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
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)
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
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: P09874 Gene ID: 142.0 Gene Symbol: PARP1 Target Organism: Homo sapiens (Human) |
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Target ID: P30542 Gene ID: 134.0 Gene Symbol: ADORA1 Target Organism: Homo sapiens (Human) |
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Target ID: P29274 Gene ID: 135.0 Gene Symbol: ADORA2A Target Organism: Homo sapiens (Human) |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
PubMed
| Title | Date | PubMed |
|---|---|---|
| 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 |
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| The effect of pregnancy on cytochrome P4501A2, xanthine oxidase, and N-acetyltransferase activities in humans. | 2001 Aug |
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| Use of novel solid-phase extraction sorbent materials for high-performance liquid chromatography quantitation of caffeine metabolism products methylxanthines and methyluric acids in samples of biological origin. | 2001 Aug 15 |
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| Urinary biomarkers for assessing dietary exposure to caffeine. | 2001 Dec |
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| Caffeine metabolism in a group of 67 patients with primary biliary cirrhosis. | 2001 Jan |
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| Uncertainty factors for chemical risk assessment. human variability in the pharmacokinetics of CYP1A2 probe substrates. | 2001 Jul |
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| Variability of cytochrome P450 1A2 activity over time in young and elderly healthy volunteers. | 2001 Nov |
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| [Research on the separation of caffeine and its nine analogues by micellar electrokinetic capillary chromatography]. | 2002 May |
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| Inducibility of CYP1A2 by omeprazole in vivo related to the genetic polymorphism of CYP1A2. | 2002 Nov |
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| 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. | 2004 |
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| Inhibition of the human organic anion transporter 1 by the caffeine metabolite 1-methylxanthine. | 2004 Jul 16 |
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| Evidence for concurrent effects of exposure to environmental cadmium and lead on hepatic CYP2A6 phenotype and renal function biomarkers in nonsmokers. | 2004 Nov |
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| Determination of methylxanthines in urine by liquid chromatography with diode array UV detection. | 2004 Nov 15 |
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| Separation, pre-concentration, and HPLC analysis of methylxanthines in urine samples. | 2004 Oct |
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| Caffeine suppresses TNF-alpha production via activation of the cyclic AMP/protein kinase A pathway. | 2004 Oct |
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| No relevant interaction with alprazolam, caffeine, tolbutamide, and digoxin by treatment with a low-hyperforin St John's wort extract. | 2005 Apr |
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| Capillary electrochromatography of caffeine and its metabolites in rat brain microdialysate. | 2005 Feb |
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| Inhibition of HIV-1 replication by caffeine and caffeine-related methylxanthines. | 2005 May 10 |
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| Artemisinin and thiabendazole are potent inhibitors of cytochrome P450 1A2 (CYP1A2) activity in humans. | 2005 Nov |
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| Effect of diet on the development of drug metabolism by cytochrome P-450 enzymes in healthy infants. | 2006 Dec |
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| Distributions of pharmaceuticals in an urban estuary during both dry- and wet-weather conditions. | 2007 Aug 15 |
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| Polymorphisms of GSTP1 and GSTT1, but not of CYP2A6, CYP2E1 or GSTM1, modify the risk for esophageal cancer in a western population. | 2007 Dec |
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| Appropriate phenotyping procedures for drug metabolizing enzymes and transporters in humans and their simultaneous use in the "cocktail" approach. | 2007 Feb |
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| Metabolite profiling of human amniotic fluid by hyphenated nuclear magnetic resonance spectroscopy. | 2008 Aug 1 |
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| Perinatal dioxin exposure, cytochrome P-450 activity, liver functions and thyroid hormones at follow-up after 7-12 years. | 2008 Feb |
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| Effects of gender and moderate smoking on the pharmacokinetics and effects of the CYP1A2 substrate tizanidine. | 2008 Jan |
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| Growth hormone does not alter CYP2A6 activity in growth hormone-deficient children. | 2008 Jan |
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| Occurrence of psychoactive stimulatory drugs in wastewaters in north-eastern Spain. | 2008 Jul 1 |
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| Assessing caffeine exposure in pregnant women. | 2008 Oct |
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
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PARAXANTHINE
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C021183
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25858
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210-271-9
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400018
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611-59-6
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4687
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Q3565Y41V7
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DTXSID2052281
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PARENT (METABOLITE ACTIVE)
SUBSTANCE RECORD
