Identification
- Summary
Xanthine is a drug used to manage uncomplicated liver dysfunction in combination with orotic acid.
- Generic Name
- Xanthine
- DrugBank Accession Number
- DB02134
- Background
A purine base found in most body tissues and fluids, certain plants, and some urinary calculi. It is an intermediate in the degradation of adenosine monophosphate to uric acid, being formed by oxidation of hypoxanthine. The methylated xanthine compounds caffeine, theobromine, and theophylline and their derivatives are used in medicine for their bronchodilator effects. (Dorland, 28th ed)
- Type
- Small Molecule
- Groups
- Experimental
- Structure
Structure for Xanthine (DB02134)
- Weight
- Average: 152.1109
Monoisotopic: 152.033425392 - Chemical Formula
- C5H4N4O2
- Synonyms
- Not Available
- External IDs
- NSC-14664
Pharmacology
- Indication
Not Available
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Associated Conditions
Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Used as adjunct in combination to treat Uncomplicated hepatic dysfunction Combination Product in combination with: Orotic acid (DB02262) •••••••••••• •••••••• ••••••••• - Contraindications & Blackbox Warnings
Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API- Pharmacodynamics
Not Available
- Mechanism of action
Target Actions Organism UPurine nucleoside phosphorylase 2 Not Available Escherichia coli (strain K12) UXanthine phosphoribosyltransferase Not Available Escherichia coli (strain K12) - Absorption
Not Available
- Volume of distribution
Not Available
- Protein binding
Not Available
- Metabolism
- Not Available
- Route of elimination
Not Available
- Half-life
Not Available
- Clearance
Not Available
- Adverse Effects
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.- Toxicity
Not Available
- Pathways
Pathway Category Adenylosuccinate Lyase Deficiency Disease Xanthine Dehydrogenase Deficiency (Xanthinuria) Disease Xanthinuria Type I Disease Mitochondrial DNA Depletion Syndrome Disease Myoadenylate Deaminase Deficiency Disease Purine Metabolism Metabolic Purine Nucleoside Phosphorylase Deficiency Disease Lesch-Nyhan Syndrome (LNS) Disease Gout or Kelley-Seegmiller Syndrome Disease Mercaptopurine Action Pathway Drug action Adenine Phosphoribosyltransferase Deficiency (APRT) Disease Adenosine Deaminase Deficiency Disease AICA-Ribosiduria Disease Molybdenum Cofactor Deficiency Disease Azathioprine Action Pathway Drug action Thioguanine Action Pathway Drug action Xanthinuria Type II Disease - 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 software1,2-Benzodiazepine The therapeutic efficacy of 1,2-Benzodiazepine can be decreased when used in combination with Xanthine. Abametapir The serum concentration of Xanthine can be increased when it is combined with Abametapir. Abatacept The metabolism of Xanthine can be increased when combined with Abatacept. Abiraterone The serum concentration of Xanthine can be increased when it is combined with Abiraterone. Acebutolol The risk or severity of adverse effects can be increased when Acebutolol is combined with Xanthine. - 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.- Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image ATOXCYNAROL® INYECTABLE Xanthine (12.5 mg) + Orotic acid (12.5 mg) Solution Intramuscular ARBOFARMA S.A.S. 2010-12-16 2022-01-31 Colombia 
BETA - NECROTON CAPSULA Xanthine (50 mg) + Orotic acid (200 mg) Capsule, coated Oral Laboratorios Incobra S.A. 2006-11-10 Not applicable Colombia NECROTON CAPSULAS Xanthine (75 mg) + Orotic acid (150 mg) Capsule, coated Oral Laboratorios Incobra S.A. 2010-07-22 Not applicable Colombia
Categories
- 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 / Vinylogous amides / Imidazoles / Heteroaromatic compounds / Ureas / Lactams / Azacyclic compounds / Organopnictogen compounds show 4 more
- Substituents
- 6-oxopurine / Alkaloid or derivatives / Aromatic heteropolycyclic compound / Azacycle / Azole / Heteroaromatic compound / Hydrocarbon derivative / Imidazole / Lactam / Organic nitrogen compound show 11 more
- Molecular Framework
- Aromatic heteropolycyclic compounds
- External Descriptors
- xanthine (CHEBI:17712) / Purine alkaloids (C00385) / a small molecule (XANTHINE)
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- 1AVZ07U9S7
- CAS number
- 69-89-6
- InChI Key
- LRFVTYWOQMYALW-UHFFFAOYSA-N
- InChI
- InChI=1S/C5H4N4O2/c10-4-2-3(7-1-6-2)8-5(11)9-4/h1H,(H3,6,7,8,9,10,11)
- IUPAC Name
- 2,3,6,7-tetrahydro-1H-purine-2,6-dione
- SMILES
- O=C1NC2=C(NC=N2)C(=O)N1
References
- Synthesis Reference
John P. Zikakis, "Preparation of high purity xanthine oxidase from bovine milk." U.S. Patent US4172763, issued October 30, 1979.
US4172763- General References
- Not Available
- External Links
- Human Metabolome Database
- HMDB0000292
- KEGG Compound
- C00385
- PubChem Compound
- 1188
- PubChem Substance
- 46507575
- ChemSpider
- 1151
- BindingDB
- 82009
- 1311085
- ChEBI
- 17712
- ChEMBL
- CHEMBL1424
- ZINC
- ZINC000013517187
- Therapeutic Targets Database
- DCL000293
- PDBe Ligand
- XAN
- Wikipedia
- Xanthine
- PDB Entries
- 1a96 / 1yr3 / 2uz9 / 2w3s / 3eub / 3l8w / 5grk / 5h9i / 5i6c / 5ruy … show 9 more
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 2 Completed Prevention Hepatic Enzymes / Metabolic Syndrome Parameters / Systolic and Diastolic Blood Pressure Levels / Uric Acid Levels 1 2 Recruiting Treatment Gout 1 1 Completed Treatment Gout / Hyperuricemia 2 Not Available Withdrawn Not Available Gout / Hyperuricemia 1
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Solution Intramuscular Injection Parenteral Injection, solution Intramuscular 12.5 mg Capsule, coated Oral - Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source water solubility 69 mg/L (at 16 °C) MERCK INDEX (1996) logP -0.73 HANSCH,C ET AL. (1995) pKa 7.53 KORTUM,G ET AL (1961) - Predicted Properties
Property Value Source Water Solubility 4.91 mg/mL ALOGPS logP -0.65 ALOGPS logP -0.21 Chemaxon logS -1.5 ALOGPS pKa (Strongest Acidic) 7.95 Chemaxon pKa (Strongest Basic) -0.7 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 3 Chemaxon Hydrogen Donor Count 3 Chemaxon Polar Surface Area 86.88 Å2 Chemaxon Rotatable Bond Count 0 Chemaxon Refractivity 36.92 m3·mol-1 Chemaxon Polarizability 12.7 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
Property Value Probability Human Intestinal Absorption + 0.9923 Blood Brain Barrier + 0.9833 Caco-2 permeable - 0.7704 P-glycoprotein substrate Non-substrate 0.6282 P-glycoprotein inhibitor I Non-inhibitor 0.9619 P-glycoprotein inhibitor II Non-inhibitor 0.9953 Renal organic cation transporter Non-inhibitor 0.9279 CYP450 2C9 substrate Non-substrate 0.7781 CYP450 2D6 substrate Non-substrate 0.7434 CYP450 3A4 substrate Non-substrate 0.7417 CYP450 1A2 substrate Inhibitor 0.575 CYP450 2C9 inhibitor Non-inhibitor 0.8946 CYP450 2D6 inhibitor Non-inhibitor 0.9138 CYP450 2C19 inhibitor Non-inhibitor 0.8748 CYP450 3A4 inhibitor Non-inhibitor 0.8998 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9936 Ames test Non AMES toxic 0.8008 Carcinogenicity Non-carcinogens 0.9579 Biodegradation Ready biodegradable 0.5112 Rat acute toxicity 2.1045 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.938 hERG inhibition (predictor II) Non-inhibitor 0.9412
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 127.7571877 predictedDarkChem Lite v0.1.0 [M-H]- 127.7886877 predictedDarkChem Lite v0.1.0 [M-H]- 127.5472877 predictedDarkChem Lite v0.1.0 [M-H]- 127.6981877 predictedDarkChem Lite v0.1.0 [M-H]- 127.23582 predictedDeepCCS 1.0 (2019) [M-H]- 127.7571877 predictedDarkChem Lite v0.1.0 [M-H]- 127.7886877 predictedDarkChem Lite v0.1.0 [M-H]- 127.5472877 predictedDarkChem Lite v0.1.0 [M-H]- 127.6981877 predictedDarkChem Lite v0.1.0 [M-H]- 127.23582 predictedDeepCCS 1.0 (2019) [M+H]+ 128.7946877 predictedDarkChem Lite v0.1.0 [M+H]+ 128.6732877 predictedDarkChem Lite v0.1.0 [M+H]+ 128.5774877 predictedDarkChem Lite v0.1.0 [M+H]+ 128.6456877 predictedDarkChem Lite v0.1.0 [M+H]+ 130.59776 predictedDeepCCS 1.0 (2019) [M+H]+ 128.7946877 predictedDarkChem Lite v0.1.0 [M+H]+ 128.6732877 predictedDarkChem Lite v0.1.0 [M+H]+ 128.5774877 predictedDarkChem Lite v0.1.0 [M+H]+ 128.6456877 predictedDarkChem Lite v0.1.0 [M+H]+ 130.59776 predictedDeepCCS 1.0 (2019) [M+Na]+ 128.2540877 predictedDarkChem Lite v0.1.0 [M+Na]+ 128.4062877 predictedDarkChem Lite v0.1.0 [M+Na]+ 128.1514877 predictedDarkChem Lite v0.1.0 [M+Na]+ 128.1232877 predictedDarkChem Lite v0.1.0 [M+Na]+ 139.62263 predictedDeepCCS 1.0 (2019) [M+Na]+ 128.2540877 predictedDarkChem Lite v0.1.0 [M+Na]+ 128.4062877 predictedDarkChem Lite v0.1.0 [M+Na]+ 128.1514877 predictedDarkChem Lite v0.1.0 [M+Na]+ 128.1232877 predictedDarkChem Lite v0.1.0 [M+Na]+ 139.62263 predictedDeepCCS 1.0 (2019)
Targets
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- Kind
- Protein
- Organism
- Escherichia coli (strain K12)
- Pharmacological action
- Unknown
- General Function
- Purine-nucleoside phosphorylase activity
- Specific Function
- The purine nucleoside phosphorylases catalyze the phosphorolytic breakdown of the N-glycosidic bond in the beta-(deoxy)ribonucleoside molecules, with the formation of the corresponding free purine ...
- Gene Name
- xapA
- Uniprot ID
- P45563
- Uniprot Name
- Purine nucleoside phosphorylase 2
- Molecular Weight
- 29834.38 Da
References
- Kind
- Protein
- Organism
- Escherichia coli (strain K12)
- Pharmacological action
- Unknown
- General Function
- Xanthine phosphoribosyltransferase activity
- Specific Function
- Acts on guanine, xanthine and to a lesser extent hypoxanthine.
- Gene Name
- gpt
- Uniprot ID
- P0A9M5
- Uniprot Name
- Xanthine phosphoribosyltransferase
- Molecular Weight
- 16970.455 Da
References
Enzymes
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- No
- Actions
- Substrate
- General Function
- Oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen, reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygen
- Specific Function
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
- Gene Name
- CYP1A2
- Uniprot ID
- P05177
- Uniprot Name
- Cytochrome P450 1A2
- Molecular Weight
- 58293.76 Da
References
- Cerasa LA, Bertino JS Jr, Ludwig EA, Savliwala M, Middleton E Jr, Slaughter RL: Lack of effect of atenolol on the pharmacokinetics of theophylline. Br J Clin Pharmacol. 1988 Dec;26(6):800-2. [Article]
- Shimada T, Gillam EM, Sutter TR, Strickland PT, Guengerich FP, Yamazaki H: Oxidation of xenobiotics by recombinant human cytochrome P450 1B1. Drug Metab Dispos. 1997 May;25(5):617-22. [Article]
- Chainuvati S, Nafziger AN, Leeder JS, Gaedigk A, Kearns GL, Sellers E, Zhang Y, Kashuba AD, Rowland E, Bertino JS Jr: Combined phenotypic assessment of cytochrome p450 1A2, 2C9, 2C19, 2D6, and 3A, N-acetyltransferase-2, and xanthine oxidase activities with the "Cooperstown 5+1 cocktail". Clin Pharmacol Ther. 2003 Nov;74(5):437-47. doi: 10.1016/S0009-9236(03)00229-7. [Article]
- Yin OQ, Lam SS, Lo CM, Chow MS: Rapid determination of five probe drugs and their metabolites in human plasma and urine by liquid chromatography/tandem mass spectrometry: application to cytochrome P450 phenotyping studies. Rapid Commun Mass Spectrom. 2004;18(23):2921-33. doi: 10.1002/rcm.1704. [Article]
- CYP1A2 interactions [File]
Drug created at June 13, 2005 13:24 / Updated at May 07, 2021 21:06