Chemical Property of Dtxcid605538
Chemical Property:
- Appearance/Colour:white to light yellow crystal powder
- Vapor Pressure:2.72E-09mmHg at 25°C
- Melting Point:313 °C
- Boiling Point:490.6oC at 760 mmHg
- Flash Point:250.5oC
- PSA：98.68000
- LogP:0.95120
- Storage Temp.:Store at 0-5
- Solubility.:INSOLUBLE
- Water Solubility.:INSOLUBLE
- Hydrogen Bond Donor Count:3
- Hydrogen Bond Acceptor Count:4
- Rotatable Bond Count:0
- Exact Mass:172.04188206
- Heavy Atom Count:11
- Complexity:222
- Purity/Quality:
-
99% *data from raw suppliers
6-Mercaptopurine Monohydrate *data from reagent suppliers
Safty Information:
- Pictogram(s):
Xn, 
Xi
- Hazard Codes:Xn,Xi
- Statements:
22-36/37/38-63-20/21/22
- Safety Statements:
22-36/37/39-45-36/37
- MSDS Files:
-
SDS file from LookChem
Total 1 MSDS from other Authors
Useful:
- Canonical SMILES:C1=NC2C(N1)C(=S)NC=N2.O
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Description
6-Mercaptopurine (6-MP) is an inhibitor of purine synthesis and interconversion. 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. It also decreases delayed-type hypersensitivity and thyroid inflammation in a guinea pig model of thyroiditis when administered pre- or post-disease onset. Formulations containing mercaptopurine have been used for maintenance therapy in patients with acute lymphoblastic leukemia.
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Uses
An immunosuppressive drug used to treat leukemia. It is also used for pediatric non-Hodgkin lymphoma, polycythemia vera, and psoriatic arthritis An immunosuppressive drug used to treat leukemia. It is also used for pediatric non-Hodgkin’s lymphoma, polycythemia vera, and psoriatic arthritis. antihypertensive, ACE inhibitor
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Indications
Mercaptopurine (Purinethol) is an analogue of hypoxanthine
and was one of the first agents shown to be active
against acute leukemias. It is now used as part of
maintenance therapy in acute lymphoblastic leukemia.
Mercaptopurine must be activated to a nucleotide by
the enzyme HGPRTase. This metabolite is capable of
inhibiting the synthesis of the normal purines adenine
and guanine at the initial aminotransferase step and inhibiting
the conversion of inosinic acid to the nucleotides
adenylate and guanylate at several steps.
Some mercaptopurine is also incorporated into DNA in
the form of thioguanine. The relative significance of
these mechanisms to the antitumor action of mercaptopurine
is not clear.
Resistance to mercaptopurine may be a result of decreased
drug activation by HGPRTase or increased inactivation
by alkaline phosphatase.
The plasma half-life of an intravenous bolus injection
of mercaptopurine is 21 minutes in children and 47
minutes in adults. After oral administration, peak
plasma levels are attained within 2 hours. The drug is
20% bound to plasma proteins and does not enter the
CSF. Xanthine oxidase is the primary enzyme involved
in the metabolic inactivation of mercaptopurine.
Mercaptopurine is used in the maintenance therapy
of acute lymphoblastic leukemia. It also displays activity
against acute and chronic myelogenous leukemias.
The major toxicities of mercaptopurine are myelosuppression,
nausea, vomiting, and hepatic toxicity.
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Clinical Use
Mercaptopurine is used in the treatment of acute lymphatic and myelogenous leukemias.
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Drug interactions
Potentially hazardous interactions with other drugs
Allopurinol: decreased rate of metabolism of
mercaptopurine - reduce dose of mercaptopurine to
a quarter of normal dose.
Antibacterials: increased risk of haematological
toxicity with co-trimoxazole and trimethoprim.
Anticoagulants: possibly reduced anticoagulant effect
of coumarins.
Antipsychotics: avoid with clozapine (increased risk
of agranulocytosis).
Febuxostat: avoid concomitant use.
