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HomeProduct name listMETHOTREXATE HYDRATE

METHOTREXATE HYDRATE

Synonym(s):L-4-Amino-N10-methylpteroylglutamic acid hydrate;L-Amethopterin hydrate;4-Amino-10-methylfolic acid hydrate;Antifolan hydrate;Methylaminopterin hydrate

  • CAS NO.:133073-73-1
  • Empirical Formula: C20H24N8O6
  • Molecular Weight: 472.46
  • MDL number: MFCD00150847
  • EINECS: 625-397-3
  • SAFETY DATA SHEET (SDS)
  • Update Date: 2023-06-08 09:02:12
METHOTREXATE HYDRATE Structural

What is METHOTREXATE HYDRATE?

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

The Uses of METHOTREXATE HYDRATE

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

The Uses of METHOTREXATE HYDRATE

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.

What are the applications of Application

Methotrexate hydrate is a cell cycle arrest agent that inhibits DHFR and modulates inflammation

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

Properties of METHOTREXATE HYDRATE

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.

Safety information for METHOTREXATE HYDRATE

Signal word Danger
Pictogram(s)
ghs
Skull and Crossbones
Acute Toxicity
GHS06
ghs
Health Hazard
GHS08
GHS Hazard Statements H301:Acute toxicity,oral
H315:Skin corrosion/irritation
H319:Serious eye damage/eye irritation
Precautionary Statement Codes P201:Obtain special instructions before use.
P202:Do not handle until all safety precautions have been read and understood.
P264:Wash hands thoroughly after handling.
P264:Wash skin thouroughly after handling.
P301+P310:IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P302+P352:IF ON SKIN: wash with plenty of soap and water.
P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

Computed Descriptors for METHOTREXATE HYDRATE

InChIKey FBOZXECLQNJBKD-ZDUSSCGKSA-N

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