mefloquine ๐Ÿถ Veterinary Use | Indications/Contra | FAERs-F | FAERs-M | Orange Bk | 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 ยตM/kg/day Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
BA (Bioavailability) 80 % Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H

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
Immune reconstitution inflammatory syndrome 80.21 44.59 15 234 5501 50599374
Product use in unapproved indication 67.48 44.59 24 225 115795 50489080
Progressive multifocal leukoencephalopathy 52.68 44.59 12 237 11445 50593430

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 83.34 64.15 19 287 8700 29565521

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 119.46 47.73 28 500 18204 64480000
JC virus infection 67.27 47.73 13 515 3342 64494862
Immune reconstitution inflammatory syndrome 60.17 47.73 15 513 12455 64485749

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
CHEBI has role CHEBI:38068 antimalarials
CHEBI has role CHEBI:149553 anticoronaviral drug
MeSH PA D000890 Anti-Infective Agents
MeSH PA D000962 Antimalarials
MeSH PA D000977 Antiparasitic Agents
MeSH PA D000981 Antiprotozoal Agents

Drug Use (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




๐Ÿถ Veterinary Drug Use

None

๐Ÿถ 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 Unclassified 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
YMZ PDB_CHEM_ID
CHEMBL411685 ChEMBL_ID
CHEMBL416956 ChEMBL_ID
CHEMBL411686 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

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
Mefloquine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0054-0025 TABLET 250 mg ORAL ANDA 24 sections
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 68071-4702 TABLET 250 mg ORAL ANDA 23 sections