A1784

Aminopterin

powder

• Synonym(s): (S)-2-{4-[(2,4-Diaminopteridin-6-yl)methylamino]benzamido}pentanedioic acid, 4-Amino-PGA, 4-Aminofolic acid, 4-Aminopteroyl-L-glutamic acid
• Empirical Formula (Hill Notation): C₁₉H₂₀N₈O₅
• CAS Number: 54-62-6
• Molecular Weight: 440.41
• Beilstein: 69045
• EC Number: 200-209-9
• UNSPSC Code: 12352200
• PubChem Substance ID: 24278186
• NACRES: NA.77

Properties

• biological source: synthetic (organic)
• Quality Level: 200
• Assay: ≥97% (TLC)
• form: powder
• color: yellow
• mp: 225 °C
• solubility: 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 (extinction coefficient): 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
• storage temp.: −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
• InChI key: TVZGACDUOSZQKY-LBPRGKRZSA-N
• Gene Information: human ... FPGS(2356) ; mouse ... Fpgs(14287)

Description

Biochem/physiol Actions

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.

Features and Benefits

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Linkage

More potent, but more toxic, than methotrexate.

Safety Information

• Pictograms: GHS06,GHS08
• Signal Word: Danger
• Hazard Statements: H300,H315,H319,H341,H360FD
• Precautionary Statements: P202 - P264 - P280 - P301 + P310 - P302 + P352 - P305 + P351 + P338
• Hazard Classifications: Acute Tox. 1 Oral - Eye Irrit. 2 - Muta. 2 - Repr. 1B - Skin Irrit. 2
• Storage Class Code: 6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials
• WGK: WGK 3
• Flash Point(F): Not applicable
• Flash Point(C): Not applicable
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves