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MedKoo Cat#: 597185 | Name: Methotrexate 1-methyl ester

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Methotrexate 1-methyl ester is an impurity of Methotrexate, a folic acid antagonist. Used as a antineoplastic and antirheumatic.

Chemical Structure

Methotrexate 1-methyl ester
Methotrexate 1-methyl ester
CAS#66147-29-3

Theoretical Analysis

MedKoo Cat#: 597185

Name: Methotrexate 1-methyl ester

CAS#: 66147-29-3

Chemical Formula: C21H24N8O5

Exact Mass: 468.1870

Molecular Weight: 468.47

Elemental Analysis: C, 53.84; H, 5.16; N, 23.92; O, 17.08

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Synonym
Methotrexate 1-methyl ester; Methotrexate alpha-methyl ester; Methotrexate related compound I;
IUPAC/Chemical Name
(S)-4-(4-(((2,4-diaminopteridin-6-yl)methyl)(methyl)amino)benzamido)-5-methoxy-5-oxopentanoic acid
InChi Key
JYFDQHNTJJOKAS-AWEZNQCLSA-N
InChi Code
InChI=1S/C21H24N8O5/c1-29(10-12-9-24-18-16(25-12)17(22)27-21(23)28-18)13-5-3-11(4-6-13)19(32)26-14(20(33)34-2)7-8-15(30)31/h3-6,9,14H,7-8,10H2,1-2H3,(H,26,32)(H,30,31)(H4,22,23,24,27,28)/t14-/m0/s1
SMILES Code
O=C(O)CC[C@@H](C(OC)=O)NC(C1=CC=C(N(CC2=NC3=C(N)N=C(N)N=C3N=C2)C)C=C1)=O
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>3 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.03.00
More Info
Product Data
Product Data
Instruction
View handling instruction
Biological target:
Methotrexate 1-methyl ester is an impurity of Methotrexate, a folic acid antagonist.
In vitro activity:
Methotrexate (0.1-10 mM) induces apoptosis of in vitro activated T cells from human peripheral blood. Methotrexate achieves clonal deletion of activated T cells in mixed lymphocyte reactions. Methotrexate can selectively delete activated peripheral blood T cells by a CD95-independent pathway. Methotrexate is taken up by cells via the reduced folate carrier and then is converted within the cells to polyglutamates. Methotrexate leads to diminished production of leukotriene B4 by neutrophils stimulated ex vivo. Methotrexate polyglutamates inhibit the enzyme aminoimidazolecarboxamidoadenosineribonucleotide (AICAR) transformylase more potently than the other enzymes involved in purine biosynthesis. Methotrexate is also known to suppress TNF activity by suppressing TNF-induced nuclear factor-κB activation in vitro, in part related to a reduction in the degradation and inactivation of an inhibitor of this factor, IκBα, and probably related to the release of adenosine. Methotrexate suppresses the production of both TNF and IFN-γ by T-cell-receptor-primed T lymphocytes from both healthy human donors and RA patients. Methotrexate treatment is associated with a significant decrease of TNF-α-positive CD4+ T cells, while the number of T cells expressing the anti-inflammatory cytokine IL-10 increased. Reference: J Clin Invest. 1998 Jul 15;102(2):322-8. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC508890/ Arthritis Res. 2002;4(4):266-73. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC128935/
In vivo activity:
Methotrexate reduces thymus and spleen indices of mice. Methotrexate markedly decreases white blood cells, thymic and splenic lymphocytes at dose greater than or equal to 5 mg/kg. However, there is a significant difference between the treatment plus control group and the model group (p<0.01). The combination of grape seed proanthocyanidins and Siberian ginseng eleutherosides obviously diminishes the effects of Methotrexate exposure on indices of thymus and spleens in mice Reference: Pharmacol Rep. 2006 Jul-Aug;58(4):473-92. http://if-pan.krakow.pl/pjp/pdf/2006/4_473.pdf

Preparing Stock Solutions

The following data is based on the product molecular weight 468.47 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
1. Karasik A, Váradi A, Szeri F. In vitro transport of methotrexate by Drosophila Multidrug Resistance-associated Protein. PLoS One. 2018 Oct 12;13(10):e0205657. doi: 10.1371/journal.pone.0205657. PMID: 30312334; PMCID: PMC6185855. 2. Yang J, Gao L, Yu P, Kosgey JC, Jia L, Fang Y, Xiong J, Zhang F. In vitro synergy of azole antifungals and methotrexate against Candida albicans. Life Sci. 2019 Oct 15;235:116827. doi: 10.1016/j.lfs.2019.116827. Epub 2019 Aug 31. PMID: 31479680. 3. Previtali V, Petrovic K, Peiró Cadahía J, Troelsen NS, Clausen MH. Auxiliary in vitro and in vivo biological evaluation of hydrogen peroxide sensitive prodrugs of methotrexate and aminopterin for the treatment of rheumatoid arthritis. Bioorg Med Chem. 2020 Jan 15;28(2):115247. doi: 10.1016/j.bmc.2019.115247. Epub 2019 Dec 6. PMID: 31843461. 4. Choi SJ, Oh JM, Chung HE, Hong SH, Kim IH, Choy JH. In vivo anticancer activity of methotrexate-loaded layered double hydroxide nanoparticles. Curr Pharm Des. 2013;19(41):7196-202. doi: 10.2174/138161281941131219123718. PMID: 23489199.
In vitro protocol:
1. Karasik A, Váradi A, Szeri F. In vitro transport of methotrexate by Drosophila Multidrug Resistance-associated Protein. PLoS One. 2018 Oct 12;13(10):e0205657. doi: 10.1371/journal.pone.0205657. PMID: 30312334; PMCID: PMC6185855. 2. Yang J, Gao L, Yu P, Kosgey JC, Jia L, Fang Y, Xiong J, Zhang F. In vitro synergy of azole antifungals and methotrexate against Candida albicans. Life Sci. 2019 Oct 15;235:116827. doi: 10.1016/j.lfs.2019.116827. Epub 2019 Aug 31. PMID: 31479680.
In vivo protocol:
1. Previtali V, Petrovic K, Peiró Cadahía J, Troelsen NS, Clausen MH. Auxiliary in vitro and in vivo biological evaluation of hydrogen peroxide sensitive prodrugs of methotrexate and aminopterin for the treatment of rheumatoid arthritis. Bioorg Med Chem. 2020 Jan 15;28(2):115247. doi: 10.1016/j.bmc.2019.115247. Epub 2019 Dec 6. PMID: 31843461. 2. Choi SJ, Oh JM, Chung HE, Hong SH, Kim IH, Choy JH. In vivo anticancer activity of methotrexate-loaded layered double hydroxide nanoparticles. Curr Pharm Des. 2013;19(41):7196-202. doi: 10.2174/138161281941131219123718. PMID: 23489199.
1: Henderson GB, Tsuji JM. Methotrexate efflux in L1210 cells. Kinetic and specificity properties of the efflux system sensitive to bromosulfophthalein and its possible identity with a system which mediates the efflux of 3',5'-cyclic AMP. J Biol Chem. 1987 Oct 5;262(28):13571-8. PubMed PMID: 2820975. 2: Gewirtz DA, Randolph JK, Jaramillo M. Induction of methotrexate release from rat hepatocytes in suspension by alpha-adrenergic agents: involvement of calcium and metabolic energy. Arch Biochem Biophys. 1985 Feb 15;237(1):237-43. PubMed PMID: 2578767.