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

Stem definitionDrug idCAS RN
quinoline derivatives 1665 53230-10-7

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • mephloquine
  • mephloquine HCl
  • mephloquine hydrochloride
  • mefloquine
  • (+/-)-Mefloquine
  • lariam
  • mefloquin
  • mephaquin
  • mefloquine hydrochloride
  • mefloquine HCl
A phospholipid-interacting antimalarial drug (ANTIMALARIALS). It is very effective against PLASMODIUM FALCIPARUM with very few side effects.
  • Molecular weight: 378.32
  • Formula: C17H16F6N2O
  • CLOGP: 3.67
  • LIPINSKI: 0
  • HAC: 3
  • HDO: 2
  • TPSA: 45.15
  • ALOGS: -4
  • ROTB: 4
  • Status: OFP
    • Legend:
    OFP - off patent
    OFM - off market
    ONP - on patent

Drug dosage:

DoseUnitRoute
1 g O

ADMET properties:

PropertyValueReference
BDDCS (Biopharmaceutical Drug Disposition Classification System) 2 Benet LZ, Broccatelli F, Oprea TI
EoM (Fraction excreted unchanged in urine) 9 % Benet LZ, Broccatelli F, Oprea TI
MRTD (Maximum Recommended Therapeutic Daily Dose) 47.20 µM/kg/day Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
BA (Bioavailability) 80 % Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H
fu (Fraction unbound in plasma) 0 % Kawashima H, Watanabe R, Esaki T, Kuroda M, Nagao C, Natsume-Kitatani Y, Ohashi R, Komura H, Mizuguchi K

Predicted pharmacokinetic/toxicological properties (PK-AZ):

PropertyDescriptionValueUnitConfidenceSimilarity
azlogd74 LogD at pH 7.4 2.433 High 1
caco2-efflux Caco-2 efflux ratio (BA/AB) 3.606 High 1
caco2-intrinsic-papp Caco-2 intrinsic apparent permeability 20.045 10^-6 cm/s High 1
dh-clint Dog hepatocyte intrinsic clearance 3.006 uL/min/10^6 cells High 1
dppb Dog plasma protein binding (% unbound) 8.380 % High 1
fcs-ppb Fetal calf serum protein binding (% unbound) 18.990 % High 1
herg hERG pIC50 5.233 pIC50 High 1
hh-clint Human hepatocyte intrinsic clearance 1.122 uL/min/10^6 cells High 1
hlm-clint Human liver microsomal intrinsic clearance 6.039 uL/min/mg protein High 1
hppb Human plasma protein binding (% unbound) 10.470 % High 1
kinase-safety-class ACVR2B,AXL,BRAF,CAMK2D,CDK5,EIF2AK3,ERBB2,GRK2,ITK,JAK3,MET,NTRK2,PDK2,PDK4,PIK3CG,PRKDC,TEK 17
kinase-selectivity-class AXL,EIF2AK3 2
mdck-mdr1-efflux MDCK-MDR1 efflux ratio 7.379 High 1
mh-clint Mouse hepatocyte intrinsic clearance 10.864 High 1
mppb Mouse plasma protein binding (% unbound) 6.760 High 1
nih-mdck-mdr1-efflux NIH MDCK-MDR1 efflux ratio 19.770 High 1
pfas-class PFAS structural alert (1 = True, 0 = False) 1
pld-class Phospholipidosis risk class (1 = positive, 0 = negative) 1 High 1
pppb Pig plasma protein binding (% unbound) 13.600 % High 1
rh-clint Rat hepatocyte intrinsic clearance 21.878 uL/min/10^6 cells High 1
rh-fuinc Rat hepatocyte fraction unbound in incubation 25.350 % High 1
rppb Rat plasma protein binding (% unbound) 7.630 % High 1
solubility-dd Solubility at pH 7.4 in DMSO 736.207 uM High 1

Approvals:

DateAgencyCompanyOrphan
May 2, 1989 FDA

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
Progressive multifocal leukoencephalopathy 125.85 45.35 26 426 15629 90612366
Immune reconstitution inflammatory syndrome 120.33 45.35 22 430 6997 90620998
JC virus infection 76.45 45.35 13 439 2706 90625289
Product use in unapproved indication 56.18 45.35 29 423 336207 90291788

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
Progressive multifocal leukoencephalopathy 122.91 58.01 27 375 11509 42609424
JC virus infection 66.91 58.01 13 389 2991 42617942

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
Progressive multifocal leukoencephalopathy 232.45 46.35 50 758 24906 110563585
JC virus infection 143.75 46.35 26 782 5264 110583227
Immune reconstitution inflammatory syndrome 131.13 46.35 29 779 16197 110572294

FDA Adverse Event Reporting System (Pediatric)

None

Pharmacologic Action:

SourceCodeDescription
ATC P01BC02 ANTIPARASITIC PRODUCTS, INSECTICIDES AND REPELLENTS
ANTIPROTOZOALS
ANTIMALARIALS
Methanolquinolines
ATC P01BF02 ANTIPARASITIC PRODUCTS, INSECTICIDES AND REPELLENTS
ANTIPROTOZOALS
ANTIMALARIALS
Artemisinin and derivatives, combinations
FDA EPC N0000175482 Antimalarial
MeSH PA D000890 Anti-Infective Agents
MeSH PA D000962 Antimalarials
MeSH PA D000977 Antiparasitic Agents
MeSH PA D000981 Antiprotozoal Agents
CHEBI has role CHEBI:38068 antimalarial
CHEBI has role CHEBI:22587 antiviral agent
CHEBI has role CHEBI:35610 antineoplastic agent
CHEBI has role CHEBI:149553 anticoronaviral agent

Related Drugs by ATC class:

P01BC Methanolquinolines 1 drug
quinine
P01BF Artemisinin and derivatives, combinations 11 drugs
amodiaquineartemetherartemisininartenimolartesunatelumefantrinepiperaquinepyrimethaminepyronaridinesulfadoxinesulfalene

Drug Use | Suggest Off label Use Form| |View source of the data|

DiseaseRelationSNOMED_IDDOID
Vivax malaria indication 27052006 DOID:12978
Chloroquine-Resistant Plasmodium Falciparum Malaria Prevention indication
Chloroquine Resistant Plasmodium Falciparum Malaria indication
Ataxia contraindication 20262006
Generalized anxiety disorder contraindication 21897009 DOID:14320
Depressive disorder contraindication 35489007
Sinus bradycardia contraindication 49710005
Schizophrenia contraindication 58214004 DOID:5419
Sinus node dysfunction contraindication 60423000
Psychotic disorder contraindication 69322001
Prolonged QT interval contraindication 111975006
Seizure disorder contraindication 128613002
Atrioventricular block contraindication 233917008 DOID:0050820
Disease of liver contraindication 235856003 DOID:409
Psychiatric Disturbance contraindication




🐶 Veterinary Drug Use

None

🐶 Veterinary products

None

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 13.95 acidic
pKa2 8.56 Basic
pKa3 4.89 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
Adenosine receptor A2a GPCR Ki 6.91 CHEMBL
Potassium voltage-gated channel subfamily H member 2 Ion channel IC50 5.25 WOMBAT-PK
Multidrug resistance protein 1 Transporter WOMBAT-PK
Adenosine receptor A1 GPCR Ki 5.91 CHEMBL
Hemoglobin subunit alpha Secreted WOMBAT-PK
Glycine receptor subunit alpha-1 Ion channel EC50 5.60 CHEMBL
Protein kinase Pfmrk Kinase IC50 4.92 CHEMBL

External reference:

IDSource
4019811 VUID
N0000147900 NUI
D00831 KEGG_DRUG
51773-92-3 SECONDARY_CAS_RN
4019498 VANDF
4019811 VANDF
C0025153 UMLSCUI
CHEBI:63609 CHEBI
CHEMBL416956 ChEMBL_ID
CHEMBL535650 ChEMBL_ID
DB00358 DRUGBANK_ID
D015767 MESH_DESCRIPTOR_UI
4046 PUBCHEM_CID
4252 IUPHAR_LIGAND_ID
3777 INN_ID
TML814419R UNII
202989 RXNORM
1710 MMSL
43453 MMSL
5035 MMSL
d00286 MMSL
003537 NDDF
004873 NDDF
387505001 SNOMEDCT_US
412243001 SNOMEDCT_US
87567009 SNOMEDCT_US
A1A1V PDB_CHEM_ID

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
Mefloquine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0555-0171 TABLET 250 mg ORAL ANDA 23 sections
Mefloquine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 21695-449 TABLET 250 mg ORAL ANDA 23 sections
Mefloquine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 21695-561 TABLET 250 mg ORAL ANDA 26 sections
Mefloquine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 50090-2396 TABLET 250 mg ORAL ANDA 23 sections
Mefloquine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 52959-803 TABLET 250 mg ORAL ANDA 26 sections
Mefloquine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 54868-5434 TABLET 250 mg ORAL ANDA 13 sections
Mefloquine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 62135-973 TABLET 250 mg ORAL ANDA 16 sections