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)
| 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
| 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 |
|---|---|---|
| Assessing caffeine exposure in pregnant women. | 2008-10 |
|
| A national reconnaissance for pharmaceuticals and other organic wastewater contaminants in the United States--II) untreated drinking water sources. | 2008-09-01 |
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| Metabolite profiling of human amniotic fluid by hyphenated nuclear magnetic resonance spectroscopy. | 2008-08-01 |
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| Occurrence of psychoactive stimulatory drugs in wastewaters in north-eastern Spain. | 2008-07-01 |
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| Biomonitoring of complex occupational exposures to carcinogens: the case of sewage workers in Paris. | 2008-03-06 |
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| Prenatal caffeine assessment: fetal and maternal biomarkers or self-reported intake? | 2008-03 |
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| Perinatal dioxin exposure, cytochrome P-450 activity, liver functions and thyroid hormones at follow-up after 7-12 years. | 2008-02 |
|
| Increases in cerebrospinal fluid caffeine concentration are associated with favorable outcome after severe traumatic brain injury in humans. | 2008-02 |
|
| Effects of gender and moderate smoking on the pharmacokinetics and effects of the CYP1A2 substrate tizanidine. | 2008-01 |
|
| Growth hormone does not alter CYP2A6 activity in growth hormone-deficient children. | 2008-01 |
|
| Interaction profile of armodafinil with medications metabolized by cytochrome P450 enzymes 1A2, 3A4 and 2C19 in healthy subjects. | 2008 |
|
| Polymorphisms of GSTP1 and GSTT1, but not of CYP2A6, CYP2E1 or GSTM1, modify the risk for esophageal cancer in a western population. | 2007-12 |
|
| Association between caffeine intake and risk of Parkinson's disease among fast and slow metabolizers. | 2007-11 |
|
| Caffeine-activated large-conductance plasma membrane cation channels in cardiac myocytes: characteristics and significance. | 2007-10 |
|
| Distributions of pharmaceuticals in an urban estuary during both dry- and wet-weather conditions. | 2007-08-15 |
|
| Reduction in non-glomerular renal clearance of the caffeine metabolite 1-methylxanthine by probenecid. | 2007-08 |
|
| Ultraperformance liquid chromatography-tandem mass spectrometry analysis of stimulatory drugs of abuse in wastewater and surface waters. | 2007-05-15 |
|
| Pharmaceuticals in on-site sewage effluent and ground water, Western Montana. | 2007-05-02 |
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| Appropriate phenotyping procedures for drug metabolizing enzymes and transporters in humans and their simultaneous use in the "cocktail" approach. | 2007-02 |
|
| 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. | 2007-02 |
|
| Development of a biosensor for caffeine. | 2007-01-23 |
|
| Pilot survey monitoring pharmaceuticals and related compounds in a sewage treatment plant located on the Mediterranean coast. | 2007-01 |
|
| Effect of diet on the development of drug metabolism by cytochrome P-450 enzymes in healthy infants. | 2006-12 |
|
| Awareness and use of caffeine by athletes competing at the 2005 Ironman Triathlon World Championships. | 2006-10 |
|
| Caffeine metabolites are inhibitors of the nuclear enzyme poly(ADP-ribose)polymerase-1 at physiological concentrations. | 2006-09-28 |
|
| Liver disease selectively modulates cytochrome P450--mediated metabolism. | 2006-09 |
|
| Immunomodulatory effects of caffeine: friend or foe? | 2006-09 |
|
| Steroid estrogens, nonylphenol ethoxylate metabolites, and other wastewater contaminants in groundwater affected by a residential septic system on Cape Cod, MA. | 2006-08-15 |
|
| Caffeine metabolites in umbilical cord blood, cytochrome P-450 1A2 activity, and intrauterine growth restriction. | 2006-06-01 |
|
| [Determination of the activity of cytochrome P-450 CYP2A6 by HPLC method with caffeine as metabolizing probe]. | 2006-03 |
|
| Oxidation of caffeine by CYP1A2: isotope effects and metabolic switching. | 2005-12 |
|
| Artemisinin and thiabendazole are potent inhibitors of cytochrome P450 1A2 (CYP1A2) activity in humans. | 2005-11 |
|
| Oral contraceptives containing ethinyl estradiol and gestodene markedly increase plasma concentrations and effects of tizanidine by inhibiting cytochrome P450 1A2. | 2005-10 |
|
| Assessment of CYP1A2 activity in clinical practice: why, how, and when? | 2005-09 |
|
| Cytochrome P450 mRNA expression in peripheral blood lymphocytes as a predictor of enzyme induction. | 2005-09 |
|
| Cyp2a6 is a principal enzyme involved in hydroxylation of 1,7-dimethylxanthine, a main caffeine metabolite, in humans. | 2005-09 |
|
| Inhibition of HIV-1 replication by caffeine and caffeine-related methylxanthines. | 2005-05-10 |
|
| No relevant interaction with alprazolam, caffeine, tolbutamide, and digoxin by treatment with a low-hyperforin St John's wort extract. | 2005-04 |
|
| Association between CYP1A2 activity and riluzole clearance in patients with amyotrophic lateral sclerosis. | 2005-03 |
|
| PCB exposure and in vivo CYP1A2 activity among Native Americans. | 2005-03 |
|
| Capillary electrochromatography of caffeine and its metabolites in rat brain microdialysate. | 2005-02 |
|
| Population pharmacokinetics of caffeine and its metabolites theobromine, paraxanthine and theophylline after inhalation in combination with diacetylmorphine. | 2005-01 |
|
| Determination of methylxanthines in urine by liquid chromatography with diode array UV detection. | 2004-11-15 |
|
| Evidence for concurrent effects of exposure to environmental cadmium and lead on hepatic CYP2A6 phenotype and renal function biomarkers in nonsmokers. | 2004-11 |
|
| Separation, pre-concentration, and HPLC analysis of methylxanthines in urine samples. | 2004-10 |
|
| Caffeine suppresses TNF-alpha production via activation of the cyclic AMP/protein kinase A pathway. | 2004-10 |
|
| Inhibition of the human organic anion transporter 1 by the caffeine metabolite 1-methylxanthine. | 2004-07-16 |
|
| 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 |
|
| Methylxanthine levels in breast milk of lactating women of different ethnic and socioeconomic classes. | 1992-04 |
|
| Simultaneous determination of caffeine and its primary demethylated metabolites in human plasma by high-performance liquid chromatography. | 1992-03-27 |
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
| Substance Class |
Chemical
Created
by
admin
on
Edited
Mon Mar 31 17:59:48 GMT 2025
by
admin
on
Mon Mar 31 17:59:48 GMT 2025
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| Record UNII |
Q3565Y41V7
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| Record Status |
Validated (UNII)
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| Record Version |
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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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611-59-6
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4687
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Q3565Y41V7
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DTXSID2052281
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| Related Record | Type | Details | ||
|---|---|---|---|---|
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PARENT -> METABOLITE ACTIVE |
| Related Record | Type | Details | ||
|---|---|---|---|---|
|
PARENT -> IMPURITY |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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PARENT -> IMPURITY |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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