Piperaquine

HCID 178840868CAS 83764-65-2
Substructure searchFind similar structures

Basic information

Standard SMILES
Clc1ccc2c(N3CCN(CCCN4CCN(c5ccnc6cc(Cl)ccc56)CC4)CC3)ccnc2c1
InChIKey
UCRHFBCYFMIWHC-UHFFFAOYSA-N
Molecular formula
C29H32Cl2N6
Average molar mass
535.5 g/mol

Overview

Piperaquine is 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. It has a role as an antimalarial. It is an organochlorine compound, an aminoquinoline and a N-arylpiperazine.

Names & identifiers

Preferred name
Piperaquine
IUPAC
7-chloro-4-[4-[3-[4-(7-chloroquinolin-4-yl)piperazin-1-yl]propyl]piperazin-1-yl]quinoline
English name
Piperaquine
Molecular formula
C29H32Cl2N6
Molecular weight
535.51058

Names & synonyms

piperaquine4085-31-8Piperaquinoline1,3-Bis(4-(7-chloroquinolin-4-yl)piperazin-1-yl)propaneQuinoline, 4,4'-(1,3-propanediyldi-4,1-piperazinediyl)bis[7-chloro-A0HV2Q956Y7-chloro-4-[4-[3-[4-(7-chloroquinolin-4-yl)piperazin-1-yl]propyl]piperazin-1-yl]quinolineCHEBI:91231DTXSID00193825Quinoline, 4,4'-(1,3-propanediyldi-4,1-piperazinediyl)bis(7-chloro-Quinoline, 4,4'-(trimethylenedi-4,1-piperazinediyl)bis(7-chloro-1,3-bis[4-(7-chloroquinolin-4-yl)piperazin-1-yl]propane
Show more names
Brn 0905079Piperaquine USP/EP/BPQuinoline, 4,4'-(1,3-propanediyldi-4,1-piperazinediyl)bis(7-chloro- (9ci)
7-chloro-4-(4-{3-[4-(7-chloroquinolin-4-yl)piperazin-1-yl]propyl}piperazin-1-yl)quinoline7-chloro-4-(4-(3-(4-(7-chloroquinolin-4-yl)piperazin-1-yl)propyl)piperazin-1-yl)quinoline1,3-bis(1-(7-chloro-4'-quinolyl)-4'-piperazinyl)propaneRefChem:174391Quinoline, 4,4'-(1,3-propanediyldi-4,1-piperazinediyl)bis(7-chloro-)DTXCID40116316Quinoline, 4,4'-(1,3-Propanediyldi-4,1-Piperazinediyl)Bis(7-Chloro)-4,4'-(propane-1,3-diyldipiperazine-4,1-diyl)bis(7-chloroquinoline)

Database identifiers

CAS
83764-65-2
ChEMBL
CHEMBL303933
ChEBI
CHEBI:91231
UNII
A0HV2Q956Y
Nikkaji
J126.229G

Properties

Computed structural properties

XLogP
5.6
Topological polar surface area
38.7 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
6
Rotatable bonds
6
Heavy atoms
37

Experimental & physicochemical properties

DrugsPharmaceuticals -> Listed in ZINC15
Human DrugsBreast Feeding; Lactation; Milk, Human; Anti-infective Agents; Antiparasitic Agents; Antimalarials; Antiprotozoal Agents

Physicochemical properties

InChIKey
UCRHFBCYFMIWHC-UHFFFAOYSA-N
SMILES
N1=C2C(C=CC(Cl)=C2)=C(N2CCN(CCCN3CCN(C4=C5C(=NC=C4)C=C(Cl)C=C5)CC3)CC2)C=C1
EWG's Food Scores
1 · 1
FDA UNII
0 HV2Q956Y · A0HV2Q956Y

Safety & regulation

Toxicology

Effects During Pregnancy and Lactation◉ Summary of Use during Lactation

Chemistry & industry

Pharmacology

Protein BindingPiperaquine's binding to plasma proteins is considered to be virtually complete. It has been measured to be >99% in humans, rats, and dogs.
PharmacodynamicsPiperaquine inhibits the P. Falciparum parasite's haem detoxification pathway.
Mechanism of ActionThe mechanism of piperaquine inhibition of the haem detoxification pathway is unknown but is expected to be similar to that of [DB00608].
Biological Half-LifeThe terminal elimination half-life was observed to be 576h or 24 days. This is thought to be due to the extensive distribution of piperaquine.
Metabolism/Metabolites · 1 item

Piperaquine undergoes N-dealkylation, separating its aliphatic bridge from one of the nitrogen-containing rings. The resulting aldehyde is then oxidized to a carboxylic acid to form metabolite 1 (M1). The same nitrogen-containing rings can also undergo hydroxylation at one of two sites to form M3 or M4. M2 is formed via N-oxidation of one of the nitrogens in the quinoline groups at either side of the molecule. M5 results when both of these nitrogens are oxidized. M1 and M2 are the major metabolism products. Each of these metabolites were observed in the urine.

MeSH Pharmacological ClassificationAgents used in the treatment of malaria. They are usually classified on the basis of their action against plasmodia at different stages in their life cycle in the human. (From AMA, Drug Evaluations Annual, 1992, p1585)

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