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tacrine 🐶 Veterinary Use | Indications/Contra | FAERs-F | FAERs-M | Orange Bk | PK/Tox | Related Drugs | BioActivity |
| Stem definition | Drug id | CAS RN |
|---|---|---|
| acridine derivatives | 2551 | 321-64-2 |
Description:
| Molecule | Description |
|---|---|
|
Synonyms:
|
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.
Legend: OFP - off patent OFM - off market ONP - on patent |
Drug dosage:
| Dose | Unit | Route |
|---|---|---|
| 0.12 | g | O |
ADMET properties:
| Property | Value | Reference |
|---|---|---|
| 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 µM/kg/day | Contrera JF, Matthews EJ, Kruhlak NL, Benz RD |
| BA (Bioavailability) | 17 % | Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H |
| 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 |
| fu (Fraction unbound in plasma) | 0.25 % | Lombardo F, Berellini G, Obach RS |
| t_half (Half-life) | 3.30 hours | Lombardo F, Berellini G, Obach RS |
| S (Water solubility) | 0.22 mg/mL | Bocci G, Oprea TI, Benet LZ |
Predicted pharmacokinetic/toxicological properties (PK-AZ):
| Property | Description | Value | Unit | Confidence | Similarity |
|---|---|---|---|---|---|
| azlogd74 | LogD at pH 7.4 | 1.030 | High | 1 | |
| caco2-efflux | Caco-2 efflux ratio (BA/AB) | 0.553 | High | 1 | |
| caco2-intrinsic-papp | Caco-2 intrinsic apparent permeability | 29.580 | 10^-6 cm/s | High | 1 |
| dh-clint | Dog hepatocyte intrinsic clearance | 27.925 | uL/min/10^6 cells | High | 1 |
| dppb | Dog plasma protein binding (% unbound) | 50.400 | % | High | 1 |
| fcs-ppb | Fetal calf serum protein binding (% unbound) | 66.310 | % | High | 1 |
| herg | hERG pIC50 | 5.238 | pIC50 | High | 1 |
| hh-clint | Human hepatocyte intrinsic clearance | 13.459 | uL/min/10^6 cells | High | 1 |
| hlm-clint | Human liver microsomal intrinsic clearance | 35.645 | uL/min/mg protein | High | 1 |
| hppb | Human plasma protein binding (% unbound) | 49.080 | % | High | 1 |
| kinase-safety-class | ACVR2A,ACVR2B,ACVRL1,AKT2,AKT3,ALK,AURKA,AURKB,AXL,BRAF,BTK,CAMK2B,CAMK2D,CDK1,CDK4,CDK5,CDK9,CHEK1,CSF1R,DDR1,DYRK1B,EGFR,EIF2AK3,EPHB4,ERBB2,FLT3,GRK1,GRK2,GRK3,GSK3B,IKBKB,IRAK1,ITK,JAK1,JAK2,JAK3,KIT,MAP2K6,MAP3K1,MAP3K10,MAP3K11,MAP3K14,MAP3K21,MAP3K7,MAP4K1,MAP4K3,MAPK1,MAPK10,MAPK12,MAPK7,MAPK9,MAPKAPK2,MARK4,MELK,MET,MTOR,NTRK2,PAK4,PDK1,PDK2,PDK4,PDPK1,PIK3CB,PIK3CD,PIM1,PIM2,PLK1,PRKCD,PRKDC,SGK1,SIK2,SIK3,STK33,SYK,TEK,TGFBR1,TTK,ULK1,ULK2,ZAP70 | 80 | |||
| kinase-selectivity-class | ACVR2B,AXL,BRAF,TTK | 4 | |||
| mdck-mdr1-bcrp-efflux | MDCK-MDR1-BCRP efflux ratio | 0.506 | High | 1 | |
| mdck-mdr1-efflux | MDCK-MDR1 efflux ratio | 1.888 | High | 1 | |
| mh-clint | Mouse hepatocyte intrinsic clearance | 72.611 | High | 1 | |
| mppb | Mouse plasma protein binding (% unbound) | 34.990 | High | 1 | |
| nih-mdck-mdr1-efflux | NIH MDCK-MDR1 efflux ratio | 1.324 | High | 1 | |
| pfas-class | PFAS structural alert (1 = True, 0 = False) | 0 | |||
| pld-class | Phospholipidosis risk class (1 = positive, 0 = negative) | 1 | High | 1 | |
| pppb | Pig plasma protein binding (% unbound) | 50.290 | % | High | 1 |
| rat-kpuu-brain | Rat brain Kpuu | 0.565 | % | High | 1 |
| rh-clint | Rat hepatocyte intrinsic clearance | 62.517 | uL/min/10^6 cells | High | 1 |
| rh-fuinc | Rat hepatocyte fraction unbound in incubation | 86.210 | % | High | 1 |
| rppb | Rat plasma protein binding (% unbound) | 46.840 | % | High | 1 |
| solubility-dd | Solubility at pH 7.4 in DMSO | 974.990 | uM | High | 1 |
Approvals:
| Date | Agency | Company | Orphan |
|---|---|---|---|
| Sept. 9, 1993 | FDA |
FDA Adverse Event Reporting System (Female)
None
FDA Adverse Event Reporting System (Male)
None
FDA Adverse Event Reporting System (Geriatric)
None
FDA Adverse Event Reporting System (Pediatric)
None
Pharmacologic Action:
| Source | Code | Description |
|---|---|---|
| ATC | N06DA01 | 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:38462 | EC 3.1.1.7 (acetylcholinesterase) inhibitor |
Related Drugs by ATC class:
N06DA Anticholinesterases 5 drugs
Drug Use | Suggest Off label Use Form| |View source of the data|
| Disease | Relation | SNOMED_ID | DOID |
|---|---|---|---|
| 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 |
🐶 Veterinary Drug Use
None
🐶 Veterinary products
None
Acid dissociation constants calculated using MoKa v3.0.0
| Dissociation level | Dissociation constant | Type (acidic/basic) |
|---|---|---|
| pKa1 | 9.6 | Basic |
Orange Book patent data (new drug applications)
None
Orange Book exclusivity data (new drug applications)
None
Bioactivity Summary:
| Target | Class | Pharos | UniProt | Action | Type | Activity value (-log[M]) | Mechanism action | Bioact source | MoA source |
|---|---|---|---|---|---|---|---|---|---|
| Acetylcholinesterase | Enzyme | INHIBITOR | Ki | 7.14 | WOMBAT-PK | CHEMBL | |||
| Cholinesterase | Enzyme | INHIBITOR | IC50 | 7.30 | SCIENTIFIC LITERATURE | SCIENTIFIC LITERATURE | |||
| Aldehyde oxidase | Enzyme | IC50 | 5.30 | WOMBAT-PK | |||||
| 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 | |||||
| Solute carrier family 22 member 1 | Transporter | IC50 | 4.66 | CHEMBL | |||||
| Potassium voltage-gated channel subfamily H member 2 | Ion channel | IC50 | 4.84 | CHEMBL | |||||
| Glutamate NMDA receptor; GRIN1/GRIN2B | Ion channel | IC50 | 4.36 | CHEMBL | |||||
| Glutamate NMDA receptor; GRIN1/GRIN2A | Ion channel | IC50 | 5.31 | CHEMBL | |||||
| Amyloid beta A4 protein | Membrane other | IC50 | 7.91 | CHEMBL | |||||
| Alpha-ketoglutarate-dependent dioxygenase FTO | Enzyme | IC50 | 5.77 | CHEMBL | |||||
| Sodium-dependent noradrenaline transporter | Transporter | Ki | 6.29 | DRUG MATRIX | |||||
| Acetylcholinesterase | Enzyme | Ki | 7.40 | CHEMBL | |||||
| Alpha-1A adrenergic receptor | GPCR | IC50 | 5.56 | CHEMBL | |||||
| Muscarinic acetylcholine receptor M2 | GPCR | IC50 | 5.68 | CHEMBL | |||||
| Acetylcholinesterase | Enzyme | Kd | 7.74 | CHEMBL | |||||
| Butyrylcholinesterase; Protein Bche | Enzyme | IC50 | 8.05 | CHEMBL | |||||
| Acetylcholinesterase | Enzyme | IC50 | 7.34 | CHEMBL | |||||
| Acetylcholinesterase | Enzyme | Ki | 8 | CHEMBL | |||||
| Acetylcholinesterase | Enzyme | Ki | 7.40 | CHEMBL | |||||
| Muscarinic acetylcholine receptor M1 | GPCR | IC50 | 5.70 | CHEMBL | |||||
| Muscarinic acetylcholine receptor M2 | GPCR | Ki | 6.66 | CHEMBL | |||||
| Amine oxidase [flavin-containing] A | Enzyme | IC50 | 7.40 | CHEMBL | |||||
| Cholinesterase | Enzyme | IC50 | 7.20 | CHEMBL | |||||
| Amine oxidase [flavin-containing] A | Enzyme | IC50 | 7.33 | CHEMBL | |||||
| Histamine N-methyltransferase | Enzyme | IC50 | 6.96 | CHEMBL | |||||
| Butyrylcholinesterase | Enzyme | Ki | 8.15 | CHEMBL | |||||
| Muscarinic acetylcholine receptor M2 | GPCR | EC50 | 5.20 | CHEMBL | |||||
| Cholinesterase | Enzyme | IC50 | 8.61 | CHEMBL | |||||
| Muscarinic acetylcholine receptor | GPCR | IC50 | 5.23 | CHEMBL | |||||
| Choline O-acetyltransferase | Enzyme | Ki | 9.82 | CHEMBL |
External reference:
| ID | Source |
|---|---|
| 4020842 | VUID |
| N0000179699 | NUI |
| D02068 | KEGG_DRUG |
| 1684-40-8 | SECONDARY_CAS_RN |
| 4020842 | VANDF |
| 4023896 | VANDF |
| C0039245 | UMLSCUI |
| CHEBI:45980 | CHEBI |
| THA | PDB_CHEM_ID |
| CHEMBL95 | ChEMBL_ID |
| DB00382 | DRUGBANK_ID |
| CHEMBL1677 | ChEMBL_ID |
| D013619 | MESH_DESCRIPTOR_UI |
| 1935 | PUBCHEM_CID |
| 6687 | IUPHAR_LIGAND_ID |
| 800 | INN_ID |
| 4VX7YNB537 | UNII |
| 10318 | RXNORM |
| 5538 | MMSL |
| 564 | MMSL |
| d03176 | MMSL |
| 004378 | NDDF |
| 004379 | NDDF |
| 108494008 | SNOMEDCT_US |
| 108495009 | SNOMEDCT_US |
| 373727000 | SNOMEDCT_US |
| 4VX7YNB537 | INXIGHT DRUGS |
Pharmaceutical products:
None