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    Tiagabine Hydrochloride

    ACTIVE PHARMA INGREDIENTS

    FINISHED DOSAGE FORMULATIONS

    DRUG PRODUCT COMPOSITIONS

    RELATED EXCIPIENT COMPANIES

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    2D Structure
    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

    2D Structure

    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]