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Details

Stereochemistry ACHIRAL
Molecular Formula C7H8N4O2
Molecular Weight 180.164
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PARAXANTHINE

SMILES

CN1C=NC2=C1C(=O)N(C)C(=O)N2

InChI

InChIKey=QUNWUDVFRNGTCO-UHFFFAOYSA-N
InChI=1S/C7H8N4O2/c1-10-3-8-5-4(10)6(12)11(2)7(13)9-5/h3H,1-2H3,(H,9,13)

HIDE SMILES / InChI

Molecular Formula C7H8N4O2
Molecular Weight 180.164
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Paraxanthine (1,7-dimethylxanthine), a metabolite of caffeine, is a central nervous stimulant and exerts anti-inflammatory effects. Paraxanthine functions as the antagonist of adenosine receptors A1 and A2a and has lower toxicity and lesser anxiogenic effects than caffeine. Also, paraxanthine acts as an inhibitor of nuclear enzyme poly(ADP-ribose) polymerase-1 (PARP-1) and may have therapeutic potential in pulmonary inflammatory diseases such as COPD. In addition, paraxanthine, and some others metabolites of caffeine differed significantly between advanced-stage non-small cell lung cancer (NSCLC) patients with poor and good survival in both discovery and validation phases. That is why was made a conclusion, that the identified small metabolites, including paraxanthine, may be useful biomarker candidates to help identify patients who may benefit from platinum-based chemotherapy.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: P09874
Gene ID: 142.0
Gene Symbol: PARP1
Target Organism: Homo sapiens (Human)
Target ID: P30542
Gene ID: 134.0
Gene Symbol: ADORA1
Target Organism: Homo sapiens (Human)
Target ID: P29274
Gene ID: 135.0
Gene Symbol: ADORA2A
Target Organism: Homo sapiens (Human)
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
PubMed

PubMed

TitleDatePubMed
Flavin monooxygenase 3 (FMO3) polymorphism in a white population: allele frequencies, mutation linkage, and functional effects on clozapine and caffeine metabolism.
1999 Oct
Rat ventral prostate xanthine oxidase bioactivation of ethanol to acetaldehyde and 1-hydroxyethyl free radicals: analysis of its potential role in heavy alcohol drinking tumor-promoting effects.
2001
The effect of pregnancy on cytochrome P4501A2, xanthine oxidase, and N-acetyltransferase activities in humans.
2001 Aug
Physiologic hyperinsulinemia enhances human skeletal muscle perfusion by capillary recruitment.
2001 Dec
Caffeine metabolism before and after liver transplantation.
2001 Feb
[Use of the paraxanthine/caffeine ratio in the saliva of patients with liver cirrhosis].
2001 Feb 1
Determination of urinary methylated purine pattern by high-performance liquid chromatography.
2001 Feb 10
7-Methylxanthine methyltransferase of coffee plants. Gene isolation and enzymatic properties.
2001 Mar 16
Variability of cytochrome P450 1A2 activity over time in young and elderly healthy volunteers.
2001 Nov
Olanzapine disposition in humans is unrelated to CYP1A2 and CYP2D6 phenotypes.
2001 Sep
CYP2A6 activity determined by caffeine phenotyping: association with colorectal cancer risk.
2002 Apr
Novel markers of susceptibility to carcinogens in diet: associations with colorectal cancer.
2002 Dec 27
Maternal serum caffeine metabolites and small-for-gestational age birth.
2002 Jan 1
[Research on the separation of caffeine and its nine analogues by micellar electrokinetic capillary chromatography].
2002 May
Effect of naturally occurring plant phenolics on the induction of drug metabolizing enzymes by o-toluidine.
2003 Apr 15
Antagonism of adenosine receptors by caffeine and caffeine metabolites in equine forebrain tissues.
2003 Feb
Paraxanthine/caffeine ratio: as an index for CYP1A2 activity in polycyclic aromatic hydrocarbons exposed subjects.
2003 Jun
Induction of the procarcinogen-activating CYP1A2 by a herbal dietary supplement in rats and humans.
2003 Jun
Isozyme-specific induction of low-dose aspirin on cytochrome P450 in healthy subjects.
2003 Mar
Salivary caffeine metabolic ratio in alcohol-dependent subjects.
2004 Apr
Catabolism of caffeine in plants and microorganisms.
2004 May 1
Separation, pre-concentration, and HPLC analysis of methylxanthines in urine samples.
2004 Oct
Assessment of CYP1A2 activity in clinical practice: why, how, and when?
2005 Sep
Cytochrome P450 mRNA expression in peripheral blood lymphocytes as a predictor of enzyme induction.
2005 Sep
[Determination of the activity of cytochrome P-450 CYP2A6 by HPLC method with caffeine as metabolizing probe].
2006 Mar
Awareness and use of caffeine by athletes competing at the 2005 Ironman Triathlon World Championships.
2006 Oct
Reduction in non-glomerular renal clearance of the caffeine metabolite 1-methylxanthine by probenecid.
2007 Aug
Polymorphisms of GSTP1 and GSTT1, but not of CYP2A6, CYP2E1 or GSTM1, modify the risk for esophageal cancer in a western population.
2007 Dec
In vivo evaluation of CYP1A2, CYP2A6, NAT-2 and xanthine oxidase activities in a Greek population sample by the RP-HPLC monitoring of caffeine metabolic ratios.
2007 Feb
Caffeine-activated large-conductance plasma membrane cation channels in cardiac myocytes: characteristics and significance.
2007 Oct
Metabolite profiling of human amniotic fluid by hyphenated nuclear magnetic resonance spectroscopy.
2008 Aug 1
Increases in cerebrospinal fluid caffeine concentration are associated with favorable outcome after severe traumatic brain injury in humans.
2008 Feb
Growth hormone does not alter CYP2A6 activity in growth hormone-deficient children.
2008 Jan
A national reconnaissance for pharmaceuticals and other organic wastewater contaminants in the United States--II) untreated drinking water sources.
2008 Sep 1
Patents

Patents

Sample Use Guides

in orexin/ataxin-3 transgenic narcoleptic mice: orexin/ataxin-3 transgenic (TG) and wild-type (WT) mice were subjected to oral administration (at ZT 2 and ZT14) of 3 doses of paraxanthine, caffeine, modafinil, or vehicle. The wake-promoting potency of 100 mg/kg p.o. of paraxanthine during the light period administration roughly corresponds to that of 200 mg/kg p.o. of modafinil. The wake-promoting potency of paraxanthine is greater and longer lasting than that of the equimolar concentration of caffeine, when the drugs were administered during the light period.
Route of Administration: Oral
In blood of COPD-patients and healthy controls ex vivo pre-incubated with a physiological concentration of 1,7-dimethylxanthine (10microM), LPS-induced production of the cytokines IL-6 and TNF-alpha was significantly suppressed.
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:31:11 GMT 2023
Edited
by admin
on Fri Dec 15 15:31:11 GMT 2023
Record UNII
Q3565Y41V7
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
PARAXANTHINE
INCI  
INCI  
Official Name English
CAFFEINE MONOHYDRATE IMPURITY F [EP IMPURITY]
Common Name English
1,7-DIMETHYLXANTHINE
Systematic Name English
PARAXANTHINE [INCI]
Common Name English
NSC-400018
Code English
1H-PURINE-2,6-DIONE, 3,7-DIHYDRO-1,7-DIMETHYL-
Systematic Name English
CAFFEINE IMPURITY F [EP IMPURITY]
Common Name English
1,7-DIMETHYL-3,7-DIHYDRO-1H-PURINE-2,6-DIONE
Systematic Name English
Code System Code Type Description
WIKIPEDIA
PARAXANTHINE
Created by admin on Fri Dec 15 15:31:11 GMT 2023 , Edited by admin on Fri Dec 15 15:31:11 GMT 2023
PRIMARY
MESH
C021183
Created by admin on Fri Dec 15 15:31:11 GMT 2023 , Edited by admin on Fri Dec 15 15:31:11 GMT 2023
PRIMARY
CHEBI
25858
Created by admin on Fri Dec 15 15:31:11 GMT 2023 , Edited by admin on Fri Dec 15 15:31:11 GMT 2023
PRIMARY
ECHA (EC/EINECS)
210-271-9
Created by admin on Fri Dec 15 15:31:11 GMT 2023 , Edited by admin on Fri Dec 15 15:31:11 GMT 2023
PRIMARY
NSC
400018
Created by admin on Fri Dec 15 15:31:11 GMT 2023 , Edited by admin on Fri Dec 15 15:31:11 GMT 2023
PRIMARY
CAS
611-59-6
Created by admin on Fri Dec 15 15:31:11 GMT 2023 , Edited by admin on Fri Dec 15 15:31:11 GMT 2023
PRIMARY
PUBCHEM
4687
Created by admin on Fri Dec 15 15:31:11 GMT 2023 , Edited by admin on Fri Dec 15 15:31:11 GMT 2023
PRIMARY
FDA UNII
Q3565Y41V7
Created by admin on Fri Dec 15 15:31:11 GMT 2023 , Edited by admin on Fri Dec 15 15:31:11 GMT 2023
PRIMARY
EPA CompTox
DTXSID2052281
Created by admin on Fri Dec 15 15:31:11 GMT 2023 , Edited by admin on Fri Dec 15 15:31:11 GMT 2023
PRIMARY
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MAJOR
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