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Progabide

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Chemistry

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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

Progabide

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 Formula	C₁₇H₁₆ClFN₂O₂
Molecular Weight	334.8 g/mol
XLogP3	3
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	4
Rotatable Bond Count	6
Exact Mass	334.0884336 g/mol
Monoisotopic Mass	334.0884336 g/mol
Topological Polar Surface Area	75.7 Å²
Heavy Atom Count	23
Formal Charge	0
Complexity	425
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

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 GABA_A and GABA_B receptors located on the terminals of primary afferent fibers. Binding to GABA_A 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 GABA_B receptors retards the influx of calcium ions into the terminals, thereby reducing the evoked release of excitatory amino acids and possibly other transmitters.