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MedKoo Cat#: 100610 | Name: Methotrexate
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Description:

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

Methotrexate is an antimetabolite and antifolate agent with antineoplastic and immunosuppressant activities. Methotrexate binds to and inhibits the enzyme dihydrofolate reductase, resulting in inhibition of purine nucleotide and thymidylate synthesis and, subsequently, inhibition of DNA and RNA syntheses. Methotrexate also exhibits potent immunosuppressant activity although the mechanism(s) of actions is unclear.

Chemical Structure

Methotrexate
Methotrexate
CAS#59-05-2 (free acid)

Theoretical Analysis

MedKoo Cat#: 100610

Name: Methotrexate

CAS#: 59-05-2 (free acid)

Chemical Formula: C20H22N8O5

Exact Mass: 454.1713

Molecular Weight: 454.44

Elemental Analysis: C, 52.86; H, 4.88; N, 24.66; O, 17.60

Price and Availability

Size Price Availability Quantity
100mg USD 90.00 Ready to ship
1g USD 150.00 Ready to ship
2g USD 250.00 Ready to ship
5g USD 550.00 Ready to ship
10g USD 950.00 Ready to ship
20g USD 1,450.00 Ready to ship
50g USD 1,950.00 Ready to ship
100g USD 2,950.00 Ready to ship
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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
CL14377; CL-14377; CL 14377; WR19039; WR-19039; WR 19039; MTX; Methotrexate; alphamethopterin; amethopterin; methylaminopterin.
IUPAC/Chemical Name
(S)-2-(4-(((2,4-diaminopteridin-6-yl)methyl)(methyl)amino)benzamido)pentanedioic acid.
InChi Key
FBOZXECLQNJBKD-ZDUSSCGKSA-N
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
SMILES Code
O=C(O)[C@@H](NC(C1=CC=C(N(CC2=NC3=C(N)N=C(N)N=C3N=C2)C)C=C1)=O)CCC(O)=O
Appearance
Yellow to orange crystalline 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, DMF, and PBS
Shelf Life
>2 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
2934.99.9001
More Info
 
Biological target:
Methotrexate is a nonspecific inhibitor of the dihydrofolate reductase(DHFR) of bacteria and cancerous cells as well as normal cells. It forms an inactive ternary complex with DHFR and NADPH. Methotrexate (MTX) induces apoptosis.
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
Soluble in DMSO, DMF, and PBS 90.0 198.05
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 454.44 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: Hope HF, Bluett J, Barton A, Hyrich KL, Cordingley L, Verstappen SM. Psychological factors predict adherence to methotrexate in rheumatoid arthritis; findings from a systematic review of rates, predictors and associations with patient-reported and clinical outcomes. RMD Open. 2016 Jan 20;2(1):e000171. doi: 10.1136/rmdopen-2015-000171. eCollection 2016. Review. PubMed PMID: 26848403; PubMed Central PMCID: PMC4731843. 2: Li D, Yang Z, Kang P, Xie X. Subcutaneous administration of methotrexate at high doses makes a better performance in the treatment of rheumatoid arthritis compared with oral administration of methotrexate: A systematic review and meta-analysis. Semin Arthritis Rheum. 2015 Dec 1. pii: S0049-0172(15)00282-6. doi: 10.1016/j.semarthrit.2015.11.004. [Epub ahead of print] Review. PubMed PMID: 26686022. 3: Hess JA, Khasawneh MK. Cancer metabolism and oxidative stress: Insights into carcinogenesis and chemotherapy via the non-dihydrofolate reductase effects of methotrexate. BBA Clin. 2015 Feb 7;3:152-61. doi: 10.1016/j.bbacli.2015.01.006. eCollection 2015 Jun. Review. PubMed PMID: 26674389; PubMed Central PMCID: PMC4661551. 4: Scherkenbach LA, Stumpf JL. Methotrexate for the Management of Crohn's Disease in Children. Ann Pharmacother. 2016 Jan;50(1):60-9. doi: 10.1177/1060028015613527. Epub 2015 Oct 27. Review. PubMed PMID: 26511908. 5: Pincus T, Bergman MJ, Yazici Y. Limitations of clinical trials in chronic diseases: is the efficacy of methotrexate (MTX) underestimated in polyarticular psoriatic arthritis on the basis of limitations of clinical trials more than on limitations of MTX, as was seen in rheumatoid arthritis? Clin Exp Rheumatol. 2015 Sep-Oct;33(5 Suppl 93):S82-93. Epub 2015 Oct 15. Review. PubMed PMID: 26472658. 6: Ianculescu I, Weisman MH. The role of methotrexate in psoriatic arthritis: what is the evidence? Clin Exp Rheumatol. 2015 Sep-Oct;33(5 Suppl 93):S94-7. Epub 2015 Oct 15. Review. PubMed PMID: 26470718. 7: Chen XM, Huang RY, Huang QC, Chu YL, Yan JY. Systemic Review and Meta-Analysis of the Clinical Efficacy and Adverse Effects of Zhengqing Fengtongning Combined with Methotrexate in Rheumatoid Arthritis. Evid Based Complement Alternat Med. 2015;2015:910376. doi: 10.1155/2015/910376. Epub 2015 Aug 24. Review. PubMed PMID: 26379753; PubMed Central PMCID: PMC4561327. 8: Sheĭkh ZhV, Krutskevich AO, Drebushevskiĭ NS, Shvaĭko SN, Dunaev AP, Alekseev VG. [Pulmonary cytotoxicity induced by bleomycin and methotrexate]. Vestn Rentgenol Radiol. 2015 May-Jun;(3):46-51. Review. Russian. PubMed PMID: 26302622. 9: Wang Y, MacDonald JK, Vandermeer B, Griffiths AM, El-Matary W. Methotrexate for maintenance of remission in ulcerative colitis. Cochrane Database Syst Rev. 2015 Aug 11;8:CD007560. doi: 10.1002/14651858.CD007560.pub3. Review. PubMed PMID: 26263042. 10: Bateman DN, Page CB. Antidotes to coumarins, isoniazid, methotrexate and thyroxine, toxins that work via metabolic processes. Br J Clin Pharmacol. 2015 Aug 9. doi: 10.1111/bcp.12736. [Epub ahead of print] Review. PubMed PMID: 26255881. 11: Evrard J, Farnier E, Carcel C, Lachenal F, Vial T, Pont E. [Proton Pump Inhibitor and High-dose Methotrexate: Two Cases Reports]. Therapie. 2015 Nov-Dec;70(6):527-35. doi: 10.2515/therapie/2015047. Epub 2015 Aug 4. Review. French. PubMed PMID: 26242498. 12: Capmas P, Fernandez H. Effectiveness of gefitinib in combination with methotrexate in the treatment of ectopic pregnancy. Int J Womens Health. 2015 Jul 3;7:673-6. doi: 10.2147/IJWH.S55556. eCollection 2015. Review. PubMed PMID: 26170723; PubMed Central PMCID: PMC4498725. 13: Scott M. Question 1: Role of methotrexate in severe atopic eczema in children. Arch Dis Child. 2015 Aug;100(8):803-6. doi: 10.1136/archdischild-2015-308917. Epub 2015 Jun 30. Review. PubMed PMID: 26130381. 14: 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. 15: Cheung VY. Local Methotrexate Injection as the First-line Treatment for Cesarean Scar Pregnancy: Review of the Literature. J Minim Invasive Gynecol. 2015 Jul-Aug;22(5):753-8. doi: 10.1016/j.jmig.2015.04.008. Epub 2015 Apr 15. Review. PubMed PMID: 25889882. 16: Park MJ. Prolonged response of meningeal carcinomatosis from non-small cell lung cancer to salvage intrathecal etoposide subsequent to failure of first-line methotrexate: a case report and literature review. Am J Case Rep. 2015 Apr 16;16:224-7. doi: 10.12659/AJCR.894061. Review. PubMed PMID: 25879815; PubMed Central PMCID: PMC4407681. 17: Pastore S, Stocco G, Favretto D, De Iudicibus S, Taddio A, d'Adamo P, Malusà N, Addobbati R, Decorti G, Lepore L, Ventura A. Genetic determinants for methotrexate response in juvenile idiopathic arthritis. Front Pharmacol. 2015 Mar 23;6:52. doi: 10.3389/fphar.2015.00052. eCollection 2015. Review. PubMed PMID: 25852556; PubMed Central PMCID: PMC4369651. 18: Yélamos O, Puig L. Systemic methotrexate for the treatment of psoriasis. Expert Rev Clin Immunol. 2015 May;11(5):553-63. doi: 10.1586/1744666X.2015.1026894. Epub 2015 Mar 16. Review. PubMed PMID: 25779551. 19: Conway R, Low C, Coughlan RJ, O'Donnell MJ, Carey JJ. Methotrexate use and risk of lung disease in psoriasis, psoriatic arthritis, and inflammatory bowel disease: systematic literature review and meta-analysis of randomised controlled trials. BMJ. 2015 Mar 13;350:h1269. doi: 10.1136/bmj.h1269. Review. PubMed PMID: 25770113; PubMed Central PMCID: PMC4358852. 20: Kaur S, Arora AK, Sekhon JS, Sood N. Nilotinib-induced psoriasis in a patient of chronic myeloid leukemia responding to methotrexate. Indian J Dermatol Venereol Leprol. 2015 Mar-Apr;81(2):216-8. doi: 10.4103/0378-6323.152311. Review. PubMed PMID: 25751356.