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Tiagabine
Also known as: 145821-59-6, Tiagabine hcl, Gabitril, Abbott 70569.hcl, Abbott-70569.1, Nnc-05-0328
Molecular Formula
C20H26ClNO2S2
Molecular Weight
412.0  g/mol
InChI Key
YUKARLAABCGMCN-PKLMIRHRSA-N
FDA UNII
DQH6T6D8OY

A nipecotic acid derivative that acts as a GABA uptake inhibitor and anticonvulsant agent. It is used in the treatment of EPILEPSY, for refractory PARTIAL SEIZURES.
1 2D Structure

Tiagabine

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
(3R)-1-[4,4-bis(3-methylthiophen-2-yl)but-3-enyl]piperidine-3-carboxylic acid;hydrochloride
2.1.2 InChI
InChI=1S/C20H25NO2S2.ClH/c1-14-7-11-24-18(14)17(19-15(2)8-12-25-19)6-4-10-21-9-3-5-16(13-21)20(22)23;/h6-8,11-12,16H,3-5,9-10,13H2,1-2H3,(H,22,23);1H/t16-;/m1./s1
2.1.3 InChI Key
YUKARLAABCGMCN-PKLMIRHRSA-N
2.1.4 Canonical SMILES
CC1=C(SC=C1)C(=CCCN2CCCC(C2)C(=O)O)C3=C(C=CS3)C.Cl
2.1.5 Isomeric SMILES
CC1=C(SC=C1)C(=CCCN2CCC[C@H](C2)C(=O)O)C3=C(C=CS3)C.Cl
2.2 Other Identifiers
2.2.1 UNII
DQH6T6D8OY
2.3 Synonyms
2.3.1 MeSH Synonyms

1. (r)-(4,4-bis(3-methyl-2-thienyl)-3-butenyl)-3-piperidinecarboxylic Acid, Hydrochloride

2. Gabitril

3. N-(4,4-di(3-methylthien-2-yl)but-3-enyl)nipecotic Acid

4. No 328

5. No 329

6. No-328

7. No-329

8. Tiagabine

9. Tiagabine, (s)-isomer

2.3.2 Depositor-Supplied Synonyms

1. 145821-59-6

2. Tiagabine Hcl

3. Gabitril

4. Abbott 70569.hcl

5. Abbott-70569.1

6. Nnc-05-0328

7. No-05-0328

8. (r)-1-(4,4-bis(3-methylthiophen-2-yl)but-3-en-1-yl)piperidine-3-carboxylic Acid Hydrochloride

9. Abt-569

10. Tiagabine (hydrochloride)

11. Tgb Hydrochloride

12. Abbott-70569.hcl

13. Gabitril Hydrochloride

14. No328 Hydrochloride

15. Dqh6t6d8oy

16. No050328 Hydrochloride

17. Abbott-705691

18. Chebi:85388

19. Abbott-70569 Hydrochloride

20. Nnc-050328

21. No-050328

22. Gabitril (tn)

23. 145821-59-6 (hcl)

24. (-)-(r)-1-[4,4-bis(3-methyl-2-thienyl)-3-butenyl]nipecotic Acid Hydrochloride

25. 3-piperidinecarboxylic Acid, 1-(4,4-bis(3-methyl-2-thienyl)-3-butenyl)-, Hydrochloride, (r)-

26. Dsstox_cid_24218

27. Dsstox_rid_80125

28. Dsstox_gsid_44218

29. (3r)-1-[4,4-bis(3-methylthiophen-2-yl)but-3-enyl]piperidine-3-carboxylic Acid;hydrochloride

30. (3r)-1-[4,4-bis(3-methylthiophen-2-yl)but-3-en-1-yl]piperidine-3-carboxylic Acid Hydrochloride

31. Cas-145821-59-6

32. Tiagabine Hydrochloride [usan]

33. Abt 569

34. Ncgc00164626-01

35. Unii-dqh6t6d8oy

36. Tiabex

37. (-)-(r)-1-(4,4-bis(3-methyl-2-thienyl)-3-butenyl)nipecotic Acid Hydrochloride

38. Tiagabine Hydrochloride [usan:usp]

39. Mfcd07369025

40. (r)-1-(4,4-bis(3-methylthiophen-2-yl)but-3-enyl)piperidine-3-carboxylic Acid Hydrochloride

41. Tiagabine Monohydrochloride

42. (-)-(r)-1-(4,4-bis(3-methyl-2-thienyl)-3-butenyl)nipecotic Acid, Hydrochloride

43. Chembl1695

44. Schembl41860

45. Mls001401367

46. Tiagabine Hydrochloride (usp)

47. Tiagabine Hydrochloride Solution

48. Dtxsid2044218

49. Hy-b0696a

50. Cep-6671

51. Tiagabine Hydrochloride [mi]

52. Tox21_112245

53. Nn-301

54. No-328

55. S4661

56. Akos024258856

57. Tox21_112245_1

58. Ccg-100885

59. H03t543

60. Ks-1217

61. Nc00135

62. Tiagabine Hydrochloride [mart.]

63. Tiagabine Hydrochloride [vandf]

64. Tiagabine Hydrochloride [usp-rs]

65. Tiagabine Hydrochloride [who-dd]

66. Ncgc00164626-02

67. 3-piperidinecarboxylic Acid, 1-(4,4-bis(3-methyl-2-thienyl)-3-buten-yl)-, Hydrochloride, (r)-

68. 3-piperidinecarboxylic Acid, 1-[4,4-bis(3-methyl-2-thienyl)-3-buten-1-yl]-, Hydrochloride (1:1), (3r)-

69. Smr000469176

70. Tiagabine Hydrochloride, >=98% (hplc)

71. T3165

72. Tiagabine Hydrochloride [orange Book]

73. Ethanone, 1-imidazo[1,2-b]pyridazin-3-yl-

74. C72768

75. D02097

76. Tiagabine Hydrochloride [usp Monograph]

77. A-70569

78. A884577

79. J-008159

80. Q27158534

81. Z2216208631

82. Tiagabine Hydrochloride 1.0 Mg/ml In Methanol (as Free Base)

83. (3r)-1-[4,4-bis(3-methyl-2-thienyl)-3-butenyl]-3-piperidinecarboxylic Acid Hydrochloride

84. (3r)-1-[4,4-bis(3-methyl-2-thienyl)but-3-en-1-yl]-3-carboxypiperidinium Chloride

85. (3r)-1-[4,4-bis(3-methyl-2-thienyl)but-3-en-1-yl]piperidine-3-carboxylic Acid Hydrochloride

86. (3r)-1-[4,4-bis(3-methyl-2-thienyl)but-3-en-1-yl]piperidine-3-carboxylic Acid Monohydrochloride

87. (r)-1-(4,4-bis(3-methylthiophen-2-yl)but-3-en-1-yl)piperidine-3-carboxylicacidhydrochloride

88. Tiagabine Hydrochloride Solution, 1.0 Mg/ml In Methanol (as Free Base), Ampule Of 1 Ml, Certified Reference Material

2.4 Create Date
2005-06-24
3 Chemical and Physical Properties
Molecular Weight 412.0 g/mol
Molecular Formula C20H26ClNO2S2
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count5
Rotatable Bond Count6
Exact Mass411.1093491 g/mol
Monoisotopic Mass411.1093491 g/mol
Topological Polar Surface Area97 Ų
Heavy Atom Count26
Formal Charge0
Complexity474
Isotope Atom Count0
Defined Atom Stereocenter Count1
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count2
4 Drug and Medication Information
4.1 Drug Information
1 of 4  
Drug NameGabitril
PubMed HealthTiagabine (By mouth)
Drug ClassesAnticonvulsant
Drug LabelGABITRIL (tiagabine HCl) is an antiepilepsy drug available as 2 mg, 4 mg, 12 mg, and 16 mg tablets for oral administration. Its chemical name is (-)-(R)-1-[4,4-Bis(3-methyl-2-thienyl)-3-butenyl]nipecotic acid hydrochloride, its molecular formula is...
Active IngredientTiagabine hydrochloride
Dosage FormTablet
RouteOral
Strength4mg; 12mg; 2mg; 16mg
Market StatusPrescription
CompanyCephalon

2 of 4  
Drug NameTiagabine hydrochloride
Drug LabelGABITRIL (tiagabine HCl) is an antiepilepsy drug available as 2 mg, 4 mg, 12 mg, and 16 mg tablets for oral administration. Its chemical name is (-)-(R)-1-[4,4-Bis(3-methyl-2-thienyl)-3-butenyl]nipecotic acid hydrochloride, its molecular formula is...
Active IngredientTiagabine hydrochloride
Dosage FormTablet
RouteOral
Strength4mg; 2mg
Market StatusPrescription
CompanySun Pharm Inds

3 of 4  
Drug NameGabitril
PubMed HealthTiagabine (By mouth)
Drug ClassesAnticonvulsant
Drug LabelGABITRIL (tiagabine HCl) is an antiepilepsy drug available as 2 mg, 4 mg, 12 mg, and 16 mg tablets for oral administration. Its chemical name is (-)-(R)-1-[4,4-Bis(3-methyl-2-thienyl)-3-butenyl]nipecotic acid hydrochloride, its molecular formula is...
Active IngredientTiagabine hydrochloride
Dosage FormTablet
RouteOral
Strength4mg; 12mg; 2mg; 16mg
Market StatusPrescription
CompanyCephalon

4 of 4  
Drug NameTiagabine hydrochloride
Drug LabelGABITRIL (tiagabine HCl) is an antiepilepsy drug available as 2 mg, 4 mg, 12 mg, and 16 mg tablets for oral administration. Its chemical name is (-)-(R)-1-[4,4-Bis(3-methyl-2-thienyl)-3-butenyl]nipecotic acid hydrochloride, its molecular formula is...
Active IngredientTiagabine hydrochloride
Dosage FormTablet
RouteOral
Strength4mg; 2mg
Market StatusPrescription
CompanySun Pharm Inds

5 Pharmacology and Biochemistry
5.1 MeSH Pharmacological Classification

Anticonvulsants

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


GABA Uptake Inhibitors

Compounds that suppress or block the plasma membrane transport of GAMMA-AMINOBUTYRIC ACID by GABA PLASMA MEMBRANE TRANSPORT PROTEINS. (See all compounds classified as GABA Uptake Inhibitors.)


5.2 FDA Pharmacological Classification
5.2.1 Pharmacological Classes
Decreased Central Nervous System Disorganized Electrical Activity [PE]; Anti-epileptic Agent [EPC]
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  • TABLET;ORAL - 12MG
  • TABLET;ORAL - 16MG
  • TABLET;ORAL - 2MG
  • TABLET;ORAL - 4MG
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