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Chemical Compound Review:

CHEMBL793 1-methyl-7,9-dihydro-3H- purine-2,6,8-trione

Synonyms: SureCN235671, AG-K-73494, SureCN3182825, CHEBI:68441, M6885_SIGMA, ...

Hildebrandt, R. et al., Tateishi, T. et al., Guo, R. et al., Yamamoto, K. et al., Bouraoui, A. et al., et al.

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Disease relevance of EINECS 211-905-7

Hypoxia decreased theophylline metabolic clearance (ClM) from 1.73+/-0.43 to 1.48+/-0.13 ml min-1 kg-1 (P<0. 05), and reduced (P<0.05) the formation clearance of theophylline metabolites, 3-methylxanthine (3MX), 1-methyluric acid (1MU) and 1,3-dimethyluric acid (1,3DMU) [1].

High impact information on EINECS 211-905-7

Theophylline and its three main metabolites, 1-methyluric acid, 3-methylxanthine, and 1,3-dimethyluric acid, were analyzed in serum and urine by HPLC [2].
Urinary and plasma metabolites (caffeine; theobromine; 3-methylxanthine; 1,3-dimethyluric acid; and 1-methyluric acid) and unchanged theophylline were analyzed with selected ion monitoring gas chromatography-mass spectrometry [3].
The urinary ratio of 1,3-dimethyluric acid (a metabolite generated by several cytochrome P450s) to 3-methylxanthine or 1-methyluric acid (metabolites generated by CYP1A2 exclusively) seemed to be relatively constant over 3 y of age; in patients under 3 y of age, these ratios were much higher than those in patients over 3 y of age [4].
Caffeine metabolites [5-acetylamino-6-formylamino-3-methyl uracil (AFMU), 1-methylxanthine, 1-methyluric acid, 1,7-methyluric acid, and 1,7-methylxanthine] were measured using HPLC [5].
The major products excreted by neonates were T, 1-methyluric acid, and 1,3-dimethyluric acid [6].

Biological context of EINECS 211-905-7

Secondary metabolism of theophylline biotransformation products in man--route of formation of 1-methyluric acid [7].

Anatomical context of EINECS 211-905-7

To evaluate the risk of neurotoxicity induced by theophylline and its main metabolites, 1-methylxanthine (1-MX), 3-methylxanthine (3-MX), 1,3-dimethyluric acid (1,3-DMUA) and 1-methyluric acid (1-MUA), we compared their convulsive potency to central nervous system (CNS) after intracerebral administration to mice [8].

Associations of EINECS 211-905-7 with other chemical compounds

No difference in the formation of metabolites before and after treatment with erythromycin was detected; the findings in urine were 40.4 +/- 5.0 vs 42.1 +/- 5.4% 1,3-dimethyluric acid, 29.6 +/- 4.6 vs 30.1 +/- 5.9% 1-methyluric acid and 13.4 +/- 3.5 vs 12.5 +/- 2.2% 3-methylxanthine before and after erythromycin treatment, respectively [9].

Gene context of EINECS 211-905-7

MEASUREMENTS AND RESULTS: The in vivo XO activity index was measured as the urinary ratio of two metabolites of caffeine: 1-methyluric acid and 1-methylxanthine [10].

Analytical, diagnostic and therapeutic context of EINECS 211-905-7

The simultaneous analysis of 5-acetylamino-6-formylamino-3-methyluracil (AFMU), 5-acetylamino-6-amino-3-methyluracil (AAMU), 1-methylxanthine (1X) and 1-methyluric acid (1U), the four urinary metabolites of caffeine employed for acetylator phenotyping in man, by micellar electrokinetic capillary chromatography (MECC) is reported [11].
Theophylline and six metabolite fractions were recognized in adult liver by thin-layer radiochromatography and high performance liquid chromatography: 1-methyluric acid; 1-methylxanthine; 1,3-dimethyluric acid and/or 3-methylxanthine; caffeine; a uracil derivative and two unknown polar compounds [12].
Western blot analysis revealed that telithromycin significantly decreased the protein levels of CYP1A2 and CYP3A2 in the liver, which could explain the observed decreases in the systemic clearance of theophylline and metabolic clearance of 1-methyluric acid and 1,3-dimethyluric acid [13].
Concerning the metabolism of theophylline in rabbits, the results showed that the oral administration of a single dose of Capsicum fruit suspension does not significantly affect the urinary excretion of theophylline and its metabolites--1,3-dimethyluric acid (1,3-DMU) and 1-methyluric acid (1-MU) [14].

References

Effect of hypoxia alone or combined with inflammation and 3-methylcholanthrene on hepatic cytochrome P450 in conscious rabbits. Kurdi, J., Maurice, H., El-Kadi, A.O., Ong, H., Dalkara, S., Bélanger, P.M., Souich, P. Br. J. Pharmacol. (1999) [Pubmed]
Cystic fibrosis: enhanced theophylline metabolism may be linked to the disease. Knoppert, D.C., Spino, M., Beck, R., Thiessen, J.J., MacLeod, S.M. Clin. Pharmacol. Ther. (1988) [Pubmed]
Developmental aspects of theophylline metabolism in premature infants. Tserng, K.Y., Takieddine, F.N., King, K.C. Clin. Pharmacol. Ther. (1983) [Pubmed]
Developmental changes in urinary elimination of theophylline and its metabolites in pediatric patients. Tateishi, T., Asoh, M., Yamaguchi, A., Yoda, T., Okano, Y.J., Koitabashi, Y., Kobayashi, S. Pediatr. Res. (1999) [Pubmed]
Caffeine acetylator phenotyping during maturation in infants. Pariente-Khayat, A., Pons, G., Rey, E., Richard, M.O., D'Athis, P., Moran, C., Badoual, J., Olive, G. Pediatr. Res. (1991) [Pubmed]
Theophylline metabolism during the first month of life and development. Bonati, M., Latini, R., Marra, G., Assael, B.M., Parini, R. Pediatr. Res. (1981) [Pubmed]
Secondary metabolism of theophylline biotransformation products in man--route of formation of 1-methyluric acid. Birkett, D.J., Miners, J.O., Attwood, J. British journal of clinical pharmacology. (1983) [Pubmed]
Neurotoxic convulsions induced by theophylline and its metabolites in mice. Yamamoto, K., Toyama, E., Kawakami, J., Sawada, Y., Iga, T. Biol. Pharm. Bull. (1996) [Pubmed]
Lack of clinically important interaction between erythromycin and theophylline. Hildebrandt, R., Gundert-Remy, U., Möller, H., Weber, E. Eur. J. Clin. Pharmacol. (1984) [Pubmed]
Xanthine oxidase activity and blood glutathione redox ratio in infants and children with septic shock syndrome. Németh, I., Boda, D. Intensive care medicine. (2001) [Pubmed]
Acetylator phenotyping via analysis of four caffeine metabolites in human urine by micellar electrokinetic capillary chromatography with multiwavelength detection. Guo, R., Thormann, W. Electrophoresis (1993) [Pubmed]
Changes in theophylline metabolism during postnatal development in rat liver slices. Gorodischer, R., Yaari, A., Margalith, M., Warszawski, D., Ben-Zvi, Z. Biochem. Pharmacol. (1986) [Pubmed]
Effect of a newly developed ketolide antibiotic, telithromycin, on metabolism of theophylline and expression of cytochrome P450 in rats. Nosaka, H., Nadai, M., Kato, M., Yasui, K., Yoshizumi, H., Miyoshi, M., Zhao, Y.L., Baba, K., Takagi, K., Hasegawa, T. Life Sci. (2006) [Pubmed]
Theophylline pharmacokinetics and metabolism in rabbits following single and repeated administration of Capsicum fruit. Bouraoui, A., Brazier, J.L., Zouaghi, H., Rousseau, M. European journal of drug metabolism and pharmacokinetics. (1995) [Pubmed]

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