A folic acid and aminopterin derivative
Technical Support & Resources

Visit our FAQ

Contact Us

Toll Free Phone (USA and Canada Only): (888) 526-5351
Direct Phone: (734) 975-3888

Request Technical Support

Technical Support Request

To streamline the process attach the appropriate questionnaire to your inquiry.

Download IHC QuestionnaireDownload WB Questionnaire

View Our Privacy Statement for details on how we use and protect your data. In addition, this site is protected by hCaptcha and its Privacy Policy and Terms of Service apply.

Methotrexate (hydrate)

Item No. 13960

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
N-[4-[[(2,4-diamino-6-pteridinyl)methyl]methylamino]benzoyl]-L-glutamic acid, hydrate
CAS Number
133073-73-1
Synonyms
  • Amethopterin
  • CL 14,377
  • EMT 25299
  • MTX
  • NSC 740
  • R 9985
Molecular Formula
C20H22N8O5 • XH2O
Formula Weight
454.4
Purity
≥98%
Formulation
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 14 mg/mlDMSO: 3 mg/mlPBS (pH 7.2): 1 mg/ml
λmax
262, 299, 377 nm
SMILES
NC1=NC(N)=C2C(N=CC(CN(C3=CC=C(C(N[C@H](C(O)=O)CCC(O)=O)=O)C=C3)C)=N2)=N1.O
InChi Code
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
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
Recommended Products

Certificates of Analysis & Batch Specific Data

Provide batch numbers separated by commas to download or request available product inserts, QC sheets, certificates of analysis, data packs, and GC-MS data.

Download most recent Certificate of Analysis for this product

    50 mg

    $28

    Add

    100 mg

    $53

    Add

    250 mg

    $104

    Add

    500 mg

    $165

    Add
    Cayman Chemical
    Visit Our Cancer Resource Center
    Find Tools & Resources to Study the Hallmarks of Cancer
    • Cancer cell signaling & regulation
    • Cancer metabolism
    • Tumor microenvironment
    EXPLORE NOW
    Product Description

    Methotrexate (MTX) is similar in structure to folic acid (Item No. 20515) and aminopterin (Item No. 21802). It acts by inhibiting the metabolism of folic acid and blocking key enzymes in the synthesis of purines and pyrimidines required for cell proliferation.1,2 MTX is known to induce adenosine release, which mediates many of its anti-inflammatory effects, including the reduction of proinflammatory cytokines.2,3,4 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.5

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Tian, H., and Cronstein, B.N. Understanding the mechanisms of action of methotrexate: Implications for the treatment of rheumatoid arthritis. Bull. NYU Hosp. Jt. Dis. 65(3), 168-173 (2007).

    2. Swierkot, J., and Szechinski, J. Methotrexate in rheumatoid arthritis. Pharmacol. Rep. 58(4), 473-492 (2006).

    3. Chan, E.S.L., and Cronstein, B.N. Molecular action of methotrexate in inflammatory diseases. Arthritis Res. 4(4), 266-273 (2002).

    4. Wessels, J.A.M., Huizinga, T.W.J., and Guchelaar, H.-J. Recent insights in the pharmacological actions of methotrexate in the treatment of rheumatoid arthritis. Rheumatology (Oxford) 47(3), 249-255 (2008).

    5. Smolen, J.S., and Steiner, G. Therapeutic strategies for rheumatoid arthritis. Nat. Rev. Drug Dis. 2(6), 473-488 (2003).

    Product Citations

    Kremer, D.M., Nelson, B.S., Lin, L., et al. GOT1 inhibition primes pancreatic cancer for ferroptosis through the autophagic release of labile iron. bioRxiv (2020).