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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

Quality Level

200

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

signalword

Danger

Hazard Classifications

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

target_organs

Liver,Bone marrow

Storage Class

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

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

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

Certificates of Analysis (COA)

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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
Methotrexate: new uses for an old drug.
Philip J Hashkes et al.
The Journal of pediatrics, 164(2), 231-236 (2013-11-30)
Johanna P Cremers et al.
Current opinion in pulmonary medicine, 19(5), 545-561 (2013-07-25)
Although glucocorticosteroids are considered the first-line treatment in sarcoidosis, refractory cases require alternatives, such as methotrexate (MTX). The aim of this study was to develop, on behalf of the World Association of Sarcoidosis and Other Granulomatous Disorders (WASOG), multinational evidence-based
Ian Joseph Cohen et al.
Pediatric blood & cancer, 61(1), 7-10 (2013-09-17)
To determine the optimal time of folinic acid rescue after methotrexate (MTX) treatment in patients with ALL, we selected and evaluated relevant studies that included doses, rescue delay, and side effects. Rescue at 42-48 hours resulted in considerable toxicity, except
Josef S Smolen et al.
Lancet (London, England), 383(9914), 321-332 (2013-10-31)
Biological agents offer good control of rheumatoid arthritis, but the long-term benefits of achieving low disease activity with a biological agent plus methotrexate or methotrexate alone are unclear. The OPTIMA trial assessed different treatment adjustment strategies in patients with early
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