6-MERCAPTOPURINE
6-Mercaptopurine is a purine analogue that interferes with nucleic acid synthesis, leading to inhibition of DNA replication and cell proliferation. It is primarily used in the treatment of acute lymphoblastic leukemia and as an immunosuppressant in certain autoimmune conditions. Advantages include durable remission support and suitability for long-term maintenance protocols. Key risks include hepatotoxicity, bone marrow suppression, and increased susceptibility to infections, requiring monitoring.
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Product Description
Mechanism of action
6‑Mercaptopurine (6‑MP) is a purine antimetabolite structurally related to hypoxanthine. It is converted intracellularly into thioinosine monophosphate and related metabolites that inhibit de novo purine synthesis and interfere with nucleic acid replication. By suppressing DNA and RNA synthesis in rapidly dividing cells, 6‑MP exerts cytotoxic and immunosuppressive effects.
Benefits and advantages
6‑MP is widely used in protocols for acute lymphoblastic leukaemia and as a maintenance immunosuppressant in certain autoimmune and inflammatory conditions when formulated appropriately. Its oral bioavailability and well‑defined pharmacology make it a versatile building block for tailored regimens in specialised care.
Side effects and risks
Major risks include myelosuppression, hepatotoxicity and gastrointestinal toxicity. Genetic polymorphisms in thiopurine S‑methyltransferase (TPMT) or NUDT15 can dramatically increase exposure to active metabolites and predispose to life‑threatening bone‑marrow suppression. Other adverse effects include increased infection risk, pancreatitis and, with long‑term use, potential secondary malignancies. Use requires specialist oversight, regular laboratory monitoring and pharmacogenetic consideration.
Datasheet
| Molecular Formula | C5H4N4S |
|---|---|
| Molecular Weight | 152.18 g/mol |
| CAS Number | 50-44-2 |
| Storage Condition | Store at 20 deg to 25 °C (68 deg to 77 °F). Store in a dry place. |
| Solubility | Solubility depends on solvent and conditions (e.g., pH). Please contact us for solvent-specific guidance. |
| Purity | Purity information is available upon request (COA). |
| Synonym | 6-Mercaptopurine; mercaptopurine; 50-44-2; Mercapurin; 6-Thiopurine |
| IUPAC/Chemical Name | 3,7-dihydropurine-6-thione |
| InChl Key | GLVAUDGFNGKCSF-UHFFFAOYSA-N |
| InChl Code | InChI=1S/C5H4N4S/c10-5-3-4(7-1-6-3)8-2-9-5/h1-2H,(H2,6,7,8,9,10) |
| References |
3D Conformer.
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