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A7019

Sigma-Aldrich

(±)Amethopterin hydrate

≥95%, powder

Synonyme(s) :

4-Amino-10-methylfolic acid, DL-4-Amino-N10-methylpteroylglutamic acid, MTX, Methylaminopterin

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About This Item

Formule empirique (notation de Hill):
C20H22N8O5 · xH2O
Numéro CAS:
60388-53-6
Poids moléculaire :
454.44 (anhydrous basis)
Numéro CE :
262-213-7
Numéro MDL:
MFCD00150845
Code UNSPSC :
12352200
ID de substance PubChem :
24891167

Pureté

≥95%

Forme

powder

Couleur

yellow to yellow with an orange cast

Solubilité

H2O: insoluble

Température de stockage

−20°C

Chaîne SMILES 

O.CN(Cc1cnc2nc(N)nc(N)c2n1)c3ccc(cc3)C(=O)NC(CCC(O)=O)C(O)=O

Informations sur le gène

human ... DHFRP1(573971) , FPGS(2356) , SLC19A1(6573) , TYMS(7298)
mouse ... Dhfr(13361)
rat ... Dhfr(24312)

Application

Amethopterin is a folic acid antagonist and potent anticancer agent. Amethopterin blocks DNA synthesis by preventing the production of tetrahydrofolate cofactors which are required to make thymidine. Amethopterin is actively transported into cells by the folate transporter where it is converted to a high molecular weight polyglutamate metabolite by folylpolyglutamate synthase, a dihydrofolate reductase inhibitor.

Actions biochimiques/physiologiques

Amethopterin is a folic acid antagonist and potent anticancer agent. Blocks DNA synthesis by blocking the production of tetrahydrofolate covactors required for the synthesis of thymidine. Amethopterin is actively transported into cells by the folate transporter. In the cell, it is converted to a high molecular weight polyglutamate metabolite by folylpolyglutamate synthase that, in turn, binds to dihydrofolate reductase and inhibits its activity. Amethopterin-polyglutamate is degraded intracellularly by γ-glutamyl hydrolase.

Reconstitution

Add a minimal amount of 0.1 N NaOH to solubilize, then dilute in neutral buffer or saline. Diluted stock is stable for 1 week refrigerated and for 1 month frozen at −20 °C. References: Cell & Tissue Culture: Laboratory Procedures, Chapter 27, Page 27D:3.2 (A. Doyle, et al., eds, John Wiley) and Cell Biology: A Laboratory Handbook, vol. 2, page 417 (Julio E. Celis, ed., Academic Press).

Pictogrammes

Skull and crossbonesHealth hazard
GHS06,GHS08

Mention d'avertissement

Danger

Mentions de danger

H301,H315,H319,H360

Classification des risques

Acute Tox. 3 Oral - Eye Irrit. 2 - Repr. 1B - Skin Irrit. 2

Code de la classe de stockage

6.1B - Non-combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials

Classe de danger pour l'eau (WGK)

WGK 3

Équipement de protection individuelle

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

Certificats d'analyse (COA)

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Consulter la Bibliothèque de documents

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
Axel Finckh et al.
Arthritis research & therapy, 16(5), 458-458 (2014-10-16)
Calcium pyrophosphate deposition (CPPD) may cause severe arthropathy, major joint destruction and treatment options are limited. The aim of this study was to test the therapeutic efficacy of methotrexate (MTX) in chronic or recurrent CPPD arthropathy. Patients with CPPD arthropathy
Anna-Birgitte Aga et al.
Annals of the rheumatic diseases, 74(2), 381-388 (2013-11-29)
To investigate whether baseline disease activity levels and responses in patients with rheumatoid arthritis (RA) changed during the period 2000-2010. Data were provided by the Norwegian disease-modifying antirheumatic drug (NOR-DMARD) study. Patients with inflammatory joint diseases starting new treatment with
Kalle Jyri Aaltonen et al.
The Journal of rheumatology, 42(3), 372-378 (2015-01-17)
Because of the role of tumor necrosis factor (TNF) in host defense, it was hypothesized that its inhibition might lead to an increased risk of malignancies and infections. The objective of our study was to assess the incidence of serious
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