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Merck

A3411

Aminopterin

powder, BioReagent, suitable for cell culture

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:
54-62-6
Molecular Weight:
440.41
PubChem Substance ID:
24890768
UNSPSC Code:
12352205
MDL number:
MFCD00036692
NACRES:
NA.75
EC Number:
200-209-9
Beilstein/REAXYS Number:
69045

Product Name

Aminopterin, powder, BioReagent, suitable for cell culture

InChI key

TVZGACDUOSZQKY-LBPRGKRZSA-N

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

SMILES string

Nc1nc(N)c2nc(CNc3ccc(cc3)C(=O)N[C@@H](CCC(O)=O)C(O)=O)cnc2n1

biological source

synthetic (organic)

product line

BioReagent

assay

≥97%

form

powder

technique(s)

cell culture | mammalian: suitable

color

yellow

solubility

2 M NaOH: 50 mg/mL
DMSO: soluble

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

shipped in

dry ice

storage temp.

−20°C

Quality Level

200

Gene Information

human ... FPGS(2356)
mouse ... Fpgs(14287)

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Application

Aminopterin has been used in the production of anti- neurogranin antibodies.

Biochem/physiol Actions

Aminopterin is found to inhibit growth, embryogenesis and has toxic effects in mice models. It serves as a abortifacient. Aminopterin is known to reduce the effects of acute leukemia in children.
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.

Other Notes

More potent, but more toxic, than methotrexate.

pictograms

Skull and crossbonesHealth hazard
GHS06,GHS08

signalword

Danger

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

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges

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Certificates of Analysis (COA)

Lot/Batch Number
0000479764
0000479764
0000415085
0000415085
0000300214

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Phase II trial of oral aminopterin for adults and children with refractory acute leukemia
Cole PD, et al.
Clinical Cancer Research, 11(22), 8089-8096 (2005)
Drugs and Nutrients: The Interactive Effects, 308-308 (1984)
Drugs and Nutrients: The Interactive Effects, 308-308 (1984)
Serum neurogranin measurement as a biomarker of acute traumatic brain injury
Yang J, et al.
Clinical Biochemistry, 48, 843-848 (2015)
M Del Campo et al.
Teratology, 60(1), 10-12 (1999-07-21)
Maternal exposures to aminopterin and methotrexate have been associated with a pattern of malformation which includes prenatal-onset growth deficiency, severe lack of ossification of the calvarium, hypoplastic supraorbital ridges, small, low-set ears, micrognathia, and limb abnormalities. We report on a
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