TAFENOQUINE

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Search structure


Synonyms	SB-252263-AAB Tafenoquine WR 238605
Status
Molecule Category	Free-form
ATC	P01BA07
UNII	262P8GS9L9


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

Structure


InChI Key	LBHLFPGPEGDCJG-UHFFFAOYSA-N
Smiles	COc1cc(C)c2c(Oc3cccc(C(F)(F)F)c3)c(OC)cc(NC(C)CCCN)c2n1
InChI	InChI=1S/C24H28F3N3O3/c1-14-11-20(32-4)30-22-18(29-15(2)7-6-10-28)13-19(31-3)23(21(14)22)33-17-9-5-8-16(12-17)24(25,26)27/h5,8-9,11-13,15,29H,6-7,10,28H2,1-4H3

Physicochemical Descriptors

Property Name	Value
Molecular Formula	C24H28F3N3O3
Molecular Weight	463.5
AlogP	5.91
Hydrogen Bond Acceptor	6.0
Hydrogen Bond Donor	2.0
Number of Rotational Bond	9.0
Polar Surface Area	78.63
Molecular species	BASE
Aromatic Rings	3.0
Heavy Atoms	33.0

Assay Description	Organism	Bioactivity	Reference
In vitro antimalarial activity dosed at 1 mg/kg against exoerythrocytic Plasmodium yoelii in mice (Mus musculus) hepatocytes	Mus musculus	39.0 %
In vitro antimalarial activity dosed at 10 mg/kg against exoerythrocytic Plasmodium yoelii in mice (Mus musculus) hepatocytes	Mus musculus	96.0 %
Antimalarial activity against mefloquine-resistant Plasmodium falciparum CDC Sierra Leone 1 D6 after 48 hrs by [3H]hypoxanthine uptake assay	Plasmodium falciparum	2.7 ug.mL-1
Antimalarial activity against mefloquine-susceptible Plasmodium falciparum CDC Indochina 3 W2 after 48 hrs by [3H]hypoxanthine uptake assay	Plasmodium falciparum	0.8 ug.mL-1
Cytotoxicity against mouse RAW264.7 cells after 24 hrs by MTT assay	Mus musculus	5.9 ug.mL-1
Antimalarial activity against mature gametocytic stage of Plasmodium falciparum assessed as inhibition of mature gamete exflagellation at 10 uM incubated for 24 hrs prior to exflagellation induction at 21 degC measured after 20 mins by microscopic analysis relative to control	Plasmodium falciparum	50.0 %
Antimalarial activity against multidrug-resistant Plasmodium falciparum W2 by SYBR green-based assay	Plasmodium falciparum	217.0 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	89.95 %
SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate	Severe acute respiratory syndrome coronavirus 2	-44.37 %
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	-0.21 %		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	-0.21 %
Antiplasmodial activity against liver stage Plasmodium cynomolgi B infected in non-human primate hepatocytes assessed as inhibition of liver schizonts development incubated for 4 days from sporozoite addition by prophylactic assay	Plasmodium cynomolgi	190.0 nM
Antiplasmodial activity against liver stage Plasmodium cynomolgi B infected in non-human primate hepatocytes assessed as inhibition of hypnozoite development incubated for 4 days from sporozoite addition by prophylactic assay	Plasmodium cynomolgi	140.0 nM

Cross References

Resources	Reference
ChEBI	141487
ChEMBL	CHEMBL298470
DrugBank	DB06608
DrugCentral	3578
FDA SRS	262P8GS9L9
Guide to Pharmacology	9722
PharmGKB	PA166115580
PubChem	115358
SureChEMBL	SCHEMBL347388

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).