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WR-238605

CAS No.:
106635-81-8
Catalog Number:
AG008WPX
Molecular Formula:
C28H34F3N3O7
Molecular Weight:
581.5807
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Product Description
Catalog Number:
AG008WPX
Chemical Name:
WR-238605
CAS Number:
106635-81-8
Molecular Formula:
C28H34F3N3O7
Molecular Weight:
581.5807
MDL Number:
MFCD00892249
IUPAC Name:
butanedioic acid;4-N-[2,6-dimethoxy-4-methyl-5-[3-(trifluoromethyl)phenoxy]quinolin-8-yl]pentane-1,4-diamine
InChI:
InChI=1S/C24H28F3N3O3.C4H6O4/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;5-3(6)1-2-4(7)8/h5,8-9,11-13,15,29H,6-7,10,28H2,1-4H3;1-2H2,(H,5,6)(H,7,8)
InChI Key:
CQBKFGJRAOXYIP-UHFFFAOYSA-N
SMILES:
OC(=O)CCC(=O)O.NCCCC(Nc1cc(OC)c(c2c1nc(OC)cc2C)Oc1cccc(c1)C(F)(F)F)C
Properties
Complexity:
690  
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
2  
Defined Atom Stereocenter Count:
0
Defined Bond Stereocenter Count:
0
Exact Mass:
581.235g/mol
Formal Charge:
0
Heavy Atom Count:
41  
Hydrogen Bond Acceptor Count:
13  
Hydrogen Bond Donor Count:
4  
Isotope Atom Count:
0
Molecular Weight:
581.589g/mol
Monoisotopic Mass:
581.235g/mol
Rotatable Bond Count:
12  
Topological Polar Surface Area:
153A^2
Undefined Atom Stereocenter Count:
1  
Undefined Bond Stereocenter Count:
0
Literature
Title Journal
Tafenoquine plus chloroquine for the treatment and relapse prevention of Plasmodium vivax malaria (DETECTIVE): a multicentre, double-blind, randomised, phase 2b dose-selection study. Lancet (London, England) 20140322
Uptake of the antileishmania drug tafenoquine follows a sterol-dependent diffusion process in Leishmania. The Journal of antimicrobial chemotherapy 20111101
Determination of tafenoquine in dried blood spots and plasma using LC and fluorescence detection. Bioanalysis 20110801
Enantiomeric separation of antimalarial drugs by capillary electrophoresis using neutral and negatively charged cyclodextrins. Journal of pharmaceutical and biomedical analysis 20110220
Radical curative efficacy of tafenoquine combination regimens in Plasmodium cynomolgi-infected Rhesus monkeys (Macaca mulatta). Malaria journal 20110101
Primaquine in vivax malaria: an update and review on management issues. Malaria journal 20110101
Risk factors for gametocyte carriage in uncomplicated falciparum malaria in children before and after artemisinin-based combination treatments. Chemotherapy 20110101
Antileishmanial and antitrypanosomal activities of the 8-aminoquinoline tafenoquine. Antimicrobial agents and chemotherapy 20101201
A randomized, double-blind, safety and tolerability study to assess the ophthalmic and renal effects of tafenoquine 200 mg weekly versus placebo for 6 months in healthy volunteers. The American journal of tropical medicine and hygiene 20090801
The efficacy and tolerability of three different regimens of tafenoquine versus primaquine for post-exposure prophylaxis of Plasmodium vivax malaria in the Southwest Pacific. Transactions of the Royal Society of Tropical Medicine and Hygiene 20081101
Tafenoquine: a promising new antimalarial agent. Expert opinion on investigational drugs 20070501
Gender differences in gastrointestinal disturbances and plasma concentrations of tafenoquine in healthy volunteers after tafenoquine administration for post-exposure vivax malaria prophylaxis. Transactions of the Royal Society of Tropical Medicine and Hygiene 20070301
Tafenoquine for the treatment of recurrent Plasmodium vivax malaria. The American journal of tropical medicine and hygiene 20070301
Treatment of acute vivax malaria with tafenoquine. Transactions of the Royal Society of Tropical Medicine and Hygiene 20050101
Efficacy of monthly tafenoquine for prophylaxis of Plasmodium vivax and multidrug-resistant P. falciparum malaria. The Journal of infectious diseases 20041015
Randomized trial of 3-dose regimens of tafenoquine (WR238605) versus low-dose primaquine for preventing Plasmodium vivax malaria relapse. Clinical infectious diseases : an official publication of the Infectious Diseases Society of America 20041015
Plasma concentrations of tafenoquine, a new long-acting antimalarial agent, in thai soldiers receiving monthly prophylaxis. Clinical infectious diseases : an official publication of the Infectious Diseases Society of America 20031215
Military aviators, special operations forces, and causal malaria prophylaxis. Military medicine 20031201
New antimalarial drugs. Angewandte Chemie (International ed. in English) 20031110
Transmission-blocking activity of tafenoquine (WR-238605) and artelinic acid against naturally circulating strains of Plasmodium vivax in Thailand. The American journal of tropical medicine and hygiene 20031101
Molecule of the month. Tafenoquine succinate. Drug news & perspectives 20030501
Blood schizontocidal activity of WR 238605 (Tafenoquine) against Plasmodium cynomolgi and Plasmodium fragile infections in rhesus monkeys. Acta tropica 20030401
The chemotherapy of rodent malaria. LXI. Drug combinations to impede the selection of drug resistance, part 4: the potential role of 8-aminoquinolines. Annals of tropical medicine and parasitology 20030401
A randomized, double-blind, placebo-controlled, dose-ranging trial of tafenoquine for weekly prophylaxis against Plasmodium falciparum. Clinical infectious diseases : an official publication of the Infectious Diseases Society of America 20030301
In-vitro interaction of tafenoquine and chloroquine in Plasmodium falciparum from northwestern Thailand. Wiener klinische Wochenschrift 20030101
In vitro activity of tafenoquine alone and in combination with artemisinin against Plasmodium falciparum. The American journal of tropical medicine and hygiene 20020701
Rapid determination of tafenoquine in small volume human plasma samples by high-performance liquid chromatography-tandem mass spectrometry. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 20020325
Comparison of tafenoquine (WR238605) and primaquine in the post-exposure (terminal) prophylaxis of vivax malaria in Australian Defence Force personnel. Transactions of the Royal Society of Tropical Medicine and Hygiene 20020101
A new primaquine analogue, tafenoquine (WR 238605), for prophylaxis against Plasmodium falciparum malaria. Clinical infectious diseases : an official publication of the Infectious Diseases Society of America 20011215
Population pharmacokinetics of the new antimalarial agent tafenoquine in Thai soldiers. British journal of clinical pharmacology 20011201
Malaria chemoprophylaxis in the age of drug resistance. II. Drugs that may be available in the future. Clinical infectious diseases : an official publication of the Infectious Diseases Society of America 20010801
Malaria prophylaxis/radical cure: recent experiences of the Australian Defence Force. Medecine tropicale : revue du Corps de sante colonial 20010101
First-time-in-humans safety and pharmacokinetics of WR 238605, a new antimalarial. The American journal of tropical medicine and hygiene 19980501
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