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/REAXYS Number: 69045
• EC Number: 200-209-9
• MDL number: MFCD00036692
• 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 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.

Features and Benefits

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Linkage

More potent, but more toxic, than methotrexate.

Safety Information

• pictograms: GHS06,GHS08
• signalword: Danger
• hcodes: H300,H315,H319,H341,H360FD
• pcodes: 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: 6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials
• wgk_germany: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable
• ppe: Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges