Tafenoquine free base
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MedKoo CAT#: 319630

CAS#: 106635-80-7 (free base)

Description: Tafenoquine, also known as WR-238605, is an oral active antimalaria drug that is being investigated as a potential treatment for malaria, as well as for malaria prevention. Tafenoquine Shows Activity against Trypanosoma brucei. Tafenoquine targets leishmania respiratory complex III and induces apoptosis. Tafenoquine has a long half-life of approximately 14 days and is generally safe and well tolerated, Malaria remains an important cause of global morbidity and mortality. As antimalarial drug resistance escalates, new safe and effective medications are necessary to prevent and treat malarial infection.


Price and Availability

Size
Price

25mg
USD 190
200mg
USD 950
2g
USD 5650
Size
Price

50mg
USD 350
500mg
USD 1950
5g
USD 8950
Size
Price

100mg
USD 550
1g
USD 3250

Tafenoquine free base, purity > 98%, is in stock. The same day shipping out after order is received.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 319630
Name: Tafenoquine free base
CAS#: 106635-80-7 (free base)
Chemical Formula: C24H28F3N3O3
Exact Mass: 463.2083
Molecular Weight: 463.5012
Elemental Analysis: C, 62.19; H, 6.09; F, 12.30; N, 9.07; O, 10.36


Related CAS #: 106635-80-7 (free base)   106635-81-8 (succinate)   1133378-83-2 (d3)    

Synonym: WR-238605, WR 238605, WR238605, Tafenoquine

IUPAC/Chemical Name: N4-(2,6-dimethoxy-4-methyl-5-(3-(trifluoromethyl)phenoxy)quinolin-8-yl)pentane-1,4-diamine

InChi Key: LBHLFPGPEGDCJG-UHFFFAOYSA-N

InChi Code: 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

SMILES Code: CC1=CC(=NC2=C1C(=C(C=C2NC(C)CCCN)OC)OC3=CC=CC(=C3)C(F)(F)F)OC


Technical Data

Appearance:
Semi-solid or waxy solid.

Purity:
>98% (or refer to the Certificate of Analysis)

Certificate of Analysis:

Safety Data Sheet (MSDS):

Shipping Condition:
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition:
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility:
Soluble in DMSO, not in water

Shelf Life:
>2 years if stored properly

Drug Formulation:
This drug may be formulated in DMSO

Stock Solution Storage:
0 - 4 C for short term (days to weeks), or -20 C for long term (months).

Harmonized System Code:
2934.99.90.01


References

1: McCarthy JS, Smith B, Reid M, Berman J, Marquart L, Dobbin C, West L, Read LT, Dow G. Blood schizonticidal activity and safety of tafenoquine when administered as chemoprophylaxis to healthy, non-immune participants followed by blood stage Plasmodium falciparum challenge: A randomized, double-blinded, placebo-controlled Phase 1b study. Clin Infect Dis. 2018 Nov 1. doi: 10.1093/cid/ciy939. [Epub ahead of print] PubMed PMID: 30388194.

2: Baird JK. Tafenoquine for travelers' malaria: evidence, rationale and recommendations. J Travel Med. 2018 Oct 31. doi: 10.1093/jtm/tay110. [Epub ahead of print] PubMed PMID: 30380095.

3: Warrasak S, Euswas A, Fukuda MM, Ittiverakul M, Miller RS, Krudsood S, Ohrt C. Comparative ophthalmic assessment of patients receiving tafenoquine or chloroquine/primaquine in a randomized clinical trial for Plasmodium vivax malaria radical cure. Int Ophthalmol. 2018 Sep 29. doi: 10.1007/s10792-018-1003-2. [Epub ahead of print] PubMed PMID: 30269312.

4: Frampton JE. Tafenoquine: First Global Approval. Drugs. 2018 Sep;78(14):1517-1523. doi: 10.1007/s40265-018-0979-2. PubMed PMID: 30229442.

5: Drugs and Lactation Database (LactMed) [Internet]. Bethesda (MD): National Library of Medicine (US); 2006-. Available from http://www.ncbi.nlm.nih.gov/books/NBK525504/ PubMed PMID: 30222296.

6: Thakkar N, Green JA, Koh GCKW, Duparc S, Tenero D, Goyal N. Population Pharmacokinetics of Tafenoquine, a Novel Antimalarial. Antimicrob Agents Chemother. 2018 Oct 24;62(11). pii: e00711-18. doi: 10.1128/AAC.00711-18. Print 2018 Nov. PubMed PMID: 30201820.

7: Tan KR, Hwang J. Tafenoquine receives regulatory approval in USA for prophylaxis of malaria and radical cure of Plasmodium vivax. J Travel Med. 2018 Jan 1;25(1). doi: 10.1093/jtm/tay071. PubMed PMID: 30137454.

8: Mathews ES, Odom John AR. Tackling resistance: emerging antimalarials and new parasite targets in the era of elimination. F1000Res. 2018 Aug 1;7. pii: F1000 Faculty Rev-1170. doi: 10.12688/f1000research.14874.1. eCollection 2018. Review. PubMed PMID: 30135714; PubMed Central PMCID: PMC6073090.

9: Das S, Dielschneider R, Chanas-LaRue A, Johnston JB, Gibson SB. Antimalarial drugs trigger lysosome-mediated cell death in chronic lymphocytic leukemia (CLL) cells. Leuk Res. 2018 Jun 7;70:79-86. doi: 10.1016/j.leukres.2018.06.005. [Epub ahead of print] PubMed PMID: 29902707.

10: Goyal N, Mohamed K, Rolfe K, Sahota S, Ernest T, Duparc S, Taylor M, Casillas L, Koh GCKW. Application of the Stable Isotope Label Approach in Clinical Development-Supporting Dissolution Specifications for a Commercial Tablet Product with Tafenoquine, a Long Half-life Compound. AAPS J. 2018 Jun 4;20(4):74. doi: 10.1208/s12248-018-0234-5. PubMed PMID: 29869298.

11: Ashley EA, Phyo AP. Drugs in Development for Malaria. Drugs. 2018 Jun;78(9):861-879. doi: 10.1007/s40265-018-0911-9. PubMed PMID: 29802605; PubMed Central PMCID: PMC6013505.

12: Bancone G, Gornsawun G, Chu CS, Porn P, Pal S, Bansil P, Domingo GJ, Nosten F. Validation of the quantitative point-of-care CareStart biosensor for assessment of G6PD activity in venous blood. PLoS One. 2018 May 8;13(5):e0196716. doi: 10.1371/journal.pone.0196716. eCollection 2018. PubMed PMID: 29738562; PubMed Central PMCID: PMC5940185.

13: Watson J, Taylor WRJ, Bancone G, Chu CS, Jittamala P, White NJ. Implications of current therapeutic restrictions for primaquine and tafenoquine in the radical cure of vivax malaria. PLoS Negl Trop Dis. 2018 Apr 20;12(4):e0006440. doi: 10.1371/journal.pntd.0006440. eCollection 2018 Apr. PubMed PMID: 29677199; PubMed Central PMCID: PMC5931686.

14: Chu CS, Bancone G, Nosten F, White NJ, Luzzatto L. Primaquine-induced haemolysis in females heterozygous for G6PD deficiency. Malar J. 2018 Mar 2;17(1):101. doi: 10.1186/s12936-018-2248-y. Review. PubMed PMID: 29499733; PubMed Central PMCID: PMC5833093.

15: Fukuda MM, Krudsood S, Mohamed K, Green JA, Warrasak S, Noedl H, Euswas A, Ittiverakul M, Buathong N, Sriwichai S, Miller RS, Ohrt C. A randomized, double-blind, active-control trial to evaluate the efficacy and safety of a three day course of tafenoquine monotherapy for the treatment of Plasmodium vivax malaria. PLoS One. 2017 Nov 9;12(11):e0187376. doi: 10.1371/journal.pone.0187376. eCollection 2017. PubMed PMID: 29121061; PubMed Central PMCID: PMC5679603.

16: Ley B, Bancone G, von Seidlein L, Thriemer K, Richards JS, Domingo GJ, Price RN. Methods for the field evaluation of quantitative G6PD diagnostics: a review. Malar J. 2017 Sep 11;16(1):361. doi: 10.1186/s12936-017-2017-3. Review. PubMed PMID: 28893237; PubMed Central PMCID: PMC5594530.

17: Kitchakarn S, Lek D, Thol S, Hok C, Saejeng A, Huy R, Chinanonwait N, Thimasarn K, Wongsrichanalai C. Implementation of G6PD testing and primaquine for P. vivax radical cure: Operational perspectives from Thailand and Cambodia. WHO South East Asia J Public Health. 2017 Sep;6(2):60-68. PubMed PMID: 28857064.

18: Bancone G, Kalnoky M, Chu CS, Chowwiwat N, Kahn M, Malleret B, Wilaisrisak P, Rénia L, Domingo GJ, Nosten F. The G6PD flow-cytometric assay is a reliable tool for diagnosis of G6PD deficiency in women and anaemic subjects. Sci Rep. 2017 Aug 29;7(1):9822. doi: 10.1038/s41598-017-10045-2. PubMed PMID: 28852037; PubMed Central PMCID: PMC5575121.

19: Rueangweerayut R, Bancone G, Harrell EJ, Beelen AP, Kongpatanakul S, Möhrle JJ, Rousell V, Mohamed K, Qureshi A, Narayan S, Yubon N, Miller A, Nosten FH, Luzzatto L, Duparc S, Kleim JP, Green JA. Hemolytic Potential of Tafenoquine in Female Volunteers Heterozygous for Glucose-6-Phosphate Dehydrogenase (G6PD) Deficiency (G6PD Mahidol Variant) versus G6PD-Normal Volunteers. Am J Trop Med Hyg. 2017 Sep;97(3):702-711. doi: 10.4269/ajtmh.16-0779. Epub 2017 Jul 27. PubMed PMID: 28749773; PubMed Central PMCID: PMC5590573.

20: Dow G, Smith B. The blood schizonticidal activity of tafenoquine makes an essential contribution to its prophylactic efficacy in nonimmune subjects at the intended dose (200 mg). Malar J. 2017 May 19;16(1):209. doi: 10.1186/s12936-017-1862-4. Review. PubMed PMID: 28526056; PubMed Central PMCID: PMC5438551.