50-44-2 6-Mercaptopurine AKSci J91223
 
 
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  J91223    
6-Mercaptopurine
, 95%
 
3H-purine-6(7H)-thione
Mercaptopurine
Mercapurin
more..




IDENTITY
CAS Number:50-44-2
MDL Number:MFCD00599524
MF:C5H4N4S
MW:152.18
EINECS:200-037-4
SPECIFICATIONS & PROPERTIES
Min. Purity Spec:95%
Physical Form:Yellow crystalline powder
Melting Point:>300°C
Long-Term Storage:Store long-term at -20°C
DOT/IATA TRANSPORT INFORMATION
Not hazardous material

BIOLOGICAL INFO
Solubility:DMSO
Application(s):DNA/RNA synthesis
Form:Free Base
Research Area:Unfection

REVIEW

 Mercaptopurine competes with hypoxanthine and guanine for the enzyme hypoxanthine-guanine phosphoribosyltransferase (HGPRTase) and is itself converted to thioinosinic acid (TIMP). This intracellular nucleotide inhibits several reactions involving inosinic acid (IMP), including the conversion of IMP to xanthylic acid (XMP) and the conversion of IMP to adenylic acid (AMP) via adenylosuccinate (SAMP). In addition, 6-methylthioinosinate (MTIMP) is formed by the methylation of TIMP. Both TIMP and MTIMP have been reported to inhibit glutamine-5-phosphoribosylpyrophosphate amidotransferase, the first enzyme unique to the de novo pathway for purine ribonucleotide synthesis. Experiments indicate that radiolabeled mercaptopurine may be recovered from the DNA in the form of deoxythioguanosine. Some mercaptopurine is converted to nucleotide derivatives of 6-thioguanine (6-TG) by the sequential actions of inosinate (IMP) dehydrogenase and xanthylate (XMP) aminase, converting TIMP to thioguanylic acid (TGMP).

REFERENCES
[1]Sahasranaman, S.; Howard, D.; Roy, S. (2008). Clinical pharmacology and pharmacogenetics of thiopurines. European Journal of Clinical Pharmacology 64 (8): 753-767. doi:10.1007/s00228-008-0478-6. PMID 18506437.
[2] Shullenberger, C. C. (1962). Long-rangetreatment of polycythemia vera with 6-mercaptopurine. Cancer chemotherapy reports. Part 1 16: 251-252. PMID 13912387

GLOBALLY HARMONIZED SYSTEM (GHS)

Pictograms

Signal Word
Warning

Hazard Statements
H302; H315; H319; H335

Precautionary Statements
P261; P264; P270; P271; P280; P301+P312; P302+P352; P304+P340; P305+P351+P338; P312; P321; P330; P332+P313; P337+P313; P362; P403+P233; P405; P501


RELATED PRODUCTS
A2666-Mercaptopurine monohydrate
H3486-Mercaptopurine

Current as of September 21, 2021


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CATEGORIES

 Heterocyclic Building Blocks > Purines
 Nucleobases > Purines
 Nucleobases > Purines


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