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MilliporeSigma

M9929

Sigma-Aldrich

Metotrexato hydrate

meets USP testing specifications

Sinónimos:

L-ametopterina hydrate, Ácido L-4-amino-N10-metilpteroilglutámico hydrate, Antifolan hydrate, MTX hydrate, Metilaminopterina hydrate, Ácido 4-amino-10-metilfólico hydrate

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About This Item

Fórmula empírica (notación de Hill):
C20H22N8O5 · xH2O
Número de CAS:
Peso molecular:
454.44 (anhydrous basis)
MDL number:
UNSPSC Code:
12352005
PubChem Substance ID:
NACRES:
NA.21

biological source

synthetic

Quality Level

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
cell based 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)

advanced drug delivery
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

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Application

Potente inhibidor de la dihidrofolato reductasa y agente para estudios antitumorales. Se utiliza para inhibir la dihidrofolato reductasa en sistemas de expresión de proteínas basados en la DHFR. También eficaz en el tratamiento de los parásitos del paludismo Plasmodium vivax resistentes a la pirimetamina.
Potente inhibidor de la dihidrofolato reductasa y agente para estudios antitumorales. Se utiliza para inhibir la dihidrofolato reductasa en sistemas de expresión de proteínas basados en la DHFR. También muestra efectos inmunodepresores, por ejemplo en la artritis reumatoide

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.

Related product

Referencia del producto
Descripción
Precios

pictograms

Skull and crossbonesHealth hazard

signalword

Danger

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

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

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


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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
Asma Achek et al.
EBioMedicine, 52, 102645-102645 (2020-02-06)
TLRs are some of the actively pursued drug-targets in immune disorders. Owing to a recent surge in the cognizance of TLR structural biology and signalling pathways, numerous therapeutic modulators, ranging from low-molecular-weight organic compounds to polypeptides and nucleic acid agents
Roy Fleischmann et al.
Annals of the rheumatic diseases, 74(6), 1132-1137 (2014-08-22)
Disease Activity Score in 28 joints calculated with C-reactive protein (DAS28-CRP) is used instead of erythrocyte sedimentation rate (DAS28-ESR) to assess rheumatoid arthritis disease activity; however, values for remission and low disease activity (LDA) for DAS28-CRP have not been validated.
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
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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Neoplastic cells are highly dependent on the de novo synthesis of nucleotides to maintain sufficient pools to support DNA replication and the production of RNA.

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