4,4'-[1,3-プロパンジイルビス(4,1-ピペラジンジイル)]ビス(7-クロロキノリン)

Piperaquine

HCID 122262
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基本情報

CAS
4085-31-8
標準SMILES
Clc1ccc2c(N3CCN(CCCN4CCN(c5ccnc6cc(Cl)ccc56)CC4)CC3)ccnc2c1
InChIKey
UCRHFBCYFMIWHC-UHFFFAOYSA-N
分子式
C29H32Cl2N6
平均分子量
535.5 g/mol
単同位体質量
534.2065504

概要

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.

名称と識別子

優先名称
Piperaquine
IUPAC
7-chloro-4-[4-[3-[4-(7-chloroquinolin-4-yl)piperazin-1-yl]propyl]piperazin-1-yl]quinoline
現地名
4,4'-[1,3-プロパンジイルビス(4,1-ピペラジンジイル)]ビス(7-クロロキノリン)
英語名
Piperaquinoline
分子式
C29H32Cl2N6
分子量
535.51

名称と別名

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
名称をさらに表示
ピペラキノリン4,4'-[1,3-プロパンジイルビス(4,1-ピペラジンジイル)]ビス(7-クロロキノリン)ピペラキン4,4′-[1,3-プロパンジイルビス(4,1-ピペラジンジイル)]ビス(7-クロロキノリン)7-クロロ-4-(4-{3-[4-(7-クロロキノリン-4-イル)ピペラジン-1-イル]プロピル}ピペラジン-1-イル)キノリン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)

データベース識別子

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

物性

構造計算による物性

XLogP
5.6
極性表面積
38.7 Ų
水素結合供与体数
0
水素結合受容体数
6
回転可能結合数
6
重原子数
37

実験および物理化学的性質

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

物理化学的性質

融点
198 · 198-200 °C
沸点
721.1 · 721.1±60.0 °C(Predicted)
比重(密度)
1.292 · 1.292±0.06 g/cm3(Predicted)
貯蔵温度
-20 °C · Store at -20°C
溶解性
0.2 mg/ml · ≤0.2mg/ml in DMSO
外見
crystalline solid

化学的性質

化学的特性To class white crystalline powder

安全と法規制

毒性情報

Effects During Pregnancy and Lactation◉ Summary of Use during Lactation

安全データ

注意喚起語
警告
危険有害性情報
コード 危険有害性情報 危険有害性クラス 区分 注意喚起語 シンボル P コード H302

化学と産業

薬理情報

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 件

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)

上流・下流製品情報

上流原料

サプライヤー100 社

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]

補足説明

定義ChEBI: 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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