Details of the Drug

General Information of Drug (ID: DM1XT4N)

Drug Name

Tafenoquine

Synonyms

106635-80-7; WR-238605; WR 238605; Etaquine; WR238605; Tafenoquine [INN:BAN

Indication

Disease Entry	ICD 11	Status	REF
Malaria	1F40-1F45	Approved	[1]
Plasmodium vivax malaria	1F41	Approved	[1]

Drug Type

Small molecular drug

Structure

3D MOL

2D MOL

#Ro5 Violations (Lipinski): 1

Molecular Weight (mw)

463.5

Topological Polar Surface Area (xlogp)

5.4

Rotatable Bond Count (rotbonds)

9

Hydrogen Bond Donor Count (hbonddonor)

2

Hydrogen Bond Acceptor Count (hbondacc)

9

ADMET Property

Absorption Tmax: The time to maximum plasma concentration (Tmax) is 13.8 h [2]
Clearance: The clearance of drug is 6 L/h [2]
Half-life: The concentration or amount of drug in body reduced by one-half in 14 days [3]
Metabolism: The drug is metabolized via the liver [2]
Vd: The volume of distribution (Vd) of drug is 2 560 L [2]

Chemical Identifiers

Formula: C24H28F3N3O3
IUPAC Name: 4-N-[2,6-dimethoxy-4-methyl-5-[3-(trifluoromethyl)phenoxy]quinolin-8-yl]pentane-1,4-diamine
Canonical SMILES: CC1=CC(=NC2=C1C(=C(C=C2NC(C)CCCN)OC)OC3=CC=CC(=C3)C(F)(F)F)OC
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
InChIKey: LBHLFPGPEGDCJG-UHFFFAOYSA-N

Cross-matching ID

PubChem CID: 115358
ChEBI ID: CHEBI:141487
CAS Number: 106635-80-7
DrugBank ID: DB06608
TTD ID: D07TWN
INTEDE ID: DR1526
ACDINA ID: D01454

Molecular Interaction Atlas of This Drug

Drug Therapeutic Target (DTT)

DTT Name	DTT ID	UniProt ID	MOA	REF
Electron transport complex III (Complex III)	TTB8JQ7	CY1_HUMAN-CYB_HUMAN	Inhibitor	[1]
Reactive oxygen species (ROS)	TTULV0X	NOUNIPROTAC	Modulator	[1]

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Drug-Metabolizing Enzyme (DME)

DME Name	DME ID	UniProt ID	MOA	REF
Cytochrome P450 2D6 (CYP2D6)_{Main DME}	DECB0K3	CP2D6_HUMAN	Substrate	[4]

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Molecular Interaction Atlas (MIA)

MIA Detail

Jump to Detail Molecular Interaction Atlas of This Drug

Drug Inactive Ingredient(s) (DIG) and Formulation(s) of This Drug

DIG

DIG Name	DIG ID	PubChem CID	Functional Classification
Mannitol	E00103	6251	Diluent; Flavoring agent; Lyophilization aid; Plasticizing agent; Tonicity agent
Hypromellose	E00634	Not Available	Coating agent
Magnesium stearate	E00208	11177	lubricant
Polyethylene glycol 4000	E00654	Not Available	Coating agent; Diluent; Ointment base; Plasticizing agent; Solvent; Suppository base; lubricant
Titanium dioxide	E00322	26042	Coating agent; Colorant; Opacifying agent
Haematite red	E00236	14833	Colorant
Cellulose microcrystalline	E00698	Not Available	Adsorbent; Suspending agent; Diluent
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⏷ Show the Full List of 7 Pharmaceutical Excipients of This Drug

Pharmaceutical Formulation

Formulation Name	Drug Dosage	Dosage Form	Route
Tafenoquine 150 mg tablet	150 mg	Tablet	Oral
Tafenoquine 100 mg tablet	100 mg	Tablet	Oral

Jump to Detail Pharmaceutical Formulation Page of This Drug

References

1	Tafenoquine: First Global Approval.Drugs. 2018 Sep;78(14):1517-1523.
2	Deshmukh R, Sharma L, Tekade M, Kesharwani P, Trivedi P, Tekade RK: Force degradation behavior of glucocorticoid deflazacort by UPLC: isolation, identification and characterization of degradant by FTIR, NMR and mass analysis. J Biomed Res. 2016 Mar;30(2):149-161. doi: 10.7555/JBR.30.20150074. Epub 2016 Feb 20.
3	Oral lipid-based nanoformulation of tafenoquine enhanced bioavailability and blood stage antimalarial efficacy and led to a reduction in human red blood cell loss in mice. Int J Nanomedicine. 2015 Feb 20;10:1493-503. doi: 10.2147/IJN.S76317. eCollection 2015.
4	Tafenoquine and its potential in the treatment and relapse prevention of Plasmodium vivax malaria: the evidence to date. Drug Des Devel Ther. 2016 Jul 26;10:2387-99.
5	Inhibitory effects of anticancer drugs on dextromethorphan-O-demethylase activity in human liver microsomes. Cancer Chemother Pharmacol. 1993;32(6):491-5.
6	Effect of genetic polymorphism on the metabolism of endogenous neuroactive substances, progesterone and p-tyramine, catalyzed by CYP2D6. Brain Res Mol Brain Res. 2004 Oct 22;129(1-2):117-23.
7	CYP2D6 polymorphisms and tamoxifen metabolism: clinical relevance. Curr Oncol Rep. 2010 Jan;12(1):7-15.
8	Metabolic interactions between acetaminophen (paracetamol) and two flavonoids, luteolin and quercetin, through in-vitro inhibition studies. J Pharm Pharmacol. 2017 Dec;69(12):1762-1772.
9	Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675.
10	Inhibition of cytochrome P450 2D6: structure-activity studies using a series of quinidine and quinine analogues. Chem Res Toxicol. 2003 Apr;16(4):450-9.
11	Effects of propofol on human hepatic microsomal cytochrome P450 activities. Xenobiotica. 1998 Sep;28(9):845-53.
12	Pharmacogenetics of schizophrenia. Am J Med Genet. 2000 Spring;97(1):98-106.
13	Roles of CYP2A6 and CYP2B6 in nicotine C-oxidation by human liver microsomes. Arch Toxicol. 1999 Mar;73(2):65-70.
14	Structure-activity relationship for human cytochrome P450 substrates and inhibitors. Drug Metab Rev. 2002 Feb-May;34(1-2):69-82.
15	Protective effect of procysteine on Acinetobacter pneumonia in hyperoxic conditions. J Antimicrob Chemother. 2013 Oct;68(10):2305-10.
16	Mitoquinone (MitoQ) Inhibits Platelet Activation Steps by Reducing ROS Levels. Int J Mol Sci. 2020 Aug 27;21(17):6192.
17	A molecular mechanism of pyruvate protection against cytotoxicity of reactive oxygen species in osteoblasts. Mol Pharmacol. 2006 Sep;70(3):925-35.