Identification
Name(S)-AMPA
Accession NumberDB02057  (EXPT00513)
TypeSmall Molecule
GroupsExperimental
Description

AMPA is a specific agonist for the AMPA receptor.

Structure
Thumb
Synonyms
(S)-alpha-amino-3-hydroxy-5-methyl-4-isoxazolepropionic acid
External IDs Not Available
Product Ingredients Not Available
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International BrandsNot Available
Brand mixturesNot Available
CategoriesNot Available
UNII9280SC28GD
CAS number83643-88-3
WeightAverage: 186.1653
Monoisotopic: 186.064056818
Chemical FormulaC7H10N2O4
InChI KeyUUDAMDVQRQNNHZ-YFKPBYRVSA-N
InChI
InChI=1S/C7H10N2O4/c1-3-4(6(10)9-13-3)2-5(8)7(11)12/h5H,2,8H2,1H3,(H,9,10)(H,11,12)/t5-/m0/s1
IUPAC Name
(2S)-2-amino-3-(3-hydroxy-5-methyl-1,2-oxazol-4-yl)propanoic acid
SMILES
CC1=C(C[C@H](N)C(O)=O)C(O)=NO1
Pharmacology
IndicationNot Available
Structured Indications Not Available
PharmacodynamicsNot Available
Mechanism of action
TargetKindPharmacological actionActionsOrganismUniProt ID
Glutamate receptor 2ProteinunknownNot AvailableHumanP42262 details
Related Articles
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organismsNot Available
PathwaysNot Available
Pharmacogenomic Effects/ADRs Not Available
Interactions
Drug Interactions Not Available
Food InteractionsNot Available
References
Synthesis Reference

Wilfried Lubisch, Berthold Behl, Hans-Peter Hofmann, Laszlo Szabo, "Pyrrolyl quinoxalindiones their production and use as AMPA receptor antagonists." U.S. Patent US6277850, issued June, 1996.

US6277850
General ReferencesNot Available
External Links
ATC CodesNot Available
AHFS CodesNot Available
PDB Entries
FDA labelNot Available
MSDSNot Available
Clinical Trials
Clinical Trials Not Available
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental PropertiesNot Available
Predicted Properties
PropertyValueSource
Water Solubility24.5 mg/mLALOGPS
logP-2.5ALOGPS
logP-2.3ChemAxon
logS-0.88ALOGPS
pKa (Strongest Acidic)1.56ChemAxon
pKa (Strongest Basic)8.9ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area109.58 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity44 m3·mol-1ChemAxon
Polarizability17.1 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9774
Blood Brain Barrier-0.5082
Caco-2 permeable-0.701
P-glycoprotein substrateNon-substrate0.5828
P-glycoprotein inhibitor INon-inhibitor0.9802
P-glycoprotein inhibitor IINon-inhibitor0.9972
Renal organic cation transporterNon-inhibitor0.9574
CYP450 2C9 substrateNon-substrate0.8715
CYP450 2D6 substrateNon-substrate0.8076
CYP450 3A4 substrateNon-substrate0.6301
CYP450 1A2 substrateNon-inhibitor0.9046
CYP450 2C9 inhibitorNon-inhibitor0.5709
CYP450 2D6 inhibitorNon-inhibitor0.9231
CYP450 2C19 inhibitorNon-inhibitor0.9026
CYP450 3A4 inhibitorNon-inhibitor0.904
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9532
Ames testNon AMES toxic0.6071
CarcinogenicityNon-carcinogens0.8944
BiodegradationNot ready biodegradable0.7339
Rat acute toxicity2.4011 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9962
hERG inhibition (predictor II)Non-inhibitor0.9661
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganic acids and derivatives
Sub ClassCarboxylic acids and derivatives
Direct ParentL-alpha-amino acids
Alternative ParentsAralkylamines / Isoxazoles / Heteroaromatic compounds / Lactams / Amino acids / Oxacyclic compounds / Monocarboxylic acids and derivatives / Carboxylic acids / Azacyclic compounds / Organopnictogen compounds
SubstituentsL-alpha-amino acid / Aralkylamine / Azole / Isoxazole / Heteroaromatic compound / Lactam / Amino acid / Carboxylic acid / Monocarboxylic acid or derivatives / Organoheterocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available

Targets

Kind
Protein
Organism
Human
Pharmacological action
unknown
General Function:
Ionotropic glutamate receptor activity
Specific Function:
Receptor for glutamate that functions as ligand-gated ion channel in the central nervous system and plays an important role in excitatory synaptic transmission. L-glutamate acts as an excitatory neurotransmitter at many synapses in the central nervous system. Binding of the excitatory neurotransmitter L-glutamate induces a conformation change, leading to the opening of the cation channel, and t...
Gene Name:
GRIA2
Uniprot ID:
P42262
Molecular Weight:
98820.32 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
  3. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235 ]
Drug created on June 13, 2005 07:24 / Updated on July 18, 2017 17:05