Mercaptopurine

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Cat Number

API154427

CAS Number

50-44-2

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CAS Number

50-44-2

EINECS

200-037-4

Storage

Store at 2-8°C

Synonyms

6-Mercaptopurine; mercaptopurine; Mercapurin; 6-Thiopurine; 6-Thioxopurine; 6-Mercaptopurin; 6-Thiohypoxanthine

Molecular Formula

C5H4N4S

Molecular Weight

152.18

Smiles

C1=NC2=C(N1)C(=S)N=CN2

Appearance

Light yellow to yellow solid powder

Melting Point

241-244°C

Boiling Point

498.6±37.0°C at 760 mmHg (Predicted)

Relative Density

1.463 (Estimate)

General Description

Mercaptopurine is a synthetic purine analogue with a thiol group, belonging to the class of antimetabolites. Its chemical structure is 3,7-dihydropurine-6-thione monohydrate. Mercaptopurine is a yellow crystalline powder, practically insoluble in water but soluble in alkaline solutions. It is a prodrug that is converted to the active nucleotide metabolites in the body.

Mechanism of Action

Mercaptopurine is converted intracellularly to 6-mercaptopurine ribonucleotide, which inhibits the enzyme amidophosphoribosyltransferase, the first step in de novo purine synthesis. This leads to the depletion of purine nucleotides and the inhibition of DNA and RNA synthesis. The drug is cell cycle-specific, affecting cells in the S-phase. It also has immunosuppressive properties.

Application

Mercaptopurine is indicated for the treatment of acute lymphoblastic leukemia (ALL), particularly in children, and for the maintenance of remission in ALL. It is also used for the treatment of inflammatory bowel disease (Crohn's disease and ulcerative colitis) and for the management of certain autoimmune disorders. The drug is effective in reducing the risk of relapse and maintaining disease control.

Genome-wide expression analysis of enteric nervous system (ENS) primary cultures revealed that LPS induced a broad spectrum of cytokines and CXCL chemokines. In enteric glial cells, Cxcl5 and Cxcl10 were confirmed as inflammatory targets. 6-Mercaptopurine (6-MP), used in inflammatory bowel disease, partly inhibited TNF-α and Cxcl5 secretion in ENS cultures but not in glial cells alone. This extends understanding of 6-MP’s anti-inflammatory properties on the ENS, though the cellular mechanisms require further study.

Fig. 1 Impact of LPS treatment on the transcriptome of ENS primary cultures. (Kneusels J, et al., 2021)

References

Kneusels J, et al. Limited Impact of 6-Mercaptopurine on Inflammation-Induced Chemokines Expression Profile in Primary Cultures of Enteric Nervous System. Neurochem Res. 2021;46(7):1781-1793.

6‑Mercaptopurine (6‑MP) loaded PLGA nanoparticles (6‑MPNs) were spherical with high encapsulation efficiency and sustained release. They improved oral bioavailability, increased intestinal absorption, reduced toxic metabolite accumulation, and enhanced anticancer efficacy in Jurkat cells and ALL model mice, prolonging survival. The nanomedicine provides a promising delivery strategy for 6‑MP with reduced systemic toxicity.

Fig. 2 Preparation of 6-mercaptopurine-loaded nanomedicines (6-MPNs) and schematic of 6-MPNs augmenting the anticancer efficiency after oral administration. (Zou Y, et al., 2021)

References

Zou Y, et al. Preparation, Characterization, Pharmacokinetic, and Therapeutic Potential of Novel 6-Mercaptopurine-Loaded Oral Nanomedicines for Acute Lymphoblastic Leukemia. Int J Nanomedicine. 2021;16:1127-1141.

Does Mercaptopurine require protection from light and oxidation during storage?

Yes, it is highly sensitive to light and oxidation. The thiol group rapidly oxidizes to disulfide dimers and light accelerates photodegradation. Store in airtight, light‑resistant containers under inert gas (nitrogen) at 2–8°C.

What is the recommended storage temperature for Mercaptopurine?

Store at 2–8°C (refrigerated). At room temperature, rapid oxidation and degradation occur, reducing therapeutic activity.

Is Mercaptopurine stable in solution for oral or injectable use?

Aqueous solutions oxidize rapidly. Use immediately after preparation. Lyophilized powder is recommended for long‑term stability.

How is the impurity mercaptopurine disulfide (an oxidation product) monitored?

This primary degradation product is specifically quantified using a stability‑indicating HPLC method with electrochemical detection, ensuring it remains below pharmacopoeial limits.