Home Other Building Blocks 6-Methylmercaptopurine

6-Methylmercaptopurine

CAS No.:
50-66-8
Catalog Number:
AG0037EB
Molecular Formula:
C6H6N4S
Molecular Weight:
166.2036
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Product Description
Catalog Number:
AG0037EB
Chemical Name:
6-Methylmercaptopurine
CAS Number:
50-66-8
Molecular Formula:
C6H6N4S
Molecular Weight:
166.2036
MDL Number:
MFCD00225354
IUPAC Name:
6-methylsulfanyl-7H-purine
InChI:
InChI=1S/C6H6N4S/c1-11-6-4-5(8-2-7-4)9-3-10-6/h2-3H,1H3,(H,7,8,9,10)
InChI Key:
UIJIQXGRFSPYQW-UHFFFAOYSA-N
SMILES:
CSc1ncnc2c1[nH]cn2
EC Number:
200-057-3
UNII:
6V404DV25O
NSC Number:
20105
Properties
Complexity:
143  
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
0
Defined Bond Stereocenter Count:
0
Exact Mass:
166.031g/mol
Formal Charge:
0
Heavy Atom Count:
11  
Hydrogen Bond Acceptor Count:
4  
Hydrogen Bond Donor Count:
1  
Isotope Atom Count:
0
Molecular Weight:
166.202g/mol
Monoisotopic Mass:
166.031g/mol
Rotatable Bond Count:
1  
Topological Polar Surface Area:
79.8A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
1.1  
Literature
Title Journal
Split-dose administration of thiopurine drugs: a novel and effective strategy for managing preferential 6-MMP metabolism. Alimentary pharmacology & therapeutics 20120901
High TPMT enzyme activity does not explain drug resistance due to preferential 6-methylmercaptopurine production in patients on thiopurine treatment. Alimentary pharmacology & therapeutics 20120501
Hepatotoxicity associated with 6-methyl mercaptopurine formation during azathioprine and 6-mercaptopurine therapy does not occur on the short-term during 6-thioguanine therapy in IBD treatment. Journal of Crohn's & colitis 20120201
Two brothers with skewed thiopurine metabolism in ulcerative colitis treated successfully with allopurinol and mercaptopurine dose reduction. Digestive diseases and sciences 20120101
A validated HPLC method for the monitoring of thiopurine metabolites in whole blood in paediatric patients with inflammatory bowel disease. International journal of immunopathology and pharmacology 20120101
Use of thiopurine testing in the management of inflammatory bowel diseases in clinical practice: a worldwide survey of experts. Inflammatory bowel diseases 20111201
Allopurinol enhances the activity of hypoxanthine-guanine phosphoribosyltransferase in inflammatory bowel disease patients during low-dose thiopurine therapy: preliminary data of an ongoing series. Nucleosides, nucleotides & nucleic acids 20111201
Evaluating the use of metabolite measurement in children receiving treatment with a thiopurine. Alimentary pharmacology & therapeutics 20111101
Detection of thiopurine methyltransferase activity in lysed red blood cells by means of lab-on-a-chip surface enhanced Raman spectroscopy (LOC-SERS). Analytical and bioanalytical chemistry 20110701
Clinical usefulness of therapeutic drug monitoring of thiopurines in patients with inadequately controlled inflammatory bowel disease. Inflammatory bowel diseases 20110601
Steady-state of azathioprine during initiation treatment of pediatric inflammatory bowel disease. Journal of Crohn's & colitis 20101201
Synthesis and SAR studies of 1,4-benzoxazine MenB inhibitors: novel antibacterial agents against Mycobacterium tuberculosis. Bioorganic & medicinal chemistry letters 20101101
A prospective evaluation of the impact of allopurinol in pediatric and adult IBD patients with preferential metabolism of 6-mercaptopurine to 6-methylmercaptopurine. Journal of Crohn's & colitis 20101101
Usefulness of the measurement of azathioprine metabolites in the assessment of non-adherence. Journal of Crohn's & colitis 20101101
Monitoring of azathioprine metabolites in pediatric patients with autoimmune hepatitis. Therapeutic drug monitoring 20100801
Limited stability of thiopurine metabolites in blood samples: relevant in research and clinical practise. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 20100601
How should thiopurine treatment be monitored?--methodological aspects. Nucleosides, nucleotides & nucleic acids 20100601
Algorithms outperform metabolite tests in predicting response of patients with inflammatory bowel disease to thiopurines. Clinical gastroenterology and hepatology : the official clinical practice journal of the American Gastroenterological Association 20100201
Usefulness of thiopurine methyltransferase and thiopurine metabolite analysis in clinical practice in patients with inflammatory bowel diseases. Acta gastro-enterologica Belgica 20100101
Patent watch. Drug metabolite claims are patentable. Nature reviews. Drug discovery 20091101
[Optimising azathioprine treatment: determination of thiopurine methyltransferase activity and thiopurine metabolites]. Anales de pediatria (Barcelona, Spain : 2003) 20090201
Initial clinical experience with allopurinol-thiopurine combination therapy in pediatric inflammatory bowel disease. Inflammatory bowel diseases 20081201
Population pharmacokinetic and pharmacogenetic analysis of 6-mercaptopurine in paediatric patients with acute lymphoblastic leukaemia. British journal of clinical pharmacology 20081201
Severe hepatotoxicity with high 6-methylmercaptopurine nucleotide concentrations after thiopurine dose escalation due to low 6-thioguanine nucleotides. European journal of gastroenterology & hepatology 20081201
Regiospecific microwave-assisted synthesis and cytotoxic activity against human breast cancer cells of (RS)-6-substituted-7- or 9-(2,3-dihydro-5H-1,4-benzodioxepin-3-yl)-7H- or -9H-purines. European journal of medicinal chemistry 20080801
Stability of thiopurine metabolites: a potential analytical bias. Clinical chemistry 20080101
Optimizing drug therapy in inflammatory bowel disease. Current gastroenterology reports 20071201
6-thioguanine nucleotide-adapted azathioprine therapy does not lead to higher remission rates than standard therapy in chronic active crohn disease: results from a randomized, controlled, open trial. Clinical chemistry 20070701
Thiopurine treatment in inflammatory bowel disease. Clinical pharmacokinetics 20070101
Utility of thiopurine methyltransferase genotyping and phenotyping, and measurement of azathioprine metabolites in the management of patients with autoimmune hepatitis. Journal of hepatology 20061001
Exposure to thiopurine drugs through breast milk is low based on metabolite concentrations in mother-infant pairs. British journal of clinical pharmacology 20061001
Molecular mechanisms underlying the enhanced sensitivity of thiopurine-resistant T-lymphoblastic cell lines to methyl mercaptopurineriboside. Biochemical pharmacology 20060928
Evolution of thiopurine use in pediatric inflammatory bowel disease in an academic center. Journal of pediatric gastroenterology and nutrition 20060901
[HPLC determination and diversity analysis of thiopurine methyltransferase activity in human and pig]. Sichuan da xue xue bao. Yi xue ban = Journal of Sichuan University. Medical science edition 20060501
Liquid chromatography-tandem mass spectrometry analysis of erythrocyte thiopurine nucleotides and effect of thiopurine methyltransferase gene variants on these metabolites in patients receiving azathioprine/6-mercaptopurine therapy. Clinical chemistry 20051101
Azathioprine and 6-mercaptopurine pharmacogenetics and metabolite monitoring in inflammatory bowel disease. Journal of gastroenterology and hepatology 20050801
Determination of mercaptopurine and its four metabolites by large-volume sample stacking with polarity switching in capillary electrophoresis. Electrophoresis 20050601
Prediction of genotoxicity of chemical compounds by statistical learning methods. Chemical research in toxicology 20050601
Monitoring of long-term thiopurine therapy among adults with inflammatory bowel disease. Scandinavian journal of gastroenterology 20041101
Therapeutic drug monitoring of thiopurine drugs in patients with inflammatory bowel disease or autoimmune hepatitis. European journal of gastroenterology & hepatology 20041101
Improved HPLC methodology for monitoring thiopurine metabolites in patients on thiopurine therapy. Clinical biochemistry 20040901
The utility of 6-thioguanine metabolite levels in managing patients with inflammatory bowel disease. The American journal of gastroenterology 20040901
Clinical significance of azathioprine active metabolite concentrations in inflammatory bowel disease. Gut 20040801
Thiopurine methyltransferase (TPMT) genotype distribution in azathioprine-tolerant and -intolerant patients with various disorders. The impact of TPMT genotyping in predicting toxicity. European journal of clinical pharmacology 20040101
Real-time RT-PCR methodology for quantification of thiopurine methyltransferase gene expression. European journal of clinical pharmacology 20030701
Mercaptopurine metabolite results in clinical gastroenterology practice. Alimentary pharmacology & therapeutics 20030101
Measurement of thiopurine S-methyltransferase activity in human blood samples based on high-performance liquid chromatography: reference values in erythrocytes from children. Annals of clinical biochemistry 20030101
6-Thioguanine seems promising in azathioprine- or 6-mercaptopurine-intolerant inflammatory bowel disease patients: a short-term safety assessment. European journal of gastroenterology & hepatology 20030101
Utility of measuring 6-methylmercaptopurine and 6-thioguanine nucleotide levels in managing inflammatory bowel disease patients treated with 6-mercaptopurine in a clinical practice setting. Journal of clinical gastroenterology 20030101
Determination of thiopurine S-methyltransferase phenotype using thin-layer chromatography and quantitative scanning. European journal of clinical pharmacology 20020401
Possible implication of thiopurine S-methyltransferase in occurrence of infectious episodes during maintenance therapy for childhood lymphoblastic leukemia with mercaptopurine. Leukemia 20011101
Determination of thiopurine methyltransferase activity in human erythrocytes by high-performance liquid chromatography: comparison with the radiochemical method. Therapeutic drug monitoring 20011001
Differing contribution of thiopurine methyltransferase to mercaptopurine versus thioguanine effects in human leukemic cells. Cancer research 20010801
Improved methods for determining the concentration of 6-thioguanine nucleotides and 6-methylmercaptopurine nucleotides in blood. Journal of chromatography. B, Biomedical sciences and applications 20010605
Therapeutic drug monitoring of azathioprine and 6-mercaptopurine metabolites in Crohn disease. Scandinavian journal of gastroenterology 20010101
Thiopurine methyltransferase activity in the erythrocytes of adults and children: and HPLC-linked assay. Clinica chimica acta; international journal of clinical chemistry 19970318
Purine analogs as potential anticytomegalovirus agents. Proceedings of the Society for Experimental Biology and Medicine. Society for Experimental Biology and Medicine (New York, N.Y.) 19690901
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