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06563

Sigma-Aldrich

Methotrexate hydrate

≥99.0% (sum of enantiomers, HPLC)

Synonym(s):

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)
EC Number:
200-413-8
MDL number:
MFCD00150847
UNSPSC Code:
12352202
PubChem Substance ID:
329748247
NACRES:
NA.77

biological source

synthetic

Assay

≥99.0% (sum of enantiomers, HPLC)

form

powder or crystals

optical activity

[α]/D +21.0±2.0°

impurities

≤0.1% sulfated ash

mp

185-204 °C

solubility

water: insoluble

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)

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General description

Methotrexateis an analog of folate. It shows anti-inflammatory effects throughseveral cellular mechanisms. The inhibition of dihydrofolate reductase reducesthe de novo synthesis of pyrimidines and purines, transmetylation ofphospholipids and proteins, and formation of polyamines.

Application

Methotrexatehydrate has been used as a disease modifyinganti-rheumatic drug (DMARD) to study its effects on Ross River virus disease (RRVD) in mice models.
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.

Other Notes

Folic acid antagonist. Potent inhibitor of dihydrofolate reductase.

Pictograms

Skull and crossbonesHealth hazard
GHS06,GHS08

Signal Word

Danger

Hazard Statements

H301,H341,H360D,H372

Hazard Classifications

Acute Tox. 3 Oral - Muta. 2 - Repr. 1B - STOT RE 1

Target Organs

Liver,Bone marrow

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

Certificates of Analysis (COA)

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B N Cronstein
Rheumatic diseases clinics of North America, 23(4), 739-755 (1997-11-15)
Because of methotrexate's well-documented efficacy in the treatment of rheumatoid arthritis, it is important that we understand the mechanism of action of this drug. There are two biochemical mechanisms by which methotrexate may modulate inflammation: (1) promotion of adenosine release
Methotrexate Treatment Causes Early Onset of Disease in a Mouse Model of Ross River Virus-Induced Inflammatory Disease through Increased Monocyte Production
Adam Taylor, et al.
PLoS ONE (2013)
D A Matthews et al.
Science (New York, N.Y.), 197(4302), 452-455 (1977-07-29)
A central eight-stranded beta-pleated sheet is the main feature of the polypeptide backbone folding in dihydrofolate reductase. The innermost four strands and two bridging helices are geometrically similar to but are connected in a different way from those in the
Edwin S L Chan et al.
Nature reviews. Rheumatology, 6(3), 175-178 (2010-03-04)
Methotrexate remains a cornerstone in the treatment of rheumatoid arthritis and other rheumatic diseases. Folate antagonism is known to contribute to the antiproliferative effects that are important in the action of methotrexate against malignant diseases, but concomitant administration of folic
Josef Singer et al.
Molecular cancer therapeutics, 13(7), 1777-1790 (2014-04-24)
Passive immunotherapy with monoclonal antibodies represents a cornerstone of human anticancer therapies, but has not been established in veterinary medicine yet. As the tumor-associated antigen EGFR (ErbB-1) is highly conserved between humans and dogs, and considering the effectiveness of the
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