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Identification
NameAMPA
Accession NumberDB02057  (EXPT00513)
TypeSmall Molecule
GroupsExperimental
Description

AMPA is a specific agonist for the AMPA receptor.

Structure
Thumb
Synonyms
SynonymLanguageCode
1-Aminomethylphosphonic acidNot AvailableNot Available
Prescription ProductsNot Available
Generic Prescription ProductsNot Available
Over the Counter ProductsNot Available
International BrandsNot Available
Brand mixturesNot Available
SaltsNot Available
CategoriesNot Available
CAS number1066-51-9
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
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentL-alpha-amino acids
Alternative Parents
Substituents
  • L-alpha-amino acid
  • Aralkylamine
  • Amino fatty acid
  • Fatty acyl
  • Heteroaromatic compound
  • Oxazole
  • Isoxazole
  • Azole
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Hydrocarbon derivative
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Carbonyl group
  • Amine
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Pharmacology
IndicationNot Available
PharmacodynamicsNot Available
Mechanism of actionNot Available
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
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
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 substrateNon-inhibitor0.5709
CYP450 2D6 substrateNon-inhibitor0.9231
CYP450 2C19 substrateNon-inhibitor0.9026
CYP450 3A4 substrateNon-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
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 FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot 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 ReferenceNot Available
External Links
ATC CodesNot Available
AHFS CodesNot Available
PDB Entries
FDA labelNot Available
MSDSNot Available
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

Targets

1. Glutamate receptor 2

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
Glutamate receptor 2 P42262 Details

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
  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
  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

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Drug created on June 13, 2005 07:24 / Updated on September 16, 2013 17:17