1,7-Dihydro-6H-Purine-6-Thionemonohydrate
6-mercaptopurine monohydrate
CAS: 6112-76-1
Molecular Formula: C5H6N4OS
1,7-Dihydro-6H-Purine-6-Thionemonohydrate - Names and Identifiers
1,7-Dihydro-6H-Purine-6-Thionemonohydrate - Physico-chemical Properties
| Molecular Formula | C5H6N4OS |
| Molar Mass | 170.19 |
| Melting Point | >300°C(lit.) |
| Boling Point | 490.6°C at 760 mmHg |
| Flash Point | 250.5°C |
| Water Solubility | INSOLUBLE |
| Solubility | Soluble in hot ethanol and slowly decompose in alkaline solution. Insoluble in water, acetone and ether. |
| Vapor Presure | 2.72E-09mmHg at 25°C |
| Appearance | Slightly yellow crystalline powder or yellow prismatic crystal |
| Color | Yellow |
| Merck | 14,5871 |
| BRN | 4012091 |
| Storage Condition | 2-8°C |
| Stability | Stable. Incompatible with strong oxidizing agents, acids, strong bases. Light sensitive. |
| MDL | MFCD03854445 |
| Physical and Chemical Properties | Monohydrate is a yellowish crystalline powder. Melting point 312-314 ℃, soluble in alkaline solution, slightly soluble in hot water, insoluble in water, acetone, ether. |
| Use | This product is for scientific research only and shall not be used for other purposes. |
| In vitro study | Mercaptopurine is widely used in the treatment of malignant tumors, rheumatic diseases, skin diseases, inflammatory bowel diseases, and solid organ transplant rejection. Mercaptopurine inhibits purine nucleotide synthesis and metabolism by inhibiting Phosphoribosyl pyrophosphate amidotransferase (PRPP amidotransferase). PRPP amidotransferase is the rate-limiting enzyme of purine and formation. It alters the synthesis and function of RNA and DNA. Mercaptopurine also interferes with nucleoside interconversion and glycoprotein synthesis. |
1,7-Dihydro-6H-Purine-6-Thionemonohydrate - Risk and Safety
| Risk Codes | R22 - Harmful if swallowed R36/37/38 - Irritating to eyes, respiratory system and skin. R63 - Possible risk of harm to the unborn child R20/21/22 - Harmful by inhalation, in contact with skin and if swallowed. |
| Safety Description | S22 - Do not breathe dust. S36/37/39 - Wear suitable protective clothing, gloves and eye/face protection. S45 - In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.) S36/37 - Wear suitable protective clothing and gloves. |
| UN IDs | UN 2811 6.1 / PGIII |
| WGK Germany | 3 |
| RTECS | UP0400000 |
| HS Code | 29335995 |
1,7-Dihydro-6H-Purine-6-Thionemonohydrate - Introduction
This product is a cell cycle specific drug that inhibits the purine synthesis pathway. Its chemical structure is similar to hypoxanthine, so it can competitively inhibit the transformation process of hypoxanthine. This product enters the body, and it must be converted from phosphoribosyltransferase to 6-mercaptopurine ribonucleotide in the cell to be active. Its main action links are:(1) Inhibition of amidotransferase through negative feedback, thus preventing the conversion of 1-pyrophosphate -5-phosphate ribose (PRPP) to 1-amino -5-phosphate ribose (PRA) The process interferes with the initial stage of purine nucleotide synthesis. (2) Inhibit the mutual transformation between complex purines, that is, it can inhibit the process of converting hypoxanthine nucleotides into adenine nucleotides and hypoxanthine nucleotides into xanthine nucleotides and guanine nucleotides. At the same time, this product also inhibits the synthesis of coenzyme I(NAD), and reduces the deoxyadenosine triphosphate (dATP) and deoxyguanosine triphosphate (dGTP) necessary for the biosynthesis of DNA, so tumor cells cannot proliferate, this product is sensitive to cells in the S proliferation cycle. In addition to inhibiting the synthesis of cell DNA, it also has a slight inhibitory effect on the synthesis of cell RNA.
Last Update：2022-10-16 17:27:05
1,7-Dihydro-6H-Purine-6-Thionemonohydrate - Reference Information
| EPA chemical substance information | information provided by: ofmpeb.epa.gov (external link) |
| Introduction | Mercaptopurine, mercaptopurine or mercaptopurine) is a thiopurine class of chemotherapy drugs and immunosuppressants. |
| indication | Mercaptopurine is mainly used for the maintenance treatment of acute leukemia (including acute myeloid leukemia and acute lymphoblastic leukemia), it is also used to treat malignant mole, choriocarcinoma, polycythemia, psoriatic arthritis, and inflammatory bowel disease (such as Crohn's disease and ulcerative colitis). Studies have shown that mercaptopurine has activity against Mycobacterium paratrachosis in vitro. |
| mechanism of action | Mercaptopurine is a purine analog belonging to the class of purine antagonist antimetabolites. It can inhibit the amide transferase, thereby interfering with purine nucleotide synthesis; Can inhibit hypoxanthine nucleotides into adenine nucleotides and hypoxanthine nucleotides into xanthine nucleotides, guanine nucleotides process; it can also inhibit the synthesis of nicotinamide adenine dinucleotide (NAD) and cause a decrease in the levels of deoxyadenosine triphosphate (dATP) and deoxyguanosine triphosphate (dGTP). This enables mercaptopurine to effectively inhibit the synthesis of DNA, thereby inhibiting the growth of tumor cells. |
| biological activity | 6-Mercaptopurine (6-MP) Monohydrate is a widely used anti-leukemia agent and immunosuppressive drug, de novo synthesis of purines can be inhibited by integration of thiopurine methyltransferase metabolites into DNA and RNA. |
| uses | intermediates of 6-mercaptopurine, oncolytic methotrexate, and azathioprine can be used as antitumor drugs. An immunosuppresive drug used to treat leukemia. It is also used for pediatric non-Hodgkin |
| production method | available from 7-aminothiazolo [5,4-d] pyrimidine, or from 6-hydroxy purine with phosphorus sulfide by substitution. |
Last Update：2024-04-10 22:29:15
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