Aminopterin

• Catalog No.: 09328
• CAS Number: 54-62-6
• M. F.: C19H20N8O5
• M. W.: 440.4127
• Purity: ≥96.0% (UV)

SYNONYMS

• Title: 氨基蝶呤
• IUPAC name: (2S)-2-[(4-{[(2,4-diaminopteridin-6-yl)methyl]amino}phenyl)formamido]pentanedioic acid
• IUPAC Traditional name: 4-aminopteroylglutamic acid
• Synonyms: 4-氨基叶酸; 4-Aminopteroyl-L-glutamic acid; 4-氨基-PGA; N-[4-[[(2,4-二氨基-6-蝶啶)甲基]氨基]苯甲酰]-L-谷氨酸; 4-Amino-PGA; 4-Aminofolic acid

DATABASE IDS

• CAS Number: 54-62-6
• Beilstein Number: 69045
• PubChem SID: 24846313
• EC Number: 200-209-9
• MDL Number: MFCD00036692

PROPERTIES

• abs.: ε1M/261 nm, 0.1 M NaOH 25,700
• abs.: ε1M/282 nm, 0.1 M NaOH 24,500
• abs.: ε1M/373 nm, 0.1 M NaOH 8,100
• Empirical Formula (Hill Notation): C19H20N8O5
• Purity: ≥96.0% (UV)
• Gene Information: human ... FPGS(2356)mouse ... Fpgs(14287)
• Melting Point: 228-235 °C (dec.)
• Optical Rotation: [α]20/D +18±2°, c = 1% in 0.1 M NaOH
• GHS Signal Word: Danger
• GHS Hazard statements: H300-H360
• European Hazard Symbols: Highly toxic (T+)
• Personal Protective Equipment: Eyeshields, Faceshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges
• GHS Precautionary statements: P201-P264-P301 + P310-P308 + P313
• RID/ADR: UN 2811 6.1/PG 1
• Risk Statements: 61-28
• RTECS: MA1050000
• Safety Statements: 53-28-36/37-45
• Storage Temperature: 2-8°C
• Hazard Class: 6.1
• UN Number: 2811
• Packing Group: 1
• German water hazard class: 3

DETAILS

Description (English)

Linkage
More potent, but more toxic, than methotrexate.
Other Notes
Folic acid antagonist.; Potent competitive inhibitor of dihydrofolate reductase1
Biochem/physiol Actions
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.

Description (简体中文)

Linkage
比甲氨喋呤更有效，但毒性也更强。
Other Notes
Folic acid antagonist.; Potent competitive inhibitor of dihydrofolate reductase1
Biochem/physiol Actions
叶酸拮抗剂。氨基蝶呤是由叶酸转运蛋白运输至细胞内的。在细胞内，它被叶酰聚谷氨酸合酶转化为一种高分子量的聚谷氨酸盐代谢物，该产物又与二氢叶酸还原酶结合并抑制其活性。氨基蝶呤-聚谷氨酸盐经 γ-谷氨酰基水解酶作用发生细胞内降解。