A1784

Aminopterin

powder

• Synonyme(s) : (S)-2-{4-[(2,4-Diaminopteridin-6-yl)methylamino]benzamido}pentanedioic acid, 4-Amino-PGA, 4-Aminofolic acid, 4-Aminopteroyl-L-glutamic acid
• Formule empirique (notation de Hill) : C₁₉H₂₀N₈O₅
• CAS Number: 54-62-6
• Poids moléculaire : 440.41
• Beilstein: 69045
• Numéro CE : 200-209-9
• Numéro MDL: MFCD00036692
• Code UNSPSC : 12352200
• ID de substance PubChem : 24278186
• Nomenclature NACRES : NA.77

Propriétés

• Source biologique: synthetic (organic)
• Niveau de qualité: 200
• Essai: ≥97% (TLC)
• Forme: powder
• Couleur: yellow
• Pf: 225 °C
• Solubilité: 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 (coefficient d'extinction): 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
• Température de stockage: −20°C
• Chaîne SMILES: 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
• Clé InChI: TVZGACDUOSZQKY-LBPRGKRZSA-N
• Informations sur le gène: human ... FPGS(2356) ; mouse ... Fpgs(14287)

Description

Actions biochimiques/physiologiques

Folic acid antagonist that binds to dihydrofolate reductase and inhibits its activity.

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.

Caractéristiques et avantages

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Liaison

More potent, but more toxic, than methotrexate.

Informations sur la sécurité

• Pictogrammes: GHS06,GHS08
• Mention d'avertissement: Danger
• Mentions de danger: H300,H315,H319,H341,H360FD
• Conseils de prudence: P202 - P264 - P280 - P301 + P310 - P302 + P352 - P305 + P351 + P338
• Classification des risques: Acute Tox. 1 Oral - Eye Irrit. 2 - Muta. 2 - Repr. 1B - Skin Irrit. 2
• Code de la classe de stockage: 6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials
• Classe de danger pour l'eau (WGK): WGK 3
• Point d'éclair (°F): Not applicable
• Point d'éclair (°C): Not applicable
• Équipement de protection individuelle: Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges