A7019
(±)-Amethopterin
≥95%, powder
Synonym(e):
4-Amino-10-methylfolsäure, DL-4-Amino-N10-methylpteroylglutaminsäure, MTX, Methotrexat, Methylaminopterin
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Empirische Formel (Hill-System):
C20H22N8O5 · xH2O
CAS-Nummer:
Molekulargewicht:
454.44 (anhydrous basis)
UNSPSC Code:
12352200
PubChem Substance ID:
EC Number:
262-213-7
MDL number:
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Unterstützung erhaltenSMILES string
O.CN(Cc1cnc2nc(N)nc(N)c2n1)c3ccc(cc3)C(=O)NC(CCC(O)=O)C(O)=O
assay
≥95%
form
powder
color
yellow to yellow with an orange cast
solubility
H2O: insoluble
storage temp.
−20°C
Gene Information
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.
Biochem/physiol Actions
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.
Preparation Note
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).
signalword
Danger
hcodes
Hazard Classifications
Acute Tox. 3 Oral - Eye Irrit. 2 - Repr. 1B - Skin Irrit. 2
Lagerklasse
6.1B - Non-combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials
wgk
WGK 3
ppe
Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges
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