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    Galantamine

    ACTIVE PHARMA INGREDIENTS

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    2D Structure
    Also known as: Galanthamine hydrobromide, 1953-04-4, Reminyl, Nivalin, Nivaline, Razadyne
    Molecular Formula
    C17H22BrNO3
    Molecular Weight
    368.3  g/mol
    InChI Key
    QORVDGQLPPAFRS-XPSHAMGMSA-N
    FDA UNII
    MJ4PTD2VVW
    A benzazepine derived from norbelladine. It is found in GALANTHUS and other AMARYLLIDACEAE. It is a cholinesterase inhibitor that has been used to reverse the muscular effects of GALLAMINE TRIETHIODIDE and TUBOCURARINE and has been studied as a treatment for ALZHEIMER DISEASE and other central nervous system disorders.
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    (1S,12S,14R)-9-methoxy-4-methyl-11-oxa-4-azatetracyclo[8.6.1.01,12.06,17]heptadeca-6(17),7,9,15-tetraen-14-ol;hydrobromide
    2.1.2 InChI
    InChI=1S/C17H21NO3.BrH/c1-18-8-7-17-6-5-12(19)9-14(17)21-16-13(20-2)4-3-11(10-18)15(16)17;/h3-6,12,14,19H,7-10H2,1-2H3;1H/t12-,14-,17-;/m0./s1
    2.1.3 InChI Key
    QORVDGQLPPAFRS-XPSHAMGMSA-N
    2.1.4 Canonical SMILES
    CN1CCC23C=CC(CC2OC4=C(C=CC(=C34)C1)OC)O.Br
    2.1.5 Isomeric SMILES
    CN1CC[C@@]23C=C[C@@H](C[C@@H]2OC4=C(C=CC(=C34)C1)OC)O.Br
    2.2 Other Identifiers
    2.2.1 UNII
    MJ4PTD2VVW
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. Galantamin

    2. Galantamine

    3. Galanthamine

    4. Galanthamine Hydrobromide

    5. Lycoremine

    6. Nivalin

    7. Nivaline

    8. Razadyne

    9. Reminyl

    2.3.2 Depositor-Supplied Synonyms

    1. Galanthamine Hydrobromide

    2. 1953-04-4

    3. Reminyl

    4. Nivalin

    5. Nivaline

    6. Razadyne

    7. Lycoremine Hydrobromide

    8. Jilkon Hydrobromide

    9. Galanthamine (hydrobromide)

    10. Galanthamine Hbr

    11. Tamilin

    12. 193146-85-9

    13. Mj4ptd2vvw

    14. 5n4sa4kqx9

    15. (-)-galantamine Hydrobromide

    16. (+/-)-galantamine Hydrobromide

    17. (+/-)-galanthamine Hydrobromide

    18. Galantamine Hydrobromide (racemic)

    19. Galantamine Hydrobromide, (+/-)-

    20. (1s,12s,14r)-9-methoxy-4-methyl-11-oxa-4-azatetracyclo[8.6.1.01,12.06,17]heptadeca-6(17),7,9,15-tetraen-14-ol;hydrobromide

    21. (4as,6r,8as)-4a,5,9,10,11,12-hexahydro-3-methoxy-11-methyl-6h-benzofuro[3a,3,2-ef][2]benzazepin-6-ol Hydrobromide

    22. Razadyne Er

    23. Reminyl (tn)

    24. (1s,12s,14r)-9-methoxy-4-methyl-11-oxa-4-azoniatetracyclo[8.6.1.01,12.06,17]heptadeca-6(17),7,9,15-tetraen-14-ol;bromide

    25. (4as,6r,8as)-3-methoxy-11-methyl-4a,5,9,10,11,12-hexahydro-6h-benzo[2,3]benzofuro[4,3-cd]azepin-6-ol Hydrobromide

    26. Galanthaminehydrobromide

    27. 1953-04-4 (hbr); 1953-04-4 (free Base).

    28. (1s,12s,14r)-9-methoxy-4-methyl-11-oxa-4-azatetracyclo[8.6.1.0^{1,12}.0^{6,17}]heptadeca-6(17),7,9,15-tetraen-14-ol Hydrobromide

    29. (4as,6r,8as)-4a,5,9,10,11,12-hexahydro-3-methoxy-11-methyl-6h-benzofuro(3a,3,2-ef)(2)benzazepin-6-ol Hydrobromide

    30. 6h-benzofuro(3a,3,2-ef)(2)benzazepin-6-ol, 4a,5,9,10,11,12-hexahydro-3-methoxy-11-methyl-, Hydrobromide (1:1), (4ar,6s,8ar)-rel-

    31. 6h-benzofuro(3a,3,2-ef)(2)benzazepin-6-ol, 4a,5,9,10,11,12-hexahydro-3-methoxy-11-methyl-, Hydrobromide (1:1), (4as,6r,8as)-

    32. Smr000449267

    33. Sr-01000597844

    34. Nivaline (pharmaceutical)

    35. C17h22brno3

    36. Anti-alzheimer

    37. Sr-05000001783

    38. Nivalin;razadyne

    39. Galantamine Hydrobromide [usan]

    40. Reminyl Xl

    41. Jilcon Hydrobromide

    42. Razadyne (tn)

    43. Prestwick_236

    44. Einecs 217-780-5

    45. Galanthamine Hydrobromide From Lycoris Sp.

    46. Mfcd00067672

    47. Unii-mj4ptd2vvw

    48. Unii-5n4sa4kqx9

    49. 1953-04-4 Unlabeled

    50. Chembl1555

    51. Galanthamine-d3 Hydrobromide

    52. Mls000758283

    53. Mls001401401

    54. Galanthamine Hydrobromide,(s)

    55. Schembl177993

    56. Spectrum1501202

    57. Hms1569f18

    58. Hms1921p21

    59. Hy-a0009

    60. Galantamine Hydrobromide (jan/usp)

    61. Ac-469

    62. Ccg-38829

    63. Galantamine Hydrobromide [mi]

    64. Galantamine Hydrobromide [usan:usp]

    65. S1339

    66. Galantamine Hydrobromide [jan]

    67. Galanthamine-o-methyl-d3 Hydrobromide

    68. Akos007930166

    69. Akos015960209

    70. Cs-0378

    71. Fd10095

    72. Galantamine Hydrobromide [hsdb]

    73. Nc00061

    74. Galantamine Hydrobromide [mart.]

    75. Galantamine Hydrobromide [vandf]

    76. Galantamine Hydrobromide [usp-rs]

    77. Galantamine Hydrobromide [who-dd]

    78. 6h-benzofuro(3a,3,2-ef)(2)benzazepin-6-ol, 4a,5,9,10,11,12-hexahydro-3-methoxy-11-methyl-, Hydrobromide, (4as,6r,8as)-

    79. As-12155

    80. Gp-37267

    81. G0293

    82. Galantamine Hydrobromide [orange Book]

    83. D02173

    84. Galantamine Hydrobromide [ep Monograph]

    85. Galantamine Hydrobromide [usp Monograph]

    86. Galantamine Hydrobromide Racemic [usp-rs]

    87. 953g044

    88. A866857

    89. A903748

    90. R-113675

    91. Sr-01000597844-1

    92. Sr-01000597844-5

    93. Sr-05000001783-3

    94. Q47495772

    95. Z1558572528

    96. Galanthamine Hydrobromide From Lycoris Sp., >=94% (tlc)

    97. (4as,6r,8as)-3-methoxy-11-methyl-5,6,9,10,11,12-hexahydro-4ah-benzo[2,3]benzofuro[4,3-cd]azepin-6-ol Hydrobromide

    98. (4as,6r,8as)-3-methoxy-11-methyl-5,6,9,10,11,12-hexahydro-4ah-benzo[2,3]benzofuro[4,3-cd]azepin-6-olhydrobromide

    99. (4as,6r,8as)-4a,5,9,10,11,12-hexahydro-3-methoxy-11-methyl-6h-benzofuro[3a,3,2-ef][2]benzazepin-6-ol, Hydrobromide

    100. (4as,6r,8as)-4a,5,9,10,11,12-hexahydro-3-methoxy-d3-11-methyl-6h-benzofuro[3a,3,2-ef][2]benzazepin-6-ol Hydrobromide

    101. 4a,5,9,10,11,12-hexahydro-3-methoxy-11-methyl-6h-benzofuro[3a,3,2-ef][2]benzazepin-6-ol Hydrobromide

    102. 6h-benzofuro(3a,3,2-ef)(2)benzazepin-6-ol, 4a,5,9,10,11,12-hexahydro-3-methoxy-11-methyl-, Hbr (1:1), (4as,6r,8as)-

    103. 6h-benzofuro(3a,3,2-ef)(2)benzazepin-6-ol, 4a,5,9,10,11,12-hexahydro-3-methoxy-11-methyl-, Hbr, (4as,6r,8as)-

    104. 6h-benzofuro(3a,3,2-ef)(2)benzazepin-6-ol, 4a,5,9,10,11,12-hexahydro-3-methoxy-11-methyl-, Hydrobromide, (4a.alpha.,6.beta.,8ar*)-

    105. 6h-benzofuro(3a,3,2-ef)(2)benzazepin-6-ol, 4a,5,9,10,11,12-hexahydro-3-methoxy-11-methyl-, Hydrobromide, (4aalpha,6beta,8ar*)-

    2.3.3 Other Synonyms

    1. Galantamine

    2. Galanthamine Hydrobromide

    3. Lycoremin

    4. Lycoremine

    5. Nivalin

    6. Razadyne

    7. Reminyl

    8. Galanthamine

    2.4 Create Date
    2005-06-24
    3 Chemical and Physical Properties
    Molecular Weight 368.3 g/mol
    Molecular Formula C17H22BrNO3
    Hydrogen Bond Donor Count2
    Hydrogen Bond Acceptor Count4
    Rotatable Bond Count1
    Exact Mass367.07831 g/mol
    Monoisotopic Mass367.07831 g/mol
    Topological Polar Surface Area41.9 Ų
    Heavy Atom Count22
    Formal Charge0
    Complexity440
    Isotope Atom Count0
    Defined Atom Stereocenter Count3
    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 NameGalantamine hydrobromide
    PubMed HealthGalantamine (By mouth)
    Drug ClassesCentral Nervous System Agent
    Drug LabelGalantamine hydrobromide is a reversible, competitive acetylcholinesterase inhibitor. Galantamine hydrobromide is known chemically as (4aS,6R,8aS)-4a,5,9,10,11,12-hexahydro-3-methoxy-11-methyl-6H-benzofuro [3a,3,2-ef][2]benzazepin-6-ol hydrobromide....
    Active IngredientGalantamine hydrobromide
    Dosage FormTablet; Capsule, extended release; Solution
    Routeoral; Oral
    Strengtheq 4mg base; 8mg; eq 12mg base; 4mg; 4mg/ml; 12mg; eq 16mg base; eq 24mg base; eq 8mg base
    Market StatusTentative Approval; Prescription
    CompanyRanbaxy; Apotex; Aurobindo Pharma; Sun Pharm Inds; Sandoz; Sun Pharma Global; Roxane; Watson Labs; Teva Pharms; Zydus Pharms Usa; Dr Reddys Labs; Mylan; Impax Labs; Barr

    2 of 4  
    Drug NameRazadyne
    Drug LabelRAZADYNE ER/RAZADYNE (galantamine hydrobromide) is galantamine hydrobromide, a reversible, competitive acetylcholinesterase inhibitor. Galantamine hydrobromide is known chemically as (4aS ,6R,8aS )-4a,5,9,10,11,12-hexahydro-3-methoxy-11-methyl-6H...
    Active IngredientGalantamine hydrobromide
    Dosage FormTablet; Solution
    RouteOral
    Strengtheq 4mg base; eq 12mg base; 4mg/ml; eq 8mg base
    Market StatusPrescription
    CompanyJanssen Pharms

    3 of 4  
    Drug NameGalantamine hydrobromide
    PubMed HealthGalantamine (By mouth)
    Drug ClassesCentral Nervous System Agent
    Drug LabelGalantamine hydrobromide is a reversible, competitive acetylcholinesterase inhibitor. Galantamine hydrobromide is known chemically as (4aS,6R,8aS)-4a,5,9,10,11,12-hexahydro-3-methoxy-11-methyl-6H-benzofuro [3a,3,2-ef][2]benzazepin-6-ol hydrobromide....
    Active IngredientGalantamine hydrobromide
    Dosage FormTablet; Capsule, extended release; Solution
    Routeoral; Oral
    Strengtheq 4mg base; 8mg; eq 12mg base; 4mg; 4mg/ml; 12mg; eq 16mg base; eq 24mg base; eq 8mg base
    Market StatusTentative Approval; Prescription
    CompanyRanbaxy; Apotex; Aurobindo Pharma; Sun Pharm Inds; Sandoz; Sun Pharma Global; Roxane; Watson Labs; Teva Pharms; Zydus Pharms Usa; Dr Reddys Labs; Mylan; Impax Labs; Barr

    4 of 4  
    Drug NameRazadyne
    Drug LabelRAZADYNE ER/RAZADYNE (galantamine hydrobromide) is galantamine hydrobromide, a reversible, competitive acetylcholinesterase inhibitor. Galantamine hydrobromide is known chemically as (4aS ,6R,8aS )-4a,5,9,10,11,12-hexahydro-3-methoxy-11-methyl-6H...
    Active IngredientGalantamine hydrobromide
    Dosage FormTablet; Solution
    RouteOral
    Strengtheq 4mg base; eq 12mg base; 4mg/ml; eq 8mg base
    Market StatusPrescription
    CompanyJanssen Pharms

    5 Pharmacology and Biochemistry
    5.1 MeSH Pharmacological Classification

    Nootropic Agents

    Drugs used to specifically facilitate learning or memory, particularly to prevent the cognitive deficits associated with dementias. These drugs act by a variety of mechanisms. (See all compounds classified as Nootropic Agents.)

    Cholinesterase Inhibitors

    Drugs that inhibit cholinesterases. The neurotransmitter ACETYLCHOLINE is rapidly hydrolyzed, and thereby inactivated, by cholinesterases. When cholinesterases are inhibited, the action of endogenously released acetylcholine at cholinergic synapses is potentiated. Cholinesterase inhibitors are widely used clinically for their potentiation of cholinergic inputs to the gastrointestinal tract and urinary bladder, the eye, and skeletal muscles; they are also used for their effects on the heart and the central nervous system. (See all compounds classified as Cholinesterase Inhibitors.)

    Parasympathomimetics

    Drugs that mimic the effects of parasympathetic nervous system activity. Included here are drugs that directly stimulate muscarinic receptors and drugs that potentiate cholinergic activity, usually by slowing the breakdown of acetylcholine (CHOLINESTERASE INHIBITORS). Drugs that stimulate both sympathetic and parasympathetic postganglionic neurons (GANGLIONIC STIMULANTS) are not included here. (See all compounds classified as Parasympathomimetics.)

    5.2 FDA Pharmacological Classification
    5.2.1 Pharmacological Classes
    Cholinesterase Inhibitors [MoA]; Cholinesterase Inhibitor [EPC]