SBR00016

Aminopterin Ready Made Solution

50 mg/mL in DMSO

• 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
• MDL number: MFCD00036692
• UNSPSC Code: 12352205
• NACRES: NA.76

Properties

• Assay: ≥85%
• Quality Level: 200
• form: liquid
• storage condition: protect from light
• concentration: 50 mg/mL in DMSO
• solubility: DMSO: 50 mg/mL
• shipped in: dry ice
• storage temp.: −20°C
• SMILES string: OC(CC[C@@H](C(O)=O)NC(C1=CC=C(NCC2=NC3=C(N)N=C(N)N=C3N=C2)C=C1)=O)=O
• 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)
• InChI key: TVZGACDUOSZQKY-UHFFFAOYSA-N

Description

Biochem/physiol Actions

Aminopterin is a synthetic derivative of pterin. It is used as a folic acid antagonist. It competitively inhibits dihydrofolate reductase (DHFR) and blocks tetrahydrofolate synthesis. This inhibition blocks DNA, RNA and protein synthesis.

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.

Aminopterin was first administered for cancer therapy, as a drug targeting metabolism, specifically in pediatric leukemia. Later on it was demonstrated to be more potent yet more toxic than methotrexate.

Safety Information

• Pictograms: GHS06,GHS08
• Signal Word: Danger
• Hazard Statements: H301,H341,H360FD
• Precautionary Statements: P202 - P264 - P270 - P280 - P301 + P310 - P405
• Hazard Classifications: Acute Tox. 3 Oral - Muta. 2 - Repr. 1B
• Storage Class Code: 6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects
• WGK: WGK 3
• Flash Point(F): 188.6 °F
• Flash Point(C): 87 °C