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

Stem definitionDrug idCAS RN
acridine derivatives 2551 321-64-2

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • tacrine hydrochloride
  • tacrine
  • tetrahydroaminacrine
  • tetrahydroaminoacridine
  • tetrahydroaminocrin
  • tetrahydroaminocrine
  • cognex
  • tacrine HCl
A cholinesterase inhibitor that crosses the blood-brain barrier. Tacrine has been used to counter the effects of muscle relaxants, as a respiratory stimulant, and in the treatment of Alzheimer's disease and other central nervous system disorders.
  • Molecular weight: 198.27
  • Formula: C13H14N2
  • CLOGP: 3.27
  • LIPINSKI: 0
  • HAC: 2
  • HDO: 1
  • TPSA: 38.91
  • ALOGS: -3.16
  • ROTB: 0

  • Status: OFM

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

Drug dosage:

DoseUnitRoute
0.12 g O

ADMET properties:

PropertyValueReference
BDDCS (Biopharmaceutical Drug Disposition Classification System) 1 Benet LZ, Broccatelli F, Oprea TI
EoM (Fraction excreted unchanged in urine) 0.50 % Benet LZ, Broccatelli F, Oprea TI
MRTD (Maximum Recommended Therapeutic Daily Dose) 11.53 ┬ÁM/kg/day Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
BA (Bioavailability) 17 % Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H
fu (Fraction unbound in plasma) 0.25 % Lombardo F, Berellini G, Obach RS
Vd (Volume of distribution) 11 L/kg Lombardo F, Berellini G, Obach RS
CL (Clearance) 56 mL/min/kg Lombardo F, Berellini G, Obach RS
t_half (Half-life) 3.30 hours Lombardo F, Berellini G, Obach RS

Approvals:

DateAgencyCompanyOrphan
Sept. 9, 1993 FDA

FDA Adverse Event Reporting System (Female)

None

FDA Adverse Event Reporting System (Male)

None

Pharmacologic Action:

SourceCodeDescription
ATC N06DA01 NERVOUS SYSTEM
PSYCHOANALEPTICS
ANTI-DEMENTIA DRUGS
Anticholinesterases
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

Drug Use (View source of the data)

DiseaseRelationSNOMED_IDDOID
Alzheimer's disease indication 26929004 DOID:10652
Peptic ulcer contraindication 13200003 DOID:750
Hyperbilirubinemia contraindication 14783006 DOID:2741
Jaundice contraindication 18165001
Parkinsonism contraindication 32798002
Sick sinus syndrome contraindication 36083008 DOID:13884
Low blood pressure contraindication 45007003
Bradycardia contraindication 48867003
Diarrhea contraindication 62315008
Gastrointestinal obstruction contraindication 126765001
Seizure disorder contraindication 128613002
Liver function tests abnormal contraindication 166603001
Asthma contraindication 195967001 DOID:2841
Disease of liver contraindication 235856003 DOID:409
Bladder outflow obstruction contraindication 236645006

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 9.6 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
Cholinesterase Enzyme INHIBITOR IC50 7.30 SCIENTIFIC LITERATURE SCIENTIFIC LITERATURE
Acetylcholinesterase Enzyme INHIBITOR Ki 7.14 WOMBAT-PK CHEMBL
Cytochrome P450 2D6 Enzyme IC50 6.52 DRUG MATRIX
Alpha-1D adrenergic receptor GPCR Ki 5.95 DRUG MATRIX
Acetylcholine receptor subunit epsilon Ion channel IC50 7.36 CHEMBL
Glutamate NMDA receptor; GRIN1/GRIN2B Ion channel IC50 4.36 CHEMBL
Glutamate NMDA receptor; GRIN1/GRIN2A Ion channel IC50 5.31 CHEMBL
Aldehyde oxidase Enzyme IC50 5.30 WOMBAT-PK
Sodium-dependent noradrenaline transporter Transporter Ki 6.29 DRUG MATRIX
Acetylcholinesterase Enzyme Kd 7.74 CHEMBL
Acetylcholinesterase Enzyme Ki 7.40 CHEMBL
Muscarinic acetylcholine receptor M2 GPCR IC50 5.68 CHEMBL
Amine oxidase [flavin-containing] A Enzyme IC50 7.40 CHEMBL
Muscarinic acetylcholine receptor M2 GPCR Ki 6.66 CHEMBL
Muscarinic acetylcholine receptor M2 GPCR EC50 5.20 CHEMBL
Acetylcholinesterase Enzyme Ki 7.40 CHEMBL
Acetylcholinesterase Enzyme Ki 8 CHEMBL
Histamine N-methyltransferase Enzyme IC50 6.96 CHEMBL
Choline O-acetyltransferase Enzyme Ki 9.82 CHEMBL
Acetylcholinesterase Enzyme IC50 7.34 CHEMBL
Butyrylcholinesterase; Protein Bche Enzyme IC50 8.05 CHEMBL
Cholinesterase Enzyme IC50 8.61 CHEMBL
Muscarinic acetylcholine receptor GPCR IC50 5.23 CHEMBL
Muscarinic acetylcholine receptor M1 GPCR IC50 5.70 CHEMBL
Butyrylcholinesterase Enzyme Ki 8.15 CHEMBL
Alpha-1A adrenergic receptor GPCR IC50 5.56 CHEMBL

External reference:

IDSource
4020842 VUID
N0000179699 NUI
C0771182 UMLSCUI
D02068 KEGG_DRUG
4966RNG0BU UNII
1684-40-8 SECONDARY_CAS_RN
800 INN_ID
108494008 SNOMEDCT_US
10318 RXNORM
373727000 SNOMEDCT_US
d03176 MMSL
4023896 VANDF
004378 NDDF
1935 PUBCHEM_CID
CHEBI:45980 CHEBI
CHEMBL95 ChEMBL_ID
DB00382 DRUGBANK_ID
CHEMBL1677 ChEMBL_ID
THA PDB_CHEM_ID
D013619 MESH_DESCRIPTOR_UI
6687 IUPHAR_LIGAND_ID

Pharmaceutical products:

None