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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2015/01/20 21:05:24」(JST)
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Tafenoquine
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| Systematic (IUPAC) name |
| N-[2,6-Dimethoxy-4-methyl-5-[3-(trifluoromethyl)phenoxy]quinolin-8-yl]pentane-1,4-diamine |
| Clinical data |
| Legal status |
?
|
| Identifiers |
| CAS number |
106635-80-7 N |
| ATC code |
None |
| PubChem |
CID 115358 |
| ChemSpider |
103196 Y |
| UNII |
262P8GS9L9 Y |
| ChEMBL |
CHEMBL298470 Y |
| NIAID ChemDB |
006901 |
| Synonyms |
Etaquine,[1] WR 238605,[1] SB-252263 |
| Chemical data |
| Formula |
C24H28F3N3O3 |
| Molecular mass |
463.493 g/mol |
SMILES
- FC(F)(F)c3cc(Oc1c(OC)cc(NC(C)CCCN)c2nc(OC)cc(c12)C)ccc3
|
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 Y
Key:LBHLFPGPEGDCJG-UHFFFAOYSA-N Y
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| N (what is this?) (verify) |
Tafenoquine is an 8-aminoquinoline drug manufactured by GlaxoSmithKline that is being investigated as a potential treatment for malaria, as well as for malaria prevention.[2][3]
The proposed indication for tafenoquine is for treatment of the hypnozoite stages of Plasmodium vivax and Plasmodium ovale that are responsible for relapse of these malaria species even when the blood stages are successfully cleared. This is only now achieved by administration of daily primaquine for 14 days. The main advantage of tafenoquine is that it has a long half-life (2–3 weeks) and therefore a single treatment may be sufficient to clear hypnozoites. The shorter regimen has been described as an advantage.[4]
Like primaquine, tafenoquine causes hemolysis in people with G-6-P deficiency.[2] Indeed, the long half-life of tafenoquine suggests that particular care should be taken to ensure that individuals with severe G-6-P deficiency do not receive the drug.
The dose of tafenoquine has not been firmly established, but for the treatment of Plasmodium vivax malaria, a dose of 800 mg over three days has been used.[5]
References
- ^ a b Peters W (1999). "The evolution of tafenoquine--antimalarial for a new millennium?". J R Soc Med 92 (7): 345–352. PMC 1297286. PMID 10615272.
- ^ a b Shanks GD, Oloo AJ, Aleman GM et al. (2001). "A New Primaquine Analogue, Tafenoquine (WR 238605), for prophylaxis against Plasmodium falciparum malaria". Clin Infect Dis 33 (12): 1968–74. doi:10.1086/324081. JSTOR 4482936. PMID 11700577.
- ^ Lell B, Faucher JF, Missinou MA et al. (2000). "Malaria chemoprophylaxis with tafenoquine: a randomised study". Lancet 355 (9220): 2041–5. doi:10.1016/S0140-6736(00)02352-7. PMID 10885356.
- ^ Elmes NJ, Nasveld PE, Kitchener SJ, Kocisko DA, Edstein MD (November 2008). "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 102 (11): 1095–101. doi:10.1016/j.trstmh.2008.04.024. PMID 18541280.
- ^ Nasvelda P, Kitchener S. (2005). "Treatment of acute vivax malaria with tafenoquine". Trans R Soc Trop Med Hyg 99 (1): 2–5. doi:10.1016/j.trstmh.2004.01.013. PMID 15550254.
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Antiparasitics – antiprotozoal agents – Chromalveolate antiparasitics (P01)
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|
Alveo-
late |
Apicom-
plexa |
Conoidasida/
(Coccidiostats) |
| Cryptosporidiosis |
|
|
| Isosporiasis |
- trimethoprim/sulfamethoxazole#
|
|
| Toxoplasmosis |
- pyrimethamine
- sulfadiazine
|
|
|
| Aconoidasida |
| Malaria |
Individual
agents |
Hemozoin
inhibitors |
| aminoquinolines |
- (4-): amodiaquine#
- chloroquine#
- (8-): primaquine#
- pamaquine
|
|
| 4-methanolquinolines |
- mefloquine#
- quinine#
- quinidine
|
|
| Other |
|
|
|
| Antifolates |
DHFR inhibitors
(antifols) |
- proguanil#
- chlorproguanil
|
|
| Sulfonamides |
- sulfadoxine
- sulfamethoxypyrazine
|
|
| Coformulation |
- sulfadoxine/pyrimethamine (SP)#
|
|
|
Sesquiterpene
lactones |
- artemether#
- artesunate#
- dihydroartemisinin
- artemotil
- artemisinin
|
|
| Other |
- atovaquone (with proguanil as Malarone)
- tetracycline
- doxycycline#
- clindamycin
- pyronaridine
- piperaquine
|
|
|
Combi-
nations |
| Fixed-dose (coformulated) ACTs |
- artemether/lumefantrine#
- artesunate/amodiaquine (ASAQ)
- artesunate/mefloquine (ASMQ)
- dihydroartemisinin/piperaquine
- artesunate/pyronaridine
|
|
Other combinations
(not co-formulated) |
- artesunate/SP
- artesunate/mefloquine
- quinine/tetracycline
- quinine/doxycycline
- quinine/clindamycin
|
|
|
|
| Babesiosis |
|
|
|
|
Cilio-
phora |
- Balantidiasis: Tetracycline
|
|
|
Hetero-
kont |
- Blastocystosis: Metronidazole
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|
- #WHO-EM
- ‡Withdrawn from market
- Clinical trials:
- †Phase III
- §Never to phase III
Index of protozoal infection
|
|
| Description |
- Alveolata
- Amoebozoa
- Excavata
- Protist
|
|
| Disease |
- Amoebozoa
- Chromalveolate
- Excavata
|
|
| Treatment |
- Drugs
- amoeboa
- chromalveolate
- excavata
|
|
|
UpToDate Contents
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English Journal
- Exposure-Response Analyses for Tafenoquine after Administration to Patients with Plasmodium vivax Malaria.
- Tenero D1, Green JA2, Goyal N3.
- Antimicrobial agents and chemotherapy.Antimicrob Agents Chemother.2015 Jul 27. pii: AAC.00718-15. [Epub ahead of print]
- Tafenoquine (TQ), a new 8-aminoquinoline with activity against all stages of the Plasmodium vivax lifecycle, is being developed for the radical cure of acute P. vivax malaria in combination with chloroquine. The efficacy and exposure data from a pivotal Phase 2b dose-ranging study were used to condu
- PMID 26248362
- The oral antimalarial drug tafenoquine shows activity against Trypanosoma brucei.
- Carvalho L1, Martínez-García M1, Pérez-Victoria I2, Manzano JI1, Yardley V3, Gamarro F4, Pérez-Victoria JM4.
- Antimicrobial agents and chemotherapy.Antimicrob Agents Chemother.2015 Jul 20. pii: AAC.00879-15. [Epub ahead of print]
- The protozoan parasite Trypanosoma brucei causes Human African Trypanosomiasis, or sleeping sickness, a neglected tropical disease that requires new, safer, and more effective treatments. Repurposing oral drugs could reduce both the time and cost involved in sleeping sickness drug discovery. Tafenoq
- PMID 26195527
- Differential cytochrome P450 2D metabolism alters tafenoquine pharmacokinetics.
- Vuong C1, Xie LH1, Potter BM1, Zhang J1, Zhang P1, Duan D1, Nolan CK1, Sciotti RJ1, Zottig VE1, Nanayakkara NP2, Tekwani BL3, Walker LA3, Smith PL1, Paris RM1, Read LT1, Li Q1, Pybus BS1, Sousa JC1, Reichard GA1, Smith B4, Marcsisin SR5.
- Antimicrobial agents and chemotherapy.Antimicrob Agents Chemother.2015 Jul;59(7):3864-9. doi: 10.1128/AAC.00343-15. Epub 2015 Apr 13.
- Cytochrome P450 (CYP) 2D metabolism is required for the liver-stage antimalarial efficacy of the 8-aminoquinoline molecule tafenoquine in mice. This could be problematic for Plasmodium vivax radical cure, as the human CYP 2D ortholog (2D6) is highly polymorphic. Diminished CYP 2D6 enzyme activity, a
- PMID 25870069
Japanese Journal
- A new primaquine analogue, tafenoquine (WR 238605), for prophylaxis against Plasmodium falciparum malaria
Related Links
- Tafenoquine Patient confirmatory Project Leader: Dr JP Kleim, GlaxoSmithKline, UK MMV Project Sponsor: Dr Wiweka Kaszubska Tafenoquine is our lead investigational medicine for the treatment of P. vivax (relapsing) malaria. It is ...
- back to the Science portfolio Patient confirmatory Project Leader: Dr JP Kleim, GlaxoSmithKline, UK MMV Project Sponsor: Dr Wiweka Kaszubska Tafenoquine is our lead investigational medicine for the treatment of P. vivax (relapsing) malaria.
Related Pictures
