Piperaquine

HCID 122262
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Grundinformationen

CAS
4085-31-8
Standard-SMILES
Clc1ccc2c(N3CCN(CCCN4CCN(c5ccnc6cc(Cl)ccc56)CC4)CC3)ccnc2c1
InChIKey
UCRHFBCYFMIWHC-UHFFFAOYSA-N
Summenformel
C29H32Cl2N6
Durchschnittliche Molmasse
535,5 g/mol
Monoisotopische Masse
534,2065504

Überblick

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.

Namen und Bezeichner

Bevorzugter Name
Piperaquine
IUPAC
7-chloro-4-[4-[3-[4-(7-chloroquinolin-4-yl)piperazin-1-yl]propyl]piperazin-1-yl]quinoline
Englischer Name
Piperaquinoline
Summenformel
C29H32Cl2N6
Molmasse
535.51

Namen und Synonyme

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
Weitere Namen anzeigen
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)

Datenbank-Bezeichner

CAS
4085-31-8
PubChem CID
122262
DTXSID
DTXSID00193825
ChEMBL
CHEMBL303933
ChEBI
CHEBI:91231
UNII
A0HV2Q956Y
Nikkaji
J126.229G

Eigenschaften

Berechnete Struktureigenschaften

XLogP
5,6
Polarare Oberfläche (TPSA)
38,7 Ų
H-Brücken-Donoren
0
H-Brücken-Akzeptoren
6
Frei drehbare Bindungen
6
Schwere Atome
37

Experimentelle und physikochemische Eigenschaften

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

Physikochemische Eigenschaften

Schmelzpunkt
198 · 198-200 °C
Siedepunkt
721.1 · 721.1±60.0 °C(Predicted)
Dichte
1.292 · 1.292±0.06 g/cm3(Predicted)
storage temp.
-20 °C · Store at -20°C
Löslichkeit
0.2 mg/ml · ≤0.2mg/ml in DMSO
Aggregatzustand
crystalline solid

Sicherheit und Regulatorisches

Toxikologische Informationen

Effects During Pregnancy and Lactation◉ Summary of Use during Lactation

Sicherheitsdaten

Alarmwort
Warnung
Gefahrenhinweise
Code Gefahrenhinweise Gefahrenklasse Abteilung Alarmwort Symbol P-Code H302

Chemie und Industrie

Pharmakologische Informationen

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 Eintrag

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)

Vor- und nachgelagerte Produkte

Vorgelagerte Rohstoffe

Anbieter100 Anbieter

湖南韵邦生物科技股份有限公司85561037 15386497078 · [email protected]
湖北威德利化学试剂有限公司181-6332-1995 18062128043 · [email protected]
武汉敬康恩生物医药科技有限公司13720134139 086-15871494362 13720134139 · [email protected]
咸宁深蓝生物医药研发有限公司18171815831 · [email protected]
陕西帕尼尔生物科技有限公司029-84385017-8003 13259417953 · [email protected]

Ergänzende Hinweise

DefinitionChEBI: 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.

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