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    Gaboxadol

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    DIGITAL CONTENT

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    2D Structure
    Also known as: Thip, 64603-91-4, Gaboxadolum, Gaboxadolum [latin], 4,5,6,7-tetrahydroisoxazolo(5,4-c)pyridin-3-ol, Mk-0928
    Molecular Formula
    C6H8N2O2
    Molecular Weight
    140.14  g/mol
    InChI Key
    ZXRVKCBLGJOCEE-UHFFFAOYSA-N
    FDA UNII
    K1M5RVL18S
    Gaboxadol also known as 4,5,6,7-tetrahydroisoxazolo(5,4-c)pyridin-3-ol (THIP) is an experimental sleep aid drug developed by Lundbeck and Merck, who reported increased deep sleep without the reinforcing effects of benzodiazepines. Development of Gaboxadol was stopped in March 2007 after concerns regarding safety and efficacy. It acts on the GABA system, but in a seemingly different way from benzodiazepines and other sedatives.
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    4,5,6,7-tetrahydro-[1,2]oxazolo[5,4-c]pyridin-3-one
    2.1.2 InChI
    InChI=1S/C6H8N2O2/c9-6-4-1-2-7-3-5(4)10-8-6/h7H,1-3H2,(H,8,9)
    2.1.3 InChI Key
    ZXRVKCBLGJOCEE-UHFFFAOYSA-N
    2.1.4 Canonical SMILES
    C1CNCC2=C1C(=O)NO2
    2.2 Other Identifiers
    2.2.1 UNII
    K1M5RVL18S
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. 4,5,6,7-tetrahydroisoxazolo(5,4-c)pyridin-3-ol

    2. Lu 2030

    3. Lu-2-030

    4. Thip

    2.3.2 Depositor-Supplied Synonyms

    1. Thip

    2. 64603-91-4

    3. Gaboxadolum

    4. Gaboxadolum [latin]

    5. 4,5,6,7-tetrahydroisoxazolo(5,4-c)pyridin-3-ol

    6. Mk-0928

    7. Lu 02-030

    8. 4,5,6,7-tetrahydro-[1,2]oxazolo[5,4-c]pyridin-3-one

    9. 4,5,6,7-tetrahydroisoxazolo[5,4-c]pyridin-3-ol

    10. Lu-02-030

    11. Prestwick-13b03

    12. Lu-02030

    13. Chebi:34373

    14. 4,5,6,7-tetrahydroisoxazolo[5,4-c]pyridin-3(2h)-one

    15. K1m5rvl18s

    16. Zinc19795995

    17. Nsc-759585

    18. Ncgc00015982-05

    19. Isoxazolo(5,4-c)pyridin-3(2h)-one, 4,5,6,7-tetrahydro-

    20. Isoxazolo[5,4-c]pyridin-3(2h)-one, 4,5,6,7-tetrahydro-

    21. Gaboxadol [usan:inn]

    22. Dsstox_cid_25206

    23. Dsstox_rid_80750

    24. Dsstox_gsid_45206

    25. Gaboxadol [inn]

    26. Cas-64603-91-4

    27. Gaboxadol (usan/inn)

    28. Einecs 264-963-0

    29. Unii-k1m5rvl18s

    30. 4,5,6,7-tetrahydroisoxazolo(5,4-c)pyridin-3(2h)-one

    31. Ei7

    32. 4,5,6,7-tetrahydroisoxazole(5,4-c)pyridin-3-ol

    33. Spectrum_001484

    34. Tocris-0807

    35. Gaboxadol [mi]

    36. Lopac-t-101

    37. Gaboxadol [usan]

    38. Prestwick0_000972

    39. Prestwick1_000972

    40. Prestwick2_000972

    41. Prestwick3_000972

    42. Spectrum2_001590

    43. Spectrum3_000728

    44. Spectrum4_000172

    45. Spectrum5_001907

    46. Biomol-nt_000235

    47. Gaboxadol [who-dd]

    48. Lopac0_001233

    49. Bspbio_001003

    50. Bspbio_002256

    51. Kbiogr_000683

    52. Kbioss_001964

    53. Divk1c_000211

    54. Spbio_001560

    55. Spbio_002914

    56. Bpbio1_000420

    57. Bpbio1_001105

    58. Chembl312443

    59. Gtpl4322

    60. Dtxsid0045206

    61. Bdbm82002

    62. Kbio1_000211

    63. Kbio2_001964

    64. Kbio2_004532

    65. Kbio2_007100

    66. Kbio3_001476

    67. Ninds_000211

    68. Bcp07031

    69. Nsc_3448

    70. Tox21_110271

    71. Bdbm50224809

    72. Mfcd05664626

    73. Ov-101

    74. Akos006282519

    75. Tox21_110271_1

    76. Ccg-205307

    77. Db06554

    78. Nsc 759585

    79. Sb18782

    80. Sdccgsbi-0051200.p004

    81. Idi1_000211

    82. Ncgc00015982-01

    83. Ncgc00015982-02

    84. Ncgc00015982-03

    85. Ncgc00015982-04

    86. Ncgc00015982-06

    87. Ncgc00015982-07

    88. Ncgc00015982-13

    89. Ncgc00024801-01

    90. Ncgc00024801-02

    91. Ncgc00024801-03

    92. Ncgc00263653-01

    93. Hy-10232

    94. Sy253214

    95. Sbi-0051200.p003

    96. Cas_64603-91-4

    97. Ab00053777

    98. Cs-0002507

    99. Ft-0774669

    100. D04282

    101. Ab00053777_07

    102. 4,5,6,7-tetrahydro-isoxazolo[5,4-c]pyridin-3-ol

    103. 4,5,6,7-tetrahydroisoxazolo[5,4-c]pyridin-3-one

    104. 4,5,6,7-tetrahydroisoxazolo[5,4-c]pyridine-3-ol

    105. 4h,5h,6h,7h-[1,2]oxazolo[5,4-c]pyridin-3-ol

    106. Q4130924

    107. 2h,3h,4h,5h,6h,7h-[1,2]oxazolo[5,4-c]pyridin-3-one

    2.4 Create Date
    2005-03-25
    3 Chemical and Physical Properties
    Molecular Weight 140.14 g/mol
    Molecular Formula C6H8N2O2
    XLogP3-0.9
    Hydrogen Bond Donor Count2
    Hydrogen Bond Acceptor Count3
    Rotatable Bond Count0
    Exact Mass140.058577502 g/mol
    Monoisotopic Mass140.058577502 g/mol
    Topological Polar Surface Area50.4 Ų
    Heavy Atom Count10
    Formal Charge0
    Complexity210
    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

    Investigated for use/treatment in sleep disorders and insomnia.

    5 Pharmacology and Biochemistry
    5.1 MeSH Pharmacological Classification

    GABA Agonists

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

    Analgesics

    Compounds capable of relieving pain without the loss of CONSCIOUSNESS. (See all compounds classified as Analgesics.)

    Anticonvulsants

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