemaxon Number of Rings 2 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
- Not Available
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS splash10-052o-9440000000-a8d9629fcf2b57351e3d Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-03di-0019000000-6b6ceab4f5031cd86bd8 Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-03di-0089000000-2477bea8a8f1d44b4427 Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-0in9-0292000000-0d5fc2d249f9d3dc2963 Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-05r4-0190000000-1d75b4ce36634050c00b Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-004i-0390000000-242f758887b1a1de78a7 Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-004i-3970000000-dd50ee8b30c9b6b78627 Predicted 1H NMR Spectrum 1D NMR Not Applicable Predicted 13C NMR Spectrum 1D NMR Not Applicable - Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 162.99144 predictedDeepCCS 1.0 (2019) [M+H]+ 165.34944 predictedDeepCCS 1.0 (2019) [M+Na]+ 171.94533 predictedDeepCCS 1.0 (2019)
Targets
- 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
- 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. [Article]
- 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
- 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. [Article]
- 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
- 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. [Article]
- 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
- 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. [Article]
- 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
- 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. [Article]
- 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
- 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. [Article]
Drug created at September 16, 2015 16:10 / Updated at December 02, 2023 07:01