Aminopterin

Title: Aminopterin
CAS Registry Number: 54-62-6
CAS Name: N-[4-[[(2,4-Diamino-6-pteridinyl)methyl]amino]benzoyl]-L-glutamic acid
Additional Names: 4-aminofolic acid; 4-aminopteroylglutamic acid; 4-amino-PGA
Molecular Formula: C19H20N8O5
Molecular Weight: 440.41
Percent Composition: C 51.82%, H 4.58%, N 25.44%, O 18.16%
Literature References: Prepd from 2,4,5,6-tetraminopyrimidine sulfate, 2,3-dibromopropionaldehyde and p-aminobenzoylglutamic acid: Seeger et al., J. Am. Chem. Soc. 69, 2567 (1947); from 6-(bromomethyl)-2,4-diaminopteridine HBr: Piper, Montgomery, J. Heterocycl. Chem. 11, 279 (1974). Purification: Loo, J. Med. Chem. 8, 139 (1965). Inhibition of dihydrofolate reductase: J. S. Erickson et al., J. Biol. Chem. 247, 5661 (1972). Use as rodenticide: US 2575168 (1951 to Am. Cyanamid).
Derivative Type: Dihydrate
Properties: Clusters of yellow needles. uv max of the 0.75 hydrate (0.1N NaOH): 261, 282, 373 (log e 4.41, 4.39, 3.91).
Absorption maximum: uv max of the 0.75 hydrate (0.1N NaOH): 261, 282, 373 (log e 4.41, 4.39, 3.91)
Use: Rodenticide.
Aminopyrine Aminoquinuride Aminorex Amioca Amiodarone

Aminopterin
Aminopterin.svg
Identifiers
CAS number 54-62-6 YesY
PubChem 2154
ChemSpider 2069 YesY
UNII JYB41CTM2Q YesY
EC number 200-209-9
ChEMBL CHEMBL274619 YesY
Jmol-3D images Image 1
Properties
Molecular formula C19H20N8O5
Molar mass 440.41 g mol−1
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Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

Aminopterin (4-aminopteroic acid), a 4-amino analog of folic acid, is an antineoplastic drug with immunosuppressive properties used in chemotherapy. Aminopterin is a synthetic derivative of pterin. Aminopterin works as an enzyme inhibitor by competing for the folate binding site of the enzyme dihydrofolate reductase. Its binding affinity for dihydrofolate reductase effectively blocks tetrahydrofolate synthesis. This results in the depletion of nucleotide precursors and inhibition of DNA, RNA, and protein synthesis.