133073-73-1

Basic information

• Product Name: METHOTREXATE HYDRATE
• Synonyms: (+)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;L-AMETHOPTERIN HYDRATE
• CAS NO: 133073-73-1
• Molecular Formula: C20H22N8O5
• Molecular Weight: 454.44
• EINECS: 200-413-8
• Mol File: 133073-73-1.mol

Chemical Properties

• Melting Point: 195 °C
• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Appearance: yellow/powder
• Density: 1.536g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Storage Temp.: −20°C
• Solubility: H2O: insoluble
• 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.
• CAS DataBase Reference: METHOTREXATE HYDRATE(CAS DataBase Reference)
• NIST Chemistry Reference: METHOTREXATE HYDRATE(133073-73-1)
• EPA Substance Registry System: METHOTREXATE HYDRATE(133073-73-1)

Safety Data

• Hazard Codes: T
• 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
• Hazardous Substances Data: 133073-73-1(Hazardous Substances Data)

Usage

Uses

Used in Anticancer Applications:
Methotrexate Hydrate is used as an antitumor agent for inhibiting dihydrofolate reductase in DHFR-based protein expression systems. It is particularly effective in the treatment of various cancers due to its ability to block cell proliferation.
Used in Autoimmune Disease Treatment:
Methotrexate Hydrate is used as an immunosuppressant for the treatment of autoimmune diseases such as rheumatoid arthritis. It is considered the gold standard of disease-modifying antirheumatic drug (DMARD) therapy, addressing both the immune-inflammatory and joint destructive processes of the condition.
Used in Ectopic Pregnancy and Medical Abortion Induction:
Methotrexate Hydrate is utilized in the management of ectopic pregnancies and for the induction of medical abortions, leveraging its effects on cell proliferation and immune modulation.
Used in Cell Culture and Assays:
Methotrexate Hydrate is used as a dihydrofolate (DHFR) inhibitor in sphere-forming assay cultures and as a component of Dulbecco's modified Eagle's medium (DMEM) for the selection of transfected cells in viability and co-culture assays. This application aids researchers in studying cell behavior and the effects of various treatments on cell growth and differentiation.

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

InChI:InChI=1/C20H22N8O5.H2O/c1-28(9-11-8-23-17-15(24-11)16(21)26-20(22)27-17)12-4-2-10(3-5-12)18(31)25-13(19(32)33)6-7-14(29)30;/h2-5,8,13H,6-7,9H2,1H3,(H,25,31)(H,29,30)(H,32,33)(H4,21,22,23,26,27);1H2/t13-;/m0./s1