M9929

Methotrexate

meets USP testing specifications

• Synonym(s): Methotrexate hydrate, 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)
• MDL number: MFCD00150847
• UNSPSC Code: 12352005
• PubChem Substance ID: 24897373
• NACRES: NA.21

Properties

• biological source: synthetic
• Quality Level: 400
• Agency: USP/NF; meets USP testing specifications
• Assay: 98.0-102.0%
• form: powder
• storage condition: (Tightly closed. Dry. Keep in a well-ventilated place. )
• technique(s): activity assay: suitable; cell based assay: suitable
• impurities: ≤0.1% Residue on ignition (Ash); ≤12.0% water (Karl Fischer)
• color: yellow to orange-yellow
• mp: 185-204 °C (365 - 399 °F)
• solubility: water: insoluble
• antibiotic activity spectrum: parasites
• application(s): advanced drug delivery; metabolomics; microbiology
• Mode of action: DNA synthesis
• 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) , DHFRP1(573971) , FPGS(2356) , SLC19A1(6573) , TYMS(7298) ; mouse ... Dhfr(13361) ; rat ... Dhfr(24312)

Description

Application

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.

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.

Other Notes

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Safety Information

• Pictograms: GHS06,GHS08
• Signal Word: Danger
• Hazard Statements: H301,H315,H319,H360FD
• Precautionary Statements: P202 - P264 - P280 - P301 + P310 - P302 + P352 - P305 + P351 + P338
• Hazard Classifications: Acute Tox. 3 Oral - Eye Irrit. 2 - Repr. 1B - Skin Irrit. 2
• 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