Primaquine

Summary

Primaquine (CHEMBL506) is an approved small-molecule antimalarial (ATC P01BA03); indicated across 7 conditions including malaria and plasmodium falciparum malaria.

At a glance

• Status: Approved (max clinical phase 4)
• Modality: Small molecule
• ATC class: P01BA03
• Indications: 7 conditions
• Clinical trials: 76
• Chemistry: 259.35 Da · C15H21N3O

Identifiers

Drug identity and classification

Field	Value
ChEMBL ID	CHEMBL506
Name	Primaquine
Type	Small molecule
Max phase	4
FDA approved	yes
PubChem CID	4908
ChEBI	CHEBI:8405
ATC	P01BA03
Molecular formula	C15H21N3O
Molecular weight	259.35
InChIKey	INDBQLZJXZLFIT-UHFFFAOYSA-N

SMILES: CC(CCCN)NC1=C2C(=CC(=C1)OC)C=CC=N2

IUPAC name: 4-N-(6-methoxyquinolin-8-yl)pentane-1,4-diamine

ChEBI definition: An N-substituted diamine that is pentane-1,4-diamine substituted by a 6-methoxyquinolin-8-yl group at the N4 position. It is a drug used in the treatment of malaria and Pneumocystis pneumonia.

Pharmacological roles (ChEBI): antimalarial.

Also known as: Kanaprim, Maliride, Neo-quipenyl, NSC-27296, Primachin, Primaquina, Primaquine, SN-13272, WR-2975, primaquine, SID24715072, SID24715073

Parent form; salt/anhydrous children: CHEMBL43128, CHEMBL3217110

Patent coverage: 3,204 distinct patent families (10,279 SureChEMBL compound mentions), from 2 matched compound structure(s). One matched structure accounts for 10,241 (100%) of the total. Mentions count patents naming the compound (not distinct inventions), so promiscuous / reference molecules inflate the mention figure — families are the dedup metric.

Targets

Targets

Broader ChEMBL bioactivity targets: 27 (assay-derived). Sample: Chloroquine resistance transporter, Alpha-2A adrenergic receptor, Amine oxidase [flavin-containing] A, Amine oxidase [flavin-containing] B, Estrogen receptor, Progesterone receptor, Beta-2 adrenergic receptor, Muscarinic acetylcholine receptor M2, Beta-1 adrenergic receptor, 5-hydroxytryptamine receptor 1A.

Bioactivity

ChEMBL activities: 15 potent at pChembl ≥ 5 of 37 total. Top 30 by potency (10 = 0.1 nM, 6 = 1 µM):

Target	pChembl	Type	Value	Unit	Activity ID
SLC6A4	8.07	Ki	8.4	nM	CHEMBL_ACT_7715784
SLC6A4	7.8	IC50	16	nM	CHEMBL_ACT_7715783
SLC6A4	7.05	AC50	89	nM	CHEMBL_ACT_25150643
SLC6A4	6.99	AC50	103.5	nM	CHEMBL_ACT_25151683
CYP1A2	6.74	IC50	182.4	nM	CHEMBL_ACT_7713611
SHMT2	6.36	IC50	436.5	nM	CHEMBL_ACT_19332956
NSD1	5.75	IC50	1800	nM	CHEMBL_ACT_29068444
PTGS1	5.57	AC50	2702	nM	CHEMBL_ACT_25206510
TST	5.54	IC50	2900	nM	CHEMBL_ACT_19209154
PDE3A	5.54	AC50	2900	nM	CHEMBL_ACT_25191014
PTGS1	5.4	AC50	3948	nM	CHEMBL_ACT_25205580
CHRM2	5.34	AC50	4541	nM	CHEMBL_ACT_25196092
ESR1	5.17	AC50	6700	nM	CHEMBL_ACT_25167581
HTR1A	5.12	AC50	7616	nM	CHEMBL_ACT_25165380
NQO2	5.12	IC50	7500	nM	CHEMBL_ACT_3603391

Target pathways

No target-pathway data for this drug (no mapped target genes).

Indications & clinical

Indications

7 indications (1 at ChEMBL trial phase 4). Phase below is the highest clinical-trial phase recorded for this drug against each disease — not the molecule’s overall approval status (that is in the Summary).

Indication	Trial phase	MONDO	EFO
malaria	4	MONDO:0005136	EFO:0001068
Plasmodium falciparum malaria	3	MONDO:0005920	EFO:0007444
Plasmodium vivax malaria	3	MONDO:0005921	EFO:0007445
pneumocystosis	3	MONDO:0019121	EFO:0007448
severe acute respiratory syndrome	2	MONDO:0005091	MONDO:0100096
obesity disorder	1	MONDO:0011122	EFO:0001073
G6PD deficiency	1	MONDO:0005775	EFO:0007287

Clinical trials

Total trials: 76.

Phase distribution

Phase	Trials
PHASE4	21
Not specified	19
PHASE3	14
PHASE2	9
PHASE1	8
PHASE1/PHASE2	4
PHASE2/PHASE3	1

Top trials by phase / activity

NCT	Phase	Status	Title
NCT07357103	PHASE4	NOT_YET_RECRUITING	Positioning Second-line Therapies for Pneumocystis Jirovecii Pneumonia (PCP Alternatives)
NCT01178021	PHASE4	COMPLETED	Estimating the Risk of Plasmodium Vivax Relapses in Afghanistan
NCT01392014	PHASE4	COMPLETED	Dihydroartemisinin-piperaquine and Primaquine for Uncomplicated Plasmodium Falciparum Cases
NCT01680406	PHASE4	COMPLETED	Ethiopia Antimalarial in Vivo Efficacy Study 2012
NCT01878357	PHASE4	COMPLETED	Surveillance and Treatment With Dihydroartemisinin-piperaquine Plus Primaquine
NCT02143934	PHASE4	COMPLETED	Effect of Liver and Blood-stage Treatment on Subsequent Plasmodium Reinfection and Morbidity
NCT02364583	PHASE4	UNKNOWN	Investigation of Short Course, High Dose Primaquine Treatment for Liver Stages of Plasmodium Vivax Infection
NCT02389374	PHASE4	COMPLETED	A Study to Assess Safety of Current Standard Malaria Treatment and an Assessment of G6PD Status in South-east Bangladesh
NCT02394197	PHASE4	COMPLETED	Effectiveness of Malaria Treatment in Mexico
NCT02434952	PHASE4	COMPLETED	Safety and Tolerability of Low Dose Primaquine
NCT02653898	PHASE4	UNKNOWN	Malaria Elimination Pilot Study in Military Forces in Cambodia
NCT02876549	PHASE4	COMPLETED	G6PD Assessment Before Primaquine for Radical Treatment of Vivax Malaria
NCT03241901	PHASE4	COMPLETED	Prolonging the Therapeutic Life Span of Artemisinin-based Combination Therapies (ACT) in Bagamoyo District, Tanzania
NCT03337152	PHASE4	TERMINATED	Assessing a Risk Model for G6PD Deficiency
NCT03352843	PHASE4	COMPLETED	Single Low-dose Primaquine Efficacy and Safety.
NCT03916003	PHASE4	COMPLETED	Reducing the Risk of P. Vivax After Falciparum Infections in Co-endemic Areas
NCT04079621	PHASE4	COMPLETED	Short Course Radical Cure of P. Vivax Malaria in Nepal
NCT04706130	PHASE4	COMPLETED	Rigorous Assessment of P. Vivax Relapses and Primaquine Efficacy for Radical Cure
NCT04984759	PHASE4	WITHDRAWN	Tafenoquine and Primaquine in Colostrum and Breast Milk
NCT06044805	PHASE4	COMPLETED	Therapeutic Efficacy of Chloroquine Plus Primaquine in the Treatment of Uncomplicated Plasmodium Vivax
NCT06191458	PHASE4	COMPLETED	Postpartum Primaquine in Breast Milk
NCT06148792	PHASE3	RECRUITING	A Revised Tafenoquine Dose to Improve Radical Cure for Vivax Malaria
NCT06666491	PHASE3	RECRUITING	An Interventional Study to Compare the Efficacy and Safety of Tafenoquine (TQ) and Primaquine (PQ) When Either Are Taken Together With Chloroquine (CQ) for the Treatment of P. Vivax Malaria in Indian Participants Aged 2 Years and Older
NCT00000640	PHASE3	COMPLETED	A Phase III Comparative Study of Dapsone / Trimethoprim and Clindamycin / Primaquine Versus Sulfamethoxazole / Trimethoprim in the Treatment of Mild-to-Moderate PCP in Patients With AIDS
NCT00158548	PHASE3	COMPLETED	ACT With Chloroquine, Amodiaquine & Sulphadoxine-pyrimethamine in Pakistan
NCT00158587	PHASE3	COMPLETED	Eight Week Primaquine Regimen for the Treatment of Vivax Malaria
NCT01074905	PHASE3	COMPLETED	Study on the Treatment of Vivax Malaria
NCT01288820	PHASE3	COMPLETED	Study of ACTs Plus Primaquine for Uncomplicated Plasmodium Vivax Malaria
NCT01365598	PHASE3	COMPLETED	Evaluation of the Gametocytocidal Efficacy and Safety of Primaquine in Uncomplicated Falciparum Malaria in Uganda
NCT01708876	PHASE3	COMPLETED	P. Knowlesi Trial of Artesunate-mefloquine Versus Chloroquine
NCT02216123	PHASE3	COMPLETED	Study to Assess the Incidence of Hemolysis, Safety, and Efficacy of Tafenoquine (SB-252263, WR238605) Versus Primaquine in Subjects With Plasmodium Vivax Malaria
NCT02259426	PHASE3	COMPLETED	Dihydroartemisinin-piperaquine With Low Dose Primaquine to Reduce Malaria Transmission
NCT02348788	PHASE3	UNKNOWN	Artemether-lumefantrine vs Chloroquine for Uncomplicated P. Vivax Malaria in Malaysia
NCT02691910	PHASE2/PHASE3	COMPLETED	Efficacy of Chloroquine (CQ) Alone Compared to Concomitant CQ and Primaquine for Plasmodium Vivax Infection
NCT02802501	PHASE3	COMPLETED	Efficacy and Safety Study of Tafenoquine (TQ) Co-administered With Dihydroartemisinin-piperaquine (DHA-PQP) for the Radical Cure of Plasmodium Vivax (P. Vivax) Malaria
NCT04411836	PHASE3	COMPLETED	Effectiveness of Novel Approaches to Radical Cure With Tafenoquine and Primaquine
NCT00959517	PHASE2	COMPLETED	Trial of Artesunate Combination Therapy in Pakistan
NCT01290601	PHASE2	TERMINATED	Study to Evaluate the Efficacy and Safety of Tafenoquine for the Treatment of Plasmodium Vivax in Adults
NCT01376167	PHASE2	COMPLETED	Ph 2B/3 Tafenoquine (TFQ) Study in Prevention of Vivax Relapse
NCT02431650	PHASE1/PHASE2	COMPLETED	Effectiveness of OZ439 as a Gametocytocidal and Transmission Blocking Agent

Clinical evidence (CIViC)

No CIViC predictive evidence (expected for non-precision-medicine drugs).

Pharmacology

Pharmacogenomics

PharmGKB dosing guidelines (1) — CPIC / DPWG genotype-guided dosing for this drug (drug × pharmacogene):

Guideline	Source	Gene(s)	Dosing	Recommendation
Annotation of CPIC Guideline for primaquine and G6PD	CPIC	G6PD		yes

PharmGKB also curates 1 clinical and 33 variant annotation(s) for this drug (gene-keyed; see PharmGKB).

Related molecules

Related molecules

No competitor molecules sharing a primary target (ChEMBL phase ≥2 or PubChem drug-class).