Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C6H6N4O2 |
| Molecular Weight | 166.1374 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
CN1C(=O)NC2=C(NC=N2)C1=O
InChI
InChIKey=MVOYJPOZRLFTCP-UHFFFAOYSA-N
InChI=1S/C6H6N4O2/c1-10-5(11)3-4(8-2-7-3)9-6(10)12/h2H,1H3,(H,7,8)(H,9,12)
| Molecular Formula | C6H6N4O2 |
| Molecular Weight | 166.1374 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| Loss of insulin-mediated microvascular perfusion in skeletal muscle is associated with the development of insulin resistance. | 2010-09 |
|
| Plant polyphenol curcumin significantly affects CYP1A2 and CYP2A6 activity in healthy, male Chinese volunteers. | 2010-06 |
|
| Is 1-methylxanthine an ideal model substrate for establishing the renal tubular transport of organic ions? | 2010-02 |
|
| Demethylation of theophylline (1,3-dimethylxanthine) to 1-methylxanthine: the first step of an antioxidising cascade. | 2010 |
|
| Simultaneous action of the flavonoid quercetin on cytochrome P450 (CYP) 1A2, CYP2A6, N-acetyltransferase and xanthine oxidase activity in healthy volunteers. | 2009-08 |
|
| Enhancement of radiotherapeutic effectiveness by temperature-sensitive liposomal 1-methylxanthine. | 2009-05-08 |
|
| Caffeine metabolic ratios for the in vivo evaluation of CYP1A2, N-acetyltransferase 2, xanthine oxidase and CYP2A6 enzymatic activities. | 2009-05 |
|
| Interleukin-6 attenuates insulin-mediated increases in endothelial cell signaling but augments skeletal muscle insulin action via differential effects on tumor necrosis factor-alpha expression. | 2009-05 |
|
| Phenotyping of N-acetyltransferase type 2 and xanthine oxidase with caffeine: when should urine samples be collected? | 2009-04 |
|
| 1-Methylxanthine enhances the radiosensitivity of tumor cells. | 2009-02 |
|
| Relaxing and contracting effects of theophylline's metabolites on the rabbit upper gastrointestinal tract. | 2008-10 |
|
| Anti-inflammatory effect of theophylline in rats and its involvement of the glucocorticoid-glucocorticoid receptor system. | 2008-04 |
|
| Point: There is capillary recruitment in active skeletal muscle during exercise. | 2008-03 |
|
| Inhibitory effects of caffeine and its metabolites on intracellular lipid accumulation in murine 3T3-L1 adipocytes. | 2008 |
|
| Theophylline and its metabolites produce a stimulating cholinergic effect on the small intestine and a nonadrenergic noncholinergic relaxing effect on the colon: a comparative study in the rabbit intestine. | 2007-12 |
|
| Reduction in non-glomerular renal clearance of the caffeine metabolite 1-methylxanthine by probenecid. | 2007-08 |
|
| Acute effects of wortmannin on insulin's hemodynamic and metabolic actions in vivo. | 2007-03 |
|
| 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 |
|
| Concordance between the deduced acetylation status generated by high-speed: real-time PCR based NAT2 genotyping of seven single nucleotide polymorphisms and human NAT2 phenotypes determined by a caffeine assay. | 2007-02 |
|
| Caffeine N3-demethylation (CYP1A2) in a population with an increased exposure to polychlorinated biphenyls. | 2006-12 |
|
| Effect of diet on the development of drug metabolism by cytochrome P-450 enzymes in healthy infants. | 2006-12 |
|
| Caffeine metabolites are inhibitors of the nuclear enzyme poly(ADP-ribose)polymerase-1 at physiological concentrations. | 2006-09-28 |
|
| Associations between CYP2E1 promoter polymorphisms and plasma 1,3-dimethyluric acid/theophylline ratios. | 2006-08 |
|
| [Determination of the activity of cytochrome P-450 CYP2A6 by HPLC method with caffeine as metabolizing probe]. | 2006-03 |
|
| Re-investigation of the concordance of human NAT2 phenotypes and genotypes. | 2005-04 |
|
| Measurement of caffeine and five of the major metabolites in urine by high-performance liquid chromatography/tandem mass spectrometry. | 2005-03 |
|
| Capillary electrochromatography of caffeine and its metabolites in rat brain microdialysate. | 2005-02 |
|
| Exercise and insulin-mediated capillary recruitment in muscle. | 2005-01 |
|
| Local methacholine but not bradykinin potentiates insulin-mediated glucose uptake in muscle in vivo by augmenting capillary recruitment. | 2004-12 |
|
| High-throughput liquid chromatography-tandem mass spectrometry assay for plasma theophylline and its metabolites. | 2004-11 |
|
| Separation, pre-concentration, and HPLC analysis of methylxanthines in urine samples. | 2004-10 |
|
| Skeletal muscle contraction stimulates capillary recruitment and glucose uptake in insulin-resistant obese Zucker rats. | 2004-10 |
|
| Inhibition of the human organic anion transporter 1 by the caffeine metabolite 1-methylxanthine. | 2004-07-16 |
|
| Phenotyping of N-acetyltransferase type 2 by caffeine from uncontrolled dietary exposure. | 2004-03 |
|
| Insulin sensitivity of muscle capillary recruitment in vivo. | 2004-02 |
|
| Acetylator phenotyping in patients with malignant lymphomas, using caffeine as the metabolic probe. | 2004-01-07 |
|
| Cytochrome P450 1A2 (CYP1A2) activity and risk factors for breast cancer: a cross-sectional study. | 2004 |
|
| Cytochrome P450 1A2 (CYP1A2) activity, mammographic density, and oxidative stress: a cross-sectional study. | 2004 |
|
| T-1032, a cyclic GMP phosphodiesterase-5 inhibitor, acutely blocks physiologic insulin-mediated muscle haemodynamic effects and glucose uptake in vivo. | 2003-12 |
|
| TNF-alpha acutely inhibits vascular effects of physiological but not high insulin or contraction. | 2003-09 |
|
| Inhibiting NOS blocks microvascular recruitment and blunts muscle glucose uptake in response to insulin. | 2003-07 |
|
| Preventive effect of zaprinast and 3-isobutyl, 1-methylxanthine (phosphodiesterase inhibitors) on gastric injury induced by nonsteroidal antiinflammatory drugs in rats. | 2003-05 |
|
| Nonnutritive flow impairs uptake of fatty acid by white muscles of the perfused rat hindlimb. | 2003-03 |
|
| Interaction of ibuprofen and probenecid with drug metabolizing enzyme phenotyping procedures using caffeine as the probe drug. | 2003-02 |
|
| Pharmacokinetics of intravenous theophylline in mutant Nagase analbuminemic rats. | 2003-01-31 |
|
| Group I aptazymes as genetic regulatory switches. | 2002-12-04 |
|
| Effects of acute renal failure induced by uranyl nitrate on the pharmacokinetics of intravenous theophylline in rats: the role of CYP2E1 induction in 1,3-dimethyluric acid formation. | 2002-12 |
|
| Insulin-mediated hemodynamic changes are impaired in muscle of Zucker obese rats. | 2002-12 |
|
| Neurotoxic convulsions induced by theophylline and its metabolites in mice. | 1996-06 |
|
| Structure-activity relationships for the binding of ligands to xanthine or guanine phosphoribosyl-transferase from Toxoplasma gondii. | 1995-11-09 |
| Substance Class |
Chemical
Created
by
admin
on
Edited
Mon Mar 31 18:53:23 GMT 2025
by
admin
on
Mon Mar 31 18:53:23 GMT 2025
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| Record UNII |
7EE8WCA32U
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| Record Status |
Validated (UNII)
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| Record Version |
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C053085
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7EE8WCA32U
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DTXSID30210271
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80220
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6136-37-4
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228-108-5
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