1-METHYLURIC ACID

Details

Stereochemistry	ACHIRAL
Molecular Formula	C6H6N4O3
Molecular Weight	182.1368
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CN1C(=O)NC2=C(NC(=O)N2)C1=O

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	182.1368
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
Effects of allopurinol on theophylline metabolism and clearance.	1979 Nov	498708
Reversed-phase liquid chromatographic investigation of UV-absorbing low-molecular-weight compounds in saliva.	1982 Dec 10	7161362
Neurotoxic convulsions induced by theophylline and its metabolites in mice.	1996 Jun	8799489
Developmental changes in urinary elimination of theophylline and its metabolites in pediatric patients.	1999 Jan	9890610
The effect of pregnancy on cytochrome P4501A2, xanthine oxidase, and N-acetyltransferase activities in humans.	2001 Aug	11503005
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	11499474
Caffeine metabolism before and after liver transplantation.	2001 Feb	11270802
Xanthine oxidase activity and blood glutathione redox ratio in infants and children with septic shock syndrome.	2001 Jan	11280638
Caffeine metabolism in a group of 67 patients with primary biliary cirrhosis.	2001 Jan	11204934
Dose dependent pharmacokinetics of theophylline: Michaelis-Menten parameters for its major metabolic pathways.	2001 Jan-Jun	11554438
[The acetylator polymorphism in a Khmer population: clinical consequences].	2001 Jul-Aug	11677864
Fluvoxamine-theophylline interaction: gap between in vitro and in vivo inhibition constants toward cytochrome P4501A2.	2001 Nov	11719727
Tegaserod coadministration does not alter the pharmacokinetics of theophylline in healthy subjects.	2001 Sep	11549104
Severe 2,3,7,8-tetrachlorodibenzo-p-dioxin (TCDD) intoxication: insights into the measurement of hepatic cytochrome P450 1A2 induction.	2002 Aug	12189363
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	12542900
Interaction of ibuprofen and probenecid with drug metabolizing enzyme phenotyping procedures using caffeine as the probe drug.	2003 Feb	12580991
Cytochrome P450 1A2 (CYP1A2) activity and risk factors for breast cancer: a cross-sectional study.	2004	15217502
Cytochrome P450 1A2 (CYP1A2) activity, mammographic density, and oxidative stress: a cross-sectional study.	2004	15217501
Phenotyping of N-acetyltransferase type 2 by caffeine from uncontrolled dietary exposure.	2004 Mar	14747882
Catabolism of caffeine in plants and microorganisms.	2004 May 1	14977550
Separation, pre-concentration, and HPLC analysis of methylxanthines in urine samples.	2004 Oct	15537072
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	15970798
Inhibition of theophylline metabolism by suplatast and its metabolites in rats.	2005 Jun	15930745
Improved HPLC assay for measuring serum vitamin C with 1-methyluric acid used as an electrochemically active internal standard.	2005 Jun	15860567
Measurement of caffeine and five of the major metabolites in urine by high-performance liquid chromatography/tandem mass spectrometry.	2005 Mar	15685651
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	16139832
An unusual patient with kidney stones composed of 1-methyluric acid.	2006 Feb	16397778
[Determination of the activity of cytochrome P-450 CYP2A6 by HPLC method with caffeine as metabolizing probe].	2006 Mar	16759004
Liver dysfunction markedly decreases the inhibition of cytochrome P450 1A2-mediated theophylline metabolism by fluvoxamine.	2006 May	16678550
Effect of a newly developed ketolide antibiotic, telithromycin, on metabolism of theophylline and expression of cytochrome P450 in rats.	2006 May 30	16423372
In vitro antioxidant activity of coffee compounds and their metabolites.	2007 Aug 22	17655324
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	17991222
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	17221922
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	17011540
Lack of effect of aciclovir on metabolism of theophylline and expression of hepatic cytochrome P450 1A2 in rats.	2007 Mar	17329857
Anti-inflammatory effect of theophylline in rats and its involvement of the glucocorticoid-glucocorticoid receptor system.	2008 Apr	18391482
Relaxing and contracting effects of theophylline's metabolites on the rabbit upper gastrointestinal tract.	2008 Oct	18844725
Phenotyping of N-acetyltransferase type 2 and xanthine oxidase with caffeine: when should urine samples be collected?	2009 Apr	19082994
Simultaneous action of the flavonoid quercetin on cytochrome P450 (CYP) 1A2, CYP2A6, N-acetyltransferase and xanthine oxidase activity in healthy volunteers.	2009 Aug	19215233
Two distinct pathways for metabolism of theophylline and caffeine are coexpressed in Pseudomonas putida CBB5.	2009 Jul	19447909
Caffeine metabolic ratios for the in vivo evaluation of CYP1A2, N-acetyltransferase 2, xanthine oxidase and CYP2A6 enzymatic activities.	2009 May	19519341

Patents

Substance Class	Chemical Created by `admin` on `Mon Mar 31 19:17:07 GMT 2025` Edited by `admin` on `Mon Mar 31 19:17:07 GMT 2025`
Record UNII	2WS4HQ639J
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

1-METHYL-2,6,8-TRIHYDROXYPURINE

Preferred Name

English

1-METHYLURIC ACID

Systematic Name

English

1-METHYL-7,9-DIHYDRO-3H-PURINE-2,6,8-TRIONE

Systematic Name

English

Code System Code Type Description

CAS

708-79-2