A metabolite of methotrexate
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Alternative(s)
332397-hydroxy Methotrexate
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7-hydroxy Methotrexate (sodium salt)

Item No. 21788

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
N-[4-[[(2,4-diamino-7,8-dihydro-7-oxo-6-pteridinyl)methyl]methylamino]benzoyl]-L-glutamic acid, trisodium salt
Synonyms
  • 7-hydroxy MTX
Molecular Formula
C20H19N8O6 • 3Na
Formula Weight
536.4
Purity
≥95%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
DMF: 14 mg/mlDMSO: 3 mg/mlPBS (pH 7.2): 1 mg/ml
SMILES
[O-]C(C(CN(C1=CC=C(C(N[C@@H](CCC([O-])=O)C([O-])=O)=O)C=C1)C)=N2)=NC3=C2C(N)=NC(N)=N3.[Na+].[Na+].[Na+]
InChi Code
InChI=1S/C20H22N8O6.3Na/c1-28(8-12-18(32)26-16-14(23-12)15(21)25-20(22)27-16)10-4-2-9(3-5-10)17(31)24-11(19(33)34)6-7-13(29)30;;;/h2-5,11H,6-8H2,1H3,(H,24,31)(H,29,30)(H,33,34)(H5,21,22,25,26,27,32);;;/q;3*+1/p-3/t11-;;;/m0.../s1
InChi Key
UGUJBPCBGFUHQR-XVSRHIFFSA-K
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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    1 mg

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    Product Description

    7-hydroxy Methotrexate (7-hydroxy MTX) is a phase I metabolite of MTX (Item No. 13960), which is converted by hepatic aldehyde oxidases.1 Elimination of 7-hydroxy MTX is associated with the multi-drug transporters Abcc2, Abcc3, and Abcg2 in transgenic mouse models. It and the parent compound rapidly accumulate when all three transporters are absent.2 Formulations containing methotrexate have been used in the treatment of cancer, autoimmune diseases, ectopic pregnancy, and for the induction of medical abortions.3,4 Various methods have been described to quantify 7-hydroxy MTX levels during cancer therapy to avoid toxicity.5,6

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Johns, D.G., Iannotti, A.T., Sartorelli, A.C., et al. The relative toxicites of methotrexate and aminopterin. Biochem. Pharmacol. 15(5), 555-561 (1966).

    2. Vlaming, M.L.H., van Esch, A., Pala, Z., et al. Abcc2 (Mrp2), Abcc3 (Mrp3), and Abcg2 (Bcrp1) are the main determinants for rapid elimination of methotrexate and its toxic metabolite 7-hydroxymethotrexate in vivo. Mol. Cancer. Ther. 8(12), 3350-3359 (2009).

    3. Cutolo, M., Sulli, A., Pizzorni, C., et al. Anti-inflammatory mechanisms of methotrexate in rheumatoid arthritis. Ann. Rheum. Dis. 60(8), 729-735 (2001).

    4. Christin-Maitre, S., Bouchard, P., and Spitz, I.M. Medical termination of pregnancy. N. Engl. J. Med. 342(13), 946-956 (2000).

    5. Schofield, R.C., Ramanathan, L.V., Murata, K., et al. Development of an assay for methotrexate and its metabolites 7-hydroxy methotrexate and DAMPA in serum by LC-MS/MS. Methods in Molecular Biology 213-222 (2016).

    6. Klapkova, E., Kukacka, J., Kotaska, K., et al. The influence of 7-OH methotrexate metabolite on clinical relevance of methotrexate determination. Clin. Lab. 57(7-8), 599-606 (2011).