Basic information
- CAS
4085-31-8- 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
- Monoisotopic mass
- 534.2065504
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
- Piperaquinoline
- Molecular formula
- C29H32Cl2N6
- Molecular weight
- 535.51
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-7-chloro-4-[4-[3-[4-(7-chloroquinolin-4-yl)piperazin-1-yl]propyl]piperazin-1-yl]quinolineA0HV2Q956YCHEBI: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
Piperaquine phosphatePIRERAQUINE PHOSPHATEpipieraquine phosphate4,4'-(1,3-Propanediyldi-4Piperaquinoline USP/EP/BPPiperaquine phosphate CP2000BULK DRUG: PIPERAQUINE PHOSPHATE (DMF GRADE)4,4'-(trimethylenedi-4,1-piperazinediyl)bis(7-chloro-quinoline)
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)
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
- Formal charge
- 0
- Complexity
- 655
Experimental & physicochemical properties
DrugsPharmaceuticals -> Listed in ZINC15
Human DrugsBreast Feeding; Lactation; Milk, Human; Anti-infective Agents; Antiparasitic Agents; Antimalarials; Antiprotozoal Agents
Physicochemical properties
- Melting point
- 198 · 198-200 °C
- Boiling point
- 721.1 · 721.1±60.0 °C(Predicted)
- Density
- 1.292 · 1.292±0.06 g/cm3(Predicted)
- storage temp.
- -20 °C · Store at -20°C
- solubility
- 0.2 mg/ml · ≤0.2mg/ml in DMSO
- form
- crystalline solid
- pka
- 8.92 · 8.92±0.50(Predicted)
- InChIKey
- UCRHFBCYFMIWHC-UHFFFAOYSA-N
- SMILES
- C(N1CCN(C2C3C(N=CC=2)=CC(Cl)=CC=3)CC1)CCN1CCN(C2C3C(N=CC=2)=CC(Cl)=CC=3)CC1
- FDA UNII
- 0 HV2Q956Y · A0HV2Q956Y
- Symbol(GHS)
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Toxicology
Effects During Pregnancy and Lactation◉ Summary of Use during Lactation
Safety data
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- Hazard statements
- H302-H315-H319-H335
- Precautionary statements
- P261-P305+P351+P338
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
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)
Absorption, Distribution and Excretion
Piperaquine is slowly absorbed and exhibits multiple peaks in its plasma concentration curve suggestive of enterohepatic recycling occurring alongside the absorption process. Due to this complication there is no discreet value for bioavailability but piperaquine is highly absorbed into systemic circulation. When taken with food, Cmax increases by 217% and mean exposure increases by 177%. Tmax is not affected by food and remains around 5 h. Piperaquine has been observed to accumulate more in females to a degree of 30-50% more than males. It also collects in red blood cells similar to [DB11638].
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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