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Details

Stereochemistry ACHIRAL
Molecular Formula C6H6N4O3
Molecular Weight 182.1371
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of 1-METHYLURIC ACID

SMILES

Cn1c(=O)c2c([nH]c(n2)O)nc1O

InChI

InChIKey=QFDRTQONISXGJA-UHFFFAOYSA-N
InChI=1S/C6H6N4O3/c1-10-4(11)2-3(9-6(10)13)8-5(12)7-2/h1H3,(H,9,13)(H2,7,8,12)

HIDE SMILES / InChI

Molecular Formula C6H6N4O3
Molecular Weight 182.1371
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Approval Year

PubMed

PubMed

TitleDatePubMed
Effects of allopurinol on theophylline metabolism and clearance.
1979 Nov
Reversed-phase liquid chromatographic investigation of UV-absorbing low-molecular-weight compounds in saliva.
1982 Dec 10
Cystic fibrosis: enhanced theophylline metabolism may be linked to the disease.
1988 Sep
Human N-acetylation genotype determination with urinary caffeine metabolites.
1990 Apr
Neurotoxic convulsions induced by theophylline and its metabolites in mice.
1996 Jun
Developmental changes in urinary elimination of theophylline and its metabolites in pediatric patients.
1999 Jan
The effect of pregnancy on cytochrome P4501A2, xanthine oxidase, and N-acetyltransferase activities in humans.
2001 Aug
Use of novel solid-phase extraction sorbent materials for high-performance liquid chromatography quantitation of caffeine metabolism products methylxanthines and methyluric acids in samples of biological origin.
2001 Aug 15
Caffeine metabolism before and after liver transplantation.
2001 Feb
Xanthine oxidase activity and blood glutathione redox ratio in infants and children with septic shock syndrome.
2001 Jan
Caffeine metabolism in a group of 67 patients with primary biliary cirrhosis.
2001 Jan
Dose dependent pharmacokinetics of theophylline: Michaelis-Menten parameters for its major metabolic pathways.
2001 Jan-Jun
[The acetylator polymorphism in a Khmer population: clinical consequences].
2001 Jul-Aug
Fluvoxamine-theophylline interaction: gap between in vitro and in vivo inhibition constants toward cytochrome P4501A2.
2001 Nov
Tegaserod coadministration does not alter the pharmacokinetics of theophylline in healthy subjects.
2001 Sep
Severe 2,3,7,8-tetrachlorodibenzo-p-dioxin (TCDD) intoxication: insights into the measurement of hepatic cytochrome P450 1A2 induction.
2002 Aug
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 Dec
Interaction of ibuprofen and probenecid with drug metabolizing enzyme phenotyping procedures using caffeine as the probe drug.
2003 Feb
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
Phenotyping of N-acetyltransferase type 2 by caffeine from uncontrolled dietary exposure.
2004 Mar
Catabolism of caffeine in plants and microorganisms.
2004 May 1
Separation, pre-concentration, and HPLC analysis of methylxanthines in urine samples.
2004 Oct
Theophylline pharmacokinetics: comparison of Cyp1a1(-/-) and Cyp1a2(-/-) knockout mice, humanized hCYP1A1_1A2 knock-in mice lacking either the mouse Cyp1a1 or Cyp1a2 gene, and Cyp1(+/+) wild-type mice.
2005 Jul
Inhibition of theophylline metabolism by suplatast and its metabolites in rats.
2005 Jun
Improved HPLC assay for measuring serum vitamin C with 1-methyluric acid used as an electrochemically active internal standard.
2005 Jun
Measurement of caffeine and five of the major metabolites in urine by high-performance liquid chromatography/tandem mass spectrometry.
2005 Mar
Simultaneous high performance liquid chromatographic separation of purines, pyrimidines, N-acetylated amino acids, and dicarboxylic acids for the chemical diagnosis of inborn errors of metabolism.
2005 Nov
An unusual patient with kidney stones composed of 1-methyluric acid.
2006 Feb
[Determination of the activity of cytochrome P-450 CYP2A6 by HPLC method with caffeine as metabolizing probe].
2006 Mar
Liver dysfunction markedly decreases the inhibition of cytochrome P450 1A2-mediated theophylline metabolism by fluvoxamine.
2006 May
Effect of a newly developed ketolide antibiotic, telithromycin, on metabolism of theophylline and expression of cytochrome P450 in rats.
2006 May 30
In vitro antioxidant activity of coffee compounds and their metabolites.
2007 Aug 22
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 Dec
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
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 Feb
Lack of effect of aciclovir on metabolism of theophylline and expression of hepatic cytochrome P450 1A2 in rats.
2007 Mar
Anti-inflammatory effect of theophylline in rats and its involvement of the glucocorticoid-glucocorticoid receptor system.
2008 Apr
Relaxing and contracting effects of theophylline's metabolites on the rabbit upper gastrointestinal tract.
2008 Oct
Simultaneous action of the flavonoid quercetin on cytochrome P450 (CYP) 1A2, CYP2A6, N-acetyltransferase and xanthine oxidase activity in healthy volunteers.
2009 Aug
Two distinct pathways for metabolism of theophylline and caffeine are coexpressed in Pseudomonas putida CBB5.
2009 Jul
Caffeine metabolic ratios for the in vivo evaluation of CYP1A2, N-acetyltransferase 2, xanthine oxidase and CYP2A6 enzymatic activities.
2009 May
Patents
Substance Class Chemical
Created
by admin
on Sat Jun 26 05:07:39 UTC 2021
Edited
by admin
on Sat Jun 26 05:07:39 UTC 2021
Record UNII
2WS4HQ639J
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
1-METHYLURIC ACID
Systematic Name English
1-METHYL-7,9-DIHYDRO-3H-PURINE-2,6,8-TRIONE
Systematic Name English
1-METHYL-2,6,8-TRIHYDROXYPURINE
Systematic Name English
Code System Code Type Description
CAS
708-79-2
Created by admin on Sat Jun 26 05:07:39 UTC 2021 , Edited by admin on Sat Jun 26 05:07:39 UTC 2021
PRIMARY
MESH
C030530
Created by admin on Sat Jun 26 05:07:39 UTC 2021 , Edited by admin on Sat Jun 26 05:07:39 UTC 2021
PRIMARY
PUBCHEM
69726
Created by admin on Sat Jun 26 05:07:39 UTC 2021 , Edited by admin on Sat Jun 26 05:07:39 UTC 2021
PRIMARY
ECHA (EC/EINECS)
211-905-7
Created by admin on Sat Jun 26 05:07:39 UTC 2021 , Edited by admin on Sat Jun 26 05:07:39 UTC 2021
PRIMARY
EPA CompTox
708-79-2
Created by admin on Sat Jun 26 05:07:39 UTC 2021 , Edited by admin on Sat Jun 26 05:07:39 UTC 2021
PRIMARY
FDA UNII
2WS4HQ639J
Created by admin on Sat Jun 26 05:07:39 UTC 2021 , Edited by admin on Sat Jun 26 05:07:39 UTC 2021
PRIMARY
Related Record Type Details
PARENT -> METABOLITE
Hepatic biotransformation prior to excretion results in about equal amounts of 1-methylxanthine and 1-methyluric acid.
PARENT -> METABOLITE INACTIVE