Basic information
- CAS
66051-74-9- Standard SMILES
CCCCN(CCCC)CCC(O)c1cc2c(Cl)cc(Cl)cc2c2cc(C(F)(F)F)ccc12- InChIKey
FOHHNHSLJDZUGQ-UHFFFAOYSA-N- Molecular formula
- C26H30Cl2F3NO
- Average molar mass
- 500.4 g/mol
- Monoisotopic mass
- 499.1656546
Overview
3-(dibutylamino)-1-[1,3-dichloro-6-(trifluoromethyl)-9-phenanthrenyl]-1-propanol is a member of phenanthrenes.
Names & identifiers
- Preferred name
- Halofantrine
- IUPAC
- 3-(dibutylamino)-1-[1,3-dichloro-6-(trifluoromethyl)phenanthren-9-yl]propan-1-ol
- English name
- HALOFANTRINE
- Molecular formula
- C26H30Cl2F3NO
- Molecular weight
- 500.42
Names & synonyms
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
Show more names
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)
Database identifiers
- 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
Properties
Computed structural properties
- XLogP
- 8.6
- Topological polar surface area
- 23.5 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 5
- Rotatable bonds
- 10
- Heavy atoms
- 33
- Formal charge
- 0
- Complexity
- 584
Experimental & physicochemical properties
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
Physicochemical properties
- Density
- 1.244 · 1.244±0.06 g/cm3 (20 ºC 760 Torr)
- storage temp.
- 2 · 2-8°C
- Water Solubility
- 0.59 mg/L · 0.59mg/L(37 ºC)
- FDA UNII
- 2 OS4303HZ · Q2OS4303HZ
- ATC code
- 1 BX01 · P01BX01
Safety & regulation
Toxicology
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
Chemistry & industry
Pharmacology
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
Applications
DescriptionHalofantrine 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%.
General DescriptionStructurally, 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.
Upstream & downstream products
Upstream raw materials
Suppliers20 total
北京华美互利生物化工010-56205725 · [email protected]
Dayang Chem (Hangzhou) Co.,Ltd.+86-0571-88938639 17705817739 · [email protected]
上海微佳禾生物科技有限公司17502176150; 17502176150 · [email protected]
LGM Pharma1-(800)-881-8210 · [email protected]
武汉易泰科技有限公司上海分公司18930552037 · [email protected]
Pure Chemistry Scientific Inc.001-857-928-2050 or 1-888-588-9418 · [email protected]
上海复和化学科技有限公司0086-21-67651709 · [email protected]
武汉海正工贸发展有限公司027-8866 0053/88660577/88660578
湖北威德利化学科技有限公司027-83989310 18627915365
上海陶术生物科技股份有限公司13564774135 · [email protected]
成都标样生物科技有限公司028-81700200 13308200041 · [email protected]
南京博米尔生物科技有限公司025-83453382-8005 · [email protected]
湖北威德利化学科技有限公司027-83991130 18627774460 · [email protected]
金锦乐(湖南)化学有限公司18001959627(微信同号) 18001959627 · [email protected]
杭州洁汉化工有限公司+86-571-86217390; +8618058761490 · [email protected]
江苏艾康生物医药研发有限公司025-58859352 15955137747 · [email protected]
career henan chemical co+86-0371-86658258 · [email protected]
ANHUI WITOP BIOTECH CO., LTD+8618071025641 · [email protected]
TargetMol中国（陶术生物）4008200310 15002144251 · [email protected]
Dideu Industries Group Limited+8617392712697 · [email protected]
Additional notes
DefinitionChEBI: 3-(dibutylamino)-1-[1,3-dichloro-6-(trifluoromethyl)-9-phenanthrenyl]-1-propanol is a member of phenanthrenes.
Related reactions
1 records
Compound notes
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