GNT

(-)-GALANTHAMINE

Created:	1999-07-08
Last modified:	2011-06-04

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6 entries where GNT is found as a standalone ligand

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Chemical Details
Formal Charge	0
Atom Count	42
Chiral Atom Count	3
Bond Count	45
Aromatic Bond Count	6

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Chemical Component Summary
Name	(-)-GALANTHAMINE
Systematic Name (OpenEye OEToolkits)	n/a
Formula	C₁₇ H₂₁ N O₃
Molecular Weight	287.354
Type	NON-POLYMER

Chemical Descriptors
Type	Program	Version	Descriptor
SMILES	ACDLabs	10.04	OC2C=CC41c3c(ccc(OC)c3OC1C2)CN(CC4)C
SMILES	CACTVS	3.341	COc1ccc2CN(C)CC[C]34C=C[CH](O)C[CH]3Oc1c24
SMILES	OpenEye OEToolkits	1.5.0	CN1CCC23C=CC(CC2Oc4c3c(ccc4OC)C1)O
Canonical SMILES	CACTVS	3.341	COc1ccc2CN(C)CC[C@@]34C=C[C@H](O)C[C@@H]3Oc1c24
Canonical SMILES	OpenEye OEToolkits	1.5.0	C[N@@]1CC[C@@]23C=C[C@@H](C[C@@H]2Oc4c3c(ccc4OC)C1)O
InChI	InChI	1.03	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
InChIKey	InChI	1.03	ASUTZQLVASHGKV-JDFRZJQESA-N

Drug Info: DrugBank

DrugBank ID	DB00674
Name	Galantamine
Groups	approved
Description	Galantamine is a tertiary alkaloid and reversible, competitive inhibitor of the acetylcholinesterase (AChE) enzyme, which is a widely studied therapeutic target used in the treatment of Alzheimer's disease.[A1018] First characterized in the early 1950s, galantamine is a tertiary alkaloid that was extracted from botanical sources, such as _Galanthus nivalis_.[A201968] Galantamine was first studied in paralytic and neuropathic conditions, such as myopathies and postpolio paralytic conditions, and for reversal of neuromuscular blockade.[A182993,A201968] Following the discovery of its AChE-inhibiting properties, the cognitive effects of galantamine were studied in a wide variety of psychiatric disorders such as mild cognitive impairment, cognitive impairment in schizophrenia and bipolar disorder, and autism; however, re-development of the drug for Alzheimer’s disease did not commence until the early 1990s due to difficulties in extraction and synthesis.[A201968] Galantamine blocks the breakdown of acetylcholine in the synaptic cleft, thereby increasing acetylcholine neurotransmission. It also acts as an allosteric modulator of the nicotinic receptor, giving its dual mechanism of action clinical significance.[A182993] The drug was approved by the FDA in 2001 for the treatment of mild to moderate dementia of the Alzheimer's type. As Alzheimer's disease is a progressive neurodegenerative disorder, galantamine is not known to alter the course of the underlying dementing process. Galantamine works to block the enzyme responsible for the breakdown of acetylcholine in the synaptic cleft, thereby enhancing cholinergic neuron function and signalling. Under this hypothesized mechanism of action, the therapeutic effects of galantamine may decrease as the disease progression advances and fewer cholinergic neurons remain functionally intact.[L13571] It is therefore not considered to be a disease-modifying drug.[A203558] Galantamine is marketed under the brand name Razadyne, and is available as oral immediate- and extended-release tablets and solution.[L13571]
Synonyms	Galantamina (-)-Galanthamine Galantamine hydrobromide Galanthamine Galantamine
Brand Names	Sandoz Galantamine ER Teva-galantamine ER Auro-galantamine ER Mylan-galantamine ER Galantamine Hydrobromide PMS-galantamine Reminyl -(8mg) Ratio-galantamine PMS-galantamine ER Galantamine hydrobromide Reminyl ER Apo-galantamine Galantamine ER Mar-galantamine ER Razadyne Pat-galantamine ER Reminyl -(12mg) Reminyl -(4mg) Galantamine Ipg-galantamine ER Pendo-galantamine ER
Indication	Galantamine is indicated for the treatment of mild to moderate dementia of the Alzheimer’s type.[L13571]
Categories	Alkaloids Amaryllidaceae Alkaloids Anti-Dementia Drugs Autonomic Agents Benzazepines Bradycardia-Causing Agents Central Nervous System Agents Cholinergic Agents Cholinesterase Inhibitors Cytochrome P-450 CYP2D6 Substrates Cytochrome P-450 CYP3A Substrates Cytochrome P-450 CYP3A4 Substrates Cytochrome P-450 Substrates Enzyme Inhibitors Heterocyclic Compounds, Fused-Ring Nervous System Neurotransmitter Agents Nootropic Agents P-glycoprotein inhibitors Parasympathomemetic (Cholinergic) Agents Parasympathomimetics Peripheral Nervous System Agents Potential QTc-Prolonging Agents Psychoanaleptics QTc Prolonging Agents
ATC-Code	N06DA04
CAS number	357-70-0

Drug Targets

Name	Target Sequence	Pharmacological Action	Actions
Acetylcholinesterase	MRPPQCLLHTPSLASPLLLLLLWLLGGGVGAEGREDAELLVTVRGGRLRG...	unknown	inhibitor
Neuronal acetylcholine receptor subunit alpha-7	MRCSPGGVWLALAASLLHVSLQGEFQRKLYKELVKNYNPLERPVANDSQP...	unknown	allosteric modulator
Muscle nicotinic acetylcholine receptor	RLVAKLFKDYSSVVRPVEDHRQVVEVTVGLQLIQLINVDEVNQIVTTNVR...	unknown	allosteric modulator
Cholinesterase	MHSKVTIICIRFLFWFLLLCMLIGKSHTEDDIIIATKNGKVRGMNLTVFG...	unknown	inhibitor
Cytochrome P450 3A4	MALIPDLAMETWLLLAVSLVLLYLYGTHSHGLFKKLGIPGPTPLPFLGNI...	unknown	substrate
Cytochrome P450 2D6	MGLEALVPLAVIVAIFLLLVDLMHRRQRWAARYPPGPLPLPGLGNLLHVD...	unknown	substrate
P-glycoprotein 1	MDLEGDRNGGAKKKNFFKLNNKSEKDKKEKKPTVSVFSMFRYSNWLDKLY...	unknown	inhibitor
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Drug Info/Drug Targets: DrugBank 3.0: a comprehensive resource for 'omics' research on drugs. Knox C, Law V, Jewison T, Liu P, Ly S, Frolkis A, Pon A, Banco K, Mak C, Neveu V, Djoumbou Y, Eisner R, Guo AC, Wishart DS. Nucleic Acids Res. 2011 Jan; 39 (Database issue):D1035-41. | PMID:21059682