Page last updated: 2024-11-04

2-amino-6-phosphonohexanoic acid

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Description

2-Amino-6-phosphonohexanoic acid (APHA) is a synthetic analogue of the neurotransmitter glutamate. It acts as a potent and selective NMDA receptor antagonist, blocking the influx of calcium ions into neurons. APHA has been studied as a potential therapeutic agent for various neurological disorders, including epilepsy, Alzheimer's disease, and stroke, due to its ability to modulate neuronal activity. Its synthesis involves several steps, including the reaction of 6-aminohexanoic acid with phosphorus oxychloride. APHA has been shown to exhibit neuroprotective effects in animal models of stroke and epilepsy, suggesting its potential as a therapeutic agent. However, further research is necessary to evaluate its safety and efficacy in humans.'
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2-amino-6-phosphonohexanoic acid: RN given refers to DL-isomer [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID2927
CHEMBL ID29587
SCHEMBL ID1978027
MeSH IDM0126974

Synonyms (24)

Synonym
2-amino-6-phosphono-hexanoic acid
6-phosphononorleucine
78944-89-5
dl-norleucine, 6-phosphono-
NCI60_025600
nsc672104
nsc-672104
2-amino-6-phosphonohexanoic acid
CHEMBL29587
dl-2-amino-6-phosphonohexanoic acid
l-ap6
norleucine,6-phosphono-
SCHEMBL1978027
dl-2-amino-6-phosphonohexanoicacid
AKOS027382530
STL526852
DTXSID00913181
FT-0706121
AKOS037494568
(r)-(-)-2-amino-6-phosphonohexanoicacidhydrate
dl-ap6
2-amino-6-phosphonohexanoicacid
CS-0020493
HY-100843
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Protein Targets (7)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Glutamate receptor ionotropic, NMDA 1 Rattus norvegicus (Norway rat)Ki0.52100.00030.86666.6900AID143147; AID143904
Glutamate receptor ionotropic, NMDA 2A Rattus norvegicus (Norway rat)Ki0.52100.00030.68056.6900AID143147; AID143904
Glutamate receptor ionotropic, NMDA 2BRattus norvegicus (Norway rat)Ki0.52100.00030.70716.6900AID143147; AID143904
Glutamate receptor ionotropic, NMDA 2CRattus norvegicus (Norway rat)Ki0.52100.00030.81966.6900AID143147; AID143904
Glutamate receptor ionotropic, NMDA 2DRattus norvegicus (Norway rat)Ki0.52100.00030.70726.6900AID143147; AID143904
Glutamate receptor ionotropic, NMDA 3BRattus norvegicus (Norway rat)Ki0.52100.00030.70726.6900AID143147; AID143904
Glutamate receptor ionotropic, NMDA 3ARattus norvegicus (Norway rat)Ki0.52100.00030.70726.6900AID143147; AID143904
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Ceullar Components (2)

Processvia Protein(s)Taxonomy
endoplasmic reticulum membraneGlutamate receptor ionotropic, NMDA 1 Rattus norvegicus (Norway rat)
plasma membraneGlutamate receptor ionotropic, NMDA 1 Rattus norvegicus (Norway rat)
endoplasmic reticulum membraneGlutamate receptor ionotropic, NMDA 2A Rattus norvegicus (Norway rat)
plasma membraneGlutamate receptor ionotropic, NMDA 2A Rattus norvegicus (Norway rat)
endoplasmic reticulum membraneGlutamate receptor ionotropic, NMDA 2BRattus norvegicus (Norway rat)
plasma membraneGlutamate receptor ionotropic, NMDA 2BRattus norvegicus (Norway rat)
endoplasmic reticulum membraneGlutamate receptor ionotropic, NMDA 2CRattus norvegicus (Norway rat)
plasma membraneGlutamate receptor ionotropic, NMDA 2CRattus norvegicus (Norway rat)
endoplasmic reticulum membraneGlutamate receptor ionotropic, NMDA 2DRattus norvegicus (Norway rat)
plasma membraneGlutamate receptor ionotropic, NMDA 2DRattus norvegicus (Norway rat)
endoplasmic reticulum membraneGlutamate receptor ionotropic, NMDA 3BRattus norvegicus (Norway rat)
plasma membraneGlutamate receptor ionotropic, NMDA 3BRattus norvegicus (Norway rat)
endoplasmic reticulum membraneGlutamate receptor ionotropic, NMDA 3ARattus norvegicus (Norway rat)
plasma membraneGlutamate receptor ionotropic, NMDA 3ARattus norvegicus (Norway rat)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (7)

Assay IDTitleYearJournalArticle
AID42542sensitization of CA1 pyramidal neurons by 2 to depolarizations by L-AP4, L-AP5 and L-AP6 before exposure to quisqualic acid1994Journal of medicinal chemistry, Nov-11, Volume: 37, Issue:23
Synthesis of oxadiazolidinedione derivatives as quisqualic acid analogues and their evaluation at a quisqualate-sensitized site in the rat hippocampus.
AID74396Concentration required to inhibit glucosamine-6-phosphate synthase (GFAT) isolated from Candida albicans2002Bioorganic & medicinal chemistry letters, Sep-16, Volume: 12, Issue:18
Multisubstrate analogue inhibitors of glucosamine-6-phosphate synthase from Candida albicans.
AID42544sensitization of CA1 pyramidal neurons to depolarizations by L-AP6 after exposure to quisqualic acid1994Journal of medicinal chemistry, Nov-11, Volume: 37, Issue:23
Synthesis of oxadiazolidinedione derivatives as quisqualic acid analogues and their evaluation at a quisqualate-sensitized site in the rat hippocampus.
AID144456Displacement of [3H]CPP from N-methyl-D-aspartate glutamate receptor in rat brain membrane1992Journal of medicinal chemistry, Apr-17, Volume: 35, Issue:8
Generation of N-methyl-D-aspartate agonist and competitive antagonist pharmacophore models. Design and synthesis of phosphonoalkyl-substituted tetrahydroisoquinolines as novel antagonists.
AID42541sensitization of CA1 pyramidal neurons by 2 to depolarizations by L-AP4, L-AP5 and L-AP6 after reversal with L-alpha-AA1994Journal of medicinal chemistry, Nov-11, Volume: 37, Issue:23
Synthesis of oxadiazolidinedione derivatives as quisqualic acid analogues and their evaluation at a quisqualate-sensitized site in the rat hippocampus.
AID143904Compound was evaluated for its ability to displace [3H]CPP ligand from N-methyl-D-aspartate (NMDA) receptor1992Journal of medicinal chemistry, May-01, Volume: 35, Issue:9
Modeling of competitive phosphono amino acid NMDA receptor antagonists.
AID143147Compound was evaluated for its ability to displace [3H]CPP or [3H]-CGS- 19755 ligand from N-methyl-D-aspartate glutamate receptor1992Journal of medicinal chemistry, May-01, Volume: 35, Issue:9
Modeling of competitive phosphono amino acid NMDA receptor antagonists.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (10)

TimeframeStudies, This Drug (%)All Drugs %
pre-19903 (30.00)18.7374
1990's5 (50.00)18.2507
2000's2 (20.00)29.6817
2010's0 (0.00)24.3611
2020's0 (0.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 11.97

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.

MetricThis Compound (vs All)
Research Demand Index11.97 (24.57)
Research Supply Index2.40 (2.92)
Research Growth Index4.37 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (11.97)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews0 (0.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other10 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]