Xanthine

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
Weight
Average: 152.1109
Monoisotopic: 152.033425392
Chemical Formula
C5H4N4O2
Synonyms
Not Available
External IDs
  • NSC-14664

Pharmacology

Indication

Not Available

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Associated Conditions
Indication TypeIndicationCombined Product DetailsApproval LevelAge GroupPatient CharacteristicsDose Form
Used as adjunct in combination to treatUncomplicated hepatic dysfunctionCombination Product in combination with: Orotic acid (DB02262)•••••••••••••••••••• •••••••••
Contraindications & Blackbox Warnings
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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UPurine nucleoside phosphorylase 2Not AvailableEscherichia coli (strain K12)
UXanthine phosphoribosyltransferaseNot AvailableEscherichia 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
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Toxicity

Not Available

Pathways
PathwayCategory
Adenylosuccinate Lyase DeficiencyDisease
Xanthine Dehydrogenase Deficiency (Xanthinuria)Disease
Xanthinuria Type IDisease
Mitochondrial DNA Depletion SyndromeDisease
Myoadenylate Deaminase DeficiencyDisease
Purine MetabolismMetabolic
Purine Nucleoside Phosphorylase DeficiencyDisease
Lesch-Nyhan Syndrome (LNS)Disease
Gout or Kelley-Seegmiller SyndromeDisease
Mercaptopurine Action PathwayDrug action
Adenine Phosphoribosyltransferase Deficiency (APRT)Disease
Adenosine Deaminase DeficiencyDisease
AICA-RibosiduriaDisease
Molybdenum Cofactor DeficiencyDisease
Azathioprine Action PathwayDrug action
Thioguanine Action PathwayDrug action
Xanthinuria Type IIDisease
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
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.
DrugInteraction
1,2-BenzodiazepineThe therapeutic efficacy of 1,2-Benzodiazepine can be decreased when used in combination with Xanthine.
AbametapirThe serum concentration of Xanthine can be increased when it is combined with Abametapir.
AbataceptThe metabolism of Xanthine can be increased when combined with Abatacept.
AbirateroneThe serum concentration of Xanthine can be increased when it is combined with Abiraterone.
AcebutololThe risk or severity of adverse effects can be increased when Acebutolol is combined with Xanthine.
Food Interactions
Not Available

Products

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Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
ATOXCYNAROL® INYECTABLEXanthine (12.5 mg) + Orotic acid (12.5 mg)SolutionIntramuscularARBOFARMA S.A.S.2010-12-162022-01-31Colombia flag
BETA - NECROTON CAPSULAXanthine (50 mg) + Orotic acid (200 mg)Capsule, coatedOralLaboratorios Incobra S.A.2006-11-10Not applicableColombia flag
NECROTON CAPSULASXanthine (75 mg) + Orotic acid (150 mg)Capsule, coatedOralLaboratorios Incobra S.A.2010-07-22Not applicableColombia flag

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
Human Metabolome Database
HMDB0000292
KEGG Compound
C00385
PubChem Compound
1188
PubChem Substance
46507575
ChemSpider
1151
BindingDB
82009
RxNav
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
PhaseStatusPurposeConditionsCount
2CompletedPreventionHepatic Enzymes / Metabolic Syndrome Parameters / Systolic and Diastolic Blood Pressure Levels / Uric Acid Levels1
2RecruitingTreatmentGout Flares1
1CompletedTreatmentGout Flares / Hyperuricemia2
Not AvailableWithdrawnNot AvailableGout Flares / Hyperuricemia1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
SolutionIntramuscular
InjectionParenteral
Injection, solutionIntramuscular12.5 mg
Capsule, coatedOral
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
water solubility69 mg/L (at 16 °C)MERCK INDEX (1996)
logP-0.73HANSCH,C ET AL. (1995)
pKa7.53KORTUM,G ET AL (1961)
Predicted Properties
PropertyValueSource
Water Solubility4.91 mg/mLALOGPS
logP-0.65ALOGPS
logP-0.21Chemaxon
logS-1.5ALOGPS
pKa (Strongest Acidic)7.95Chemaxon
pKa (Strongest Basic)-0.7Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count3Chemaxon
Hydrogen Donor Count3Chemaxon
Polar Surface Area86.88 Å2Chemaxon
Rotatable Bond Count0Chemaxon
Refractivity36.92 m3·mol-1Chemaxon
Polarizability12.7 Å3Chemaxon
Number of Rings2Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9923
Blood Brain Barrier+0.9833
Caco-2 permeable-0.7704
P-glycoprotein substrateNon-substrate0.6282
P-glycoprotein inhibitor INon-inhibitor0.9619
P-glycoprotein inhibitor IINon-inhibitor0.9953
Renal organic cation transporterNon-inhibitor0.9279
CYP450 2C9 substrateNon-substrate0.7781
CYP450 2D6 substrateNon-substrate0.7434
CYP450 3A4 substrateNon-substrate0.7417
CYP450 1A2 substrateInhibitor0.575
CYP450 2C9 inhibitorNon-inhibitor0.8946
CYP450 2D6 inhibitorNon-inhibitor0.9138
CYP450 2C19 inhibitorNon-inhibitor0.8748
CYP450 3A4 inhibitorNon-inhibitor0.8998
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9936
Ames testNon AMES toxic0.8008
CarcinogenicityNon-carcinogens0.9579
BiodegradationReady biodegradable0.5112
Rat acute toxicity2.1045 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.938
hERG inhibition (predictor II)Non-inhibitor0.9412
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)GC-MSsplash10-0f6t-0924000000-9b80e0a2a60c73ca0180
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSsplash10-0kai-7900000000-2dc30b0fc4cff2239dbe
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-0f6t-0924000000-9b80e0a2a60c73ca0180
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-0f6t-0924000000-30dc5892eecde860846a
Mass Spectrum (Electron Ionization)MSsplash10-0udi-7900000000-2d5ab5d5db8ff4981467
MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)LC-MS/MSsplash10-0udi-0900000000-a70539989d121bfacee0
MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)LC-MS/MSsplash10-0a4i-6900000000-b047b06406308dbaeda8
MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)LC-MS/MSsplash10-0a4i-9300000000-ed480ed920c3e9b576ec
LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , NegativeLC-MS/MSsplash10-0zfr-0900000000-efb049914c9bce596267
LC-MS/MS Spectrum - LC-ESI-QTOF , negativeLC-MS/MSsplash10-0zfr-0900000000-efb049914c9bce596267
MS/MS Spectrum - , negativeLC-MS/MSsplash10-0udi-0900000000-5fee91293851bb02193e
LC-MS/MS Spectrum - LC-ESI-IT , positiveLC-MS/MSsplash10-000i-0900000000-4568a814903ff411923a
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0udi-0900000000-05c870c00cd24706ea38
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0w2i-0900000000-71ddbfb82053fc2b2921
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0udi-0900000000-cf9c92a903ac3bcea6a4
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-1000-9700000000-0e5760f5b0cc760a2c17
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0zfu-5900000000-be9d95837bf4c81834d7
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0006-9000000000-652d5b66e22c25ca3490
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0udi-0900000000-f08567ad948469a5a5da
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0udi-0900000000-861debae7596feb7999a
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0w29-0900000000-4e1c48ad6e24a3d9226d
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-052f-9700000000-ec1f7e019a3ed93be0ff
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-014i-9100000000-e28b587f9e9ad168f29d
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0006-9000000000-7c146e82a6827c7126fc
1H NMR Spectrum1D NMRNot Applicable
13C NMR Spectrum1D NMRNot Applicable
1H NMR Spectrum1D NMRNot Applicable
13C NMR Spectrum1D NMRNot Applicable
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
[1H,1H] 2D NMR Spectrum2D NMRNot Applicable
[1H,13C] 2D NMR Spectrum2D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-127.7571877
predicted
DarkChem Lite v0.1.0
[M-H]-127.7886877
predicted
DarkChem Lite v0.1.0
[M-H]-127.5472877
predicted
DarkChem Lite v0.1.0
[M-H]-127.6981877
predicted
DarkChem Lite v0.1.0
[M-H]-127.23582
predicted
DeepCCS 1.0 (2019)
[M-H]-127.7571877
predicted
DarkChem Lite v0.1.0
[M-H]-127.7886877
predicted
DarkChem Lite v0.1.0
[M-H]-127.5472877
predicted
DarkChem Lite v0.1.0
[M-H]-127.6981877
predicted
DarkChem Lite v0.1.0
[M-H]-127.23582
predicted
DeepCCS 1.0 (2019)
[M+H]+128.7946877
predicted
DarkChem Lite v0.1.0
[M+H]+128.6732877
predicted
DarkChem Lite v0.1.0
[M+H]+128.5774877
predicted
DarkChem Lite v0.1.0
[M+H]+128.6456877
predicted
DarkChem Lite v0.1.0
[M+H]+130.59776
predicted
DeepCCS 1.0 (2019)
[M+H]+128.7946877
predicted
DarkChem Lite v0.1.0
[M+H]+128.6732877
predicted
DarkChem Lite v0.1.0
[M+H]+128.5774877
predicted
DarkChem Lite v0.1.0
[M+H]+128.6456877
predicted
DarkChem Lite v0.1.0
[M+H]+130.59776
predicted
DeepCCS 1.0 (2019)
[M+Na]+128.2540877
predicted
DarkChem Lite v0.1.0
[M+Na]+128.4062877
predicted
DarkChem Lite v0.1.0
[M+Na]+128.1514877
predicted
DarkChem Lite v0.1.0
[M+Na]+128.1232877
predicted
DarkChem Lite v0.1.0
[M+Na]+139.62263
predicted
DeepCCS 1.0 (2019)
[M+Na]+128.2540877
predicted
DarkChem Lite v0.1.0
[M+Na]+128.4062877
predicted
DarkChem Lite v0.1.0
[M+Na]+128.1514877
predicted
DarkChem Lite v0.1.0
[M+Na]+128.1232877
predicted
DarkChem Lite v0.1.0
[M+Na]+139.62263
predicted
DeepCCS 1.0 (2019)

Targets

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insights and accelerate drug research.
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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
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]
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
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]

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
  1. 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]
  2. 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]
  3. 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]
  4. 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]
  5. CYP1A2 interactions [File]

Drug created at June 13, 2005 13:24 / Updated at May 07, 2021 21:06