Galantamine hydrobromideProduct ingredient for Galantamine

Name
Galantamine hydrobromide
Drug Entry
Galantamine

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.1 First characterized in the early 1950s, galantamine is a tertiary alkaloid that was extracted from botanical sources, such as Galanthus nivalis.5 Galantamine was first studied in paralytic and neuropathic conditions, such as myopathies and postpolio paralytic conditions, and for reversal of neuromuscular blockade.7,5 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.5 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.7

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.10 It is therefore not considered to be a disease-modifying drug.8 Galantamine is marketed under the brand name Razadyne, and is available as oral immediate- and extended-release tablets and solution.10

Accession Number
DBSALT000316
Structure
Synonyms
Not Available
UNII
MJ4PTD2VVW
CAS Number
1953-04-4
Weight
Average: 368.265
Monoisotopic: 367.078306222
Chemical Formula
C17H22BrNO3
InChI Key
QORVDGQLPPAFRS-XPSHAMGMSA-N
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
IUPAC Name
(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
SMILES
Br.[H][C@]12C[C@@H](O)C=C[C@]11CCN(C)CC3=C1C(O2)=C(OC)C=C3
PubChem Compound
121587
ChemSpider
108491
ChEBI
543255
ChEMBL
CHEMBL1555
Wikipedia
Galantamine
Predicted Properties
PropertyValueSource
logP1.16Chemaxon
pKa (Strongest Acidic)14.81Chemaxon
pKa (Strongest Basic)8.58Chemaxon
Physiological Charge1Chemaxon
Hydrogen Acceptor Count4Chemaxon
Hydrogen Donor Count1Chemaxon
Polar Surface Area41.93 Å2Chemaxon
Rotatable Bond Count1Chemaxon
Refractivity82.3 m3·mol-1Chemaxon
Polarizability31.5 Å3Chemaxon
Number of Rings4Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon