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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
Pricing and availability is not currently available.

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.

related product

Product No.
Description
Pricing

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
0000395825
0000394537
0000386554
0000385317
0000375990

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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
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
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
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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Questions

1–9 of 9 Questions  

  1. How can I determine the shelf life / expiration / retest date of this product?

    1 answer

    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf

      Helpful?

  2. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer

    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

      Helpful?

  3. To prepare methotrexate stock solution, should methotrexate, product M9929, be dissolved in 0.1 M sodium hydroxide or 1 M?

    1 answer

    1. Methotrexate is typically dissolved in a 0.1 M sodium hydroxide solution to prepare a stock solution. This concentration is sufficient to ensure complete dissolution, as methotrexate is slightly soluble in water. Using a 1 M sodium hydroxide solution may be too strong and could potentially alter the stability of methotrexate.

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

    1 answer

    1. 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.

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  5. Can Product M9929, Methotrexate, be stored?

    1 answer

    1. 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.

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

    1 answer

    1. 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).

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

    1 answer

    1. Solutions can be sterile filtered.

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

    1 answer

    1. 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.

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

    1 answer

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

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