China Original Largest Manufacturer sales 6-Mercaptopurine monohydrate CAS 6112-76-1 CAS NO.6112-76-1

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6-Mercaptopurine monohydrate Basic information Product Name: 6-Mercaptopurine monohydrate Synonyms: 1,7-dihydro-6h-purin-6-thion,monohydrat;1,7-dihydro-6h-purine-6-thionemonohydrate;1,7-dihydro-6h-purine-6-thionmonohydrate;6h-purin-6-thion,monohydrat;6-merkaptopurin,monohydrat;3,7-Dihydro-purine-6-thione Monohydrate;6-MERCAPTOPURINE extrapure;6-Purinethiol, 6-Thiohypoxanthine CAS: 6112-76-1 MF: C5H6N4OS MW: 170.19 EINECS: 612-090-4 Product Categories: inhibitor;ALTACE;Nucleic acids;Bases & Related Reagents;Heterocycles;Nucleotides;Pyridines, Pyrimidines, Purines and Pteredines;Purine;Heterocyclic Compounds;Antitumors for Research and Experimental Use;Biochemistry;Nucleobases and their analogs;Nucleosides, Nucleotides & Related Reagents;Sulfur & Selenium Compounds Mol File: 6112-76-1.mol   6-Mercaptopurine monohydrate Chemical Properties Melting point  >300 °C(lit.) storage temp.  2-8°C solubility  INSOLUBLE form  Fine Powder color  Yellow Water Solubility  INSOLUBLE Merck  14,5871 BRN  4012091 Stability: Stable. Incompatible with strong oxidizing agents, acids, strong bases. Light sensitive. CAS DataBase Reference 6112-76-1(CAS DataBase Reference) EPA Substance Registry System Mercaptopurine monohydrate (6112-76-1)   Safety Information Hazard Codes  Xn,Xi Risk Statements  22-36/37/38-63-20/21/22 Safety Statements  22-36/37/39-45-36/37 RIDADR  UN 2811 6.1 / PGIII WGK Germany  3 RTECS  UP0400000 HS Code  29335995 MSDS Information Provider Language 6-Mercaptopurine monohydrate English SigmaAldrich English ACROS English ALFA English   6-Mercaptopurine monohydrate Usage And Synthesis 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. Chemical Properties white to light yellow crystal powder Uses An immunosuppressive drug used to treat leukemia. It is also used for pediatric non-Hodgkin lymphoma, polycythemia vera, and psoriatic arthritis Uses An immunosuppressive drug used to treat leukemia. It is also used for pediatric non-Hodgkin’s lymphoma, polycythemia vera, and psoriatic arthritis. Uses 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. Brand name Purinethol (Teva). General Description The drug is available as a 50-mg tablet for oral use. The primaryuses of mercaptopurine are in the treatment of lymphoblasticleukemia, acute lymphocytic leukemia, and Crohndisease. The mechanism of action includes incorporation ofmercaptopurine into DNA and RNA via the triphosphatemetabolite. This incorporation inhibits synthesis and functionof the resulting modified DNA or RNA. The parent drug isinactive and requires phosphorylation for activity. Resistancecan occur via decreased expression of the activating enzymesor increased expression of the major catabolic enzymes.Oral absorption is generally incomplete (about 50%) andthe drug does not enter the CNS in therapeutic quantities.Mercaptopurine is metabolized by methylation, and themethylated product has anticancer activity. Oxidation byxanthine oxidase yields inactive metabolites. The concurrentuse of xanthine oxidase inhibitors such as allopurinol can enhancethe potency of mercaptopurine by inhibiting its catabolicbreakdown. The toxicities for mercaptopurine includemyelosuppression, immunosuppression, nausea, vomiting,diarrhea, dry skin, urticaria, and photosensitivity. General Description Odorless light yellow to yellow crystalline powder. Becomes anhydrous at 284°F. Air & Water Reactions 6-Mercaptopurine monohydrate is sensitive to light and oxidation. Insoluble in water. Reactivity Profile 6-Mercaptopurine monohydrate reacts with strong oxidizing agents, strong bases and strong acids. Fire Hazard Flash point data for 6-Mercaptopurine monohydrate are not available. 6-Mercaptopurine monohydrate is probably combustible. Mechanism of action Because the major mechanism of action of mercaptopurine is inhibition of de novo purine nucleotide biosynthesis rather than apoptosis secondary to the incorporation of false nucleotides into DNA, there is a lower risk for mutagenesis and secondary malignancy compared to thioguanine. Clinical Use Mercaptopurine is used in the treatment of acute lymphatic and myelogenous leukemias. Side effects Bone marrow suppression is the major use-limiting toxicity, although the drug can be hepatotoxic in high doses. Dosage adjustments should be considered in the face of renal or hepatic impairment. Chemical Synthesis Mercaptopurine, 6-purinthiol, is made from uric acid (30.1.2.5), which is synthesized from barbituric acid (30.1.2.1). Barbituric acid (30.1.2.1) is easily made by condensing urea with malonic ester and then nitrosylating it with nitrous acid. The nitrosoderivative (30.1.2.2) is reduced by hydrogen (obtained in situ by reacting tin with hydrochloric acid) to an amine (uramil) (30.1.2.3), and then reacted with isocyanic acid, which forms pseudouric acid (30.1.2.4). This undergoes cyclization to uric acid (30.1.2.5) when heated in the presence of hydrochloric acid. Upon reacting phosphorous pentachloride with uric acid, 2,6,8-trichloropurine (30.1.2.6) is formed. The three chlorine atoms in trichloropurine differ significantly in terms of reactivity for nucleophilic substitution. The chlorine atom at C6 is much more active than the chlorine atom at C2, and this is more active than the chlorine atom at C8, which allows subsequent manipulation by them. Interaction of 2,6,8-trichloropurine (30.1.2.6) with sodium hydroxide allows to replace the chlorine atom at C6, forming the dichloro-derivative (30.1.2.7), which is then reduced by hydriodic acid to hypoxanthine (30.1.2.8). Upon reaction with phosphorous pentasulfide, hypoxanthine is transformed into mercaptopurine (30.1.2.9). 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. Metabolism It is available in an oral dosage form, but absorption can be erratic and is reduced by the presence of food. The drug is extensively metabolized on first pass and excreted by the kidneys. Purification Methods Crystallise 6-mercaptopurine from pyridine (30mL/g), wash it with pyridine, then triturate with water (25mL/g) and adjust to pH 5 by adding M HCl. Recrystallise it by heating, then cooling, the solution. Filter off the solid, wash it with water and dry it at 110o. It has also been crystallised from water (charcoal) as yellow crystals of the monohydrate which become anhydrous on drying at 140o. It has UV: at 230 and 312nm ( 14,000 and 19,600) in 0.1N NaOH; 222 and 327nm ( 9,2400 max and 21,300), and 216 and 329nm ( 8,740 and 19,300) in MeOH. It forms a 1:1 complex with Zn2+ , Pb2+ , Co2+, and Ni2+ in aqueous dioxan. It is an antineoplastic. [Albert & Brown J Chem Soc 2060 1954, IR: Brown & Mason J Chem Soc 682 1957, UV: Fox et al. J Am Chem Soc 80 1669 1958, UV: Mason J Chem Soc 2071 1954, Beilstein 26 III/IV 2097.]

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Leader Biochemical Group is a large leader incorporated industry manufacturers and suppliers of advanced refined raw materials From the year of 1996 when our factory was put into production to year of 2020, our group has successively invested in more than 52 factories with shares and subordinates.We focus on manufacture Pharm & chemicals, functional active ingredients, nutritional Ingredients, health care products, cosmetics, pharmaceutical and refined feed, oil, natural plant ingredients industries to provide top quality of GMP standards products.All the invested factories' product lines cover API and intermediates, vitamins, amino acids, plant extracts, daily chemical products, cosmetics raw materials, nutrition and health care products, food additives, feed additives, essential oil products, fine chemical products and agricultural chemical raw materials And flavors and fragrances. Especially in the field of vitamins, amino acids, pharmaceutical raw materials and cosmetic raw materials, we have more than 20 years of production and sales experience. All products meet the requirements of high international export standards and have been recognized by customers all over the world. Our manufacture basement & R&D center located in National Aerospace Economic & Technical Development Zone Xi`an Shaanxi China. Now not only relying on self-cultivation and development as well as maintains good cooperative relations with many famous research institutes and universities in China. Now, we have closely cooperation with Shanghai Institute of Organic Chemistry of Chinese Academy of Science, Beijing Institute of Material Medical of Chinese Academy of Medical Science, China Pharmaceutical University, Zhejiang University. Closely cooperation with them not only integrating Science and technology resources, but also increasing the R&D speed and improving our R&D power. Offering Powerful Tech supporting Platform for group development. Keep serve the manufacture and the market as the R&D central task, focus on the technical research.  Now there are 3 technology R & D platforms including biological extract, microorganism fermentation and chemical synthesis, and can independently research and develop kinds of difficult APIs and pharmaceutical intermediates. With the strong support of China State Institute of Pharmaceutical Industry (hereinafter short for CSIPI), earlier known as Shanghai Institute of Pharmaceutical Industry (SIPI), we have unique advantages in the R & D and industrialization of high-grade, precision and advanced products.  Now our Group technical force is abundant, existing staff more that 1000 people, senior professional and technical staff accounted for more than 50% of the total number of employees, including 15 PhD research and development personnel, 5 master′ S degree in technical and management personnel 9 people. We have advanced equipment like fermentation equipment and technology also extraction, isolation, purification, synthesis with rich production experience and strict quality control system, According to the GMP required, quickly transforming the R&D results to industrial production in time, it is our advantages and our products are exported to North and South America, Europe, Middle East, Africa, and other five continents and scale the forefront in the nation, won good international reputation.  We believe only good quality can bring good cooperation, quality is our key spirit during our production, we are warmly welcome clients and partner from all over the world contact us for everlasting cooperation, Leader will be your strong, sincere and reliable partner in China.

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6-Mercaptopurine monohydrate Basic information Product Name: 6-Mercaptopurine monohydrate Synonyms: 1,7-dihydro-6h-purin-6-thion,monohydrat;1,7-dihydro-6h-purine-6-thionemonohydrate;1,7-dihydro-6h-purine-6-thionmonohydrate;6h-purin-6-thion,monohydrat;6-merkaptopurin,monohydrat;3,7-Dihydro-purine-6-thione Monohydrate;6-MERCAPTOPURINE extrapure;6-Purinethiol, 6-Thiohypoxanthine CAS: 6112-76-1 MF: C5H6N4OS MW: 170.19 EINECS: 612-090-4 Product Categories: inhibitor;ALTACE;Nucleic acids;Bases & Related Reagents;Heterocycles;Nucleotides;Pyridines, Pyrimidines, Purines and Pteredines;Purine;Heterocyclic Compounds;Antitumors for Research and Experimental Use;Biochemistry;Nucleobases and their analogs;Nucleosides, Nucleotides & Related Reagents;Sulfur & Selenium Compounds Mol File: 6112-76-1.mol   6-Mercaptopurine monohydrate Chemical Properties Melting point  >300 °C(lit.) storage temp.  2-8°C solubility  INSOLUBLE form  Fine Powder color  Yellow Water Solubility  INSOLUBLE Merck  14,5871 BRN  4012091 Stability: Stable. Incompatible with strong oxidizing agents, acids, strong bases. Light sensitive. CAS DataBase Reference 6112-76-1(CAS DataBase Reference) EPA Substance Registry System Mercaptopurine monohydrate (6112-76-1)   Safety Information Hazard Codes  Xn,Xi Risk Statements  22-36/37/38-63-20/21/22 Safety Statements  22-36/37/39-45-36/37 RIDADR  UN 2811 6.1 / PGIII WGK Germany  3 RTECS  UP0400000 HS Code  29335995 MSDS Information Provider Language 6-Mercaptopurine monohydrate English SigmaAldrich English ACROS English ALFA English   6-Mercaptopurine monohydrate Usage And Synthesis 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. Chemical Properties white to light yellow crystal powder Uses An immunosuppressive drug used to treat leukemia. It is also used for pediatric non-Hodgkin lymphoma, polycythemia vera, and psoriatic arthritis Uses An immunosuppressive drug used to treat leukemia. It is also used for pediatric non-Hodgkin’s lymphoma, polycythemia vera, and psoriatic arthritis. Uses 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. Brand name Purinethol (Teva). General Description The drug is available as a 50-mg tablet for oral use. The primaryuses of mercaptopurine are in the treatment of lymphoblasticleukemia, acute lymphocytic leukemia, and Crohndisease. The mechanism of action includes incorporation ofmercaptopurine into DNA and RNA via the triphosphatemetabolite. This incorporation inhibits synthesis and functionof the resulting modified DNA or RNA. The parent drug isinactive and requires phosphorylation for activity. Resistancecan occur via decreased expression of the activating enzymesor increased expression of the major catabolic enzymes.Oral absorption is generally incomplete (about 50%) andthe drug does not enter the CNS in therapeutic quantities.Mercaptopurine is metabolized by methylation, and themethylated product has anticancer activity. Oxidation byxanthine oxidase yields inactive metabolites. The concurrentuse of xanthine oxidase inhibitors such as allopurinol can enhancethe potency of mercaptopurine by inhibiting its catabolicbreakdown. The toxicities for mercaptopurine includemyelosuppression, immunosuppression, nausea, vomiting,diarrhea, dry skin, urticaria, and photosensitivity. General Description Odorless light yellow to yellow crystalline powder. Becomes anhydrous at 284°F. Air & Water Reactions 6-Mercaptopurine monohydrate is sensitive to light and oxidation. Insoluble in water. Reactivity Profile 6-Mercaptopurine monohydrate reacts with strong oxidizing agents, strong bases and strong acids. Fire Hazard Flash point data for 6-Mercaptopurine monohydrate are not available. 6-Mercaptopurine monohydrate is probably combustible. Mechanism of action Because the major mechanism of action of mercaptopurine is inhibition of de novo purine nucleotide biosynthesis rather than apoptosis secondary to the incorporation of false nucleotides into DNA, there is a lower risk for mutagenesis and secondary malignancy compared to thioguanine. Clinical Use Mercaptopurine is used in the treatment of acute lymphatic and myelogenous leukemias. Side effects Bone marrow suppression is the major use-limiting toxicity, although the drug can be hepatotoxic in high doses. Dosage adjustments should be considered in the face of renal or hepatic impairment. Chemical Synthesis Mercaptopurine, 6-purinthiol, is made from uric acid (30.1.2.5), which is synthesized from barbituric acid (30.1.2.1). Barbituric acid (30.1.2.1) is easily made by condensing urea with malonic ester and then nitrosylating it with nitrous acid. The nitrosoderivative (30.1.2.2) is reduced by hydrogen (obtained in situ by reacting tin with hydrochloric acid) to an amine (uramil) (30.1.2.3), and then reacted with isocyanic acid, which forms pseudouric acid (30.1.2.4). This undergoes cyclization to uric acid (30.1.2.5) when heated in the presence of hydrochloric acid. Upon reacting phosphorous pentachloride with uric acid, 2,6,8-trichloropurine (30.1.2.6) is formed. The three chlorine atoms in trichloropurine differ significantly in terms of reactivity for nucleophilic substitution. The chlorine atom at C6 is much more active than the chlorine atom at C2, and this is more active than the chlorine atom at C8, which allows subsequent manipulation by them. Interaction of 2,6,8-trichloropurine (30.1.2.6) with sodium hydroxide allows to replace the chlorine atom at C6, forming the dichloro-derivative (30.1.2.7), which is then reduced by hydriodic acid to hypoxanthine (30.1.2.8). Upon reaction with phosphorous pentasulfide, hypoxanthine is transformed into mercaptopurine (30.1.2.9). 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. Metabolism It is available in an oral dosage form, but absorption can be erratic and is reduced by the presence of food. The drug is extensively metabolized on first pass and excreted by the kidneys. Purification Methods Crystallise 6-mercaptopurine from pyridine (30mL/g), wash it with pyridine, then triturate with water (25mL/g) and adjust to pH 5 by adding M HCl. Recrystallise it by heating, then cooling, the solution. Filter off the solid, wash it with water and dry it at 110o. It has also been crystallised from water (charcoal) as yellow crystals of the monohydrate which become anhydrous on drying at 140o. It has UV: at 230 and 312nm ( 14,000 and 19,600) in 0.1N NaOH; 222 and 327nm ( 9,2400 max and 21,300), and 216 and 329nm ( 8,740 and 19,300) in MeOH. It forms a 1:1 complex with Zn2+ , Pb2+ , Co2+, and Ni2+ in aqueous dioxan. It is an antineoplastic. [Albert & Brown J Chem Soc 2060 1954, IR: Brown & Mason J Chem Soc 682 1957, UV: Fox et al. J Am Chem Soc 80 1669 1958, UV: Mason J Chem Soc 2071 1954, Beilstein 26 III/IV 2097.]