Deoxyaminopteroic acid (DAAP) is a synthetic analogue of pteroic acid, a precursor to tetrahydrofolic acid (THF), an essential coenzyme in many metabolic pathways. DAAP acts as an inhibitor of dihydrofolate reductase (DHFR), an enzyme responsible for the conversion of dihydrofolate to THF. The inhibition of DHFR by DAAP leads to a depletion of THF, disrupting various metabolic processes, including DNA synthesis, RNA synthesis, and amino acid metabolism. DAAP has been studied as a potential anticancer agent due to its ability to inhibit tumor cell growth. Its mechanism of action involves the disruption of folate metabolism, which is often dysregulated in cancer cells. However, DAAP has not yet been approved for clinical use. Despite its potential as an anticancer agent, DAAP has also been found to exhibit toxicity in animal models, which has limited its further development.'
deoxyaminopteroic acid: carboxypeptidase cleavage product of methotrexate (minus glutamic acid); RN given refers to parent cpd; structure [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]
| ID Source | ID |
|---|---|
| PubMed CID | 72441 |
| CHEMBL ID | 3544676 |
| SCHEMBL ID | 221621 |
| MeSH ID | M0040248 |
| Synonym |
|---|
| nsc-133723 |
| 4-[[(2,4-diamino-6-pteridinyl)methyl](methyl)amino]benzenecarboxylic acid |
| nsc131463 |
| 19741-14-1 |
| nsc-131463 |
| 4-[(2,4-diaminopteridin-6-yl)methyl-methyl-amino]benzoic acid |
| dc326 |
| benzoic acid, p-[[(2,4-diamino-6-pteridinyl)methyl]methylamino]- |
| sd-096947 |
| deoxyaminopteroic acid |
| benzoic acid, 4-[(2,4-diamino-6-pteridinylmethyl)methylamino]- |
| 4-[(2,4-diaminopteridin-6-yl)methyl-methylamino]benzoic acid |
| AKOS005110876 |
| FT-0665459 |
| unii-p7ovp484dx |
| 4-deoxy-4-amino-n(10)-methylpteroic acid |
| 2,4-diamino-n(10)-methylpteroic acid |
| nsc 131463 |
| n-10-methyl-4-deoxy-4-aminopteroate |
| p7ovp484dx , |
| 4-(((2,4-diamino-6-pteridinyl)methyl)methylamino)benzoic acid |
| 2,4-apa |
| BCP9000998 |
| nsc 133723 |
| dampa |
| nsc131463(nsc133723) |
| BCP0726000313 |
| 4-(n-(2,4-diamino-6-pteridinylmethyl)-n-methylamino)benzoic acid |
| GEO-03114 |
| methotrexate impurity e [ep impurity] |
| 4-amino-4-deoxy-n10-methylpteroic acid |
| benzoic acid, 4-(((2,4-diamino-6-pteridinyl)methyl)methylamino)- |
| 4-(n-((2,4-diaminopyrimido(4,5-b)pyrazin-6-yl)methyl)-n-methylamino)benzoic acid |
| 4-(((2,4-diaminopteridin-6-yl)methyl)methylamino)benzoic acid |
| SCHEMBL221621 |
| SS-3399 |
| 4-[n-[(2,4-diamino-6-pteridinyl)methyl]-n-methylamino]benzoic acid |
| 4-(n-((2,4-diaminopteridin-6-yl)methyl)-n-methylamino)benzoic acid |
| LWCXZSDKANNOAR-UHFFFAOYSA-N |
| 4-(((2,4-diaminopteridin-6-yl)methyl)(methyl)amino)benzoic acid |
| 4-[n-(2,4-diamino-6-pteridinylmethyl)-n-methylamino]benzoic acid |
| DTXSID20173427 |
| CHEMBL3544676 |
| C90286 |
| 4[n-(2,4-diamino-6-pteridinylme-thyl)-n-methylamino]benzoic acid |
| nsc 131463(nsc 133723) |
| 4-(((2,4-diaminopteridin-6-yl)methyl)(methyl)amino)benzoicacid |
| mfcd00075774 |
| nsc131463;dampa;nsc-131463;deoxyaminopteroic acid;methotrexate impurity e;4-amino-4-deoxy-10-methylpteroic acid |
| BCP02884 |
| EX-A7646 |
| methotrexate metabolite |
| CS-0027733 |
| HY-108251 |
| Q27286329 |
| 4-[n-(2,4-diamino-6-pteridinylmethyl)-n-methylamino]benzoicacid |
| 4-[[(2,4-diaminopteridin-6-yl)methyl]methylamino]benzoic acid (4-amino-n10-methylpteroic acid; apa) |
| 4-[[(2,4-diaminopteridin-6-yl)methyl](methyl)amino]benzoic acid |
| SY337270 |
| methotrexate ep impurity e |
| Excerpt | Reference | Relevance |
|---|---|---|
| " The 7-OHMTX level increased during each infusion and a Cmax of 19 mumol." | ( Pharmacokinetic study of methotrexate, folinic acid and their serum metabolites in children treated with high-dose methotrexate and leucovorin rescue. Breithaupt, H; Hartmann, R; Henze, G; Hepp, R; Wolfrom, C, 1990) | 0.28 |
| "9 l/kg/h and the mean terminal half-life was 51 min." | ( Pharmacokinetics and metabolism of the methotrexate metabolite 2, 4-diamino-N(10)-methylpteroic acid. Adamson, PC; Anderson, L; Balis, FM; Hawkins, M; McCully, C; Monitjo, KS; Salzer, WL; Sung, E; Widemann, BC, 2000) | 0.31 |
| Timeframe | Studies, This Drug (%) | All Drugs % |
|---|---|---|
| pre-1990 | 10 (43.48) | 18.7374 |
| 1990's | 4 (17.39) | 18.2507 |
| 2000's | 2 (8.70) | 29.6817 |
| 2010's | 6 (26.09) | 24.3611 |
| 2020's | 1 (4.35) | 2.80 |
| [information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] | ||
According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be weak demand-to-supply ratio for research on this compound.
| This Compound (11.51) All Compounds (24.57) |
| Publication Type | This drug (%) | All Drugs (%) |
|---|---|---|
| Trials | 0 (0.00%) | 5.53% |
| Reviews | 0 (0.00%) | 6.00% |
| Case Studies | 1 (4.35%) | 4.05% |
| Observational | 0 (0.00%) | 0.25% |
| Other | 22 (95.65%) | 84.16% |
| [information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] | ||