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

Stem definitionDrug idCAS RN
acridine derivatives 2338 83-89-6

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • quinacrin
  • quinacrine
  • mepacrine
  • atabrine
  • acrinamine
  • acriquine
  • quinacrine dihydrochloride hydrate
  • quinacrine dihydrochloride
  • quinacrine hydrochloride
  • quinacrine HCl
An acridine derivative formerly widely used as an antimalarial but superseded by chloroquine in recent years.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.
  • Molecular weight: 399.96
  • Formula: C23H30ClN3O
  • CLOGP: 6.72
  • LIPINSKI: 1
  • HAC: 4
  • HDO: 1
  • TPSA: 37.39
  • ALOGS: -5.22
  • ROTB: 9

Drug dosage:

DoseUnitRoute
0.30 g O

ADMET properties:

PropertyValueReference
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 ┬ÁM/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

Approvals:

DateAgencyCompanyOrphan
Jan. 1, 1933 YEAR INTRODUCED

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
Lupus vasculitis 161.39 68.32 21 340 452 46685249
Lupus nephritis 128.69 68.32 21 340 2225 46683476
Mitral valve incompetence 84.14 68.32 21 340 18831 46666870

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

Pharmacologic Action:

SourceCodeDescription
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:38068 antimalarials
CHEBI has role CHEBI:77402 trypanothione reductase inhibitors

Drug Use (View source of the data)

DiseaseRelationSNOMED_IDDOID
Giardiasis indication 58265007 DOID:10718
Pneumothorax off-label use 36118008
Discoid lupus erythematosus off-label use 200938002

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (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:

TargetClassPharosUniProtActionTypeActivity value
(-log[M])
Mechanism
action
Bioact sourceMoA 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 6.44 DRUG MATRIX
Muscarinic acetylcholine receptor M2 GPCR Ki 6.46 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
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
Aldehyde oxidase Enzyme IC50 5.48 WOMBAT-PK
Major prion protein Surface antigen EC50 6.52 CHEMBL
Sodium channel alpha subunits; brain (Types I, II, III) Ion channel IC50 5.48 CHEMBL
Alpha-1B adrenergic receptor GPCR Ki 5.72 DRUG MATRIX
Trypanothione reductase Enzyme Ki 4.72 CHEMBL
Bacterial DNA-directed RNA polymerase Enzyme IC50 4.70 CHEMBL
Phospholipase A2 group 1B Unclassified IC50 4 CHEMBL
Phospholipase A2 group 1B Enzyme IC50 4 CHEMBL
Cholinesterase Enzyme IC50 5.35 CHEMBL
Riboflavin-binding protein Unclassified Kd 6.58 CHEMBL
Cyclooxygenase Enzyme IC50 4.49 CHEMBL

External reference:

IDSource
4019924 VUID
N0000148009 NUI
D08179 KEGG_DRUG
6151-30-0 SECONDARY_CAS_RN
4018230 VANDF
4019924 VANDF
C0699546 UMLSCUI
CHEBI:8711 CHEBI
QUN PDB_CHEM_ID
237 PUBCHEM_CID
CHEMBL7568 ChEMBL_ID
CHEMBL554190 ChEMBL_ID
CHEMBL2105615 ChEMBL_ID
CHEMBL556980 ChEMBL_ID
D011796 MESH_DESCRIPTOR_UI
DB01103 DRUGBANK_ID
10172 IUPHAR_LIGAND_ID
396 INN_ID
H0C805XYDE UNII
82092 RXNORM
10011 MMSL
d00158 MMSL
002937 NDDF
004871 NDDF
350225009 SNOMEDCT_US
387363006 SNOMEDCT_US
387445007 SNOMEDCT_US

Pharmaceutical products:

None