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A6770

Sigma-Aldrich

Methotrexate hydrate

≥98% (HPLC), powder

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Synonym(s):
4-Amino-10-methylfolic acid hydrate, L-4-Amino-N10-methylpteroylglutamic acid hydrate, L-Amethopterin hydrate, Antifolan hydrate, MTX hydrate, Methylaminopterin hydrate
Empirical Formula (Hill Notation):
C20H22N8O5 · xH2O
CAS Number:
133073-73-1
Molecular Weight:
454.44 (anhydrous basis)
MDL number:
MFCD00150847
UNSPSC Code:
12352202
PubChem Substance ID:
57653876
NACRES:
NA.77

biological source

synthetic (organic)

Quality Level

200

Assay

≥98% (HPLC)

form

powder

color

, yellow to very dark yellow to very dark orange

mp

185-204  °C

solubility

H2O: 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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Application

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.

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

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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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
Yingjuan J Lu et al.
Cell reports. Medicine, 2(10), 100422-100422 (2021-11-11)
Provoked by sterile/nonsterile insults, prolonged monocyte mobilization and uncontrolled monocyte/macrophage activation can pose imminent or impending harm to the affected organs. Curiously, folate receptor beta (FRβ), with subnanomolar affinity for the vitamin folic acid (FA), is upregulated during immune activation
Irina Kalashnikova et al.
Theranostics, 10(26), 11863-11880 (2020-11-19)
Rheumatoid arthritis (RA) is an autoimmune disease that affects 1-2% of the human population worldwide, and effective therapies with targeted delivery for local immune suppression have not been described. We address this problem by developing a novel theranostic nanoparticle for
Bokyeong Ryu et al.
Frontiers in veterinary science, 8, 587659-587659 (2021-10-05)
The gastrointestinal tract is the most common exposure route of xenobiotics, and intestinal toxicity can result in systemic toxicity in most cases. It is important to develop intestinal toxicity assays mimicking the human system; thus, stem cells are rapidly being
Methotrexate: new uses for an old drug.
Philip J Hashkes et al.
The Journal of pediatrics, 164(2), 231-236 (2013-11-30)
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