An internal standard for the quantification of methotrexate
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Unlabeled Version(s)
13960Methotrexate (hydrate)
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Methotrexate-d3

Item No. 22378

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
N-[4-[[(2,4-diamino-6-pteridinyl)methyl]methyl-d3-amino]benzoyl]-L-glutamic acid
CAS Number
432545-63-6
Synonyms
  • Amethopterin-d3
  • MTX-d3
Molecular Formula
C20H19D3N8O5
Formula Weight
457.5
Purity
≥99% deuterated forms (d1-d3)
Formulation
A solid
Solubility(Learn about Variance in Solubility)
DMF: 14 mg/mlDMSO: 3 mg/mlPBS (pH 7.2): 1 mg/ml
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([2H])([2H])[2H])=N2)=N1
InChi Code
InChI=1S/C20H22N8O5/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)/t13-/m0/s1/i1D3
InChi Key
FBOZXECLQNJBKD-FUPFOCIHSA-N
Shipping & Storage Information
Storage
4°C
Shipping
Room temperature in continental US; may vary elsewhere
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    500 µg

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    Product Description

    Methotrexate-d3 is intended for use as an internal standard for the quantification of MTX (Item No. 13960) by GC- or LC-MS. 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 in the treatment of cancer, autoimmune diseases, ectopic pregnancy, and for the induction of medical abortions. MTX formulations are 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).