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Product Description
Mechanism of action
Aminopterin is a potent classical antifolate structurally related to methotrexate. It inhibits dihydrofolate reductase (DHFR), preventing conversion of dihydrofolate to tetrahydrofolate—an essential cofactor for thymidylate and purine synthesis. This halts DNA replication in rapidly dividing cells. Aminopterin also inhibits several folate‑dependent transaminases, giving it broad antimetabolite activity.
Benefits and advantages
While largely superseded clinically, aminopterin is still widely used in molecular biology in HAT selection medium, allowing survival only of cells with intact hypoxanthine salvage pathways. Its sharply defined antifolate mechanism makes it a model compound in oncopharmacology and folate biochemistry.
Side effects and risks
Severe mucositis, pancytopenia, hepatotoxicity, teratogenicity and acute renal injury. It must be handled in cytotoxic‑approved facilities with closed transfer systems.
Datasheet
| Molecular Formula | C19H20N8O5 |
|---|---|
| Molecular Weight | 440.4 g/mol |
| CAS Number | 54-62-6 |
| Storage Condition | Store in a cool, dry place. Keep container tightly closed. Protect from moisture and light. |
| Solubility | 3.0X103 mg/L |
| Purity | Purity information is available upon request (COA). |
| Synonym | aminopterin; 4-Aminofolic acid; 54-62-6; 4-Amino-PGA; Aminopterine |
| IUPAC/Chemical Name | (2S)-2-[[4-[(2,4-diaminopteridin-6-yl)methylamino]benzoyl]amino]pentanedioic acid |
| InChl Key | TVZGACDUOSZQKY-LBPRGKRZSA-N |
| InChl Code | 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 |
| References |
3D Conformer.
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