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Aminopterin

Aminopterin is a folic acid analog and derivative of pterin; it is very similar to methotrexate in structure. Aminopterin exhibits anticancer chemotherapeutic and immunosuppressive activities. Like other folic acid analogs, aminopterin inhibits dihydrofolate reductase, depleting nucleotide pools and inhibiting synthesis of DNA and RNA. Aminopterin was one of the first compounds to successfully induce remission in childhood leukemia and was clinically used to treat rheumatoid arthritis, but has since been replaced by methotrexate.

References PubMed ID::http://www.ncbi.nlm.nih.gov/pubmed/18837785

Cas No.

54-62-6

Purity

≥95%

Formula

C19H20N8O5

Formula Wt.

440.41

Chemical Name

N-[4-[[(2,4-Diamino-6-pteridinyl)methyl]amino]benzoyl]-L-glutamic acid

IUPAC Name

2-[[4-[(2,4-diaminopteridin-6-yl)methylamino]benzoyl]amino]pentanedioicacid

Synonym

4-Aminofolic acid

Melting Point

230-235°C (dec)

Solubility

Soluble in DMSO or 2 N NaOH (50mg/mL).

Appearance

Dark Yellow-Brown Powder

Visentin M, Zhao R, Goldman ID. The antifolates. Hematol Oncol Clin North Am. 2012 Jun;26(3):629-48. PMID: 22520983.

McGuire JJ. Anticancer antifolates: current status and future directions. Curr Pharm Des. 2003;9(31):2593-613. PMID: 14529544.

Baggott JE, Morgan SL, Ha TS, et al. Antifolates in rheumatoid arthritis: a hypothetical mechanism of action. Clin Exp Rheumatol. 1993 Mar-Apr;11 Suppl 8:S101-5. PMID: 8324932.

PF-06463922