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Chemical Compound Review:

NSC-46380 6-sulfanylidene-7,9-dihydro- 3H-purine-2,8...

Synonyms: AC1MHU36, NSC46380, NSC 46380, AKOS006273461, AKOS015904793, ...

Tamta, H. et al., Ravis, W.R. et al., Tawa, R. et al., Hwang, I.Y. et al., Rudy, J.L. et al., et al.

Tamta, Kalra, Thilagavathi, Chakraborti, Mukhopadhyay,

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High impact information on NSC 46380

When rats were given S-(6-purinyl)-L-cysteine (31.2 mg/kg i.p.) and were sacrificed at 30 min after treatments, 6-mercaptopurine, 6-methyl-mercaptopurine and 6-thiouric acid were detected in the kidney, liver or plasma.(ABSTRACT TRUNCATED AT 250 WORDS)[1]
Varying the concentration of 6-mercaptopurine from 0.24 to 5.88 mM demonstrated saturability of the biotransformation of 6-mercaptopurine to 6-thiouric acid with a maximum rate of 1.6 X 10(-5) mmoles per min g for jejunal portions [2].
With in situ loops perfused with 1.47 mM drug, collection of mesentery blood showed that absorption rates of 6-thiouric acid were 0.67 that of the parent drug [2].
A convenient HPLC assay, which allows for the simultaneous measurement in extracellular fluids of 6-mercaptopurine and four of its metabolites, 6-thioguanine, 6-mercaptopurine riboside, 6-thioxanthine and 6-thiouric acid is described [3].
Enzymatic hydroxylation of 6-MP forms 6-thiouric acid in two steps involving 6-TX as the intermediate, whereas 2-MP is converted to 8-hydroxy-2-mercaptopurine as the expected end product in one step [4].

Biological context of NSC 46380

Biological monitoring included plasma chloramphenicol levels, plasma 6-mercaptopurine and urine 6-thiouric acid levels [5].

Associations of NSC 46380 with other chemical compounds

Xanthine oxidase oxidized pure 6-MP, and its bismuth complex to 6-thiouric acid, in vitro [6].

Gene context of NSC 46380

Xanthine oxidase (XO) can transform 6-MP into 6-thioxanthine (6-TX) and 6-thiouric acid (6-TUA), which have no therapeutic value [7].

Analytical, diagnostic and therapeutic context of NSC 46380

The plasma concentrations of 6MP and its major metabolite, 6-thiouric acid, were assayed by high-performance liquid chromatography [8].
6-mercaptopurine (MP) and 6-thiouric acid (TUA) in plasma and urine were analyzed simultaneously by reversed-phase HPLC with a sensitivity of 5 ng/ml [9].
The rate constants for conversion of 6MP into the final product (6-thiouric acid) and the apparent Michaelis constant were also determined by a nonlinear regression analysis based on the integrated Michaelis-Menten equation using the ultraviolet absorbance data and the simplified complementary tristimulus colorimetry [10].

References

Cysteine S-conjugates may act as kidney-selective prodrugs: formation of 6-mercaptopurine by the renal metabolism of S-(6-purinyl)-L-cysteine. Hwang, I.Y., Elfarra, A.A. J. Pharmacol. Exp. Ther. (1989) [Pubmed]
Intestinal absorption and metabolism of 6-mercaptopurine in the rat small intestine. Ravis, W.R., Wang, J.S., Feldman, S. Biochem. Pharmacol. (1984) [Pubmed]
HPLC analysis of 6-mercaptopurine and metabolites in extracellular body fluids. Rudy, J.L., Argyle, J.C., Winick, N., Van Dreal, P. Ann. Clin. Biochem. (1988) [Pubmed]
Nature and position of functional group on thiopurine substrates influence activity of xanthine oxidase - enzymatic reaction pathways of 6-mercaptopurine and 2-mercaptopurine are different. Tamta, H., Kalra, S., Thilagavathi, R., Chakraborti, A.K., Mukhopadhyay, A.K. Biochemistry Mosc. (2007) [Pubmed]
Assessment of exposure to chloramphenicol and azathioprine among workers in a South African pharmaceutical plant. Jeebhay, M., Mbuli, S., Uebel, R. International archives of occupational and environmental health. (1993) [Pubmed]
In vitro oxidation of 6-MP and its metallo complexes by xanthine oxidase. Lewis, R.W., Olivier, G. Res. Commun. Chem. Pathol. Pharmacol. (1977) [Pubmed]
Milk could decrease the bioavailability of 6-mercaptopurine. Rivard, G.E., Lin, K.T., Leclerc, J.M., David, M. The American journal of pediatric hematology/oncology. (1989) [Pubmed]
Effect of allopurinol on the pharmacokinetics of 6-mercaptopurine in rabbits. Tterlikkis, L., Day, J.L., Brown, D.A., Schroeder, E.C. Cancer Res. (1983) [Pubmed]
HPLC analysis of azathioprine metabolites in red blood cells, plasma and urine in renal transplant recipients. Weller, S., Thürmann, P., Rietbrock, N., Gossmann, J., Scheuermann, E.H. International journal of clinical pharmacology and therapeutics. (1995) [Pubmed]
The use of xanthine oxidase for a specific and sensitive fluorimetric determination of 6-mercaptopurine in serum. Tawa, R., Takeshima, S., Hirose, S. Biochemical medicine. (1984) [Pubmed]

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