Piperaquine
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Also known as Piperaquinoline
Summary
Piperaquine (CHEMBL303933) is a phase-3 clinical-stage small-molecule antimalarial; indicated across 4 conditions including malaria and plasmodium falciparum malaria.
At a glance
- Status: Max clinical phase 3 (not approved)
- Modality: Small molecule
- Indications: 4 conditions
- Clinical trials: 21
- Chemistry: 535.5 Da · C29H32Cl2N6
Identifiers
Drug identity and classification
| Field | Value |
|---|---|
| ChEMBL ID | CHEMBL303933 |
| Name | Piperaquine |
| Type | Small molecule |
| Max phase | 3 |
| FDA approved | no |
| PubChem CID | 122262 |
| ChEBI | CHEBI:91231 |
| Molecular formula | C29H32Cl2N6 |
| Molecular weight | 535.5 |
| InChIKey | UCRHFBCYFMIWHC-UHFFFAOYSA-N |
SMILES: C1CN(CCN1CCCN2CCN(CC2)C3=C4C=CC(=CC4=NC=C3)Cl)C5=C6C=CC(=CC6=NC=C5)Cl
IUPAC name: 7-chloro-4-[4-[3-[4-(7-chloroquinolin-4-yl)piperazin-1-yl]propyl]piperazin-1-yl]quinoline
ChEBI definition: An aminoquinoline that is 1,3-di(piperazin-1-yl)propane in which the nitrogen at position 4 of each of the piperazine moieties is replaced by a 7-chloroquinolin-4-yl group.
Pharmacological roles (ChEBI): antimalarial.
Also known as: Piperaquine, Piperaquinoline, piperaquine, PIPERAQUINE
Parent form; salt/anhydrous children: CHEMBL539666, CHEMBL1652442
Patent coverage: 585 distinct patent families (1,554 SureChEMBL compound mentions), from 2 matched compound structure(s). One matched structure accounts for 1,500 (97%) 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: 8 (assay-derived). Sample: Muscarinic acetylcholine receptor M1, D(3) dopamine receptor, Kappa-type opioid receptor, Voltage-gated inwardly rectifying potassium channel KCNH2, cGMP-inhibited 3’,5’-cyclic phosphodiesterase 3A, Histamine H3 receptor, 3’,5’-cyclic-AMP phosphodiesterase 4D, Cytochrome P450 3A4.
Bioactivity
ChEMBL activities: 6 potent at pChembl ≥ 5 of 8 total. Top 30 by potency (10 = 0.1 nM, 6 = 1 µM):
| Target | pChembl | Type | Value | Unit | Activity ID |
|---|---|---|---|---|---|
| CYP3A4 | 7.05 | Ki | 90 | nM | CHEMBL_ACT_19145083 |
| KCNH2 | 5.59 | AC50 | 2560 | nM | CHEMBL_ACT_25118039 |
| CHRM1 | 5.42 | AC50 | 3800 | nM | CHEMBL_ACT_25135575 |
| PDE3A | 5.33 | AC50 | 4700 | nM | CHEMBL_ACT_25190814 |
| HRH3 | 5.21 | AC50 | 6100 | nM | CHEMBL_ACT_25200685 |
| DRD3 | 5.05 | AC50 | 9000 | nM | CHEMBL_ACT_25193646 |
Target pathways
No target-pathway data for this drug (no mapped target genes).
Indications & clinical
Indications
4 indications (0 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 | 3 | MONDO:0005136 | EFO:0001068 |
| Plasmodium falciparum malaria | 3 | MONDO:0005920 | EFO:0007444 |
| Plasmodium vivax malaria | 3 | MONDO:0005921 | EFO:0007445 |
1 further indication record had no mapped disease name (EFO/MeSH-only) or were duplicates, and are omitted.
Clinical trials
Total trials: 21.
Phase distribution
| Phase | Trials |
|---|---|
| PHASE3 | 5 |
| PHASE4 | 4 |
| PHASE2 | 3 |
| Not specified | 3 |
| PHASE2/PHASE3 | 2 |
| PHASE1 | 2 |
| PHASE1/PHASE2 | 1 |
| EARLY_PHASE1 | 1 |
Top trials by phase / activity
| NCT | Phase | Status | Title |
|---|---|---|---|
| NCT07322068 | PHASE4 | NOT_YET_RECRUITING | Perennial Malaria Chemoprevention in the Malaria Vaccine Era |
| NCT01075945 | PHASE4 | UNKNOWN | Dihydroartemisinin- Piperaquine Versus Artemether- Lumefantrine in the Treatment Uncomplicated Plasmodium Falciparum Malaria in Sudan |
| NCT01887821 | PHASE4 | COMPLETED | Antimalarial Drug Susceptibility and Molecular Characterization of Plasmodium Vivax Isolates in Vietnam |
| NCT04767191 | PHASE4 | COMPLETED | Malaria Therapeutic Efficacy Study (TES) Kenya |
| NCT00561899 | PHASE2/PHASE3 | COMPLETED | Comparison of Three Drug Combinations for Intermittent Treatment of Malaria in Children |
| NCT01722539 | PHASE3 | COMPLETED | Impact IPT With Sulfadoxine-pyrimethamine or Sulfadoxine-pyrimethamine Plus Piperaquine in Schoolchildren |
| NCT01899820 | PHASE3 | UNKNOWN | Evaluation of the Efficacy of Artemisinin Combination Therapy in Kenya |
| NCT02974348 | PHASE3 | COMPLETED | Antimalaria Drugs Susceptibility Testing for an Effective Management of Infected Patients in Sub-Sahara Africa |
| NCT03939104 | PHASE3 | COMPLETED | A Trial to Compare the Efficacy, Safety and Tolerability of Combinations of 3 Anti-malarial Drugs Against Combinations of 2 Anti-malarial Drugs (Asia) |
| NCT04049916 | PHASE2/PHASE3 | COMPLETED | Pyronaridine-artesunate With Low Dose Primaquine for Preventing P. Falciparum Transmission |
| NCT04844099 | PHASE3 | COMPLETED | Dihydroartemisinin-Piperaquine or Sulphadoxine-Pyrimethamine for the Chemoprevention of Malaria in Sickle Cell Anaemia |
| NCT04280692 | PHASE1/PHASE2 | SUSPENDED | Controlled Human Malaria Infection Transmission Model - Phase A |
| NCT04609098 | PHASE2 | COMPLETED | Single Low Dose Tafenoquine to Reduce P. Falciparum Transmission in Mali (NECTAR2) |
| NCT05829187 | PHASE2 | COMPLETED | Momordica Charantia and Dihydroartemisinin-piperaquined-primaquine for Uncomplicated Plasmodium Falciparum Malaria Patients in Southwest Sumba Regency |
| NCT06036030 | PHASE2 | COMPLETED | Combination Momordica Charantia Extract and Primaquine Againts Plasmodium Falciparum Uncomplicated and Plasmodium Vivax Uncomplicated Treatment in Manokwari, West Papua |
| NCT07470424 | PHASE1 | NOT_YET_RECRUITING | A Clinical Study of Piperaquine, Pyronaridine, and Artesunate Administered in Combination in Healthy Adults |
| NCT02431637 | PHASE1 | COMPLETED | Experimental Falciparum Transmission to Anopheles |
| NCT07021430 | EARLY_PHASE1 | NOT_YET_RECRUITING | Focal Mass Drug Administration for the Prevention of Malaria in Pregnancy |
| NCT06870344 | Not specified | ACTIVE_NOT_RECRUITING | IGHID 12334 - After the Flood: Optimal Strategies to Prevent Malaria Epidemics Caused by Severe Flooding |
| NCT01280162 | Not specified | COMPLETED | Malaria Active Epidemiology and Treatment Study |
| NCT02199951 | Not specified | UNKNOWN | Introduction of Eurartesim® in Burkina Faso, Mozambique, Ghana and Tanzania |
Clinical evidence (CIViC)
No CIViC predictive evidence (expected for non-precision-medicine drugs).
Pharmacology
Pharmacogenomics
No CPIC/DPWG dosing guideline or drug-level clinical/variant annotations in PharmGKB for this molecule.
Related molecules
Related molecules
No competitor molecules sharing a primary target (ChEMBL phase ≥2 or PubChem drug-class).