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mepacrine 🐶 Veterinary Use | Indications/Contra | FAERs-F | FAERs-M | Orange Bk | PK/Tox | Related Drugs | BioActivity |
| Stem definition | Drug id | CAS RN |
|---|---|---|
| acridine derivatives | 2338 | 83-89-6 |
Description:
| Molecule | Description |
|---|---|
|
Synonyms:
|
An acridine derivative formerly widely used as an antimalarial but superseded by chloroquine in recent years. It has also been used as an anthelmintic and in the treatment of giardiasis and malignant effusions. It is used in cell biological experiments as an inhibitor of phospholipase A2.
|
Drug dosage:
| Dose | Unit | Route |
|---|---|---|
| 0.30 | g | O |
ADMET properties:
| Property | Value | Reference |
|---|---|---|
| BDDCS (Biopharmaceutical Drug Disposition Classification System) | 1 | Benet LZ, Broccatelli F, Oprea TI |
| S (Water solubility) | 28.57 mg/mL | Benet LZ, Broccatelli F, Oprea TI |
| MRTD (Maximum Recommended Therapeutic Daily Dose) | 12.50 µM/kg/day | Contrera JF, Matthews EJ, Kruhlak NL, Benz RD |
| Vd (Volume of distribution) | 45 L/kg | Lombardo F, Berellini G, Obach RS |
| CL (Clearance) | 5.10 mL/min/kg | Lombardo F, Berellini G, Obach RS |
| fu (Fraction unbound in plasma) | 0.13 % | Lombardo F, Berellini G, Obach RS |
| t_half (Half-life) | 120 hours | Lombardo F, Berellini G, Obach RS |
| BA (Bioavailability) | 2 % |
Predicted pharmacokinetic/toxicological properties (PK-AZ):
| Property | Description | Value | Unit | Confidence | Similarity |
|---|---|---|---|---|---|
| azlogd74 | LogD at pH 7.4 | 2.397 | High | 1 | |
| caco2-efflux | Caco-2 efflux ratio (BA/AB) | 1.892 | High | 1 | |
| caco2-intrinsic-papp | Caco-2 intrinsic apparent permeability | 15.885 | 10^-6 cm/s | High | 1 |
| dh-clint | Dog hepatocyte intrinsic clearance | 8.260 | uL/min/10^6 cells | High | 1 |
| dppb | Dog plasma protein binding (% unbound) | 10.560 | % | High | 1 |
| fcs-ppb | Fetal calf serum protein binding (% unbound) | 29.810 | % | High | 1 |
| herg | hERG pIC50 | 6.773 | pIC50 | High | 1 |
| hh-clint | Human hepatocyte intrinsic clearance | 2.080 | uL/min/10^6 cells | High | 1 |
| hlm-clint | Human liver microsomal intrinsic clearance | 39.264 | uL/min/mg protein | High | 1 |
| hppb | Human plasma protein binding (% unbound) | 13.380 | % | High | 1 |
| kinase-safety-class | ACVR2A,ACVR2B,ACVRL1,AKT1,AKT2,AKT3,ALK,AURKA,AURKB,AXL,BRAF,BTK,CAMK2B,CAMK2D,CDK1,CDK4,CDK5,CDK9,CHEK1,CSF1R,DDR1,DYRK1B,EGFR,EIF2AK3,EPHA2,EPHB4,ERBB2,FLT3,GAK,GRK2,GSK3B,INSR,IRAK1,ITK,JAK1,JAK2,JAK3,KDR,KIT,MAP2K6,MAP3K1,MAP3K10,MAP3K11,MAP3K21,MAP3K7,MAP4K1,MAP4K3,MAP4K5,MAPK10,MAPK12,MAPK7,MAPK9,MAPKAPK2,MARK4,MELK,MET,MTOR,NTRK2,PDK1,PDK2,PDK4,PDPK1,PIK3CA,PIK3CB,PIK3CD,PIM2,PRKCD,PRKDC,SIK2,SIK3,SRC,STK33,SYK,TEK,TTK,TYRO3,ULK1,ULK2,ZAP70 | 79 | |||
| kinase-selectivity-class | AXL,CAMK2D,DYRK1B,EIF2AK3,PDK4,STK33,TTK | 7 | |||
| mdck-mdr1-efflux | MDCK-MDR1 efflux ratio | 5.070 | High | 1 | |
| mh-clint | Mouse hepatocyte intrinsic clearance | 42.462 | High | 1 | |
| mppb | Mouse plasma protein binding (% unbound) | 6.350 | High | 1 | |
| nih-mdck-mdr1-efflux | NIH MDCK-MDR1 efflux ratio | 28.119 | 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) | 20.450 | % | High | 1 |
| rh-clint | Rat hepatocyte intrinsic clearance | 31.189 | uL/min/10^6 cells | High | 1 |
| rh-fuinc | Rat hepatocyte fraction unbound in incubation | 14.890 | % | High | 1 |
| rppb | Rat plasma protein binding (% unbound) | 9.940 | % | High | 1 |
| solubility-dd | Solubility at pH 7.4 in DMSO | 889.201 | uM | High | 1 |
Approvals:
| Date | Agency | Company | Orphan |
|---|---|---|---|
| Jan. 1, 1933 | YEAR INTRODUCED |
FDA Adverse Event Reporting System (Female)
| MedDRA adverse event term | Likelihood ratio | Likelihood ratio threshold | Patients taking drug having adverse event | Patients taking drug not having adverse event | Patients not taking drug having adverse event | Patients not taking drug not having adverse event |
|---|---|---|---|---|---|---|
| Lupus vasculitis | 203.95 | 60.00 | 26 | 546 | 582 | 90627293 |
| Lupus nephritis | 156.90 | 60.00 | 27 | 545 | 4805 | 90623070 |
| Mitral valve incompetence | 110.17 | 60.00 | 26 | 546 | 22498 | 90605377 |
| Febrile neutropenia | 60.28 | 60.00 | 26 | 546 | 158323 | 90469552 |
FDA Adverse Event Reporting System (Male)
None
FDA Adverse Event Reporting System (Geriatric)
| MedDRA adverse event term | Likelihood ratio | Likelihood ratio threshold | Patients taking drug having adverse event | Patients taking drug not having adverse event | Patients not taking drug having adverse event | Patients not taking drug not having adverse event |
|---|---|---|---|---|---|---|
| Lupus vasculitis | 211.24 | 56.60 | 26 | 494 | 592 | 110588187 |
| Lupus nephritis | 165.97 | 56.60 | 27 | 493 | 4618 | 110584161 |
| Mitral valve incompetence | 107.71 | 56.60 | 26 | 494 | 33303 | 110555476 |
| Gastrointestinal disorder | 57.10 | 56.60 | 26 | 494 | 241926 | 110346853 |
FDA Adverse Event Reporting System (Pediatric)
None
Pharmacologic Action:
| Source | Code | Description |
|---|---|---|
| ATC | P01AX05 | ANTIPARASITIC PRODUCTS, INSECTICIDES AND REPELLENTS ANTIPROTOZOALS AGENTS AGAINST AMOEBIASIS AND OTHER PROTOZOAL DISEASES Other agents against amoebiasis and other protozoal diseases |
| MeSH PA | D000871 | Anthelmintics |
| MeSH PA | D000890 | Anti-Infective Agents |
| MeSH PA | D000923 | Anticestodal Agents |
| MeSH PA | D000962 | Antimalarials |
| MeSH PA | D000969 | Antinematodal Agents |
| MeSH PA | D000970 | Antineoplastic Agents |
| MeSH PA | D000977 | Antiparasitic Agents |
| MeSH PA | D000980 | Antiplatyhelmintic Agents |
| MeSH PA | D000981 | Antiprotozoal Agents |
| MeSH PA | D004791 | Enzyme Inhibitors |
| CHEBI has role | CHEBI:35610 | antineoplastic agent |
| CHEBI has role | CHEBI:38068 | antimalarial |
| CHEBI has role | CHEBI:77402 | EC 1.8.1.12 (trypanothione-disulfide reductase) inhibitor |
| CHEBI has role | CHEBI:171664 | antiamoebic agent |
Related Drugs by ATC class:
P01AX Other agents against amoebiasis and other protozoal diseases 9 drugs
Drug Use | Suggest Off label Use Form| |View source of the data|
| Disease | Relation | SNOMED_ID | DOID |
|---|---|---|---|
| Giardiasis | indication | 58265007 | DOID:10718 |
| Pneumothorax | off-label use | 36118008 | |
| Discoid lupus erythematosus | off-label use | 200938002 |
🐶 Veterinary Drug Use
None
🐶 Veterinary products
None
Acid dissociation constants calculated using MoKa v3.0.0
| Dissociation level | Dissociation constant | Type (acidic/basic) |
|---|---|---|
| pKa1 | 10.19 | Basic |
| pKa2 | 8.11 | 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 |
|---|---|---|---|---|---|---|---|---|---|
| Alpha-2A adrenergic receptor | GPCR | Ki | 6.07 | DRUG MATRIX | |||||
| Sodium-dependent noradrenaline transporter | Transporter | Ki | 5.54 | DRUG MATRIX | |||||
| 5-hydroxytryptamine receptor 2A | GPCR | Ki | 6.12 | DRUG MATRIX | |||||
| Alpha-2B adrenergic receptor | GPCR | Ki | 6.08 | DRUG MATRIX | |||||
| D(3) dopamine receptor | GPCR | Ki | 6.35 | DRUG MATRIX | |||||
| Histamine H2 receptor | GPCR | Ki | 5.46 | DRUG MATRIX | |||||
| Muscarinic acetylcholine receptor M1 | GPCR | Ki | 6.45 | DRUG MATRIX | |||||
| Muscarinic acetylcholine receptor M2 | GPCR | Ki | 6.47 | DRUG MATRIX | |||||
| Muscarinic acetylcholine receptor M3 | GPCR | Ki | 6.58 | DRUG MATRIX | |||||
| Muscarinic acetylcholine receptor M4 | GPCR | Ki | 6.56 | DRUG MATRIX | |||||
| Muscarinic acetylcholine receptor M5 | GPCR | Ki | 5.57 | DRUG MATRIX | |||||
| Aldehyde oxidase | Enzyme | IC50 | 5.48 | WOMBAT-PK | |||||
| Alpha-2C adrenergic receptor | GPCR | Ki | 6.25 | DRUG MATRIX | |||||
| Alpha-1D adrenergic receptor | GPCR | Ki | 5.99 | DRUG MATRIX | |||||
| Acetylcholinesterase | Enzyme | IC50 | 5.57 | DRUG MATRIX | |||||
| Major prion protein | Surface antigen | EC50 | 6.52 | CHEMBL | |||||
| Sodium channel alpha subunits; brain (Types I, II, III) | Ion channel | IC50 | 5.48 | CHEMBL | |||||
| Cyclic GMP-AMP synthase | Enzyme | IC50 | 5.16 | CHEMBL | |||||
| Trypanothione reductase | Enzyme | Ki | 4.72 | CHEMBL | |||||
| Alpha-1B adrenergic receptor | GPCR | Ki | 5.72 | DRUG MATRIX | |||||
| Cholinesterase | Enzyme | IC50 | 5.35 | CHEMBL | |||||
| Riboflavin-binding protein | Secreted | Kd | 6.58 | CHEMBL | |||||
| Cyclooxygenase | Enzyme | IC50 | 4.49 | CHEMBL | |||||
| Bacterial DNA-directed RNA polymerase | Enzyme | IC50 | 4.70 | CHEMBL | |||||
| Phospholipase A2 group 1B | Enzyme | IC50 | 4 | CHEMBL | |||||
| Phospholipase A2 group 1B | Enzyme | IC50 | 4 | CHEMBL | |||||
| Major prion protein | Surface antigen | IC50 | 7.02 | CHEMBL |
External reference:
| ID | Source |
|---|---|
| 4019924 | VUID |
| N0000148009 | NUI |
| D08179 | KEGG_DRUG |
| 4018230 | VANDF |
| 4019924 | VANDF |
| C0034403 | UMLSCUI |
| CHEBI:8711 | CHEBI |
| QUN | PDB_CHEM_ID |
| CHEMBL7568 | ChEMBL_ID |
| DB01103 | DRUGBANK_ID |
| 237 | PUBCHEM_CID |
| 10172 | IUPHAR_LIGAND_ID |
| 6151-30-0 | SECONDARY_CAS_RN |
| 82092 | RXNORM |
| 10011 | MMSL |
| d00158 | MMSL |
| 002937 | NDDF |
| 004871 | NDDF |
| 350225009 | SNOMEDCT_US |
| 387363006 | SNOMEDCT_US |
| 387445007 | SNOMEDCT_US |
| D011796 | MESH_DESCRIPTOR_UI |
| CHEMBL554190 | ChEMBL_ID |
| CHEMBL2105615 | ChEMBL_ID |
| 396 | INN_ID |
| H0C805XYDE | UNII |
Pharmaceutical products:
None