Compounds > 2-amino-5-phosphonomethyl(1,1'-biphenyl)-3-propanoic acid
Page last updated: 2024-12-08

2-amino-5-phosphonomethyl(1,1'-biphenyl)-3-propanoic acid

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Description

2-amino-5-phosphonomethyl(1,1'-biphenyl)-3-propanoic acid: structure in first source; NMDA receptor antagonist [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID159489
CHEMBL ID1907813
SCHEMBL ID794085
MeSH IDM0208393

Synonyms (10)

Synonym
sdz eab 515
118077-09-1
(2s)-2-amino-3-[3-phenyl-5-(phosphonomethyl)phenyl]propanoic acid
(1,1'-biphenyl)-3-propanoic acid, alpha-amino-5-(phosphonomethyl)-, (s)-
2-amino-5-phosphonomethyl(1,1'-biphenyl)-3-propanoic acid
sdz-eab-515
eab 515
CHEMBL1907813
SCHEMBL794085
(s)-alpha-amino-5-phosphonomethyl[1,1'-biphenyl]-3-propanoic acid

Research Excerpts

Bioavailability

ExcerptReferenceRelevance
" The lead compound SDZ EAB 515 was found to inhibit L-phenylalanine uptake by the large neutral amino acid carrier in vitro and in vivo; active transport may thus confer a good bioavailability to this class of compounds."( Biphenyl-derivatives of 2-amino-7-phosphono-heptanoic acid, a novel class of potent competitive N-methyl-D-aspartate receptor antagonists--II. Pharmacological characterization in vivo.
Campbell, E; Fricker, G; Jenner, P; Lemaire, M; McAllister, KH; Müller, W; Neijt, HC; Park, CK; Perkins, M; Rudin, M; Sauter, A; Smith, L; Urwyler, S; Wiederhold, KH, 1996)		0.29

Dosage Studied

ExcerptRelevanceReference
" Upon intracerebroventricular administration, the observed steady-state cortical extracellular fluid concentrations of EAB 515 were over 100-fold higher than those observed following intravenous administration, when normalized for the dosing rate."( Modeling the route of administration-based enhancement in the brain delivery of EAB 515, studied by microdialysis.
Brundage, RC; Lemaire, M; Malhotra, BK; Sawchuk, RJ, 1997)		0.3
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (16)

Assay IDTitleYearJournalArticle
AID118471Maximal electroshock (MES) results in mice by iv administration of 10 mg/kg expressed as number of animals protected by total 5 animals tested after 15 min was reported1995Journal of medicinal chemistry, May-26, Volume: 38, Issue:11
Potent, orally active, competitive N-methyl-D-aspartate (NMDA) receptor antagonists are substrates for a neutral amino acid uptake system in Chinese hamster ovary cells.
AID118473Maximal electroshock (MES) results in mice by iv administration of 10 mg/kg expressed as number of animals protected by total 5 animals tested after 2 hr was reported1995Journal of medicinal chemistry, May-26, Volume: 38, Issue:11
Potent, orally active, competitive N-methyl-D-aspartate (NMDA) receptor antagonists are substrates for a neutral amino acid uptake system in Chinese hamster ovary cells.
AID118475Maximal electroshock (MES) results in mice by iv administration of 3 mg/kg expressed as number of animals protected by total 5 animals tested after 1 hr was reported1995Journal of medicinal chemistry, May-26, Volume: 38, Issue:11
Potent, orally active, competitive N-methyl-D-aspartate (NMDA) receptor antagonists are substrates for a neutral amino acid uptake system in Chinese hamster ovary cells.
AID118476Maximal electroshock (MES) results in mice by iv administration of 3 mg/kg expressed as number of animals protected by total 5 animals tested after 2 hr was reported1995Journal of medicinal chemistry, May-26, Volume: 38, Issue:11
Potent, orally active, competitive N-methyl-D-aspartate (NMDA) receptor antagonists are substrates for a neutral amino acid uptake system in Chinese hamster ovary cells.
AID110233Maximal electroshock (MES) results in mice by iv administration of 10 mg/kg expressed as number of animals with ataxia total 5 animals tested after 1 hr was reported1995Journal of medicinal chemistry, May-26, Volume: 38, Issue:11
Potent, orally active, competitive N-methyl-D-aspartate (NMDA) receptor antagonists are substrates for a neutral amino acid uptake system in Chinese hamster ovary cells.
AID144770Inhibition of NMDA receptor binding affinity in rat brain synaptosomal membrane using [3H]glutamate as radioligand1995Journal of medicinal chemistry, May-26, Volume: 38, Issue:11
Potent, orally active, competitive N-methyl-D-aspartate (NMDA) receptor antagonists are substrates for a neutral amino acid uptake system in Chinese hamster ovary cells.
AID110235Maximal electroshock (MES) results in mice by iv administration of 3 mg/kg expressed as number of animals with ataxia by total 5 animals tested after 15 min was reported1995Journal of medicinal chemistry, May-26, Volume: 38, Issue:11
Potent, orally active, competitive N-methyl-D-aspartate (NMDA) receptor antagonists are substrates for a neutral amino acid uptake system in Chinese hamster ovary cells.
AID143313Inhibition of receptor binding affinity in rat brain synaptosomal membrane measured using LDH release1995Journal of medicinal chemistry, May-26, Volume: 38, Issue:11
Potent, orally active, competitive N-methyl-D-aspartate (NMDA) receptor antagonists are substrates for a neutral amino acid uptake system in Chinese hamster ovary cells.
AID144772Inhibition of NMDA receptor binding affinity in rat brain synaptosomal membrane using [3H]glycine as radioligand1995Journal of medicinal chemistry, May-26, Volume: 38, Issue:11
Potent, orally active, competitive N-methyl-D-aspartate (NMDA) receptor antagonists are substrates for a neutral amino acid uptake system in Chinese hamster ovary cells.
AID110232Maximal electroshock (MES) results in mice by iv administration of 10 mg/kg expressed as number of animals with ataxia total 5 animals tested after 15 min was reported1995Journal of medicinal chemistry, May-26, Volume: 38, Issue:11
Potent, orally active, competitive N-methyl-D-aspartate (NMDA) receptor antagonists are substrates for a neutral amino acid uptake system in Chinese hamster ovary cells.
AID110236Maximal electroshock (MES) results in mice by iv administration of 3 mg/kg expressed as number of animals with ataxia by total 5 animals tested after 1 hr was reported1995Journal of medicinal chemistry, May-26, Volume: 38, Issue:11
Potent, orally active, competitive N-methyl-D-aspartate (NMDA) receptor antagonists are substrates for a neutral amino acid uptake system in Chinese hamster ovary cells.
AID118474Maximal electroshock (MES) results in mice by iv administration of 3 mg/kg expressed as number of animals protected by total 5 animals tested after 15 min was reported1995Journal of medicinal chemistry, May-26, Volume: 38, Issue:11
Potent, orally active, competitive N-methyl-D-aspartate (NMDA) receptor antagonists are substrates for a neutral amino acid uptake system in Chinese hamster ovary cells.
AID110237Maximal electroshock (MES) results in mice by iv administration of 3 mg/kg expressed as number of animals with ataxia total 5 animals tested after 2 hr was reported1995Journal of medicinal chemistry, May-26, Volume: 38, Issue:11
Potent, orally active, competitive N-methyl-D-aspartate (NMDA) receptor antagonists are substrates for a neutral amino acid uptake system in Chinese hamster ovary cells.
AID144898Inhibition of receptor binding affinity in rat brain synaptosomal membrane was determined by [3H]-CGP- 39653 as radioligand1995Journal of medicinal chemistry, May-26, Volume: 38, Issue:11
Potent, orally active, competitive N-methyl-D-aspartate (NMDA) receptor antagonists are substrates for a neutral amino acid uptake system in Chinese hamster ovary cells.
AID118472Maximal electroshock (MES) results in mice by iv administration of 10 mg/kg expressed as number of animals protected by total 5 animals tested after 1 hr was reported1995Journal of medicinal chemistry, May-26, Volume: 38, Issue:11
Potent, orally active, competitive N-methyl-D-aspartate (NMDA) receptor antagonists are substrates for a neutral amino acid uptake system in Chinese hamster ovary cells.
AID110234Maximal electroshock (MES) results in mice by iv administration of 10 mg/kg expressed as number of animals with ataxia total 5 animals tested after 2 hr was reported1995Journal of medicinal chemistry, May-26, Volume: 38, Issue:11
Potent, orally active, competitive N-methyl-D-aspartate (NMDA) receptor antagonists are substrates for a neutral amino acid uptake system in Chinese hamster ovary cells.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (9)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's9 (100.00)18.2507
2000's0 (0.00)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: 12.15

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 Index12.15 (24.57)
Research Supply Index2.30 (2.92)
Research Growth Index4.45 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (12.15)

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%
Other9 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
glycine
[no description available]		1.9810alpha-amino acid;
amino acid zwitterion;
proteinogenic amino acid;
serine family amino acid		EC 2.1.2.1 (glycine hydroxymethyltransferase) inhibitor;
fundamental metabolite;
hepatoprotective agent;
micronutrient;
neurotransmitter;
NMDA receptor agonist;
nutraceutical
2-amino-5-phosphonovalerate
2-Amino-5-phosphonovalerate: The D-enantiomer is a potent and specific antagonist of NMDA glutamate receptors (RECEPTORS, N-METHYL-D-ASPARTATE). The L form is inactive at NMDA receptors but may affect the AP4 (2-amino-4-phosphonobutyrate; APB) excitatory amino acid receptors.		2.6830non-proteinogenic alpha-amino acidNMDA receptor antagonist
3-(2-carboxypiperazin-4-yl)propyl-1-phosphonic acid
3-(2-carboxypiperazin-4-yl)propyl-1-phosphonic acid: structure given in first source; NMDA receptor antagonist		1.9810
2-amino-7-phosphonoheptanoic acid
2-amino-7-phosphonoheptanoic acid: (D)-isomer active as an antagonist of N-methyl-D-aspartate excitation of central neurons; (L)-isomer inactive; RN given refers to cpd without isomeric designation		1.9810
probenecid
Probenecid: The prototypical uricosuric agent. It inhibits the renal excretion of organic anions and reduces tubular reabsorption of urate. Probenecid has also been used to treat patients with renal impairment, and, because it reduces the renal tubular excretion of other drugs, has been used as an adjunct to antibacterial therapy.. probenecid : A sulfonamide in which the nitrogen of 4-sulfamoylbenzoic acid is substituted with two propyl groups.		1.9810benzoic acids;
sulfonamide		uricosuric drug
levodopa
Levodopa: The naturally occurring form of DIHYDROXYPHENYLALANINE and the immediate precursor of DOPAMINE. Unlike dopamine itself, it can be taken orally and crosses the blood-brain barrier. It is rapidly taken up by dopaminergic neurons and converted to DOPAMINE. It is used for the treatment of PARKINSONIAN DISORDERS and is usually given with agents that inhibit its conversion to dopamine outside of the central nervous system.. L-dopa : An optically active form of dopa having L-configuration. Used to treat the stiffness, tremors, spasms, and poor muscle control of Parkinson's disease		1.9910amino acid zwitterion;
dopa;
L-tyrosine derivative;
non-proteinogenic L-alpha-amino acid		allelochemical;
antidyskinesia agent;
antiparkinson drug;
dopaminergic agent;
hapten;
human metabolite;
mouse metabolite;
neurotoxin;
plant growth retardant;
plant metabolite;
prodrug
phenylalanine
Phenylalanine: An essential aromatic amino acid that is a precursor of MELANIN; DOPAMINE; noradrenalin (NOREPINEPHRINE), and THYROXINE.. L-phenylalanine : The L-enantiomer of phenylalanine.. phenylalanine : An aromatic amino acid that is alanine in which one of the methyl hydrogens is substituted by a phenyl group.		1.9810amino acid zwitterion;
erythrose 4-phosphate/phosphoenolpyruvate family amino acid;
L-alpha-amino acid;
phenylalanine;
proteinogenic amino acid		algal metabolite;
EC 3.1.3.1 (alkaline phosphatase) inhibitor;
Escherichia coli metabolite;
human xenobiotic metabolite;
micronutrient;
mouse metabolite;
nutraceutical;
plant metabolite;
Saccharomyces cerevisiae metabolite
n-methylaspartate
N-Methylaspartate: An amino acid that, as the D-isomer, is the defining agonist for the NMDA receptor subtype of glutamate receptors (RECEPTORS, NMDA).. N-methyl-D-aspartic acid : An aspartic acid derivative having an N-methyl substituent and D-configuration.		1.9810amino dicarboxylic acid;
D-alpha-amino acid;
D-aspartic acid derivative;
secondary amino compound		neurotransmitter agent
glutamic acid
Glutamic Acid: A non-essential amino acid naturally occurring in the L-form. Glutamic acid is the most common excitatory neurotransmitter in the CENTRAL NERVOUS SYSTEM.. glutamic acid : An alpha-amino acid that is glutaric acid bearing a single amino substituent at position 2.		1.9810glutamic acid;
glutamine family amino acid;
L-alpha-amino acid;
proteinogenic amino acid		Escherichia coli metabolite;
ferroptosis inducer;
micronutrient;
mouse metabolite;
neurotransmitter;
nutraceutical
selfotel
selfotel: a N-methyl-D-aspartate (NMDA) antagonist; used to treat stroke-induced impairment		1.9910non-proteinogenic alpha-amino acid
npc 12626
NPC 12626: N-methyl-D-aspartate receptor antagonist; structure given in first source; NPC 17742, the (2R,4R,5S)-isomer, is the most potent isomer in the mixture NPC 12626		1.9910
sdz 220-581
alpha-amino-2'-chloro-5-(phosphonomethyl)(1,1'-biphenyl)-3-propanoic acid: structure given in first source; RN given refers to (S)-isomer		210
ly 274614
LY 235959: RN refers to (3S-(3alpha,4aalpha,6beta,8aalpha))-isomer		1.9910
homoquinolinic acid
homoquinolinic acid: structure given in first source		1.9910
3-(2-carboxypiperazine-4-yl)-1-propenyl-1-phosphonic acid
SDZ EAA 494: N-methyl-D-aspartate receptor antagonist		2.420
cgp 39653
CGP 39653: NMDA receptor antagonist; structure given in first source		1.9810
ConditionIndicatedRelationship StrengthStudiesTrials
Sensitivity and Specificity
Binary classification measures to assess test results. Sensitivity or recall rate is the proportion of true positives. Specificity is the probability of correctly determining the absence of a condition. (From Last, Dictionary of Epidemiology, 2d ed)		01.9910
Hyperactivity, Motor
[description not available]		0210