galantamine Indications/Contra | FAERs-F | FAERs-M | Orange Bk | BioActivity |

Stem definitionDrug idCAS RN
1272 357-70-0

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • galantamine
  • galantamin
  • galantamina
  • lycoremin
  • lycoremine
  • galanthamine
  • (-)-Galantamine
  • (-)-Galanthamine
  • galantamine hydrobromide
  • galanthamine hydrobromide
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.
  • Molecular weight: 287.36
  • Formula: C17H21NO3
  • CLOGP: 1.02
  • LIPINSKI: 0
  • HAC: 4
  • HDO: 1
  • TPSA: 41.93
  • ALOGS: -2.23
  • ROTB: 1

  • Status: OFP

  • Legend:
    OFP - off patent
    OFM - off market
    ONP - on patent

Drug dosage:

DoseUnitRoute
16 mg O

ADMET properties:

PropertyValueReference
BDDCS (Biopharmaceutical Drug Disposition Classification System) 1 Benet LZ, Broccatelli F, Oprea TI
S (Water solubility) 10 mg/mL Benet LZ, Broccatelli F, Oprea TI
EoM (Fraction excreted unchanged in urine) 20 % Benet LZ, Broccatelli F, Oprea TI
MRTD (Maximum Recommended Therapeutic Daily Dose) 1.45 ┬ÁM/kg/day Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
BA (Bioavailability) 99 % Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H
Vd (Volume of distribution) 2.30 L/kg Lombardo F, Berellini G, Obach RS
CL (Clearance) 5.60 mL/min/kg Lombardo F, Berellini G, Obach RS
fu (Fraction unbound in plasma) 0.83 % Lombardo F, Berellini G, Obach RS
t_half (Half-life) 5.30 hours Lombardo F, Berellini G, Obach RS

Approvals:

DateAgencyCompanyOrphan
Feb. 28, 2001 FDA JANSSEN PHARMS

FDA Adverse Event Reporting System (Female)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Sedation complication 348.97 31.21 78 4169 3567 46678248
Orthostatic hypotension 310.10 31.21 107 4140 24551 46657264
Creatinine renal clearance decreased 289.61 31.21 76 4171 6844 46674971
Sedation 286.42 31.21 99 4148 22811 46659004
Cognitive disorder 282.12 31.21 111 4136 36772 46645043
Balance disorder 222.50 31.21 111 4136 64410 46617405
Blood calcium decreased 220.30 31.21 74 4173 15599 46666216
Fall 196.01 31.21 191 4056 328906 46352909
Depressed level of consciousness 185.29 31.21 89 4158 47480 46634335
Mobility decreased 124.25 31.21 74 4173 60520 46621295
Constipation 124.02 31.21 112 4135 173985 46507830
Hypotension 112.34 31.21 121 4126 232468 46449347
Product dispensing error 64.16 31.21 26 4221 9207 46672608
Toxicity to various agents 60.95 31.21 85 4162 211681 46470134
Pleurothotonus 59.42 31.21 15 4232 1150 46680665
Marasmus 49.90 31.21 11 4236 468 46681347
Dementia 46.35 31.21 24 4223 14906 46666909
Drug ineffective 37.67 31.21 8 4239 677830 46003985
Hallucination 37.07 31.21 33 4214 49918 46631897

FDA Adverse Event Reporting System (Male)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Fall 66.51 23.72 83 2712 181789 29767894
Compartment syndrome 39.39 23.72 13 2782 2514 29947169
Post-traumatic stress disorder 36.37 23.72 11 2784 1604 29948079
Dementia 35.30 23.72 19 2776 12442 29937241
Fracture 34.90 23.72 15 2780 5991 29943692
Increased bronchial secretion 33.82 23.72 10 2785 1349 29948334
Agitation 32.29 23.72 32 2763 54041 29895642
Dysphagia 31.01 23.72 32 2763 56666 29893017
Miosis 28.19 23.72 14 2781 7762 29941921
Hallucination 27.38 23.72 28 2767 49031 29900652
Hallucination, visual 25.78 23.72 17 2778 16096 29933587
Aggression 24.19 23.72 23 2772 36884 29912799
Coombs negative haemolytic anaemia 23.97 23.72 5 2790 159 29949524
Bradycardia 23.93 23.72 30 2765 65496 29884187
Loss of consciousness 23.83 23.72 33 2762 79342 29870341
Pneumonia aspiration 23.73 23.72 23 2772 37757 29911926

Pharmacologic Action:

SourceCodeDescription
ATC N06DA04 NERVOUS SYSTEM
PSYCHOANALEPTICS
ANTI-DEMENTIA DRUGS
Anticholinesterases
FDA MoA N0000000177 Cholinesterase Inhibitors
FDA EPC N0000175723 Cholinesterase Inhibitor
MeSH PA D002491 Central Nervous System Agents
MeSH PA D018678 Cholinergic Agents
MeSH PA D002800 Cholinesterase Inhibitors
MeSH PA D004791 Enzyme Inhibitors
MeSH PA D018377 Neurotransmitter Agents
MeSH PA D018697 Nootropic Agents
MeSH PA D010277 Parasympathomimetics
MeSH PA D018373 Peripheral Nervous System Agents
CHEBI has role CHEBI:37733 bche inhibitor
CHEBI has role CHEBI:38323 cholinergic drugs
CHEBI has role CHEBI:38462 acetylcholinesterase inhibitors
CHEBI has role CHEBI:74530 curare antidote
CHEBI has role CHEBI:76924 plant metabolites

Drug Use (View source of the data)

DiseaseRelationSNOMED_IDDOID
Alzheimer's disease indication 26929004 DOID:10652
Diffuse Lewy body disease off-label use 80098002
Moderate to Severe Alzheimer's Type Dementia off-label use
Peptic ulcer contraindication 13200003 DOID:750
Chronic obstructive lung disease contraindication 13645005 DOID:3083
Gastrointestinal ulcer contraindication 40845000
Bradycardia contraindication 48867003
Duodenal ulcer disease contraindication 51868009 DOID:1724
Acute nephropathy contraindication 58574008
Hepatic failure contraindication 59927004
Epilepsy contraindication 84757009 DOID:1826
Kidney disease contraindication 90708001 DOID:557
Asthma contraindication 195967001 DOID:2841
Atrioventricular block contraindication 233917008 DOID:0050820
Disease of liver contraindication 235856003 DOID:409
Bladder outflow obstruction contraindication 236645006
Congenital long QT syndrome contraindication 442917000

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 8.14 Basic

Orange Book patent data (new drug applications)

None

Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

TargetClassPharosUniProtActionTypeActivity value
(-log[M])
Mechanism
action
Bioact sourceMoA source
Acetylcholinesterase Enzyme INHIBITOR Ki 7.21 CHEMBL CHEMBL
Cholinesterase Enzyme Ki 6.72 CHEMBL
Acetylcholinesterase Enzyme IC50 6.44 CHEMBL
Acetylcholinesterase Enzyme Ki 6.37 CHEMBL
Acetylcholinesterase Enzyme IC50 6.27 CHEMBL
Acetylcholinesterase Enzyme IC50 5.60 CHEMBL
Butyrylcholinesterase; Protein Bche Enzyme IC50 5.23 CHEMBL
Cholinesterase Enzyme Ki 5.03 CHEMBL
Acetylcholinesterase Enzyme IC50 5.06 CHEMBL
Butyrylcholinesterase Enzyme Ki 5.10 CHEMBL

External reference:

IDSource
4021250 VUID
N0000148691 NUI
D02173 KEGG_DRUG
1953-04-4 SECONDARY_CAS_RN
4021250 VANDF
4021251 VANDF
C0016967 UMLSCUI
CHEBI:42944 CHEBI
GNT PDB_CHEM_ID
9651 PUBCHEM_CID
CHEMBL659 ChEMBL_ID
CHEMBL1555 ChEMBL_ID
DB00674 DRUGBANK_ID
D005702 MESH_DESCRIPTOR_UI
6693 IUPHAR_LIGAND_ID
1392 INN_ID
0D3Q044KCA UNII
4637 RXNORM
147848 MMSL
15913 MMSL
d04750 MMSL
007026 NDDF
007027 NDDF
129482002 SNOMEDCT_US
323377002 SNOMEDCT_US
395727007 SNOMEDCT_US

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
Galantamine Hydrobromide HUMAN PRESCRIPTION DRUG LABEL 1 0054-0137 SOLUTION 4 mg ORAL ANDA 24 sections
Galantamine HUMAN PRESCRIPTION DRUG LABEL 1 0591-3496 CAPSULE, EXTENDED RELEASE 8 mg ORAL ANDA 24 sections
Galantamine HUMAN PRESCRIPTION DRUG LABEL 1 0591-3497 CAPSULE, EXTENDED RELEASE 16 mg ORAL ANDA 24 sections
Galantamine HUMAN PRESCRIPTION DRUG LABEL 1 0591-3498 CAPSULE, EXTENDED RELEASE 24 mg ORAL ANDA 24 sections
galantamine hydrobromide HUMAN PRESCRIPTION DRUG LABEL 1 10147-0881 TABLET, FILM COATED 4 mg ORAL NDA 26 sections
galantamine hydrobromide HUMAN PRESCRIPTION DRUG LABEL 1 10147-0882 TABLET, FILM COATED 8 mg ORAL NDA 26 sections
galantamine hydrobromide HUMAN PRESCRIPTION DRUG LABEL 1 10147-0883 TABLET, FILM COATED 12 mg ORAL NDA 26 sections
galantamine hydrobromide HUMAN PRESCRIPTION DRUG LABEL 1 10147-0891 CAPSULE, EXTENDED RELEASE 8 mg ORAL NDA 26 sections
galantamine hydrobromide HUMAN PRESCRIPTION DRUG LABEL 1 10147-0892 CAPSULE, EXTENDED RELEASE 16 mg ORAL NDA 26 sections
galantamine hydrobromide HUMAN PRESCRIPTION DRUG LABEL 1 10147-0893 CAPSULE, EXTENDED RELEASE 24 mg ORAL NDA 26 sections
RAZADYNE HUMAN PRESCRIPTION DRUG LABEL 1 21695-184 TABLET, FILM COATED 8 mg ORAL NDA 20 sections
RAZADYNE HUMAN PRESCRIPTION DRUG LABEL 1 21695-591 TABLET, FILM COATED 12 mg ORAL NDA 20 sections
Galantamine hydrobromide HUMAN PRESCRIPTION DRUG LABEL 1 43353-984 CAPSULE, EXTENDED RELEASE 16 mg ORAL ANDA 20 sections
Galantamine Hydrobromide Human Prescription Drug Label 1 47335-835 CAPSULE, EXTENDED RELEASE 8 mg ORAL ANDA 24 sections
Galantamine Hydrobromide Human Prescription Drug Label 1 47335-836 CAPSULE, EXTENDED RELEASE 16 mg ORAL ANDA 24 sections
Galantamine Hydrobromide Human Prescription Drug Label 1 47335-837 CAPSULE, EXTENDED RELEASE 24 mg ORAL ANDA 24 sections
RAZADYNE HUMAN PRESCRIPTION DRUG LABEL 1 50458-387 CAPSULE, EXTENDED RELEASE 8 mg ORAL NDA 25 sections
RAZADYNE HUMAN PRESCRIPTION DRUG LABEL 1 50458-388 CAPSULE, EXTENDED RELEASE 16 mg ORAL NDA 25 sections
RAZADYNE HUMAN PRESCRIPTION DRUG LABEL 1 50458-389 CAPSULE, EXTENDED RELEASE 24 mg ORAL NDA 25 sections
RAZADYNE HUMAN PRESCRIPTION DRUG LABEL 1 50458-396 TABLET, FILM COATED 4 mg ORAL NDA 25 sections
RAZADYNE HUMAN PRESCRIPTION DRUG LABEL 1 50458-397 TABLET, FILM COATED 8 mg ORAL NDA 25 sections
RAZADYNE HUMAN PRESCRIPTION DRUG LABEL 1 50458-398 TABLET, FILM COATED 12 mg ORAL NDA 25 sections
Galantamine Hydrobromide HUMAN PRESCRIPTION DRUG LABEL 1 51990-111 TABLET, FILM COATED 4 mg ORAL NDA 26 sections
Galantamine Hydrobromide HUMAN PRESCRIPTION DRUG LABEL 1 51990-112 TABLET, FILM COATED 8 mg ORAL NDA 26 sections
Galantamine Hydrobromide HUMAN PRESCRIPTION DRUG LABEL 1 51990-113 TABLET, FILM COATED 12 mg ORAL NDA 26 sections
Galantamine Human Prescription Drug Label 1 57237-049 TABLET, FILM COATED 4 mg ORAL ANDA 24 sections
Galantamine Human Prescription Drug Label 1 57237-050 TABLET, FILM COATED 8 mg ORAL ANDA 24 sections
Galantamine Human Prescription Drug Label 1 57237-051 TABLET, FILM COATED 12 mg ORAL ANDA 24 sections
Galantamine HUMAN PRESCRIPTION DRUG LABEL 1 60505-2542 TABLET, FILM COATED 4 mg ORAL ANDA 18 sections
Galantamine HUMAN PRESCRIPTION DRUG LABEL 1 60505-2543 TABLET, FILM COATED 8 mg ORAL ANDA 18 sections