6-Mercaptopurine (monohydrate) Usage and Synthesis |
Introduction |
Mercaptopurine (6-MP, also known as 6-mercaptopurine, mercaptopurine or azathiopurine) is a thiopurine chemotherapy drug and immunosuppressant. |
Indications |
Mercaptopurine is mainly used for the maintenance treatment of acute leukemia (including acute myeloid leukemia and acute lymphocytic leukemia).
It is also used to treat malignant hydatidiform mole, choriocarcinoma, polycythemia vera, psoriatic arthritis, and inflammatory bowel disease (such as Crohn's disease and ulcerative colitis).
Studies have shown that mercaptopurine has anti-Mycobacterium paratuberculosis activity in vitro. |
Mechanism of Action |
Mercaptopurine is a purine analogue and belongs to the class of purine antagonist antimetabolites. It can inhibit amidotransferase, thereby interfering with purine nucleotide synthesis;
it can inhibit the conversion of inosine nucleotides to adenine nucleotides and inosine nucleotides to xanthine nucleotides and guanine nucleotides;
it can also inhibit the synthesis of nicotinamide adenine dinucleotide (NAD+) and cause a decrease in the levels of deoxyadenosine triphosphate (dATP) and deoxyguanosine triphosphate (dGTP).
This allows mercaptopurine to effectively inhibit DNA synthesis, thereby inhibiting the growth of tumor cells. |
Biological Activity |
6-Mercaptopurine (6-MP) Monohydrate is a widely used anti-leukemic agent and immunosuppressant that inhibits de novo purine synthesis
by incorporating mercaptopurine methyltransferase metabolites into DNA and RNA. |
In vitro studies |
Mercaptopurine is widely used to treat malignancies, rheumatic diseases, skin diseases, inflammatory bowel disease, and solid organ transplant rejection.
Mercaptopurine inhibits purine nucleotide synthesis and metabolism by inhibiting phosphoribosyl pyrophosphate amidotransferase (PRPP amidotransferase). PRPP amidotransferase
is the rate-limiting enzyme in purine synthesis. It alters the synthesis and function of RNA and DNA. Mercaptopurine also interferes with nucleoside interconversion and glycoprotein synthesis. |
Chemical properties |
The monohydrate is a light yellow crystalline powder. Melting point 312-314℃, easily soluble in alkaline solution, slightly soluble in hot water, insoluble in water, acetone, and ether. |
Uses |
An intermediate of 6-mercaptopurine, lysopurine, and thiopurine, and can be used as an anti-tumor drug. |
Production method |
It can be prepared from 7-aminothiazolo[5,4-d]pyrimidine, or from 6-hydroxypurine by substitution with phosphorus sulfide. |
