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    Progabide

    INTERMEDIATES

    PharmaCompass
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    2D Structure
    Also known as: 62666-20-0, Halogabide, Gabren, Gabrene, Progabidum [inn-latin], Progabida [inn-spanish]
    Molecular Formula
    C17H16ClFN2O2
    Molecular Weight
    334.8  g/mol
    InChI Key
    IBALRBWGSVJPAP-UHFFFAOYSA-N
    FDA UNII
    38C836J57Z
    Progabide 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. In clinical trials, progabide has been investigated for Parkinson's disease, schizophrenia, clinical depression and anxiety disorder; its therapeutic effectiveness in these conditions is not fully elucidated.
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    4-[[(4-chlorophenyl)-(5-fluoro-2-hydroxyphenyl)methylidene]amino]butanamide
    2.1.2 InChI
    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/h3-8,10,22H,1-2,9H2,(H2,20,23)
    2.1.3 InChI Key
    IBALRBWGSVJPAP-UHFFFAOYSA-N
    2.1.4 Canonical SMILES
    C1=CC(=CC=C1C(=NCCCC(=O)N)C2=C(C=CC(=C2)F)O)Cl
    2.2 Other Identifiers
    2.2.1 UNII
    38C836J57Z
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. Gabrene

    2. Sl 76002

    2.3.2 Depositor-Supplied Synonyms

    1. 62666-20-0

    2. Halogabide

    3. Gabren

    4. Gabrene

    5. Progabidum [inn-latin]

    6. Progabida [inn-spanish]

    7. 4-(((4-chlorophenyl)(5-fluoro-2-hydroxyphenyl)methylene)amino)butanamide

    8. Sl 76002

    9. Progabide, (z)-

    10. Sl-76002

    11. Sl 76 002

    12. 112e50torv

    13. 4-[[(e)-(4-chlorophenyl)-(3-fluoro-6-oxocyclohexa-2,4-dien-1-ylidene)methyl]amino]butanamide

    14. Butanamide, 4-(((4-chlorophenyl)(5-fluoro-2-hydroxyphenyl)methylene)amino)-

    15. 38c836j57z

    16. Progabida

    17. Progabidum

    18. Progabide [usan:ban:inn]

    19. Progabide [usan:inn:ban]

    20. Progabide (usan/inn)

    21. Sl 76-002

    22. Butanamide, 4-(((4-chlorophenyl)(5-fluoro-2-hydroxyphenyl)methylene)amino)-, (z)-

    23. Butanamide, 4-[[(4-chlorophenyl)(5-fluoro-2-hydroxyphenyl)methylene]amino]-, (e)-

    24. 104880-78-6

    25. 90656-51-2

    26. Gabren (tn)

    27. Einecs 263-679-4

    28. Brn 2339306

    29. Unii-38c836j57z

    30. 4-((alpha-(p-chlorophenyl)-5-fluorosalicylidene)amino)butyramide

    31. 4-(alpha-(p-chlorophenyl)-5-fluoro-2-hydroxybenzylideneamino)butyramide

    32. 4-[[(z)-(4-chlorophenyl)-(3-fluoro-6-oxocyclohexa-2,4-dien-1-ylidene)methyl]amino]butanamide

    33. Progabide [inn]

    34. Progabide [mi]

    35. Progabide [usan]

    36. Progabide [mart.]

    37. Butyramide, 4-(alpha-(p-chlorophenyl)-5-fluoro-2-hydroxybenzylideneamino)-

    38. Progabide [who-dd]

    39. Unii-112e50torv

    40. Schembl35328

    41. Schembl35329

    42. Schembl340485

    43. Schembl341677

    44. Chembl287631

    45. Chembl4796538

    46. Dtxsid00878140

    47. Chebi:135422

    48. Hy-a0173

    49. Zinc13519914

    50. Zinc18153101

    51. Akos016013958

    52. Db00837

    53. Cs-0017513

    54. Ft-0674038

    55. D05621

    56. 666p200

    57. A833914

    58. Q426524

    59. 4-((.alpha.-(p-chlorophenyl)-5-fluorosalicylidene)amino)butyramide

    60. 4-[(4-chlorophenyl) (5-fluoro-2-hydroxy-phenyl)-methylene]amino Butanamide

    61. 4-[[(4-chlorophenyl)-(5-fluoro-2-hydroxyphenyl)methylidene]amino]butanamide

    62. 4-[[(4-chlorophenyl)( 5-fluoro-2-hydroxyphenyl)-methylene]amino ]butanamide

    63. 4-[[(z)-(4-chlorophenyl)-(3-fluoro-6-oxo-cyclohexa-2,4-dien-1-ylidene)methyl]amino]butanamide;progabide

    64. 4-{[(4-chlorophenyl)[(1e)-3-fluoro-6-oxocyclohexa-2,4-dien-1-ylidene]methyl]amino}butanamide

    2.4 Create Date
    2005-08-08
    3 Chemical and Physical Properties
    Molecular Weight 334.8 g/mol
    Molecular Formula C17H16ClFN2O2
    XLogP33
    Hydrogen Bond Donor Count2
    Hydrogen Bond Acceptor Count4
    Rotatable Bond Count6
    Exact Mass334.0884336 g/mol
    Monoisotopic Mass334.0884336 g/mol
    Topological Polar Surface Area75.7 Ų
    Heavy Atom Count23
    Formal Charge0
    Complexity425
    Isotope Atom Count0
    Defined Atom Stereocenter Count0
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    4 Drug and Medication Information
    4.1 Drug Indication

    Indicated for the treatment of epilepsy.

    5 Pharmacology and Biochemistry
    5.1 Pharmacology

    Progabide, a fatty acid derivative, is a GABA receptor agonist used to treat the symptoms of epilepsy.

    5.2 MeSH Pharmacological Classification

    Anticonvulsants

    Drugs used to prevent SEIZURES or reduce their severity. (See all compounds classified as Anticonvulsants.)

    Antidepressive Agents

    Mood-stimulating drugs used primarily in the treatment of affective disorders and related conditions. Several MONOAMINE OXIDASE INHIBITORS are useful as antidepressants apparently as a long-term consequence of their modulation of catecholamine levels. The tricyclic compounds useful as antidepressive agents (ANTIDEPRESSIVE AGENTS, TRICYCLIC) also appear to act through brain catecholamine systems. A third group (ANTIDEPRESSIVE AGENTS, SECOND-GENERATION) is a diverse group of drugs including some that act specifically on serotonergic systems. (See all compounds classified as Antidepressive Agents.)

    GABA Agonists

    Endogenous compounds and drugs that bind to and activate GAMMA-AMINOBUTYRIC ACID receptors (RECEPTORS, GABA). (See all compounds classified as GABA Agonists.)

    Antiparkinson Agents

    Agents used in the treatment of Parkinson's disease. The most commonly used drugs act on the dopaminergic system in the striatum and basal ganglia or are centrally acting muscarinic antagonists. (See all compounds classified as Antiparkinson Agents.)

    5.3 ATC Code

    N - Nervous system

    N03 - Antiepileptics

    N03A - Antiepileptics

    N03AG - Fatty acid derivatives

    N03AG05 - Progabide

    5.4 Absorption, Distribution and Excretion

    Absorption

    Well absorbed with a bioavailability of 60%

    5.5 Metabolism/Metabolites

    Hepatic

    5.6 Biological Half-Life

    4 hours

    5.7 Mechanism of Action

    Progabide 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.