Galantamine

Galantamine
Clinical data
Trade names	Razadyne, Reminyl, others
AHFS/Drugs.com	Monograph
MedlinePlus	a699058
License data	US DailyMed: Razadyne;
Pregnancy; category	AU: B1;
Routes of; administration	By mouth
ATC code	N06DA04 (WHO) ;
Legal status
Legal status	BR: Class C1 (Other controlled substances); EU: Rx-only; In general: ℞ (Prescription only);
Pharmacokinetic data
Bioavailability	80–100%
Protein binding	18%
Metabolism	Liver partially CYP450:CYP2D6/3A4 substrate
Elimination half-life	7 hours
Excretion	Kidney (95%, of which 32% unchanged), fecal (5%)
Identifiers
	IUPAC name (4aS,6R,8aS)-5,6,9,10,11,12-Hexahydro-3-methoxy-11-methyl-4aH-[1]benzofuro[3a,3,2-ef][2]benzazepin-6-ol;
CAS Number	357-70-0 ;
PubChem CID	9651;
IUPHAR/BPS	6693;
DrugBank	DB00674 ;
ChemSpider	9272 ;
UNII	0D3Q044KCA;
KEGG	D04292 ;
ChEBI	CHEBI:42944 ;
ChEMBL	ChEMBL659 ;
PDB ligand	GNT (PDBe, RCSB PDB);
CompTox Dashboard (EPA)	DTXSID2045606 ;
ECHA InfoCard	100.118.289
Chemical and physical data
Formula	C17H21NO3
Molar mass	287.359 g·mol−1
3D model (JSmol)	Interactive image;
Melting point	126.5 °C (259.7 °F)
	SMILES O(c2c1O[C@H]4C[C@@H](O)/C=C\[C@@]43c1c(cc2)CN(C)CC3)C;
	InChI InChI=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 ; Key:ASUTZQLVASHGKV-JDFRZJQESA-N ;
	(verify)

Galantamine is used for the treatment of cognitive decline in mild to moderate Alzheimer's disease and various other memory impairments. It is an alkaloid extracted from the bulbs and flowers of Galanthus nivalis (common snowdrop), Galanthus caucasicus (Caucasian snowdrop), Galanthus woronowii (Voronov's snowdrop), and other members of the family Amaryllidaceae, such as Narcissus (daffodil), Leucojum aestivum (snowflake), and Lycoris including Lycoris radiata (red spider lily). It can also be produced synthetically.

Galantamine was isolated for the first time from bulbs of Galanthus nivalis (common snowdrop) by the Bulgarian chemist Dimitar Paskov and his team in 1956. The active ingredient was extracted, identified, and studied, in particular in relation to acetylcholinesterase (AChE)-inhibiting properties. The first industrial process was developed in 1959. However, it was not until the 1990s when full-scale synthesis was upscaled and optimized.

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