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Chemical Compound Review:

AFMU N-(4-formamido-1-methyl-2,6- dioxo-3H...

Synonyms: AG-H-43745, CHEBI:32643, HMDB11105, CTK8D4667, AR-1G6930, ...

Kaufmann, G.R. et al., el-Yazigi, A. et al., Becquemont, L. et al., Roots, I. et al., Bechtel, Y.C. et al., et al.

Becquemont, Chazouilleres, Serfaty, Poirier, Broly, Jaillon, Poupon, Funck-Brentano,

Welcome! If you are familiar with the subject of this article, you can contribute to this open access knowledge base by deleting incorrect information, restructuring or completely rewriting any text. Read more.

Disease relevance of Acetamide, N-(4-(formylamino)-1,2,3,6-tetrahydro-1-methyl-2,6-dioxo-5-pyrimidinyl)-

In 220 of the lung cancer patients the N-acetyltransferase polymorphism was evaluated by means of the molar ratio of 5-acetylamino-6-formylamino-3-methyluracil and 1-methylxanthine in urine after ingestion of caffeine (coffee) [1].

High impact information on Acetamide, N-(4-(formylamino)-1,2,3,6-tetrahydro-1-methyl-2,6-dioxo-5-pyrimidinyl)-

Phenotypic acetylation capacity was expressed as the ratio of 5-acetylamino-6-formylamino-3-methyluracil and 1-methylxanthine in urine after caffeine intake [2].
CYP3A4, CYP2D6, and NAT2 activities were assessed by use of urinary metabolic ratios of 3-methoxymorphinan/dextromethorphan, dextrorphan/dextromethorphan, and 5-acetylamino-6-formylamino-3-methyluracil (AFMU)/1-methylxanthine(1X) [3].
The NAT2 genotype was assessed by polymerase chain reaction and restriction fragment length polymorphism, the NAT2 phenotype was determined by caffeine test (urinary metabolic ratio of the caffeine metabolites 5-acetylamino-6-formylamino-3-methyluracil and 1-methylxanthine) [4].
The acetylator status was established from the urinary metabolic ratio of 5-acetylamino-6-formylamino-3-methyluracil to 1-methylxanthine (AFMU/1X) after oral administration of caffeine [5].
Caffeine has also been shown to undergo 3-demethylation by CYP1A2, and it is further acetylated to 5-acetylamino-6-formylamino-3-methyluracil (AFMU) by the polymorphic NAT2 [6].

Biological context of Acetamide, N-(4-(formylamino)-1,2,3,6-tetrahydro-1-methyl-2,6-dioxo-5-pyrimidinyl)-

We describe a simplified liquid-chromatographic test in which acetylator phenotype is determined by measuring the peak height ratio of two urinary caffeine metabolites, 5-acetylamino-6-formylamino-3-methyluracil and 1-methylxanthine [7].

Associations of Acetamide, N-(4-(formylamino)-1,2,3,6-tetrahydro-1-methyl-2,6-dioxo-5-pyrimidinyl)- with other chemical compounds

At neutral to basic pH however, 5-acetylamino-6-formylamino-3-methyluracil (AFMU), a metabolite of caffeine, spontaneously decomposes to 5-acetylamino-6-amino-3-methyluracil (AAMU) [8].

References

Debrisoquine hydroxylation phenotype, acetylation phenotype, and ABO blood groups as genetic host factors of lung cancer risk. Roots, I., Drakoulis, N., Ploch, M., Heinemeyer, G., Loddenkemper, R., Minks, T., Nitz, M., Otte, F., Koch, M. Klin. Wochenschr. (1988) [Pubmed]
Arylamine N-acetyltransferase (NAT2) mutations and their allelic linkage in unrelated Caucasian individuals: correlation with phenotypic activity. Cascorbi, I., Drakoulis, N., Brockmöller, J., Maurer, A., Sperling, K., Roots, I. Am. J. Hum. Genet. (1995) [Pubmed]
Effect of interferon alpha-ribavirin bitherapy on cytochrome P450 1A2 and 2D6 and N-acetyltransferase-2 activities in patients with chronic active hepatitis C. Becquemont, L., Chazouilleres, O., Serfaty, L., Poirier, J.M., Broly, F., Jaillon, P., Poupon, R., Funck-Brentano, C. Clin. Pharmacol. Ther. (2002) [Pubmed]
N-acetyltransferase 2 polymorphism in patients infected with human immunodeficiency virus. Kaufmann, G.R., Wenk, M., Taeschner, W., Peterli, B., Gyr, K., Meyer, U.A., Haefeli, W.E. Clin. Pharmacol. Ther. (1996) [Pubmed]
A population and family study of N-acetyltransferase using caffeine urinary metabolites. Bechtel, Y.C., Bonaiti-Pellie, C., Poisson, N., Magnette, J., Bechtel, P.R. Clin. Pharmacol. Ther. (1993) [Pubmed]
Determination of CYP1A2 and NAT2 phenotypes in human populations by analysis of caffeine urinary metabolites. Butler, M.A., Lang, N.P., Young, J.F., Caporaso, N.E., Vineis, P., Hayes, R.B., Teitel, C.H., Massengill, J.P., Lawsen, M.F., Kadlubar, F.F. Pharmacogenetics (1992) [Pubmed]
A simplified and rapid test for acetylator phenotyping by use of the peak height ratio of two urinary caffeine metabolites. el-Yazigi, A., Chaleby, K., Martin, C.R. Clin. Chem. (1989) [Pubmed]
Extractionless method for the simultaneous high-performance liquid chromatographic determination of urinary caffeine metabolites for N-acetyltransferase 2, cytochrome P450 1A2 and xanthine oxidase activity assessment. Nyéki, A., Biollaz, J., Kesselring, U.W., Décosterd, L.A. J. Chromatogr. B Biomed. Sci. Appl. (2001) [Pubmed]

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