An inhibitor of purine synthesis and interconversion
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Metabolite(s)
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6-Mercaptopurine (hydrate)

Item No. 23675

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
1,2,3,9-tetrahydro-6H-purine-6-thione, monohydrate
CAS Number
6112-76-1
Synonyms
  • 6-MP
Molecular Formula
C5H4N4S • H2O
Formula Weight
170.2
Purity
≥98%
Formulation
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 5 mg/mlDMSO: 5 mg/mlDMSO:PBS(pH7.2) (1:1): 0.5 mg/mlEthanol: 0.2 mg/ml
λmax
202, 330 nm
SMILES
S=C1C2=C(NC=N2)N=CN1.O
InChi Code
InChI=1S/C5H4N4S.H2O/c10-5-3-4(7-1-6-3)8-2-9-5;/h1-2H,(H2,6,7,8,9,10);1H2
InChi Key
WFFQYWAAEWLHJC-UHFFFAOYSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    5 g

    $75

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    25 g

    $295

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    Cayman Chemical
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    Product Description

    6-Mercaptopurine (6-MP) is an inhibitor of purine synthesis and interconversion.1 It is rapidly converted to 6-mercaptopurine ribonucleoside-5'-monophosphate, which inhibits phosphoribosyl pyrophosphate (PRPP) amidotransferase, the rate-limiting enzyme in purine synthesis. It also inhibits the conversion of IMP to adenylosuccinic acid and xanthylic acid and blocks AMP formation in vitro. 6-MP (30 mg/kg) inhibits growth of sarcoma 180, adenocarcinoma E 0771, and adenocarcinoma 755 tumors and reduces the size of leukemia L1210 subcutaneous growths in mice.2 It also decreases delayed-type hypersensitivity and thyroid inflammation in a guinea pig model of thyroiditis when administered pre- or post-disease onset.3 Formulations containing mercaptopurine have been used for maintenance therapy in patients with acute lymphoblastic leukemia.4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Brockman, R.W. Biochemical aspects of mercaptopurine inhibition and resistance. Cancer Res. 23(8), 1191-1201 (1963).

    2. Skipper, H.E., Thomson, J.R., Elion, G.B., et al. Observations on the anticancer activity of 6-mercaptopurine. Cancer Res. 14(4), 294-298 (1954).

    3. Spiegelberg, H.L., and Miescher, P.A. The effect of 6-mercaptopurine and aminopterin on experimental immune thyroiditis in guinea pigs. J. Exp. Med. 118(5), 869-890 (1963).

    4. Alsous, M., Abu Farha, R., Alefishat, E., et al. Adherence to 6-mercaptopurine in children and adolescents with acute lymphoblastic leukemia. PLoS One 12(9), e0183119 (2017).