Galantamine

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Product Details:

  • CAS No: 357-70-0
  • AHFC code: 12:04.0
  • Synonyms: (-)-Galantamine, (-)-Galanthamine, 4-27-00-02184 (Beilstein Handbook Reference), BRN 0093736, Galantamin, Galantamina, Galantamina [INN-Spanish], Galantamine, Galantaminum, Galantaminum [INN-Latin], Galanthamine, Galanthaminum, HSDB 7361, Jilkon, Lycoremin, Lycoremine, Nivalin, Nivaline, NSC 100058, Reminyl, UNII-0D3Q044KCA
  • ATC Code: N06DA04
  • Chemical Formula: C17-H21-N-O3
  • Molecular Weight: 287.3569
  • Assay/Purity: Typically NLT 98%
  • DrugBank: DB00674 (APRD00206, EXPT01628)
  • SMILES: CN1CC[C,,]23C=C[C,,H](C[C,,H]2Oc4c3c(ccc4OC)C1)O
  • InChl: 1S/C17H21NO3/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/t12-,14-,17-/m0/s1
  • PubChem: 9651
  • IUPAC: (4aS,6R,8aS)-4a,5,9,10,11,12-Hexahydro-3-methoxy-11-methyl-6H-benzofuro(3a,3,2-ef)(2)benzazepin-6-ol 6H-Benzofuro(3a,3,2-ef)(2)benzazepin-6-ol, 4a,5,9,10,11,12-hexahydro-3-methoxy-11-methyl-, (4aS,6R,8aS)- Galanthamine

Additional Details

Indication:
For the treatment of mild to moderate dementia of the Alzheimer's type. Has also been investigated in patients with mild cognitive impairment who did not meet the diagnostic criteria for Alzheimer's disease.
Pharmacodynamics:
Galantamine is a parasympathomimetic, specifically, a reversible cholinesterase inhibitor. It is indicated for the treatment of mild to moderate dementia of the Alzheimer's type. An early pathophysiological feature of Alzheimer's disease that is associated with memory loss and cognitive deficits is a deficiency of acetylcholine as a result of selective loss of cholinergic neurons in the cerebral cortex, nucleus basalis, and hippocampus. Galantamine is postulated to exert its therapeutic effect by enhancing cholinergic function. This is accomplished by increasing the concentration of acetylcholine through reversible inhibition of its hydrolysis by acetylcholinesterase. If this proposed mechanism of action is correct, Galantamine's effect may lessen as the disease progresses and fewer cholinergic neurons remain functionally intact. There is no evidence that Galantamine alters the course of the underlying dementing process.
Mode of Action:
Galantamine is a phenanthrene alkaloid and a reversible, competitive acetylcholinesterase inhibitor. It is not structurally related to other acetylcholinesterase inhibitors. Galantamine's proposed mechanism of action involves the reversible inhibition of acetylcholinesterase, which prevents the hydrolysis of acetycholine, leading to an increased concentration of acetylcholine at cholinergic synapses. Galantamine also binds allosterically with nicotinic acetylcholine receptors and may possibly potentiate the action of agonists (such as acetylcholine) at these receptors.
Metabolism:
Toxicity:
LD50=75 mg/kg (rat)
General Reference:
Scott LJ, Goa KL: Galantamine: a review of its use in Alzheimerês disease. Drugs. 2000 Nov;60(5):1095-122. Pubmed Greenblatt HM, Kryger G, Lewis T, Silman I, Sussman JL: Structure of acetylcholinesterase complexed with (-)-galanthamine at 2.3 A resolution. FEBS Lett. 1999 Dec 17;463(3):321-6. Pubmed Woodruff-Pak DS, Vogel RW 3rd, Wenk GL: Galantamine: effect on nicotinic receptor binding, acetylcholinesterase inhibition, and learning. Proc Natl Acad Sci U S A. 2001 Feb 13;98(4):2089-94. Epub 2001 Feb 6. Pubmed Birks J: Cholinesterase inhibitors for Alzheimerês disease. Cochrane Database Syst Rev. 2006 Jan 25;(1):CD005593. Pubmed# Lilienfeld S: Galantamineãa novel cholinergic drug with a unique dual mode of action for the treatment of patients with Alzheimerês disease. CNS Drug Rev. 2002 Summer;8(2):159-76. Pubmed Olin J, Schneider L: Galantamine for Alzheimerês disease. Cochrane Database Syst Rev. 2002;(3):CD001747. Pubmed# Scott LJ, Goa KL: Galantamine: a review of its use in Alzheimerês disease. Drugs. 2000 Nov;60(5):1095-122. Pubmed
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