Aminopterin Ready Made Solution

SIGMA/SBR00016 - 50 mg/mL in DMSO

Synonym: (S)-2-{4-[(2,4-Diaminopteridin-6-yl)methylamino]benzamido}pentanedioic acid; 4-Amino-PGA; 4-Aminofolic acid; 4-Aminopteroyl-L-glutamic acid

CAS Number: 54-62-6
Empirical Formula (Hill Notation): C₁₉H₂₀N₈O₅
Molecular Weight: 440.41
MDL Number: MFCD00036692
Linear Formula: C₁₉H₂₀N₈O₅
Product Type: Chemical

Catalog Number	PKG Qty.	Price


45-SBR00016-1ML	1 mL	$470.00 1/EA	Add To Favorites

Properties
Descriptions
Safety Info.
Basic Data

assay	≥85%
concentration	50 mg/mL in DMSO
form	liquid
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
Quality Level	200
shipped in	dry ice
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
solubility	DMSO: 50 mg/mL
storage condition	protect from light
storage temp.	−20°C

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.

Symbol	GHS06,GHS08
Signal word	Danger
Hazard statements	H301 - H360
Precautionary statements	P201 - P280 - P301 + P330 + P331 + P310 - P308 + P313
RIDADR	UN 2810 6.1 / PGIII
WGK Germany	WGK 3
Flash Point(F)	188.6 °F
Flash Point(C)	87 °C

Purity	≥85%
Storage Temp.	−20°C
UNSPSC	12352200

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