Mercaptopurine

Base Information

• Chemical Name: Mercaptopurine
• CAS No.: 50-44-2
• Deprecated CAS: 5759-99-9,5818-33-7,5818-60-0,39454-94-9,111079-50-6,39454-94-9,5818-33-7,5818-60-0
• Molecular Formula: C5H4N4S
• Molecular Weight: 152.18
• Hs Code.: 2933599090
• European Community (EC) Number: 200-037-4
• NSC Number: 759614,755
• UNII: PKK6MUZ20G
• DSSTox Substance ID: DTXSID0020810
• Nikkaji Number: J2.298E
• Wikipedia: Mercaptopurine
• Wikidata: Q418529
• NCI Thesaurus Code: C61832
• RXCUI: 1546028
• Pharos Ligand ID: GVGMMZSCWXZJ
• Metabolomics Workbench ID: 43275
• ChEMBL ID: CHEMBL1425
• Mol file: 50-44-2.mol

Synonyms:1,7-Dihydro-6H-purine-6-thione;6 Mercaptopurine;6 Mercaptopurine Monohydrate;6 Thiohypoxanthine;6 Thiopurine;6-Mercaptopurine;6-Mercaptopurine Monohydrate;6-Thiohypoxanthine;6-Thiopurine;6H-Purine-6-thione, 1,7-dihydro-;BW 57 323H;BW 57-323H;BW 57323H;Leupurin;Mecaptopurine Anhydrous;Mercaptopurina Wellcome;Mercaptopurine;Puri-Nethol;Purimethol;Purinethol

Chemical Property of Mercaptopurine

Chemical Property:

• Appearance/Colour: yellowish-greenish solid
• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 241-244 °C
• Refractive Index: 1.828
• Boiling Point: 471.018 °C at 760 mmHg
• PKA: 7.77, 11.17(at 25℃)
• Flash Point: 238.663 °C
• PSA: 89.45000
• Density: 1.82 g/cm³
• LogP: 1.01550
• Storage Temp.: Store at RT
• Water Solubility.: 124mg/L(25 oC)
• XLogP3: 0
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 152.01566732
• Heavy Atom Count: 10
• Complexity: 190

Purity/Quality:

99% ^*data from raw suppliers

6-Mercaptopurine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Drug Classes: Antineoplastic Agents
• Canonical SMILES: C1=NC2=C(N1)C(=S)N=CN2
• Recent ClinicalTrials: Combination Chemotherapy in Treating Young Patients With Newly Diagnosed T-Cell Acute Lymphoblastic Leukemia or T-cell Lymphoblastic Lymphoma
• Recent EU Clinical Trials: A multicentre, randomized trial in adults with de novo Philadelphia-Chromosome positive acute lymphoblastic leukemia to assess the efficacy of ponatinib versus imatinib in combination with low-intensity chemotherapy, to compare end of therapy with indication for SCT versus TKI, blinatumomab and chemotherapy in optimal responders and to evaluate blinatumomab in suboptimal responders (GMALL-EVOLVE)
• Recent NIPH Clinical Trials: Efficacy of mercaptopurine in leukemia patients with relapse after allogeneic stem cell transplantation
• General Description: 6-Mercaptopurine is a purine analogue and antimetabolite chemotherapeutic agent used primarily in the treatment of leukemia. It functions by interfering with nucleic acid synthesis, inhibiting the proliferation of cancer cells. Structurally, it is a thiol-substituted purine derivative, and its cytotoxic activity has been extensively studied, often serving as a reference compound in the development of novel antitumor agents. Derivatives and analogues of 6-mercaptopurine, such as those explored in the cited studies, aim to enhance its therapeutic efficacy or reduce side effects while retaining its core mechanism of action.

Technology Process of Mercaptopurine

There total 27 articles about Mercaptopurine 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: 85.0%

hypoxanthine (68-94-0) → 6-mercaptopurine (50-44-2)

Guidance literature:

With pyridin-1-ium-1-yl[pyridin-1-ium-1-yl(sulfido)phosphinothioyl]sulfanyl-sulfido-thioxo-phosphane; In dimethylsulfone; at 165 - 175 ℃; for 0.25h;

DOI:10.1021/jo101865y

Reference yield:

N-(4-amino-6-thioxo-1,6-dihydro-pyrimidin-5-yl)-formamide (500542-05-2) → 6H-purine-6-thione (50-44-2)

Guidance literature:

With formamide; at 200 ℃;

DOI:10.1021/ja01593a062

Reference yield:

1,7-dihydro-6H-purin-6-one (68-94-0) → 6H-purine-6-thione (50-44-2)

Guidance literature:

With tetraphosphorus decasulfide; tetralin;

DOI:10.1021/ja01122a037

upstream raw materials:

2,6,8-trichloro-7H-purine

[1,3]thiazolo[5,4-d]pyrimidin-7-amine

formamide

6-amino-5-formylamino-3H-pyrimidin-4-one

Downstream raw materials:

6-furfurylmercapto-7(9)H-purine

6-[2]thienylmethylsulfanyl-7(9)H-purine

6-isopropylmercapto-7(9)H-purine

6-n-butylthiopurine

Refernces

Synthesis and cytotoxic activity of imidazo[1,2-a]-1,3,5-triazine analogues of 6-mercaptopurine

10.1002/ardp.200700176

The research focuses on the synthesis and cytotoxic activity evaluation of imidazo[1,2-a]-1,3,5-triazine analogues, which are structurally related to the chemotherapeutic drug 6-mercaptopurine. The study involved the preparation of 2-substituted imidazo[1,2-a]-1,3,5-triazines using various aliphatic and aromatic amines as reactants. The synthesized compounds were characterized using IR, 1H-NMR, and elemental analysis. The cytotoxic activity of these compounds was assessed through in-vitro studies on five human cancer cell lines, with one active compound further tested on 12 human cancer cell lines. The experiments utilized a microtiter assay based on crystal violet staining to determine antiproliferative activity, and the IC50 values were calculated from the results of three independent experiments. The study aimed to develop new antitumor agents and compared the cytotoxic activity of the synthesized compounds with that of 6-mercaptopurine and thioguanine, two established anticancer drugs.

Aminomethylation and hydroxymethylation of purine-6(1H)-thione and 6-alkylthiopurines.

10.1021/jm00313a025

The research focuses on the chemical synthesis and analysis of various purine derivatives, specifically 6-(alkylthio)-9-(hydroxymethyl)-SH-purines. The study investigates the hydroxymethylation of purine-6(1H)-thione and its derivatives, revealing that substitution occurs at the 9 position of the purine ring. Key chemicals involved include ethyl acetate, ligroin, benzene, ethyl alcohol, and petroleum ether, used as solvents in the synthesis and analysis processes. The researchers also utilized aqueous formaldehyde and sodium carbonate for hydroxymethylation reactions. Additionally, the study examines the infrared and ultraviolet spectra of these compounds, as well as their stability and reactivity with isocyanates. One of the synthesized compounds was screened for antitumor activity, showing promising results in certain leukemia models. The research provides valuable insights into the structure and potential applications of these purine derivatives.