galantamine 🐶 Veterinary Use | Indications/Contra | FAERs-F | FAERs-M | Orange Bk | PK/Tox | Related Drugs | 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 µM/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

Predicted pharmacokinetic/toxicological properties (PK-AZ):

PropertyDescriptionValueUnitConfidenceSimilarity
azlogd74 LogD at pH 7.4 0.621 High 1
caco2-efflux Caco-2 efflux ratio (BA/AB) 1.901 High 1
caco2-intrinsic-papp Caco-2 intrinsic apparent permeability 8.954 10^-6 cm/s High 1
dh-clint Dog hepatocyte intrinsic clearance 11.995 uL/min/10^6 cells High 1
dppb Dog plasma protein binding (% unbound) 80.030 % High 1
fcs-ppb Fetal calf serum protein binding (% unbound) 81.290 % High 1
herg hERG pIC50 4.343 pIC50 High 1
hh-clint Human hepatocyte intrinsic clearance 2.218 uL/min/10^6 cells High 1
hlm-clint Human liver microsomal intrinsic clearance 6.871 uL/min/mg protein High 1
hppb Human plasma protein binding (% unbound) 76.680 % High 1
kinase-safety-class ACVR2B,AKT2,AKT3,AXL,BRAF,BTK,CAMK2B,CAMK2D,CDK4,CDK5,CDK9,DDR1,DYRK1B,EIF2AK3,EPHB4,ERBB2,GRK2,ITK,JAK2,JAK3,MAP3K7,MAPK10,MAPK7,MAPKAPK2,MET,NTRK2,PDK2,PDK4,PDPK1,PIK3CA,PIK3CB,PIM2,PRKDC,SIK2,SIK3,STK33,TEK,TGFBR1,ZAP70 39
kinase-selectivity-class EIF2AK3 1
mdck-mdr1-efflux MDCK-MDR1 efflux ratio 4.018 High 1
mh-clint Mouse hepatocyte intrinsic clearance 38.019 High 1
mppb Mouse plasma protein binding (% unbound) 75.210 High 1
nih-mdck-mdr1-efflux NIH MDCK-MDR1 efflux ratio 11.350 High 1
pfas-class PFAS structural alert (1 = True, 0 = False) 0
pppb Pig plasma protein binding (% unbound) 80.940 % High 1
rh-clint Rat hepatocyte intrinsic clearance 38.282 uL/min/10^6 cells High 1
rh-fuinc Rat hepatocyte fraction unbound in incubation 87.820 % High 1
rppb Rat plasma protein binding (% unbound) 68.730 % High 1
solubility-dd Solubility at pH 7.4 in DMSO 909.913 uM High 1

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
Creatinine renal clearance decreased 1556.14 39.37 368 9327 18531 90600221
Orthostatic hypotension 1528.66 39.37 426 9269 41401 90577351
Sedation complication 1505.56 39.37 351 9344 16593 90602159
Sedation 1380.46 39.37 406 9289 47765 90570987
Blood calcium decreased 1370.72 39.37 365 9330 29817 90588935
Cognitive disorder 1323.93 39.37 428 9267 68979 90549773
Balance disorder 1183.15 39.37 428 9267 96652 90522100
Depressed level of consciousness 1100.64 39.37 377 9318 72407 90546345
Constipation 753.37 39.37 430 9265 279965 90338787
Fall 726.23 39.37 512 9183 481298 90137454
Hypotension 701.66 39.37 433 9262 324964 90293788
Mobility decreased 602.25 39.37 358 9337 250376 90368376
Toxicity to various agents 594.30 39.37 373 9322 287473 90331279
Pain 179.51 39.37 353 9342 995988 89622764
Renal function test abnormal 172.24 39.37 53 9642 7138 90611614
Creatinine renal clearance increased 159.40 39.37 42 9653 3239 90615513
Multiple drug therapy 152.51 39.37 48 9647 6961 90611791
Fatigue 64.04 39.37 22 9673 1154001 89464751
Overdose 58.49 39.37 78 9617 157631 90461121
Pleurothotonus 54.97 39.37 15 9680 1320 90617432
Drug interaction 54.13 39.37 102 9593 276351 90342401
Drug ineffective 52.49 39.37 43 9652 1384255 89234497
Drug abuse 49.23 39.37 52 9643 82295 90536457
Hallucination 45.51 39.37 45 9650 65914 90552838
Headache 45.16 39.37 18 9677 862728 89756024
Rash 44.37 39.37 15 9680 796085 89822667
Marasmus 42.20 39.37 11 9684 812 90617940
Thyroid atrophy 41.30 39.37 9 9686 307 90618445

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 78.97 24.63 94 3233 234426 42383582
Dysphagia 38.19 24.63 37 3290 72682 42545326
Hallucination 35.46 24.63 32 3295 57475 42560533
Post-traumatic stress disorder 34.54 24.63 11 3316 2274 42615734
Compartment syndrome 34.41 24.63 12 3315 3277 42614731
Fracture 33.16 24.63 15 3312 8088 42609920
Agitation 32.40 24.63 32 3295 64282 42553726
Aggression 32.10 24.63 27 3300 44136 42573872
Increased bronchial secretion 26.25 24.63 9 3318 2337 42615671
Delirium 26.20 24.63 26 3301 52493 42565515
Pneumonia aspiration 25.37 24.63 25 3302 50053 42567955
Bradycardia 24.94 24.63 32 3295 85452 42532556

FDA Adverse Event Reporting System (Geriatric)

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
Creatinine renal clearance decreased 1532.81 27.42 376 11782 21439 110555702
Sedation complication 1511.19 27.42 365 11793 19490 110557651
Orthostatic hypotension 1346.58 27.42 432 11726 65817 110511324
Blood calcium decreased 1333.83 27.42 373 11785 35472 110541669
Cognitive disorder 1259.39 27.42 440 11718 87071 110490070
Sedation 1256.31 27.42 415 11743 69268 110507873
Balance disorder 1114.96 27.42 434 11724 116126 110461015
Depressed level of consciousness 1006.42 27.42 399 11759 111879 110465262
Fall 757.15 27.42 581 11577 602901 109974240
Constipation 668.49 27.42 440 11718 357346 110219795
Mobility decreased 639.40 27.42 369 11789 237053 110340088
Hypotension 558.06 27.42 459 11699 523390 110053751
Toxicity to various agents 457.37 27.42 395 11763 480160 110096981
Pain 204.00 27.42 370 11788 954585 109622556
Renal function test abnormal 159.40 27.42 53 12105 8893 110568248
Creatinine renal clearance increased 154.09 27.42 42 12116 3583 110573558
Multiple drug therapy 144.87 27.42 48 12110 7966 110569175
Overdose 53.78 27.42 94 12064 233700 110343441
Drug ineffective 49.34 27.42 57 12101 1520483 109056658
Amyloid related imaging abnormality-oedema/effusion 47.68 27.42 14 12144 1561 110575580
Pleurothotonus 45.29 27.42 15 12143 2483 110574658
Marasmus 42.41 27.42 13 12145 1678 110575463
Fatigue 42.25 27.42 43 12115 1215915 109361226
Thyroid atrophy 41.31 27.42 9 12149 298 110576843
Bladder disorder 39.92 27.42 21 12137 11116 110566025
Pneumonia aspiration 38.39 27.42 46 12112 81187 110495954
Drug interaction 37.07 27.42 130 12028 500053 110077088
Headache 36.98 27.42 26 12132 882351 109694790
Bradycardia 36.35 27.42 63 12095 155454 110421687
Hallucination 36.24 27.42 50 12108 101382 110475759
Rash 36.00 27.42 23 12135 820941 109756200
Poriomania 32.45 27.42 7 12151 221 110576920
Agitation 32.09 27.42 50 12108 113001 110464140
Weight increased 30.09 27.42 5 12153 419639 110157502
Arthralgia 30.06 27.42 25 12133 779607 109797534
Alopecia 29.38 27.42 3 12155 364750 110212391
Drug hypersensitivity 29.25 27.42 7 12151 454083 110123058
Cerebral infarction 28.94 27.42 32 12126 51806 110525335
Drug intolerance 28.80 27.42 5 12153 406507 110170634
Fracture 28.80 27.42 23 12135 24765 110552376
Loss of consciousness 28.33 27.42 65 12093 196241 110380900
Dementia 27.78 27.42 25 12133 31648 110545493

FDA Adverse Event Reporting System (Pediatric)

None

Pharmacologic Action:

SourceCodeDescription
ATC N06DA04 NERVOUS SYSTEM
PSYCHOANALEPTICS
ANTI-DEMENTIA DRUGS
Anticholinesterases
FDA MoA N0000000177 Cholinesterase Inhibitors
MeSH PA D002800 Cholinesterase Inhibitors
MeSH PA D004791 Enzyme Inhibitors
MeSH PA D010277 Parasympathomimetics
MeSH PA D018377 Neurotransmitter Agents
MeSH PA D018678 Cholinergic Agents
MeSH PA D018697 Nootropic Agents
FDA EPC N0000175723 Cholinesterase Inhibitor
CHEBI has role CHEBI:35469 antidepressant
CHEBI has role CHEBI:35474 anxiolytic drug
CHEBI has role CHEBI:35476 antipsychotic agent
CHEBI has role CHEBI:37733 EC 3.1.1.8 (cholinesterase) inhibitor
CHEBI has role CHEBI:38323 cholinergic drug
CHEBI has role CHEBI:38462 EC 3.1.1.7 (acetylcholinesterase) inhibitor
CHEBI has role CHEBI:50514 vasoconstrictor agent
CHEBI has role CHEBI:64946 anti-HIV agent
CHEBI has role CHEBI:66980 nootropic agent
CHEBI has role CHEBI:74518 anti-obesity agent
CHEBI has role CHEBI:74530 antidote to curare poisoning
CHEBI has role CHEBI:76924 plant metabolite

Related Drugs by ATC class:

N06DA Anticholinesterases 5 drugs
donepezilipidacrinememantinerivastigminetacrine

Drug Use | Suggest Off label Use Form| |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




🐶 Veterinary Drug Use

None

🐶 Veterinary products

None

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
0D3Q044KCA INXIGHT DRUGS

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
Galantamine Hydrobromide HUMAN PRESCRIPTION DRUG LABEL 1 0054-0137 SOLUTION 4 mg ORAL ANDA 25 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 HUMAN PRESCRIPTION DRUG LABEL 1 24979-722 TABLET, FILM COATED 4 mg ORAL ANDA 26 sections
Galantamine HUMAN PRESCRIPTION DRUG LABEL 1 24979-723 TABLET, FILM COATED 8 mg ORAL ANDA 26 sections
Galantamine HUMAN PRESCRIPTION DRUG LABEL 1 24979-724 TABLET, FILM COATED 12 mg ORAL ANDA 26 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
Galantamine HUMAN PRESCRIPTION DRUG LABEL 1 51407-906 TABLET, FILM COATED 4 mg ORAL ANDA 26 sections
Galantamine HUMAN PRESCRIPTION DRUG LABEL 1 51407-907 TABLET, FILM COATED 8 mg ORAL ANDA 26 sections
Galantamine HUMAN PRESCRIPTION DRUG LABEL 1 51407-908 TABLET, FILM COATED 12 mg ORAL ANDA 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
Galantamine Hydrobromide HUMAN PRESCRIPTION DRUG LABEL 1 63629-2364 CAPSULE, EXTENDED RELEASE 8 mg ORAL ANDA 25 sections
Galantamine Hydrobromide HUMAN PRESCRIPTION DRUG LABEL 1 63629-2365 CAPSULE, EXTENDED RELEASE 16 mg ORAL ANDA 25 sections
Galantamine Human Prescription Drug Label 1 65862-458 TABLET, FILM COATED 4 mg ORAL ANDA 25 sections
Galantamine Human Prescription Drug Label 1 65862-459 TABLET, FILM COATED 8 mg ORAL ANDA 25 sections
Galantamine Human Prescription Drug Label 1 65862-460 TABLET, FILM COATED 12 mg ORAL ANDA 25 sections
Galantamine Human Prescription Drug Label 1 65862-744 CAPSULE, EXTENDED RELEASE 8 mg ORAL ANDA 25 sections
Galantamine Human Prescription Drug Label 1 65862-745 CAPSULE, EXTENDED RELEASE 16 mg ORAL ANDA 25 sections
Galantamine Human Prescription Drug Label 1 65862-746 CAPSULE, EXTENDED RELEASE 24 mg ORAL ANDA 25 sections
Galantamine HUMAN PRESCRIPTION DRUG LABEL 1 68084-729 TABLET, FILM COATED 4 mg ORAL ANDA 24 sections
Galantamine HUMAN PRESCRIPTION DRUG LABEL 1 70436-004 TABLET, FILM COATED 4 mg ORAL ANDA 27 sections
Galantamine HUMAN PRESCRIPTION DRUG LABEL 1 70436-005 TABLET, FILM COATED 8 mg ORAL ANDA 27 sections