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 751.44 36.38 171 5723 6995 53336177
Orthostatic hypotension 729.12 36.38 224 5670 29529 53313643
Creatinine renal clearance decreased 714.20 36.38 177 5717 10474 53332698
Sedation 687.31 36.38 214 5680 29461 53313711
Cognitive disorder 654.59 36.38 228 5666 44550 53298622
Blood calcium decreased 596.65 36.38 175 5719 19619 53323553
Balance disorder 545.54 36.38 228 5666 72979 53270193
Depressed level of consciousness 475.00 36.38 190 5704 54238 53288934
Fall 373.84 36.38 310 5584 358130 52985042
Mobility decreased 366.65 36.38 175 5719 76096 53267076
Constipation 331.54 36.38 228 5666 198184 53144988
Hypotension 302.61 36.38 238 5656 253838 53089334
Toxicity to various agents 207.08 36.38 180 5714 219418 53123754
Pain 72.61 36.38 183 5711 588215 52754957
Drug ineffective 61.10 36.38 9 5885 817236 52525936
Product dispensing error 56.69 36.38 26 5868 10214 53332958
Pleurothotonus 54.02 36.38 15 5879 1364 53341808
Marasmus 46.22 36.38 11 5883 541 53342631
Dementia 41.98 36.38 25 5869 16725 53326447
Fatigue 40.84 36.38 15 5879 730491 52612681
Hallucination 38.51 36.38 38 5856 53800 53289372

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 66.32 24.54 84 2804 196117 32314521
Compartment syndrome 39.77 24.54 13 2875 2564 32508074
Dysphagia 37.52 24.54 36 2852 61440 32449198
Fracture 37.35 24.54 16 2872 6663 32503975
Post-traumatic stress disorder 35.30 24.54 11 2877 1860 32508778
Dementia 34.90 24.54 19 2869 13367 32497271
Agitation 32.08 24.54 32 2856 57204 32453434
Increased bronchial secretion 31.75 24.54 10 2878 1751 32508887
Hallucination 28.71 24.54 29 2859 52590 32458048
Miosis 27.35 24.54 14 2874 8690 32501948
Hallucination, visual 25.57 24.54 17 2871 17142 32493496
Bradycardia 24.58 24.54 31 2857 71531 32439107

Pharmacologic Action:

SourceCodeDescription
ATC N06DA04 NERVOUS SYSTEM
PSYCHOANALEPTICS
ANTI-DEMENTIA DRUGS
Anticholinesterases
FDA MoA N0000000177 Cholinesterase Inhibitors
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
FDA EPC N0000175723 Cholinesterase Inhibitor
CHEBI has role CHEBI:37733 BChE inhibitor
CHEBI has role CHEBI:38323 cholinergic agent
CHEBI has role CHEBI:38462 acetylcholine esterase inhibitor
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 IC50 5.60 CHEMBL
Butyrylcholinesterase; Protein Bche Enzyme IC50 5.23 CHEMBL
Acetylcholinesterase Enzyme IC50 6.27 CHEMBL
Acetylcholinesterase Enzyme Ki 6.37 CHEMBL
Acetylcholinesterase Enzyme IC50 5.06 CHEMBL
Butyrylcholinesterase Enzyme Ki 5.10 CHEMBL
Cholinesterase Enzyme Ki 5.03 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
CHEMBL659 ChEMBL_ID
DB00674 DRUGBANK_ID
CHEMBL1555 ChEMBL_ID
D005702 MESH_DESCRIPTOR_UI
9651 PUBCHEM_CID
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 HUMAN PRESCRIPTION DRUG LABEL 1 0904-7104 TABLET, FILM COATED 4 mg ORAL ANDA 26 sections
galantamine hydrobromide HUMAN PRESCRIPTION DRUG LABEL 1 10147-0881 TABLET, FILM COATED 4 mg ORAL NDA 27 sections
galantamine hydrobromide HUMAN PRESCRIPTION DRUG LABEL 1 10147-0882 TABLET, FILM COATED 8 mg ORAL NDA 27 sections
galantamine hydrobromide HUMAN PRESCRIPTION DRUG LABEL 1 10147-0883 TABLET, FILM COATED 12 mg ORAL NDA 27 sections
galantamine hydrobromide HUMAN PRESCRIPTION DRUG LABEL 1 10147-0891 CAPSULE, EXTENDED RELEASE 8 mg ORAL NDA 27 sections
galantamine hydrobromide HUMAN PRESCRIPTION DRUG LABEL 1 10147-0892 CAPSULE, EXTENDED RELEASE 16 mg ORAL NDA 27 sections
galantamine hydrobromide HUMAN PRESCRIPTION DRUG LABEL 1 10147-0893 CAPSULE, EXTENDED RELEASE 24 mg ORAL NDA 27 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 25 sections
Galantamine Hydrobromide Human Prescription Drug Label 1 47335-836 CAPSULE, EXTENDED RELEASE 16 mg ORAL ANDA 25 sections
Galantamine Hydrobromide Human Prescription Drug Label 1 47335-837 CAPSULE, EXTENDED RELEASE 24 mg ORAL ANDA 25 sections
RAZADYNE HUMAN PRESCRIPTION DRUG LABEL 1 50458-387 CAPSULE, EXTENDED RELEASE 8 mg ORAL NDA 26 sections
RAZADYNE HUMAN PRESCRIPTION DRUG LABEL 1 50458-388 CAPSULE, EXTENDED RELEASE 16 mg ORAL NDA 26 sections
RAZADYNE HUMAN PRESCRIPTION DRUG LABEL 1 50458-389 CAPSULE, EXTENDED RELEASE 24 mg ORAL NDA 26 sections
RAZADYNE HUMAN PRESCRIPTION DRUG LABEL 1 50458-396 TABLET, FILM COATED 4 mg ORAL NDA 26 sections
RAZADYNE HUMAN PRESCRIPTION DRUG LABEL 1 50458-397 TABLET, FILM COATED 8 mg ORAL NDA 26 sections
RAZADYNE HUMAN PRESCRIPTION DRUG LABEL 1 50458-398 TABLET, FILM COATED 12 mg ORAL NDA 26 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 25 sections
Galantamine Human Prescription Drug Label 1 57237-050 TABLET, FILM COATED 8 mg ORAL ANDA 25 sections
Galantamine Human Prescription Drug Label 1 57237-051 TABLET, FILM COATED 12 mg ORAL ANDA 25 sections
Galantamine Hydrobromide HUMAN PRESCRIPTION DRUG LABEL 1 63629-2363 CAPSULE, EXTENDED RELEASE 24 mg ORAL ANDA 25 sections