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Merck
CN

M9929

Sigma-Aldrich

Methotrexate

meets USP testing specifications

Synonym(s):

Methotrexate hydrate, 4-Amino-10-methylfolic acid hydrate, L-4-Amino-N10-methylpteroylglutamic acid hydrate, L-Amethopterin hydrate, Antifolan hydrate, MTX hydrate, Methylaminopterin hydrate

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About This Item

Empirical Formula (Hill Notation):
C20H22N8O5 · xH2O
CAS Number:
133073-73-1
Molecular Weight:
454.44 (anhydrous basis)
MDL number:
MFCD00150847
UNSPSC Code:
12352005
PubChem Substance ID:
24897373
NACRES:
NA.21

Key Documents

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biological source

synthetic

Quality Level

400

Agency

USP/NF
meets USP testing specifications

Assay

98.0-102.0%

form

powder

storage condition

(Tightly closed. Dry. Keep in a well-ventilated place. )

technique(s)

activity assay: suitable

impurities

≤0.1% Residue on ignition (Ash)
≤12.0% water (Karl Fischer)

color

yellow to orange-yellow

mp

185-204 °C (365 - 399 °F)

solubility

water: insoluble

antibiotic activity spectrum

parasites

application(s)

metabolomics
microbiology

Mode of action

DNA synthesis

storage temp.

−20°C

SMILES string

[H]O[H].CN(Cc1cnc2nc(N)nc(N)c2n1)c3ccc(cc3)C(=O)N[C@@H](CCC(O)=O)C(O)=O

InChI

1S/C20H22N8O5.H2O/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);1H2/t13-;/m0./s1

InChI key

FPJYMUQSRFJSEW-ZOWNYOTGSA-N

Gene Information

human ... DHFR(1719), DHFRP1(573971), FPGS(2356), SLC19A1(6573), TYMS(7298)
mouse ... Dhfr(13361)
rat ... Dhfr(24312)

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Application

Potent inhibitor of dihydrofolate reductase and agent for antitumor studies. Use to inhibit dihydrofolate reductase in DHFR-based protein expression systems.
Potent inhibitor of dihydrofolate reductase and agent for antitumor studies. Use to inhibit dihydrofolate reductase in DHFR-based protein expression systems. Also effective in treatment of pyrimethamine-resistant Plasmodium vivax malaria parasites.
Potent inhibitor of dihydrofolate reductase and agent for antitumor studies. Use to inhibit dihydrofolate reductase in DHFR-based protein expression systems. Also shows immunosuppressive effects in, e.g., rheumatoid arthritis.

Biochem/physiol Actions

Methotrexate is an allosteric inhibititor of dihydrofolate reductase (DHFR), the enzyme that catalyzes the conversion of dihydrofolate to tetrahydrofolate. Since tetrahydrolfolate is required for purine and pyrimidine synthesis, methotrexate treatment results in the inhibition of DNA and RNA synthesis.

Other Notes

For additional information on our range of Biochemicals, please complete this form.

Pictograms

Skull and crossbonesHealth hazard
GHS06,GHS08

Signal Word

Danger

Hazard Statements

H301,H315,H319,H360FD

Hazard Classifications

Acute Tox. 3 Oral - Eye Irrit. 2 - Repr. 1B - Skin Irrit. 2

Storage Class Code

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
0000492902
0000492902
0000476090
0000476090
0000439794

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  1. Which document(s) contains shelf-life or expiration date information for a given product?

    If available for a given product, the recommended re-test date or the expiration date can be found on the Certificate of Analysis.

  2. How do I get lot-specific information or a Certificate of Analysis?

    The lot specific COA document can be found by entering the lot number above under the "Documents" section.

  3. How do I find price and availability?

    There are several ways to find pricing and availability for our products. Once you log onto our website, you will find the price and availability displayed on the product detail page. You can contact any of our Customer Sales and Service offices to receive a quote.  USA customers:  1-800-325-3010 or view local office numbers.

  4. What is the Department of Transportation shipping information for this product?

    Transportation information can be found in Section 14 of the product's (M)SDS.To access the shipping information for this material, use the link on the product detail page for the product. 

  5. What is the solubility of Methotrexate, Product M9929?

    Methotrexate is practically insoluble in water.  It does dissolve in solutions of mineral acids (such as HCl) and in dilute solutions of alkali hydroxides. A solution can be prepared in 0.1 M sodium hydroxide at 20 mg/ml (may require some heating).

  6. Can Product M9929, Methotrexate, be stored?

    Alkaline stock solutions can decompose. It is best to prepare stock solutions in a minimal amount of of 1 M sodium hydroxide, then dilute with saline or medium. Solutions can be stored at -20°C for about one month. Solutions can be stored for about 1 week at 2-8°C.

  7. How can I sterilize Product M9929, Methotrexate solutions?

    Solutions can be sterile filtered.

  8. What does the description of "meets USP testing specification" signify?

    The product has been tested according to the specifications in the monograph of the United States Pharmacopoeia.

  9. Has Product M9929, Methotrexate, been tested for cell culture applications?

    Product M9929 has not been cell culture tested. Product M8407, Methotrexate hydrate, has been both mammalian and insect cell culture tested and is recommended to use for these applications.

  10. My question is not addressed here, how can I contact Technical Service for assistance?

    Ask a Scientist here.

Hany Elsawy et al.
Bioscience reports, 40(6) (2020-05-28)
Methotrexate (MTX) is an efficient chemotherapeutic and immunosuppressant drug, but the hepatotoxicity of MTX limits its clinical use. Naringin (Nar) is a flavonoid derived from Citrus paradise, and has been shown to possess several pharmacological activities, including free-radical scavenging and
Shih-Chao Lin et al.
Plants (Basel, Switzerland), 9(11) (2020-11-14)
Crotonoside, a guanosine analog originally isolated from Croton tiglium, is reported to be a potent tyrosine kinase inhibitor with immunosuppressive effects on immune cells. Due to its potential immunotherapeutic effects, we aimed to evaluate the anti-arthritic activity of crotonoside and
Acharya Balkrishna et al.
Scientific reports, 9(1), 8025-8025 (2019-05-31)
Rheumatoid arthritis (RA) is a chronic inflammatory autoimmune disorder that affects joints of hands and feet and introduces injury in secondary organs such as cardiac tissue. In the present study, we induced RA in male Balb/c mice (CAIA) using collagen-antibody
Asma Achek et al.
EBioMedicine, 52, 102645-102645 (2020-02-06)
TLRs are some of the actively pursued drug-targets in immune disorders. Owing to a recent surge in the cognizance of TLR structural biology and signalling pathways, numerous therapeutic modulators, ranging from low-molecular-weight organic compounds to polypeptides and nucleic acid agents
Jun-Young Park et al.
International journal of nanomedicine, 16, 4943-4957 (2021-07-31)
Understanding structural interactions between the active drug and conjugated nanoparticles is critical for optimizing intracellular drug transport and for increasing nano drug efficacy. In this regard, analyzing the conformational deformation of conjugated drugs surrounding nanoparticles is essential to understand the
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