HALOFANTRINE

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Search structure


Synonyms	DL-WR-171669 Halofantrine
Status
Molecule Category	UNKNOWN
ATC	P01BX01
UNII	R7ADS21FSN
EPA CompTox	DTXSID0023119


Active Pharmaceutical Ingredients Bioactive chemicals	Exact Similarity SubStructure	Threshold (%) >= 70

Structure


InChI Key	FOHHNHSLJDZUGQ-UHFFFAOYSA-N
Smiles	CCCCN(CCCC)CCC(O)c1cc2c(Cl)cc(Cl)cc2c2cc(C(F)(F)F)ccc12
InChI	InChI=1S/C26H30Cl2F3NO/c1-3-5-10-32(11-6-4-2)12-9-25(33)23-16-22-21(14-18(27)15-24(22)28)20-13-17(26(29,30)31)7-8-19(20)23/h7-8,13-16,25,33H,3-6,9-12H2,1-2H3

Physicochemical Descriptors

Property Name	Value
Molecular Formula	C26H30Cl2F3NO
Molecular Weight	500.43
AlogP	8.64
Hydrogen Bond Acceptor	2.0
Hydrogen Bond Donor	1.0
Number of Rotational Bond	10.0
Polar Surface Area	23.47
Molecular species	BASE
Aromatic Rings	3.0
Heavy Atoms	33.0

Assay Description	Organism	Bioactivity	Reference
K+ channel blocking activity in Chinese hamster ovary cells expressing HERG Kv11.1	None	196.0 nM
Inhibitory activity against Plasmodium falciparum Dd2 in erythrocytes	Plasmodium falciparum	9.3 nM
Inhibition of human Potassium channel HERG expressed in mammalian cells	Homo sapiens	199.53 nM
Inhibitory concentration against IKr potassium channel	None	40.0 nM
Inhibitory concentration against potassium channel HERG	None	199.53 nM
Inhibition of human voltage-gated potassium channel subunit Kv11.1 (ERG K+ channel) in open state	Homo sapiens	199.53 nM
Inhibition of human cloned ERG	Homo sapiens	40.0 nM
Inhibition of human ERG expressed in CHO cells by whole cell patch clamp technique	Homo sapiens	199.53 nM
Inhibition of human ERG in MCF7 cells	Homo sapiens	199.53 nM
Antimalarial activity against early trophozoite-stage Plasmodium falciparum 3D7 infected in erythrocyte assessed as reduction in parasite hemoglobin content at 5 times IC50 after 8 hrs	Plasmodium falciparum	64.0 %
Antiplasmodial activity against multidrug-resistant Plasmodium falciparum VS/1 by [3H]hypoxanthine incorporation assay	Plasmodium falciparum VS/1	9.0 nM
Inhibition of human ERG	Homo sapiens	194.98 nM
Antimalarial activity against chloroquine-resistant Plasmodium falciparum K1 assessed as incorporation of [3H]hypoxanthine after 48 hr microdilution method	Plasmodium falciparum K1	2.8 nM
Antimalarial activity against chloroquine-sensitive Plasmodium falciparum 3D7 assessed as incorporation of [3H]hypoxanthine after 48 hr microdilution method	Plasmodium falciparum 3D7	5.8 nM
Inhibition of human ERG expressed in CHL cells assessed as tail current at 10 uM after 7 mins by patch clamp assay relative to control	Homo sapiens	100.0 %
Inhibition of human ERG by fluorescence polarization assay	Homo sapiens	156.0 nM
Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of Caco-2 cells at 10 uM after 48 hours by high content imaging	Homo sapiens	-22.52 %
SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate	Severe acute respiratory syndrome coronavirus 2	36.22 %		SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate	Severe acute respiratory syndrome coronavirus 2	10.12 %
Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging	Chlorocebus sabaeus	93.0 %		Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging	Chlorocebus sabaeus	0.17 %		Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging	Chlorocebus sabaeus	93.0 %		Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging	Chlorocebus sabaeus	0.17 %

Cross References

Resources	Reference
ChEBI	94392
ChEMBL	CHEMBL1107
DrugBank	DB01218
DrugCentral	1350
FDA SRS	R7ADS21FSN
Human Metabolome Database	HMDB0015349
Guide to Pharmacology	10019
PharmGKB	PA449839
PubChem	37393
SureChEMBL	SCHEMBL43795

CONTENTS

PREMIER has received funding from the Innovative Medicines Initiative 2 Joint Undertaking (JU) under grant agreement No 875508. The JU receives support from the EU’s Horizon 2020 research and innovation programme and the European Federation of Pharmaceutical Industries and Associations (EFPIA). The views reflect only the authors’ perspective and the JU is not responsible for any use that may be made of the information this manuscript contains.

Elements of the website have been developed under projects PREMIER and the Biocenter Finland Drug Discovery and Chemical Biology network. CSC-IT is thanked for providing computational resources. Content of the website is provided without guarantee for correctness. Data has been collected and integrated from multiple public sources, for the largest: FDA, HUGO Gene Nomenclature Committee, ChEMBL, IUPHAR/BPS guide to pharmacology, Reactome, UniProt, and Ensembl. Credit is given to Ensembl for collecting species images (provided under public domain licences such as Wikimedia and NHGRI).