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Chemical Compound Review:

AC1L3XMS 5-(hydroxymethyl)-1-methyl-2- phenyl...

Synonyms: AC1Q6IJS, CTK8D4576, ZINC06072259, AR-1G5612, 3-Hmap, ...

Teunissen, M.W. et al., Lanchote, V.L. et al., Posner, J. et al., Teunissen, M.W. et al., Shrewsbury, R.P. et al., et al.

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Disease relevance of 3-Hmap

In contrast, the clearance of antipyrine was not significantly different (1.0 +/- 0.7 versus 0.8 +/- 0.3 ml/min/kg), but the formation clearance for 3-hydroxymethylantipyrine was significantly greater in patients with cystic fibrosis [1].
Antipyrine salivary clearance and half-life and the rate of formation of three principal metabolites of antipyrine (4-hydroxyantipyrine, 3-hydroxymethylantipyrine and norantipyrine) were assessed in nine children with congenital adrenal hyperplasia, six of whom were salt-losers and three of whom were non-salt-losers [2].

High impact information on 3-Hmap

Formation of 3-hydroxymethylantipyrine is mediated by CYP1A2 and CYP2C9 [3].
Urinary 3-hydroxymethylantipyrine (HMA) and free antipyrine were present in greater quantities in 48 h urine in the elderly (P less than 0.001 and P less than 0.05) while the amounts of 4-hydroxyantipyrine (OHA) were almost identical in the two age groups [4].
This difference was mainly due to a 35% higher clearance for production of 3-hydroxymethylantipyrine (HMA), while clearance for production of norantipyrine (NORA) and 4-hydroxyantipyrine (OHA) was not significantly different from the control group [5].
This "cocktail" approach made it possible to characterize in vivo the activities of different forms of cytochrome P450 in a single-study protocol using the total clearance of nifedipine and clearance for production of 3-hydroxymethylantipyrine (HMA), 4-hydroxyantipyrine (OHA) and norantipyrine (NORA) [6].
Alterations in antipyrine clearance (Cl) and 3-hydroxymethylantipyrine (3OHME) formation clearance (ClF) show that the extent of Fluosol hemodilution influences both the time and pattern of change in cytochrome P-450 isoenzyme activity [7].

Analytical, diagnostic and therapeutic context of 3-Hmap

We investigated antipyrine clearance and urinary excretion of 4-hydroxyantipyrine, 3-hydroxymethylantipyrine and nor-antipyrine in rats after 70% partial hepatectomy [8].
The concentration of antipyrine and its 3 main metabolites (norantipyrine (NORA), 4-hydroxyantipyrine (OHA), 3-hydroxymethylantipyrine (HMA)) in plasma and urine were measured by high-performance liquid chromatography (HPLC) [9].

References

Hepatic drug clearance in patients with mild cystic fibrosis. Kearns, G.L., Crom, W.R., Karlson, K.H., Mallory, G.B., Evans, W.E. Clin. Pharmacol. Ther. (1996) [Pubmed]
Antipyrine clearance and metabolite formation in children with congenital adrenal hyperplasia. Teunissen, M.W., Bruining, G.J., De Jongh, B.M., Tenkate-Westerhof, E.W., Breimer, D.D. British journal of clinical pharmacology. (1985) [Pubmed]
Antipyrine as a probe for human oxidative drug metabolism: identification of the cytochrome P450 enzymes catalyzing 4-hydroxyantipyrine, 3-hydroxymethylantipyrine, and norantipyrine formation. Engel, G., Hofmann, U., Heidemann, H., Cosme, J., Eichelbaum, M. Clin. Pharmacol. Ther. (1996) [Pubmed]
The disposition of antipyrine and its metabolites in young and elderly healthy volunteers. Posner, J., Danhof, M., Teunissen, M.W., Breimer, D.D., Whiteman, P.D. British journal of clinical pharmacology. (1987) [Pubmed]
Antipyrine metabolism in patients with disseminated testicular cancer and the influence of cytostatic treatment. Teunissen, M.W., Willemse, P.H., Sleijfer, D.T., Sluiter, W.J., Breimer, D.D. Cancer Chemother. Pharmacol. (1984) [Pubmed]
Influence of renal failure on cytochrome P450 activity in hypertensive patients using a "cocktail" of antipyrine and nifedipine. Lanchote, V.L., Ping, W.C., Santos, S.R. Eur. J. Clin. Pharmacol. (1996) [Pubmed]
Evaluation of cytochrome P-450 mediated metabolism of antipyrine in the rat at different extents of fluosol-DA hemodilution. Shrewsbury, R.P., White, L.G. Res. Commun. Chem. Pathol. Pharmacol. (1990) [Pubmed]
Antipyrine metabolism during hepatic regeneration in the rat. Poulsen, H.E., Pilsgaard, H. Liver (1985) [Pubmed]
Effect of fusidic acid on the hepatic cytochrome P450 enzyme system. Reimann, G., Barthel, B., Rockstroh, J.K., Spatz, D., Brockmeyer, N.H. International journal of clinical pharmacology and therapeutics. (1999) [Pubmed]

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