Methotrexate disodium | CAS#7413-34-5 | antimetabolite

MedKoo Cat#: 558622 | Name: Methotrexate disodium

Featured

Description:

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

Methotrexate is an antineoplastic antimetabolite with immunosuppressant properties. It is an inhibitor of tetrahydrofoltae dehydrogenase and prevents the formation of tetrahydrofolate, necessary for synthesis of thymidylate, an essential component of DNA.

Chemical Structure

Methotrexate disodium

CAS#7413-34-5 (disodium)

Theoretical Analysis

MedKoo Cat#: 558622

Name: Methotrexate disodium

CAS#: 7413-34-5 (disodium)

Chemical Formula: C20H20N8Na2O5

Exact Mass: 0.0000

Molecular Weight: 498.41

Elemental Analysis: C, 48.20; H, 4.04; N, 22.48; Na, 9.23; O, 16.05

Price and Availability

Size	Price	Availability
100mg	USD 250.00	2 Weeks
500mg	USD 550.00	2 Weeks
1g	USD 850.00	2 Weeks

Bulk Inquiry

Buy Now

Add to Cart

Related CAS #

7413-34-5 (disodium) 7532-09-4 (monosodium) 15475-56-6 (sodium) 59-05-2 (free acid) 6745-93-3 (monohydrate) 133073-73-1 (hydrate)

Synonym

Methotrexate; Antifolan; Brimexate; Metrotex; Mexate;

IUPAC/Chemical Name

(4-(((2,4-diaminopteridin-6-yl)methyl)(methyl)amino)benzoyl)-L-glutamate disodium

InChi Key

DASQOOZCTWOQPA-GXKRWWSZSA-L

InChi Code

InChI=1S/C20H22N8O5.2Na/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);;/q;2*+1/p-2/t13-;;/m0../s1

SMILES Code

O=C([O-])CC[C@@H](C([O-])=O)NC(C1=CC=C(N(CC2=NC3=C(N)N=C(N)N=C3N=C2)C)C=C1)=O.[Na+].[Na+]

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 (Amethopterin) disodium, an antimetabolite and antifolate agent, inhibits the enzyme dihydrofolate reductase, thereby preventing the conversion of folic acid into tetrahydrofolate, and inhibiting DNA synthesis.

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

	Solvent	mg/mL	mM	comments
Solubility
	Water	74.5	149.48

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 498.41 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.

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:

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: Řiháček M, Pilatova K, Štěrba J, Pilný R, Valík D. [New Indings in Methotrexate Pharmacology - Diagnostic Possibilities and Impact on Clinical Care]. Klin Onkol. 2015;28(3):163-70. Review. Czech. PubMed PMID: 26062617. 2: Mohamed HJ, Sorich MJ, Kowalski SM, McKinnon R, Proudman SM, Cleland L, Wiese MD. The role and utility of measuring red blood cell methotrexate polyglutamate concentrations in inflammatory arthropathies--a systematic review. Eur J Clin Pharmacol. 2015 Apr;71(4):411-23. doi: 10.1007/s00228-015-1819-x. Epub 2015 Feb 18. Review. PubMed PMID: 25687918. 3: Widemann BC, Schwartz S, Jayaprakash N, Christensen R, Pui CH, Chauhan N, Daugherty C, King TR, Rush JE, Howard SC. Efficacy of glucarpidase (carboxypeptidase g2) in patients with acute kidney injury after high-dose methotrexate therapy. Pharmacotherapy. 2014 May;34(5):427-39. doi: 10.1002/phar.1360. Epub 2013 Oct 17. PubMed PMID: 24132809; PubMed Central PMCID: PMC3990659. 4: Nogueira E, Lager F, Le Roux D, Nogueira P, Freitas J, Charvet C, Renault G, Loureiro A, Almeida CR, Ohradanova-Repic A, Machacek C, Bernardes GJ, Moreira A, Stockinger H, Burnet M, Carmo AM, Gomes AC, Preto A, Bismuth G, Cavaco-Paulo A. Enhancing Methotrexate Tolerance with Folate Tagged Liposomes in Arthritic Mice. J Biomed Nanotechnol. 2015 Dec;11(12):2243-52. PubMed PMID: 26510317. 5: Reeves D, DiDominick S, Finn S, Kim HJ, Shake A. Methotrexate Elimination When Coadministered With Levetiracetam. Ann Pharmacother. 2016 Dec;50(12):1016-1022. Epub 2016 Aug 10. PubMed PMID: 27511814. 6: Korell J, Duffull SB, Dalrymple JM, Drake J, Zhang M, Barclay ML, Stamp LK. Comparison of intracellular methotrexate kinetics in red blood cells with the kinetics in other cell types. Br J Clin Pharmacol. 2014 Mar;77(3):493-7. doi: 10.1111/bcp.12209. PubMed PMID: 23844933; PubMed Central PMCID: PMC3952723. 7: Csordas K, Hegyi M, Eipel OT, Muller J, Erdelyi DJ, Kovacs GT. Comparison of pharmacokinetics and toxicity after high-dose methotrexate treatments in children with acute lymphoblastic leukemia. Anticancer Drugs. 2013 Feb;24(2):189-97. doi: 10.1097/CAD.0b013e32835b8662. PubMed PMID: 23187460. 8: Szczerkowska-Dobosz A. [Subcutaneous methotrexate in psoriasis and psoriatic arthritis treatment]. Wiad Lek. 2016;69(4):675-679. Review. Polish. PubMed PMID: 27941209. 9: Rodin I, Braun A, Stavrianidi A, Shpigun O. A validated LC-MS/MS method for rapid determination of methotrexate in human saliva and its application to an excretion evaluation study. J Chromatogr B Analyt Technol Biomed Life Sci. 2013 Oct 15;937:1-6. doi: 10.1016/j.jchromb.2013.07.026. Epub 2013 Aug 15. PubMed PMID: 24008118. 10: Klapkova E, Kukacka J, Kotaska K, Suchanska I, Urinovska R, Prusa R. The influence of 7-OH methotrexate metabolite on clinical relevance of methotrexate determination. Clin Lab. 2011;57(7-8):599-606. PubMed PMID: 21888024. 11: Bianchi G, Caporali R, Todoerti M, Mattana P. Methotrexate and Rheumatoid Arthritis: Current Evidence Regarding Subcutaneous Versus Oral Routes of Administration. Adv Ther. 2016 Mar;33(3):369-78. doi: 10.1007/s12325-016-0295-8. Epub 2016 Feb 4. Review. PubMed PMID: 26846283; PubMed Central PMCID: PMC4833794. 12: Bertram A, Ivanyi P, Hafer C, Matthias K, Peest D, Ganser A, Schmidt BM. High cut-off dialysis as a salvage therapy option in high-dose methotrexate chemotherapy? Ann Hematol. 2014 Jun;93(6):1053-5. doi: 10.1007/s00277-013-1909-8. Epub 2013 Oct 6. PubMed PMID: 24097083. 13: Kuleva SA. [Delayed elimination of methotrexate after high-dose infusion]. Vopr Onkol. 2013;59(1):126-31. Russian. PubMed PMID: 23814840. 14: Weekly oral methotrexate therapy: raise awareness of fatal dosing errors. Prescrire Int. 2013 May;22(138):126. PubMed PMID: 23819175. 15: Brandhonneur N, Noury F, Bruyère A, Saint-Jalmes H, Le Corre P. PBPK model of methotrexate in cerebrospinal fluid ventricles using a combined microdialysis and MRI acquisition. Eur J Pharm Biopharm. 2016 Jul;104:117-30. doi: 10.1016/j.ejpb.2016.04.012. Epub 2016 Apr 30. PubMed PMID: 27142258. 16: Bauters T, Lammens T, Belin P, Benoit Y, Robays H, de Moerloose B. Delayed elimination of methotrexate by cola beverages in a pediatric acute lymphoblastic leukemia population. Leuk Lymphoma. 2013 May;54(5):1094-6. doi: 10.3109/10428194.2012.737918. Epub 2012 Nov 15. PubMed PMID: 23061529. 17: Tamura R, Nakamura Y, Kuroshima Y. Arthrorheumatism with methotrexate-associated lymphoproliferative disorder in the brain. J Neurosurg Sci. 2016 Sep;60(3):400-401. PubMed PMID: 28097831. 18: Ganti V, Walker EA, Nagar S. Pharmacokinetic application of a bio-analytical LC-MS method developed for 5-fluorouracil and methotrexate in mouse plasma, brain and urine. Biomed Chromatogr. 2013 Aug;27(8):994-1002. doi: 10.1002/bmc.2893. Epub 2013 Mar 12. PubMed PMID: 23494628; PubMed Central PMCID: PMC4347818. 19: Singh VK, Subudhi BB. Development and characterization of lysine-methotrexate conjugate for enhanced brain delivery. Drug Deliv. 2016 Sep;23(7):2327-2337. Epub 2014 Dec 5. PubMed PMID: 25475953. 20: Woolf RT, West SL, Arenas-Hernandez M, Hare N, Peters van Ton AM, Lewis CM, Marinaki AM, Barker JN, Smith CH. Methotrexate polyglutamates as a marker of patient compliance and clinical response in psoriasis: a single-centre prospective study. Br J Dermatol. 2012 Jul;167(1):165-73. doi: 10.1111/j.1365-2133.2012.10881.x. PubMed PMID: 22309614.