Progabide (CHEM002285)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesTargets (3)XML
Record Information
Version1.0
Creation Date2009-07-21 20:27:47 UTC
Update Date2026-05-14 16:50:16 UTC
Accession NumberCHEM002285
Identification
Common NameProgabide
ClassSmall Molecule
DescriptionProgabide is an analog and prodrug of gamma-aminobutyric acid. It is commonly used in the treatment of epilepsy. It has agonistic activity for both the GABAA and GABAB receptors. Progabide has been investigated for many diseases besides epilepsy, including Parkinson's disease, schizophrenia, clinical depression and anxiety disorder with varying success.
Contaminant Sources
  • HMDB Contaminants - Urine
  • STOFF IDENT Compounds
  • T3DB toxins
Contaminant Type
  • Amide
  • Amine
  • Anticonvulsant
  • Antidepressant
  • Antidepressive Agent
  • Antidyskinetic
  • Antiparkinson Agent
  • Drug
  • Ester
  • GABA Agonist
  • Ketone
  • Metabolite
  • Organic Compound
  • Organochloride
  • Organofluoride
  • Synthetic Compound
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
HalogabideHMDB
GabreneHMDB
4-{[(4-chlorophenyl)[(1E)-3-fluoro-6-oxocyclohexa-2,4-dien-1-ylidene]methyl]amino}butanimidateGenerator
ProgabideMeSH
Chemical FormulaC17H16ClFN2O2
Average Molecular Mass334.773 g/mol
Monoisotopic Mass334.088 g/mol
CAS Registry Number62666-20-0
IUPAC Name4-{[(4-chlorophenyl)(5-fluoro-2-hydroxyphenyl)methylidene]amino}butanimidic acid
Traditional Nameprogabide
SMILESNC(=O)CCCN\C(C1=CC=C(Cl)C=C1)=C1/C=C(F)C=CC1=O
InChI IdentifierInChI=1S/C17H16ClFN2O2/c18-12-5-3-11(4-6-12)17(21-9-1-2-16(20)23)14-10-13(19)7-8-15(14)22/h3-8,10,21H,1-2,9H2,(H2,20,23)/b17-14+
InChI KeyDWEQWXSKOHHBNT-SAPNQHFASA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as o-quinomethanes. These are organic compounds containing a benzene ring conjugated to a methylidene group and a ketone at carbon atoms 1 and 2, respectively.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbonyl compounds
Direct ParentO-quinomethanes
Alternative Parents
Substituents
  • O-quinomethane
  • Chlorobenzene
  • Halobenzene
  • Aryl chloride
  • Aryl halide
  • Monocyclic benzene moiety
  • Benzenoid
  • Vinylogous amide
  • Carboximidic acid
  • Carboximidic acid derivative
  • Secondary aliphatic amine
  • Enamine
  • Fluoroalkene
  • Haloalkene
  • Secondary amine
  • Vinyl fluoride
  • Vinyl halide
  • Organopnictogen compound
  • Organic oxide
  • Amine
  • Organohalogen compound
  • Organochloride
  • Organofluoride
  • Organonitrogen compound
  • Hydrocarbon derivative
  • Organic nitrogen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting Point133-135°C
Boiling PointNot Available
Solubility70.9 mg/L
Predicted Properties
PropertyValueSource
Water Solubility0.0044 g/LALOGPS
logP2.68ALOGPS
logP1.8ChemAxon
logS-4.9ALOGPS
pKa (Strongest Acidic)15.32ChemAxon
pKa (Strongest Basic)4.01ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area72.19 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity91.22 m³·mol⁻¹ChemAxon
Polarizability33.21 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-000x-5091000000-45493775f8e316fed345Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00kr-1029000000-fc0da8ed87727a709a1fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-5059000000-63dcad42741a847ae8ffSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000f-9520000000-da113f6ba6c4a6d23a82Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0129000000-3de1ea119383317ba355Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000y-6289000000-b086ccb10b99604720a8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9330000000-2be76f698dbbc120b6b1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0009000000-513fcdf8c10f3b29cd13Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0f80-0094000000-8c5c8a6b47f57d482e91Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01q9-0090000000-990d46a622dd2ff2264dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0029000000-8d3aa9ae2fda5750dbf2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000t-2196000000-d2a509d2c58ae1850d29Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-01qj-3490000000-5a245325ccd99decd7c9Spectrum
Toxicity Profile
Route of ExposureWell absorbed with a bioavailability of 60%
Mechanism of ToxicityProgabide binds to both GABAA and GABAB receptors located on the terminals of primary afferent fibers. Binding to GABAA results in an increased affinity of the GABA receptor for the amino acid, an augmented flux of chloride ions across the terminal membrane, and an increase in the amount of presynaptic inhibition. Activation of the GABAB receptors retards the influx of calcium ions into the terminals, thereby reducing the evoked release of excitatory amino acids and possibly other transmitters.
MetabolismHepatic Half Life: 4 hours
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesIndicated for the treatment of epilepsy.
Minimum Risk LevelNot Available
Health EffectsMay cause a potentially dangerous rash that may develop into Stevens Johnson syndrome, an extremely rare but potentially fatal skin disease.
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0014975
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkProgabide
Chemspider ID4514729
ChEBI IDNot Available
PubChem Compound ID5361323
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Bartholini G, Scatton B, Zivkovic B, Lloyd KG: GABA receptor agonists and extrapyramidal motor function: therapeutic implications for Parkinson's disease. Adv Neurol. 1987;45:79-83.