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Record Information
Version4.0
Creation Date2012-09-06 15:16:50 UTC
Update Date2017-09-27 08:27:46 UTC
HMDB IDHMDB0014975
Secondary Accession Numbers
  • HMDB14975
Metabolite Identification
Common NameProgabide
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.
Structure
Thumb
Synonyms
ValueSource
HalogabideHMDB
GabreneMeSH
Chemical FormulaC17H16ClFN2O2
Average Molecular Weight334.773
Monoisotopic Molecular Weight334.088433678
IUPAC Name4-{[(4-chlorophenyl)[(1E)-3-fluoro-6-oxocyclohexa-2,4-dien-1-ylidene]methyl]amino}butanamide
Traditional Nameprogabide
CAS Registry Number62666-20-0
SMILES
NC(=O)CCCN\C(C1=CC=C(Cl)C=C1)=C1/C=C(F)C=CC1=O
InChI Identifier
InChI=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
DescriptionThis compound belongs to the class of chemical entities 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.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganic oxygen compounds
Sub ClassOrganooxygen 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
Ontology
Disposition

Biological Location:

  Subcellular:

  Biofluid and excreta:

Role

Industrial application:

  Pharmaceutical industry:

Indirect biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point133 - 135 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.0044 g/LNot Available
LogP2.6Not Available
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 RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00kr-1029000000-fc0da8ed87727a709a1fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-5059000000-63dcad42741a847ae8ffView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000f-9520000000-da113f6ba6c4a6d23a82View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0129000000-3de1ea119383317ba355View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000y-6289000000-b086ccb10b99604720a8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9330000000-2be76f698dbbc120b6b1View in MoNA
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid Locations
  • Blood
  • Urine
Tissue LocationNot Available
PathwaysNot Available
NameSMPDB/PathwhizKEGG
No entries found
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00837 details
UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00837 details
Abnormal Concentrations
Not Available
Predicted Concentrations
BiofluidValueOriginal ageOriginal sexOriginal conditionComments
Blood0-3 uMAdult (>18 years old)BothNormalPredicted based on drug qualities
Blood0-1 umol/mmol creatinineAdult (>18 years old)BothNormalPredicted based on drug qualities
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00837
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID4514729
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkProgabide
METLIN IDNot Available
PubChem Compound5361323
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not 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. [PubMed:3030072 ]

Enzymes

General function:
Involved in G-protein coupled receptor activity
Specific function:
Isoform 1E function may be to regulate the availability of functional GABA-B-R1A/GABA-B-R2 heterodimers by competing for GABA-B-R2 dimerization. This could explain the observation that certain small molecule ligands exhibit differential affinity for central versus peripheral sites
Gene Name:
GABBR1
Uniprot ID:
Q9UBS5
Molecular weight:
108319.4
References
  1. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
  2. Agmo A, Belzung C: Interactions between dopamine and GABA in the control of ambulatory activity and neophobia in the mouse. Pharmacol Biochem Behav. 1998 Jan;59(1):239-47. [PubMed:9443561 ]
  3. Fadda F, Mosca E, Meloni R, Gessa GL: Suppression by progabide of ethanol withdrawal syndrome in rats. Eur J Pharmacol. 1985 Mar 12;109(3):321-5. [PubMed:2985405 ]
General function:
Involved in ion transport
Specific function:
GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel
Gene Name:
GABRA1
Uniprot ID:
P14867
Molecular weight:
51801.4
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. Agmo A, Belzung C: Interactions between dopamine and GABA in the control of ambulatory activity and neophobia in the mouse. Pharmacol Biochem Behav. 1998 Jan;59(1):239-47. [PubMed:9443561 ]
  4. Grech DM, Balster RL: Pentobarbital-like discriminative stimulus effects of direct GABA agonists in rats. Psychopharmacology (Berl). 1993;110(3):295-301. [PubMed:7831422 ]
  5. Fadda F, Mosca E, Meloni R, Gessa GL: Suppression by progabide of ethanol withdrawal syndrome in rats. Eur J Pharmacol. 1985 Mar 12;109(3):321-5. [PubMed:2985405 ]