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M9929

Methotrexate

Name: Methotrexate
Brand: SIAL

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)

NACRES:

NA.21

PubChem Substance ID:

24897373

UNSPSC Code:

12352005

MDL number:

MFCD00150847

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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)

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

GHS06,GHS08

signalword

Danger

hcodes

H301,H315,H319,H360FD

pcodes

P202 - P264 - P280 - P301 + P310 - P302 + P352 - P305 + P351 + P338

Hazard Classifications

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

Storage Class

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

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges

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Certificates of Analysis (COA)

Lot/Batch Number

0000523959

0000513219

0000509795

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A peptide derived from the core β-sheet region of TIRAP decoys TLR4 and reduces inflammatory and autoimmune symptoms in murine models.

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Alleviation of Collagen-Induced Arthritis by Crotonoside through Modulation of Dendritic Cell Differentiation and Activation.

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

Herbo-mineral formulation 'Ashwashila' attenuates rheumatoid arthritis symptoms in collagen-antibody-induced arthritis (CAIA) mice model.

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

Naringin alleviates methotrexate-induced liver injury in male albino rats and enhances its antitumor efficacy in HepG2 cells.

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

Deep sequencing reveals different compositions of mRNA transcribed from the F8 gene in a panel of FVIII-producing CHO cell lines.

Christian S Kaas et al.

Biotechnology journal, 10(7), 1081-1089 (2015-05-13)

Coagulation factor VIII (FVIII) is one of the most complex biopharmaceuticals due to the large size, poor protein stability and extensive post-translational modifications. As a consequence, efficient production of FVIII in mammalian cells poses a major challenge, with typical yields

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