Dtxcid605538

Base Information

• Chemical Name: Dtxcid605538
• CAS No.: 6112-76-1
• Molecular Formula: C5H4N4S.H2O
• Molecular Weight: 170.195
• Hs Code.: 29335995
• DSSTox Substance ID: DTXSID9025538
• ChEMBL ID: CHEMBL1495381
• Mol file: 6112-76-1.mol

Synonyms:DTXSID9025538;DTXCID605538;CHEMBL1495381;Tox21_200994;NCGC00258547-01;CAS-6112-76-1

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
• 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.
• 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
• 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.
• Clinical Use: Mercaptopurine is used in the treatment of acute lymphatic and myelogenous leukemias.
• 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.

Technology Process of Dtxcid605538

There total 2 articles about Dtxcid605538 which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 83.28%

6-chloro-7H-purine (87-42-3,111055-92-6) + thiourea (17356-08-0) → 6-mercaptopurine (6112-76-1)

Guidance literature:

With formic acid; In ethanol; at 78 - 80 ℃; for 1h;

Reference yield:

→ 6-mercaptopurine (6112-76-1)

Guidance literature:

Reference yield: 85.0%

5-Chloro-2-chloromethyl-3-(2-chlorophenyl)-3H-quinazolin-4-one (371243-84-4) + 6-mercaptopurine monohydrate (6112-76-1) → 5-chloro-3-(2-chlorophenyl)-2-(9H-purin-6-ylsulfanylmethyl)-3H-quinazolin-4-one

Guidance literature:

With potassium carbonate; In N,N-dimethyl-formamide;

upstream raw materials:

6-chloro-7H-purine

thiourea

Downstream raw materials:

Allopurinol

purine-6-sulphonate potassium salt