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
Product dispensing error 126.45 44.27 25 382 2516 2355162
Fall 81.03 44.27 33 374 47066 2310612
Pleurothotonus 78.75 44.27 12 395 254 2357424
Medication error 64.39 44.27 17 390 6114 2351564
Orthostatic hypotension 55.47 44.27 13 394 2866 2354812
Cognitive disorder 52.09 44.27 14 393 5367 2352311
Decreased appetite 52.01 44.27 21 386 28870 2328808
Sedation 48.38 44.27 12 395 3350 2354328
Hyponatraemia 47.36 44.27 16 391 13309 2344369
Loss of consciousness 45.66 44.27 17 390 18750 2338928

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
Post-traumatic stress disorder 66.77 35.91 11 310 296 1746164
Increased bronchial secretion 55.67 35.91 9 312 214 1746246
Compartment syndrome 53.92 35.91 10 311 539 1745921
Agitation 46.25 35.91 16 305 11010 1735450
Miosis 44.05 35.91 10 311 1468 1744992
Bradycardia 43.06 35.91 15 306 10519 1735941

Pharmacologic Action:

SourceCodeDescription
ATC N06DA04 NERVOUS SYSTEM
PSYCHOANALEPTICS
ANTI-DEMENTIA DRUGS
Anticholinesterases
FDA EPC N0000175723 Cholinesterase Inhibitor
CHEBI has role CHEBI:74530 antidote to curare poisoning
CHEBI has role CHEBI:38323 cholinergic drug
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

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

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
Galantamine HUMAN PRESCRIPTION DRUG LABEL 1 0054-0090 TABLET 4 mg ORAL ANDA 16 sections
Galantamine HUMAN PRESCRIPTION DRUG LABEL 1 0054-0091 TABLET 8 mg ORAL ANDA 16 sections
Galantamine HUMAN PRESCRIPTION DRUG LABEL 1 0054-0092 TABLET 12 mg ORAL ANDA 16 sections
Galantamine Hydrobromide HUMAN PRESCRIPTION DRUG LABEL 1 0054-0137 SOLUTION 4 mg ORAL ANDA 16 sections
Galantamine HUMAN PRESCRIPTION DRUG LABEL 1 0591-3496 CAPSULE, EXTENDED RELEASE 8 mg ORAL ANDA 16 sections
Galantamine HUMAN PRESCRIPTION DRUG LABEL 1 0591-3497 CAPSULE, EXTENDED RELEASE 16 mg ORAL ANDA 16 sections
Galantamine HUMAN PRESCRIPTION DRUG LABEL 1 0591-3498 CAPSULE, EXTENDED RELEASE 24 mg ORAL ANDA 16 sections
galantamine hydrobromide HUMAN PRESCRIPTION DRUG LABEL 1 10147-0881 TABLET, FILM COATED 4 mg ORAL NDA 17 sections
galantamine hydrobromide HUMAN PRESCRIPTION DRUG LABEL 1 10147-0882 TABLET, FILM COATED 8 mg ORAL NDA 17 sections
galantamine hydrobromide HUMAN PRESCRIPTION DRUG LABEL 1 10147-0883 TABLET, FILM COATED 12 mg ORAL NDA 17 sections
galantamine hydrobromide HUMAN PRESCRIPTION DRUG LABEL 1 10147-0891 CAPSULE, EXTENDED RELEASE 8 mg ORAL NDA 17 sections
galantamine hydrobromide HUMAN PRESCRIPTION DRUG LABEL 1 10147-0892 CAPSULE, EXTENDED RELEASE 16 mg ORAL NDA 17 sections
galantamine hydrobromide HUMAN PRESCRIPTION DRUG LABEL 1 10147-0893 CAPSULE, EXTENDED RELEASE 24 mg ORAL NDA 17 sections
RAZADYNE HUMAN PRESCRIPTION DRUG LABEL 1 21695-184 TABLET, FILM COATED 8 mg ORAL NDA 12 sections
RAZADYNE HUMAN PRESCRIPTION DRUG LABEL 1 21695-591 TABLET, FILM COATED 12 mg ORAL NDA 12 sections
Galantamine hydrobromide HUMAN PRESCRIPTION DRUG LABEL 1 43353-984 CAPSULE, EXTENDED RELEASE 16 mg ORAL ANDA 13 sections
Galantamine Hydrobromide HUMAN PRESCRIPTION DRUG LABEL 1 47335-835 CAPSULE, EXTENDED RELEASE 8 mg ORAL ANDA 16 sections
Galantamine Hydrobromide HUMAN PRESCRIPTION DRUG LABEL 1 47335-836 CAPSULE, EXTENDED RELEASE 16 mg ORAL ANDA 16 sections
Galantamine Hydrobromide HUMAN PRESCRIPTION DRUG LABEL 1 47335-837 CAPSULE, EXTENDED RELEASE 24 mg ORAL ANDA 16 sections
RAZADYNE HUMAN PRESCRIPTION DRUG LABEL 1 50458-387 CAPSULE, EXTENDED RELEASE 8 mg ORAL NDA 17 sections
RAZADYNE HUMAN PRESCRIPTION DRUG LABEL 1 50458-388 CAPSULE, EXTENDED RELEASE 16 mg ORAL NDA 17 sections
RAZADYNE HUMAN PRESCRIPTION DRUG LABEL 1 50458-389 CAPSULE, EXTENDED RELEASE 24 mg ORAL NDA 17 sections
RAZADYNE HUMAN PRESCRIPTION DRUG LABEL 1 50458-396 TABLET, FILM COATED 4 mg ORAL NDA 17 sections
RAZADYNE HUMAN PRESCRIPTION DRUG LABEL 1 50458-397 TABLET, FILM COATED 8 mg ORAL NDA 17 sections
RAZADYNE HUMAN PRESCRIPTION DRUG LABEL 1 50458-398 TABLET, FILM COATED 12 mg ORAL NDA 17 sections
Galantamine Hydrobromide HUMAN PRESCRIPTION DRUG LABEL 1 51990-111 TABLET, FILM COATED 4 mg ORAL NDA 17 sections
Galantamine Hydrobromide HUMAN PRESCRIPTION DRUG LABEL 1 51990-112 TABLET, FILM COATED 8 mg ORAL NDA 17 sections
Galantamine Hydrobromide HUMAN PRESCRIPTION DRUG LABEL 1 51990-113 TABLET, FILM COATED 12 mg ORAL NDA 17 sections
Galantamine HUMAN PRESCRIPTION DRUG LABEL 1 57237-049 TABLET, FILM COATED 4 mg ORAL ANDA 16 sections
Galantamine HUMAN PRESCRIPTION DRUG LABEL 1 57237-050 TABLET, FILM COATED 8 mg ORAL ANDA 16 sections