A1784

Aminopterin

powder

• Synonym(e): (S)-2-{4-[(2,4-Diaminopteridin-6-yl)-methylamino]-benzamido}-pentandisäure, 4-Amino-pteroyl-L-glutaminsäure, 4-Aminofolsäure, erythro-2-Amino-1-phenyl-1-propanol -hydrochlorid
• Empirische Formel (Hill-System): C₁₉H₂₀N₈O₅
• CAS-Nummer: 54-62-6
• Molekulargewicht: 440.41
• Beilstein: 69045
• EG-Nummer: 200-209-9
• UNSPSC-Code: 12352200
• PubChem Substanz-ID: 24278186
• NACRES: NA.77

Eigenschaften

• Biologische Quelle: synthetic (organic)
• Qualitätsniveau: 200
• Assay: ≥97% (TLC)
• Form: powder
• Farbe: yellow
• mp (Schmelzpunkt): 225 °C
• Löslichkeit: 2 M NaOH: 50 mg/mL (Solutions may be stored for 1-2 days at 4°C.); DMSO: soluble (Solutions may be stored for 1-2 days at 4°C.)
• ε (Extinktionskoeffizient): 24,500 at 282 nm in 0.1 M NaOH at 1 M; 25,700 at 261 nm in 0.1 M NaOH at 1 M; 8,100 at 373 nm in 0.1 M NaOH at 1 M
• Lagertemp.: −20°C
• SMILES String: Nc1nc(N)c2nc(CNc3ccc(cc3)C(=O)N[C@@H](CCC(O)=O)C(O)=O)cnc2n1
• InChI: 1S/C19H20N8O5/c20-15-14-16(27-19(21)26-15)23-8-11(24-14)7-22-10-3-1-9(2-4-10)17(30)25-12(18(31)32)5-6-13(28)29/h1-4,8,12,22H,5-7H2,(H,25,30)(H,28,29)(H,31,32)(H4,20,21,23,26,27)/t12-/m0/s1
• InChIKey: TVZGACDUOSZQKY-LBPRGKRZSA-N
• Angaben zum Gen: human ... FPGS(2356) ; mouse ... Fpgs(14287)

Beschreibung

Biochem./physiol. Wirkung

Folic acid antagonist. Aminopterin 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. Aminopterin-polyglutamate is degraded intracellularly by γ-glutamyl hydrolase.

Leistungsmerkmale und Vorteile

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Verlinkung

Wirksamer aber auch toxischer als Methotrexat

Sicherheitshinweise

• Piktogramme: GHS06,GHS08
• Signalwort: Danger
• H-Sätze: H300,H315,H319,H341,H360FD
• P-Sätze: P202 - P264 - P280 - P301 + P310 - P302 + P352 - P305 + P351 + P338
• Gefahreneinstufungen: Acute Tox. 1 Oral - Eye Irrit. 2 - Muta. 2 - Repr. 1B - Skin Irrit. 2
• Lagerklassenschlüssel: 6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials
• WGK: WGK 3
• Flammpunkt (°F): Not applicable
• Flammpunkt (°C): Not applicable
• Persönliche Schutzausrüstung: Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges