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PubChem
| Name: | 6-Mercaptopurine |
|---|---|
| PubChem Compound ID: | 2724350 |
| Description: | An antimetabolite antineoplastic agent with immunosuppressant properties. It interferes with nucleic acid synthesis by inhibiting purine metabolism and is used, usually in combination with other drugs, in the treatment of or in remission maintenance programs for leukemia. |
| Molecular formula: | C5H6N4OS |
| Molecular weight: | 170.193 g/mol |
| Synonyms: |
Mercaptopurine hydrate; 6H-Purine-6-thione, 1,7-dihydro-, monohydrate; Mercaptopurine hydrate (JP15); CCRIS 5819; Purine-6-thiol, monohydrate; Purine-6-thiol monohydrate; 1,7-Dihydro-6H-purin-6-thion, monohydrat [Czech]; 6-Mercaptopurine monohydrate; 6-Merkaptopurin, monohydrat [Czech]; Mercaptopurine [BAN:INN:JAN].
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DrugBank
Identification
| Name: | 6-Mercaptopurine |
|---|---|
| Name (isomeric): | DB01033 |
| Drug Type: | small molecule |
| Description: | An antimetabolite antineoplastic agent with immunosuppressant properties. It interferes with nucleic acid synthesis by inhibiting purine metabolism and is used, usually in combination with other drugs, in the treatment of or in remission maintenance programs for leukemia. |
| Synonyms: |
6-Mercaptopurine; MP; 6 MP; Mercapurin; Mercaptopurine Monohydrate
|
| Brand: | Puri-Nethol, Leukerin, Ismipur, Mern, Mercaleukim, Mercaleukin, Purimethol, Purinethol, Leupurin |
| Category: | Antimetabolites, Antimetabolites, Antineoplastic, Antineoplastic Agents, Purine analogues, Immunosuppressive Agents, Nucleic Acid Synthesis Inhibitors |
| CAS number: | 50-44-2 |
Pharmacology
| Indication: | For remission induction and maintenance therapy of acute lymphatic leukemia. |
|---|---|
| Pharmacology: |
Mercaptopurine is one of a large series of purine analogues which interfere with nucleic acid biosynthesis and has been found active against human leukemias. It is an analogue of the purine bases adenine and hypoxanthine. It is not known exactly which of any one or more of the biochemical effects of mercaptopurine and its metabolites are directly o...
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| Mechanism of Action: |
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 ...
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| Absorption: | Clinical studies have shown that the absorption of an oral dose of mercaptopurine in humans is incomplete and variable, averaging approximately 50% of the administered dose. The factors influencing absorption are unknown. |
| Protein binding: | Plasma protein binding averages 19% over the concentration range 10 to 50 µg/mL (a concentration only achieved by intravenous administration of mercaptopurine at doses exceeding 5 to 10 mg/kg). |
| Biotransformation: | Hepatic. Degradation primarily by xanthine oxidase. The catabolism of mercaptopurine and its metabolites is complex. In humans, after oral administration of 35S-6-mercaptopurine, urine contains intact mercaptopurine, thiouric acid (formed by direct oxidation by xanthine oxidase, probably via 6-mercapto-8-hydroxypurine), and a number of 6-methylated thiopurines. The methylthiopurines yield appreciable amounts of inorganic sulfate. |
| Half Life: | Triphasic: 45 minutes, 2.5 hours, and 10 hours. |
| Toxicity: | Signs and symptoms of overdosage may be immediate such as anorexia, nausea, vomiting, and diarrhea; or delayed such as myelosuppression, liver dysfunction, and gastroenteritis. The oral LD50 of mercaptopurine was determined to be 480 mg/kg in the mouse and 425 mg/kg in the rat. |
| Affected organisms: | Humans and other mammals |
Interactions
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Targets
Enzymes
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