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 |
|---|---|---|
| Methylxanthine levels in breast milk of lactating women of different ethnic and socioeconomic classes. | 1992 Apr |
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| Simultaneous determination of caffeine and its primary demethylated metabolites in human plasma by high-performance liquid chromatography. | 1992 Mar 27 |
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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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| Oxidation of caffeine by CYP1A2: isotope effects and metabolic switching. | 2005 Dec |
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| Capillary electrochromatography of caffeine and its metabolites in rat brain microdialysate. | 2005 Feb |
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| Population pharmacokinetics of caffeine and its metabolites theobromine, paraxanthine and theophylline after inhalation in combination with diacetylmorphine. | 2005 Jan |
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| Association between CYP1A2 activity and riluzole clearance in patients with amyotrophic lateral sclerosis. | 2005 Mar |
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| PCB exposure and in vivo CYP1A2 activity among Native Americans. | 2005 Mar |
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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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| Oral contraceptives containing ethinyl estradiol and gestodene markedly increase plasma concentrations and effects of tizanidine by inhibiting cytochrome P450 1A2. | 2005 Oct |
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| Assessment of CYP1A2 activity in clinical practice: why, how, and when? | 2005 Sep |
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| Cytochrome P450 mRNA expression in peripheral blood lymphocytes as a predictor of enzyme induction. | 2005 Sep |
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| Cyp2a6 is a principal enzyme involved in hydroxylation of 1,7-dimethylxanthine, a main caffeine metabolite, in humans. | 2005 Sep |
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| Steroid estrogens, nonylphenol ethoxylate metabolites, and other wastewater contaminants in groundwater affected by a residential septic system on Cape Cod, MA. | 2006 Aug 15 |
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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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| Caffeine metabolites in umbilical cord blood, cytochrome P-450 1A2 activity, and intrauterine growth restriction. | 2006 Jun 1 |
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| [Determination of the activity of cytochrome P-450 CYP2A6 by HPLC method with caffeine as metabolizing probe]. | 2006 Mar |
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| Awareness and use of caffeine by athletes competing at the 2005 Ironman Triathlon World Championships. | 2006 Oct |
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| Liver disease selectively modulates cytochrome P450--mediated metabolism. | 2006 Sep |
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| Immunomodulatory effects of caffeine: friend or foe? | 2006 Sep |
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| Caffeine metabolites are inhibitors of the nuclear enzyme poly(ADP-ribose)polymerase-1 at physiological concentrations. | 2006 Sep 28 |
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| Reduction in non-glomerular renal clearance of the caffeine metabolite 1-methylxanthine by probenecid. | 2007 Aug |
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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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| 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 |
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| Pilot survey monitoring pharmaceuticals and related compounds in a sewage treatment plant located on the Mediterranean coast. | 2007 Jan |
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| Development of a biosensor for caffeine. | 2007 Jan 23 |
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| Ultraperformance liquid chromatography-tandem mass spectrometry analysis of stimulatory drugs of abuse in wastewater and surface waters. | 2007 May 15 |
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| Pharmaceuticals in on-site sewage effluent and ground water, Western Montana. | 2007 May-Jun |
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| Association between caffeine intake and risk of Parkinson's disease among fast and slow metabolizers. | 2007 Nov |
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| Caffeine-activated large-conductance plasma membrane cation channels in cardiac myocytes: characteristics and significance. | 2007 Oct |
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| Interaction profile of armodafinil with medications metabolized by cytochrome P450 enzymes 1A2, 3A4 and 2C19 in healthy subjects. | 2008 |
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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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| Increases in cerebrospinal fluid caffeine concentration are associated with favorable outcome after severe traumatic brain injury in humans. | 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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| Prenatal caffeine assessment: fetal and maternal biomarkers or self-reported intake? | 2008 Mar |
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| Biomonitoring of complex occupational exposures to carcinogens: the case of sewage workers in Paris. | 2008 Mar 6 |
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| Assessing caffeine exposure in pregnant women. | 2008 Oct |
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| A national reconnaissance for pharmaceuticals and other organic wastewater contaminants in the United States--II) untreated drinking water sources. | 2008 Sep 1 |
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
