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 |
|---|---|---|
| Methylxanthine levels in breast milk of lactating women of different ethnic and socioeconomic classes. | 1992 Apr |
|
| Validation of a high-performance liquid chromatography assay for quantification of caffeine and paraxanthine in human serum in the context of CYP1A2 phenotyping. | 1999 Jun |
|
| 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 |
|
| Structural basis for the binding affinity of xanthines with the DNA intercalator acridine orange. | 2001 Dec 20 |
|
| [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 |
|
| Comparison of the potency of adenosine as an agonist at human adenosine receptors expressed in Chinese hamster ovary cells. | 2001 Feb 15 |
|
| Cytosolic xanthine oxidoreductase mediated bioactivation of ethanol to acetaldehyde and free radicals in rat breast tissue. Its potential role in alcohol-promoted mammary cancer. | 2001 Mar 7 |
|
| Variability of cytochrome P450 1A2 activity over time in young and elderly healthy volunteers. | 2001 Nov |
|
| Effects of phenothiazine neuroleptics on the rate of caffeine demethylation and hydroxylation in the rat liver. | 2001 Nov-Dec |
|
| CYP2A6 activity determined by caffeine phenotyping: association with colorectal cancer risk. | 2002 Apr |
|
| Severe 2,3,7,8-tetrachlorodibenzo-p-dioxin (TCDD) intoxication: insights into the measurement of hepatic cytochrome P450 1A2 induction. | 2002 Aug |
|
| Caffeine potentiates the discriminative-stimulus effects of nicotine in rats. | 2002 Aug |
|
| Effects of exercise and thermal stress on caffeine pharmacokinetics in men and eumenorrheic women. | 2002 Oct |
|
| Effect of naturally occurring plant phenolics on the induction of drug metabolizing enzymes by o-toluidine. | 2003 Apr 15 |
|
| The Karolinska cocktail for phenotyping of five human cytochrome P450 enzymes. | 2003 Jun |
|
| Isozyme-specific induction of low-dose aspirin on cytochrome P450 in healthy subjects. | 2003 Mar |
|
| 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 |
|
| Serum metabolite/caffeine ratios as a test for liver function. | 2004 Apr |
|
| Salivary caffeine metabolic ratio in alcohol-dependent subjects. | 2004 Apr |
|
| Catabolism of caffeine in plants and microorganisms. | 2004 May 1 |
|
| Determination of methylxanthines in urine by liquid chromatography with diode array UV detection. | 2004 Nov 15 |
|
| Separation, pre-concentration, and HPLC analysis of methylxanthines in urine samples. | 2004 Oct |
|
| Caffeine suppresses TNF-alpha production via activation of the cyclic AMP/protein kinase A pathway. | 2004 Oct |
|
| Capillary electrochromatography of caffeine and its metabolites in rat brain microdialysate. | 2005 Feb |
|
| Steroid estrogens, nonylphenol ethoxylate metabolites, and other wastewater contaminants in groundwater affected by a residential septic system on Cape Cod, MA. | 2006 Aug 15 |
|
| Effect of diet on the development of drug metabolism by cytochrome P-450 enzymes in healthy infants. | 2006 Dec |
|
| Awareness and use of caffeine by athletes competing at the 2005 Ironman Triathlon World Championships. | 2006 Oct |
|
| Caffeine metabolites are inhibitors of the nuclear enzyme poly(ADP-ribose)polymerase-1 at physiological concentrations. | 2006 Sep 28 |
|
| Polymorphisms of GSTP1 and GSTT1, but not of CYP2A6, CYP2E1 or GSTM1, modify the risk for esophageal cancer in a western population. | 2007 Dec |
|
| Association between caffeine intake and risk of Parkinson's disease among fast and slow metabolizers. | 2007 Nov |
|
| Interaction profile of armodafinil with medications metabolized by cytochrome P450 enzymes 1A2, 3A4 and 2C19 in healthy subjects. | 2008 |
|
| Effects of gender and moderate smoking on the pharmacokinetics and effects of the CYP1A2 substrate tizanidine. | 2008 Jan |
|
| Biomonitoring of complex occupational exposures to carcinogens: the case of sewage workers in Paris. | 2008 Mar 6 |
|
| 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
| 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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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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|---|---|---|---|---|
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PARENT -> IMPURITY |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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PARENT -> IMPURITY |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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