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| METHOTREXATE HYDRATE Basic information |
| Product Name: | METHOTREXATE HYDRATE | | Synonyms: | L-Glutamic acid,N-[4-[[(2,4-diamino-6-pteridinyl)methyl]methylamino]benzoyl]-, hydrate (9CI);(+)AMETHOPTERINE HYDRATE;(+)-AMETHOPTERIN HYDRATE;4-AMINO-10-METHYLFOLIC ACID HYDRATE;METHYLAMINOPTERIN HYDRATE;METHOTREXATE HYDRATE;L-4-AMINO-N10-METHYLPTEROYL-GLUTAMIC ACID HYDRATE;L-(+)-AMETHOPTERIN HYDRATE | | CAS: | 133073-73-1 | | MF: | C20H24N8O6 | | MW: | 472.46 | | EINECS: | 625-397-3 | | Product Categories: | | Mol File: | 133073-73-1.mol |
| METHOTREXATE HYDRATE Chemical Properties |
| Melting point | 195 °C | | storage temp. | -20°C | | solubility | H2O: insoluble | | form | powder | | color | yellow | | optical activity | [α]/D +21.0±2.0° | | Stability: | Stable for 2 years from date of purchase as supplied. Solutions in DMSO may be stored at -20°C for up to 3 months. | | InChIKey | FBOZXECLQNJBKD-ZDUSSCGKSA-N |
| METHOTREXATE HYDRATE Usage And Synthesis |
| Description | Methotrexate (MTX) is similar in structure to folic acid and aminopterin . It acts by inhibiting the metabolism of folic acid and blocking key enzymes in the synthesis of purines and pyrimidines required for cell proliferation. MTX is known to induce adenosine release, which mediates many of its anti-inflammatory effects, including the reduction of proinflammatory cytokines. Formulations containing MTX have been used as immunosuppressants, in the treatment of cancer, autoimmune disease, ectopic pregnancy, and for the induction of medical abortions. MTX formulations have been considered the gold standard of disease-modifying antirheumatic drug (DMARD) therapy to treat both the immune-inflammatory and joint destructive processes of rheumatoid arthritis. | | Chemical Properties | yellow to orange crystalline powder | | Uses | Potent inhibitor of dihydrofolate reductase and agent for antitumor studies. Use to inhibit dihydrofolate reductase in DHFR-based protein expression systems. Also shows immunosuppressive effects in, e.g., rheumatoid arthritis. | | Uses | Methotrexate hydrate has been used:- as a dihydrofolate (DHFR)?inhibitor in sphere forming assay culture
- as a component of dulbecco′ modified Eagle′s medium (DMEM) for selection of transfected cells
- in viability and co-culture assays
| | Biochem/physiol Actions | Methotrexate is an allosteric inhibititor of dihydrofolate reductase (DHFR), the enzyme that catalyzes the conversion of dihydrofolate to tetrahydrofolate. Since tetrahydrolfolate is required for purine and pyrimidine synthesis, methotrexate treatment results in the inhibition of DNA and RNA synthesis. | | References | Wessels et al. (2008), Recent insights in the pharmacological actions of methotrexate in the treatment of rheumatoid arthritis; Rheumatology (Oxford), 47 249
Allegra et al. (1987), Evidence for direct inhibition of de novo purine synthesis in human MCF-7 breast cells as a principal mode of metabolic inhibition by methotrexate; Biol. Chem., 262 13520
Chu et al. (1990), Mechanism of thymidylate synthase inhibition by methotrexate in human neoplastic cell lines and normal human myeloid progenitor cells; Biol. Chem., 265 8470
Gerards et al. (2003), Inhibition of cytokine production by methotrexate. Studies in healthy volunteers and patients with rheumatoid arthritis; Rheumatology (Oxford), 42 1189
Friedman and Cronstein (2019), Methotrexate mechanism in treatment of rheumatoid arthritis; Joint Bone Spine, 86 301
Smolen and Steiner (2003), Therapeutic strategies for rheumatoid arthritis; Rev. Drug Discov., 2 473 |
| METHOTREXATE HYDRATE Preparation Products And Raw materials |
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