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

Stem definitionDrug idCAS RN
quinoline derivatives 2266 90-34-6

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • primaquine
  • primachin
  • primaquin
  • dl-Primaquine
  • (+/-)-Primaquine
  • primaquine phosphate
  • primaquine diphosphate
An aminoquinoline that is given by mouth to produce a radical cure and prevent relapse of vivax and ovale malarias following treatment with a blood schizontocide. It has also been used to prevent transmission of falciparum malaria by those returning to areas where there is a potential for re-introduction of malaria. Adverse effects include anemias and GI disturbances. (From Martindale, The Extra Pharmacopeia, 30th ed, p404)
  • Molecular weight: 259.35
  • Formula: C15H21N3O
  • CLOGP: 2.60
  • LIPINSKI: 0
  • HAC: 4
  • HDO: 2
  • TPSA: 60.17
  • ALOGS: -3.66
  • ROTB: 6

  • Status: OFP

  • Legend:
    OFP - off patent
    OFM - off market
    ONP - on patent

Drug dosage:

DoseUnitRoute
15 mg O

ADMET properties:

PropertyValueReference
BDDCS (Biopharmaceutical Drug Disposition Classification System) 1 Benet LZ, Broccatelli F, Oprea TI
EoM (Fraction excreted unchanged in urine) 1 % Benet LZ, Broccatelli F, Oprea TI
MRTD (Maximum Recommended Therapeutic Daily Dose) 2.89 ┬ÁM/kg/day Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
BA (Bioavailability) 96 % Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H
Vd (Volume of distribution) 4 L/kg Lombardo F, Berellini G, Obach RS
CL (Clearance) 5.80 mL/min/kg Lombardo F, Berellini G, Obach RS
t_half (Half-life) 7.10 hours Lombardo F, Berellini G, Obach RS

Approvals:

DateAgencyCompanyOrphan
Jan. 23, 1952 FDA SANOFI AVENTIS US

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
Methaemoglobinaemia 94.15 53.53 13 74 2259 53346720

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
Methaemoglobinaemia 195.40 39.69 34 435 2842 32510215
Pneumocystis jirovecii pneumonia 71.00 39.69 21 448 18849 32494208
Cyanosis 60.70 39.69 17 452 12536 32500521
Plasmodium vivax infection 48.41 39.69 5 464 3 32513054
Drug clearance increased 43.92 39.69 6 463 96 32512961

Pharmacologic Action:

SourceCodeDescription
ATC P01BA03 ANTIPARASITIC PRODUCTS, INSECTICIDES AND REPELLENTS
ANTIPROTOZOALS
ANTIMALARIALS
Aminoquinolines
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 antimalarials

Drug Use (View source of the data)

DiseaseRelationSNOMED_IDDOID
Vivax malaria indication 27052006 DOID:12978
Ovale malaria off-label use 19341001 DOID:12919
Pneumocystosis jiroveci pneumonia off-label use 415125002 DOID:11339
Plasmodium Ovale Malaria Prevention off-label use
Hemolytic anemia contraindication 61261009 DOID:583
Anemia due to enzyme deficiency contraindication 111577008
Deficiency of glucose-6-phosphate dehydrogenase contraindication 124134002 DOID:2862
Deficiency of cytochrome-b>5< reductase contraindication 124184009
Pregnancy, function contraindication 289908002
Neutropenic disorder contraindication 303011007 DOID:1227
Bone marrow depression contraindication 307762000

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 10.77 Basic
pKa2 3.96 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
Potassium voltage-gated channel subfamily H member 2 Ion channel IC50 4.67 WOMBAT-PK
Sodium-dependent serotonin transporter Transporter Ki 8.08 DRUG MATRIX
Hemoglobin subunit alpha Secreted WOMBAT-PK
Amine oxidase [flavin-containing] B Enzyme IC50 4.02 CHEMBL
Ribosyldihydronicotinamide dehydrogenase [quinone] Enzyme IC50 5.12 CHEMBL
Cytochrome P450 1A2 Enzyme IC50 6.74 DRUG MATRIX
Amine oxidase [flavin-containing] A Enzyme IC50 4.12 CHEMBL
Glucose-6-phosphate 1-dehydrogenase Enzyme WOMBAT-PK
Heat shock protein HSP 90-alpha Cytosolic other IC50 8.22 WOMBAT-PK
Aryl hydrocarbon receptor Transcription factor IC50 5.33 WOMBAT-PK
Serine hydroxymethyltransferase, mitochondrial Enzyme IC50 6.36 CHEMBL
Reverse transcriptase/RNaseH Enzyme IC50 4 CHEMBL
Reverse transcriptase Enzyme IC50 4 CHEMBL
Chloroquine resistance transporter Transporter IC50 4.17 CHEMBL

External reference:

IDSource
4019903 VUID
N0000147988 NUI
D02126 KEGG_DRUG
63-45-6 SECONDARY_CAS_RN
4018229 VANDF
4019903 VANDF
C0033126 UMLSCUI
CHEBI:8405 CHEBI
1PQ PDB_CHEM_ID
CHEMBL506 ChEMBL_ID
CHEMBL43128 ChEMBL_ID
DB01087 DRUGBANK_ID
D011319 MESH_DESCRIPTOR_UI
218 INN_ID
4908 PUBCHEM_CID
9952 IUPHAR_LIGAND_ID
MVR3634GX1 UNII
8687 RXNORM
386 MMSL
5354 MMSL
d00351 MMSL
002941 NDDF
004904 NDDF
36391008 SNOMEDCT_US
426320005 SNOMEDCT_US
429663004 SNOMEDCT_US

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
Primaquine Phosphate HUMAN PRESCRIPTION DRUG LABEL 1 0024-1596 TABLET, FILM COATED 15 mg ORAL NDA 21 sections
Primaquine Phosphate HUMAN PRESCRIPTION DRUG LABEL 1 33261-671 TABLET 15 mg ORAL ANDA 18 sections
PRIMAQUINE PHOSPHATE HUMAN PRESCRIPTION DRUG LABEL 1 42291-510 TABLET, FILM COATED 15 mg ORAL ANDA 17 sections
Primaquine Phosphate HUMAN PRESCRIPTION DRUG LABEL 1 43063-225 TABLET, FILM COATED 15 mg ORAL NDA 21 sections
Primaquine Phosphate HUMAN PRESCRIPTION DRUG LABEL 1 43063-721 TABLET 15 mg ORAL ANDA 22 sections
PRIMAQUINE PHOSPHATE HUMAN PRESCRIPTION DRUG LABEL 1 50742-191 TABLET, FILM COATED 15 mg ORAL ANDA 18 sections
Primaquine Phosphate HUMAN PRESCRIPTION DRUG LABEL 1 60429-035 TABLET 15 mg ORAL ANDA 22 sections
Primaquine Phosphate HUMAN PRESCRIPTION DRUG LABEL 1 76385-102 TABLET 15 mg ORAL ANDA 22 sections