A metabolite of methotrexate
Related Products
Alternative(s)
217887-hydroxy Methotrexate (sodium salt)
Parent Compound(s)
13960Methotrexate (hydrate)
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7-hydroxy Methotrexate

Item No. 33239

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
CAS Number
5939-37-7
Synonyms
  • NSC 380962
  • 7-hydroxy MTX
Molecular Formula
C20H22N8O6
Formula Weight
470.4
Purity
≥98%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
DMSO: slightly solubleEthanol: slightly soluble
λmax
266, 304, 354 nm
SMILES
NC1=C2C(NC(C(CN(C3=CC=C(C=C3)C(N[C@H](C(O)=O)CCC(O)=O)=O)C)=N2)=O)=NC(N)=N1
InChi Code
InChI=1S/C20H22N8O6/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)/t11-/m0/s1
InChi Key
HODZDDDNGRLGSI-NSHDSACASA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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    500 µg

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    Product Description

    7-hydroxy Methotrexate (7-hydroxy MTX) is the major metabolite of the folic acid derivative MTX (Item No. 13960).1 It is formed by the 7-oxidation of MTX by hepatic aldehyde oxidases. Unlike MTX, 7-hydroxy MTX does not inhibit thymidylate synthase in isolated human acute myeloid and acute lymphoblastic leukemia cells.2 7-hydroxy MTX has a maximum tolerated dose of 0.1 g/kg, which is 30- to 50-fold lower than MTX, in rats.3 Serum levels of 7-hydroxy MTX have been used as a marker of MTX toxicity during chemotherapy.4,5

    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. Lingg, R.M., Hempel, G., Rots, M.G., et al. Effects and interaction of 7-hydroxy methotrexate and methotrexate in leukaemic cells ex vivo measured by the thymidylate synthase inhibition assay. Cancer Chemother. Pharmacol. 56(3), 322-327 (2005).

    3. Fuskevåg, O.M., Kristiansen, C., Lindal, S., et al. Maximum tolerated doses of methotrexate and 7-hydroxy-methotrexate in a model of acute toxicity in rats. Cancer Chemother. Pharmacol. 46(1), 69-73 (2000).

    4. 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).

    5. 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).