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Key Documents

M8407

Sigma-Aldrich

Methotrexate hydrate

powder, suitable for cell culture, BioReagent

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:
Molecular Weight:
454.44 (anhydrous basis)
MDL number:
UNSPSC Code:
12352207
PubChem Substance ID:
NACRES:
NA.75

product name

Methotrexate hydrate, powder, BioReagent, suitable for cell culture, ≥98% (HPLC)

product line

BioReagent

Assay

≥98% (HPLC)

form

powder

technique(s)

cell culture | mammalian: suitable

solubility

H2O: insoluble

antibiotic activity spectrum

neoplastics
parasites

Mode of action

enzyme | inhibits

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

Methotrexate hydrate has been used:
  • as a dihydrofolate (DHFR) inhibitor in sphere forming assay culture
  • as a component of dulbecco′ modified Eagle′s medium (DMEM) for selection of transfected cells
  • in viability and co-culture assays

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 a folic acid antagonist.
Methotrexate used to inhibit dihyrofolate reductase and select for DHFR overexpresssion.

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Pictograms

Skull and crossbonesHealth hazard

Signal Word

Danger

Hazard Statements

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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Folate supplementation during methotrexate therapy for patients with psoriasis
Strober BE and Menon K
Journal of the American Academy of Dermatology, 53(4), 652-659 (2005)
Methylthioadenosine (MTA) Rescues Methylthioadenosine Phosphorylase (MTAP)-deficient tumors from purine synthesis inhibition in vivo via non-autonomous adenine supply
Ruefli-Brasse A, et al.
Journal of Cancer Therapy, 2(4), 523-523 (2011)
Comparative metabolic analysis of CHO cell clones obtained through cell engineering, for IgG productivity, growth and cell longevity
Wilkens CA and Gerdtzen ZP
Testing, 10(3), e0119053-e0119053 (2015)
Localizations of Na+-d-glucose cotransporters SGLT1 and SGLT2 in human kidney and of SGLT1 in human small intestine, liver, lung, and heart
Vrhovac I, et al.
Pflugers Archiv : European Journal of Physiology, 467(9), 1881-1898 (2015)
Yunqian Qiao et al.
Nature communications, 12(1), 6360-6360 (2021-11-06)
Expression of the cell surface receptor CD137 has been shown to enhance anti-cancer T cell function via engagement with its natural ligand 4-1BBL. CD137 ligation with engineered ligands has emerged as a cancer immunotherapy strategy, yet clinical development of agonists

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