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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| Biotransformation of caffeine, paraxanthine, theobromine and theophylline by cDNA-expressed human CYP1A2 and CYP2E1. | 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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| Flavin monooxygenase 3 (FMO3) polymorphism in a white population: allele frequencies, mutation linkage, and functional effects on clozapine and caffeine metabolism. | 1999 Oct |
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| 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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| High-performance liquid chromatographic assay for acetaminophen glucuronide in human liver microsomes. | 2001 Apr 5 |
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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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| Physiologic hyperinsulinemia enhances human skeletal muscle perfusion by capillary recruitment. | 2001 Dec |
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| Caffeine metabolism before and after liver transplantation. | 2001 Feb |
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| Comparison of the potency of adenosine as an agonist at human adenosine receptors expressed in Chinese hamster ovary cells. | 2001 Feb 15 |
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| Caffeine metabolism in a group of 67 patients with primary biliary cirrhosis. | 2001 Jan |
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| In vivo effect of clarithromycin on multiple cytochrome P450s. | 2001 Jul |
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| Uncertainty factors for chemical risk assessment: interspecies differences in the in vivo pharmacokinetics and metabolism of human CYP1A2 substrates. | 2001 Jul |
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| 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 |
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| Variability of cytochrome P450 1A2 activity over time in young and elderly healthy volunteers. | 2001 Nov |
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| Olanzapine disposition in humans is unrelated to CYP1A2 and CYP2D6 phenotypes. | 2001 Sep |
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| Determination of theophylline by HPLC and GC-IDMS, the effect of chemically similar xanthine derivatives on the specificity of the method and the possibility of paracetamol as interfering substance. | 2002 |
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| Novel markers of susceptibility to carcinogens in diet: associations with colorectal cancer. | 2002 Dec 27 |
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| Differences in caffeine and paraxanthine metabolism between human and murine CYP1A2. | 2002 Jun 15 |
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| Inducibility of CYP1A2 by omeprazole in vivo related to the genetic polymorphism of CYP1A2. | 2002 Nov |
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| Effect of naturally occurring plant phenolics on the induction of drug metabolizing enzymes by o-toluidine. | 2003 Apr 15 |
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| Effects of caffeine intake on the pharmacokinetics of melatonin, a probe drug for CYP1A2 activity. | 2003 Dec |
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| Antagonism of adenosine receptors by caffeine and caffeine metabolites in equine forebrain tissues. | 2003 Feb |
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| Paraxanthine/caffeine ratio: as an index for CYP1A2 activity in polycyclic aromatic hydrocarbons exposed subjects. | 2003 Jun |
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| The Karolinska cocktail for phenotyping of five human cytochrome P450 enzymes. | 2003 Jun |
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| Two novel methods for the determination of CYP1A2 activity using the paraxanthine/caffeine ratio. | 2003 Jun |
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| Induction of the procarcinogen-activating CYP1A2 by a herbal dietary supplement in rats and humans. | 2003 Jun |
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| Salivary caffeine metabolic ratio in alcohol-dependent subjects. | 2004 Apr |
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| Effect of caffeine-containing versus decaffeinated coffee on serum clozapine concentrations in hospitalised patients. | 2004 Jan |
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| Regarding "An unexpected distribution of sodium concentration in serum specimens stored for more than 30 years". | 2004 Jan |
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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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| Catabolism of caffeine in plants and microorganisms. | 2004 May 1 |
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| Artemisinin and thiabendazole are potent inhibitors of cytochrome P450 1A2 (CYP1A2) activity in humans. | 2005 Nov |
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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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| Caffeine-activated large-conductance plasma membrane cation channels in cardiac myocytes: characteristics and significance. | 2007 Oct |
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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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| 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
