tafenoquine   Click here for help

GtoPdb Ligand ID: 9722

Synonyms: Arakoda® | etaquine | Krintafel® | WR238605
Approved drug Antimalarial Ligand
tafenoquine is an approved drug (FDA (2018))
Compound class: Synthetic organic
Comment: Tafenoquine is an 8-aminoquinoline derivative that has potent antimalarial activity and is a synthetic analogue of primaquine.
The INN record for tafenoquine indicates that it is a racemic mixture. We show the chemical structure without stereochemistry to represent the mixture. The non-isomeric structure is also represented in the PubChem and ChEMBL entries listed in the links table below, while the two enantiomers forming the racemate are represented by PubChem CID 76969187 and PubChem CID 76969188.

The Malaria tab on this ligand page provides additional curator comments of relevance to the Guide to MALARIA PHARMACOLOGY.
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Ligand Activity Visualisation Charts

These are box plot that provide a unique visualisation, summarising all the activity data for a ligand taken from ChEMBL and GtoPdb across multiple targets and species. Click on a plot to see the median, interquartile range, low and high data points. A value of zero indicates that no data are available. A separate chart is created for each target, and where possible the algorithm tries to merge ChEMBL and GtoPdb targets by matching them on name and UniProt accession, for each available species. However, please note that inconsistency in naming of targets may lead to data for the same target being reported across multiple charts.

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View interactive charts of activity data across species
2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Click here for structure editor
Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the CDK toolkit. All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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Hydrogen bond acceptors 3
Hydrogen bond donors 2
Rotatable bonds 10
Topological polar surface area 78.63
Molecular weight 463.21
XLogP 5.3
No. Lipinski's rules broken 1
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

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Canonical SMILES NCCCC(Nc1cc(OC)c(c2c1nc(OC)cc2C)Oc1cccc(c1)C(F)(F)F)C
Isomeric SMILES NCCCC(Nc1cc(OC)c(c2c1nc(OC)cc2C)Oc1cccc(c1)C(F)(F)F)C
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
InChI Key LBHLFPGPEGDCJG-UHFFFAOYSA-N
Classification Click here for help
Compound class Synthetic organic
Ligand families/groups Antimalarial ligands
Approved drug? Yes (FDA (2018))
IUPAC Name Click here for help
N-[2,6-dimethoxy-4-methyl-5-[3-(trifluoromethyl)phenoxy]quinolin-8-yl]pentane-1,4-diamine
International Nonproprietary Names Click here for help
INN number INN
7835 tafenoquine
Synonyms Click here for help
Arakoda® | etaquine | Krintafel® | WR238605
Database Links Click here for help
CAS Registry No. 106635-80-7 (source: Scifinder)
ChEMBL Ligand CHEMBL298470
DrugCentral Ligand 3578
GtoPdb PubChem SID 374883823
PubChem CID 115358
Search Google for chemical match using the InChIKey LBHLFPGPEGDCJG-UHFFFAOYSA-N
Search Google for chemicals with the same backbone LBHLFPGPEGDCJG
Search PubMed clinical trials tafenoquine
Search PubMed titles tafenoquine
Search PubMed titles/abstracts tafenoquine
Search UniChem for chemical match using the InChIKey LBHLFPGPEGDCJG-UHFFFAOYSA-N
Search UniChem for chemicals with the same backbone LBHLFPGPEGDCJG
Wikipedia Tafenoquine