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

Safety Information

Hazard Codes 

T

Risk Statements 

61-25-36/38-46

Safety Statements 

53-26-36/37-45-36

RIDADR 

UN 2811 6.1/PG 3

WGK Germany 

3

RTECS 

MA1225000

HS Code 

29339980

MSDS

• Language:English Provider:SigmaAldrich

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

Definition

ChEBI: Methotrexate hydrate is a member of folic acids.

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

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