06563

Methotrexate hydrate

≥99.0% (sum of enantiomers, HPLC)

• Synonym(s): 4-Amino-10-methylfolic acid hydrate, L-4-Amino-N¹⁰-methylpteroylglutamic acid hydrate, L-Amethopterin hydrate, Antifolan hydrate, MTX hydrate, Methylaminopterin hydrate
• Empirical Formula (Hill Notation): C₂₀H₂₂N₈O₅ · xH₂O
• CAS Number: 133073-73-1
• Molecular Weight: 454.44 (anhydrous basis)
• EC Number: 200-413-8
• MDL number: MFCD00150847
• UNSPSC Code: 12352202
• PubChem Substance ID: 329748247
• NACRES: NA.77

Properties

• biological source: synthetic
• Assay: ≥99.0% (sum of enantiomers, HPLC)
• form: powder or crystals
• optical activity: [α]/D +21.0±2.0°
• impurities: ≤0.1% sulfated ash
• mp: 185-204 °C
• solubility: water: insoluble
• storage temp.: −20°C
• SMILES string: [H]O[H].CN(Cc1cnc2nc(N)nc(N)c2n1)c3ccc(cc3)C(=O)N[C@@H](CCC(O)=O)C(O)=O
• InChI: 1S/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
• InChI key: FPJYMUQSRFJSEW-ZOWNYOTGSA-N
• Gene Information: human ... DHFR(1719)

Description

General description

Methotrexateis an analog of folate. It shows anti-inflammatory effects throughseveral cellular mechanisms. The inhibition of dihydrofolate reductase reducesthe de novo synthesis of pyrimidines and purines, transmetylation ofphospholipids and proteins, and formation of polyamines.

Application

Methotrexatehydrate has been used as a disease modifyinganti-rheumatic drug (DMARD) to study its effects on Ross River virus disease (RRVD) in mice models.

Potent inhibitor of dihydrofolate reductase and agent for antitumor studies. Use to inhibit dihydrofolate reductase in DHFR-based protein expression systems. Also effective in treatment of pyrimethamine-resistant Plasmodium vivax malaria parasites.

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.

Other Notes

Folic acid antagonist. Potent inhibitor of dihydrofolate reductase.

Safety Information

• Pictograms: GHS06,GHS08
• Signal Word: Danger
• Hazard Statements: H301,H341,H360D,H372
• Precautionary Statements: P202 - P260 - P264 - P280 - P301 + P310 - P405
• Hazard Classifications: Acute Tox. 3 Oral - Muta. 2 - Repr. 1B - STOT RE 1
• Target Organs: Liver,Bone marrow
• Storage Class Code: 6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects
• WGK: WGK 3
• Flash Point(F): Not applicable
• Flash Point(C): Not applicable
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves