ハロファントリン
Halofantrine
基本情報
- CAS
66051-74-9- 標準SMILES
CCCCN(CCCC)CCC(O)c1cc2c(Cl)cc(Cl)cc2c2cc(C(F)(F)F)ccc12- InChIKey
FOHHNHSLJDZUGQ-UHFFFAOYSA-N- 分子式
- C26H30Cl2F3NO
- 平均分子量
- 500.4 g/mol
- 単同位体質量
- 499.1656546
概要
3-(dibutylamino)-1-[1,3-dichloro-6-(trifluoromethyl)-9-phenanthrenyl]-1-propanol is a member of phenanthrenes.
名称と識別子
- 優先名称
- Halofantrine
- IUPAC
- 3-(dibutylamino)-1-[1,3-dichloro-6-(trifluoromethyl)phenanthren-9-yl]propan-1-ol
- 現地名
- ハロファントリン
- 英語名
- HALOFANTRINE
- 分子式
- C26H30Cl2F3NO
- 分子量
- 500.42
名称と別名
Halofantrine69756-53-2Halofantrinum3-(dibutylamino)-1-[1,3-dichloro-6-(trifluoromethyl)phenanthren-9-yl]propan-1-ol3-(Dibutylamino)-1-(1,3-dichloro-6-(trifluoromethyl)phenanthren-9-yl)propan-1-olQ2OS4303HZDL-WR-171669DTXSID0023119WR-171699RefChem:783364DTXCID403119P01BX01
名称をさらに表示
ハロファントリン1,3-ジクロロ-α-[2-(ジブチルアミノ)エチル]-6-(トリフルオロメチル)-9-フェナントレンメタノール1,3-ジクロロ-α-[2-(ジブチルアミノ)エチル]-6-トリフルオロメチル-9-フェナントレンメタノール3-(ジブチルアミノ)-1-[1,3-ジクロロ-6-(トリフルオロメチル)フェナントレン-9-イル]プロパン-1-オールHalofanWR-171669SKF-102886Halofantrine D18HALOFANTRINE USP/EP/BPHalofantrine hydrochloride CRS3-(Dibutylamino)-1-(1,3-dichloro-6-(trifluoromethyl)-phenanthren-9-yl)propan-1-ol1，3-Dichloro-α-[2-(dibutylamino)ethyl]-6-(trifluoromethyl)-9-phenanthrenemethanol3-DIBUTYLAMINO-1-(1,3-DICHLORO-6-TRIFLUOROMETHYL-PHENANTHREN-9-YL)-PROPAN-1-OL HCL
274-104-1Halofantrine, (-)-Halofantrinum [INN-Latin]Halofantrina [INN-Spanish]66051-76-1dl-WR 171669(+)-HalofantrineHalofantrine (INN)
データベース識別子
- CAS
66051-74-9、66051-76-1、69756-53-2- PubChem CID
- 37393
- DTXSID
DTXSID0023119- ChEMBL
CHEMBL1107- ChEBI
CHEBI:94392- UNII
- Q2OS4303HZ
- EC Number
- 274-104-1
- Nikkaji
- J18.879D
物性
構造計算による物性
- XLogP
- 8.6
- 極性表面積
- 23.5 Ų
- 水素結合供与体数
- 1
- 水素結合受容体数
- 5
- 回転可能結合数
- 10
- 重原子数
- 33
- 形式電荷
- 0
- 複雑度
- 584
実験および物理化学的性質
DrugsPharmaceuticals -> Antiparasitic products, insecticides and repellents -> Antiprotozoals
LogP8.9
Solubility1.11e-04 g/L
Human DrugsBreast Feeding; Lactation; Milk, Human; Anti-infective Agents; Antiparasitic Agents; Antimalarials; Antiprotozoal Agents
Physical DescriptionSolid
物理化学的性質
- 比重(密度)
- 1.244 · 1.244±0.06 g/cm3 (20 ºC 760 Torr)
- 貯蔵温度
- 2 · 2-8°C
- 水溶解度
- 0.59 mg/L · 0.59mg/L(37℃)
安全と法規制
安全情報は参考情報です。供給元の安全データシート（SDS）、適用法令、専門家による評価に代わるものではありません。
毒性情報
Drug Induced Liver Injury
Drug-Induced Liver Injury Severity and Toxicity (DILIst)
Halofantrine
DILI Positive
DOI:10.1016/j.drudis.2019.09.022
Effects During Pregnancy and Lactation◉ Summary of Use during Lactation
化学と産業
薬理情報
ATC CodeP - Antiparasitic products, insecticides and repellents
Protein Binding60-70%;
PharmacodynamicsHalofantrine is a synthetic antimalarial which acts as a blood schizonticide. It is effective against multi drug resistant (including mefloquine resistant) <i>P. falciparum</i> malaria.
Mechanism of ActionThe mechanism of action of Halofantrine may be similar to that of chloroquine, quinine, and mefloquine; by forming toxic complexes with ferritoporphyrin IX that damage the membrane of the parasite.
Biological Half-Life6-10 days
Metabolism/MetabolitesHepatic
FDA Pharmacological Classification
Q2OS4303HZ
HALOFANTRINE
Established Pharmacologic Class [EPC] - Antimalarial
Halofantrine is an Antimalarial.
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)
Cellular LocationsMembrane
応用分野
説明Halofantrine is an orally-active blood schizonticide reportedly highly effective in the treatment of fulcipurum malaria and other types of parasitemia. Cure rate is claimed to be over 95%.
一般的な説明Structurally, halofantrine differs from allother antimalarial drugs. It is a good example of drug designthat incorporates bioisosteric principles as evidenced by thetrifluromethyl moiety. Halofantrine is a schizonticide and has no affect on the sporozoite, gametocyte,or hepatic stages. Both the parent compound and Ndesbutylmetabolite are equally active in vitro. Halfantrine’sspecific mechanism of action against the parasite is notknown. There is contradictory evidence that its mechanismranges from requiring heme to disrupting the mitochondria.There is a prominent warning that halfantrine can affectnerve conduction in cardiac tissue.
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