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Key Documents

SBR00016

Sigma-Aldrich

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

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About This Item

Empirical Formula (Hill Notation):
C19H20N8O5
CAS Number:
Molecular Weight:
440.41
MDL number:
UNSPSC Code:
12352205
NACRES:
NA.76

Assay

≥85%

Quality Level

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

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.

Pictograms

Skull and crossbonesHealth hazard

Signal Word

Danger

Hazard Statements

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


Certificates of Analysis (COA)

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A quantitative comparison of the antileukemic effectiveness of two folic acid antagonists in mice.
A GOLDIN et al.
Journal of the National Cancer Institute, 15(6), 1657-1664 (1955-06-01)
Michele Visentin et al.
Hematology/oncology clinics of North America, 26(3), 629-648 (2012-04-24)
This article focuses on the cellular, biochemical, and molecular pharmacology of antifolates and how a basic understanding of the mechanism of action of methotrexate, its cytotoxic determinants, mechanisms of resistance, and transport into and out of cells has led to
Temporary remissions in acute leukemia in children produced by folic acid antagonist, 4-aminopteroyl-glutamic acid.
S FARBER et al.
The New England journal of medicine, 238(23), 787-793 (1948-06-03)
Antagonist for pteroylglutamic acid.
D R SEEGER et al.
Journal of the American Chemical Society, 69(10), 2567-2567 (1947-10-01)

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