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Updating {{drugbox}} (changes to verified fields - updated 'DrugBank_Ref', 'ChEBI_Ref', 'KEGG_Ref', 'ChEBI_Ref') per Chem/Drugbox validation (report [[Wikipedia talk:WikiProject_Pharmacology|erro
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{{drugbox
{{Drugbox
| Verifiedfields = changed
| Verifiedfields = changed
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| verifiedrevid = 418130041
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| UNII_Ref = {{fdacite|changed|FDA}}
⚫
| UNII = 262P8GS9L9| verifiedrevid = 418130041
|
| IUPAC_name = ''N''-[2,6-dimethoxy-4-methyl-5-[3-(trifluoromethyl)<br>phenoxy]quinolin-8-yl]pentane-1,4-diamine
| IUPAC_name = ''N''-[2,6-dimethoxy-4-methyl-5-[3-(trifluoromethyl)<br>phenoxy]quinolin-8-yl]pentane-1,4-diamine
| image = Tafenoquine.svg
| image = Tafenoquine.svg

<!--Clinical data-->
| tradename =
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<!--Pharmacokinetic data-->
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| bioavailability =
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| protein_bound =
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| metabolism =
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| elimination_half-life =
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| excretion =

<!--Identifiers-->
⚫
| CAS_number = 106635-80-7
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| ATC_prefix = none
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| ATC_suffix =
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| PubChem = 115358
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| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
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| UNII_Ref = {{fdacite|changed|FDA}}
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| InChI = 1/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
| UNII = 262P8GS9L9
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| InChIKey = LBHLFPGPEGDCJG-UHFFFAOYAE
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| smiles = FC(F)(F)c3cc(Oc1c(OC)cc(NC(C)CCCN)c2nc(OC)cc(c12)C)ccc3
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 298470
| ChEMBL = 298470

<!--Chemical data-->
⚫
| C=24 | H=28 | F=3 | N=3 | O=3
⚫
| molecular_weight = 463.493 g/mol
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| smiles = FC(F)(F)c3cc(Oc1c(OC)cc(NC(C)CCCN)c2nc(OC)cc(c12)C)ccc3
⚫
| InChI = 1/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
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| StdInChI = 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
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| StdInChIKey = LBHLFPGPEGDCJG-UHFFFAOYSA-N
| StdInChIKey = LBHLFPGPEGDCJG-UHFFFAOYSA-N
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| CAS_number = 106635-80-7
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| ATC_prefix = none
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| ATC_suffix =
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| PubChem = 115358
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| C = 24 | H = 28 | F = 3 | N = 3 | O = 3
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| molecular_weight = 463.493 g/mol
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| bioavailability =
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| metabolism =
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| pregnancy_category =
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| legal_status =
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| routes_of_administration =
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}}
'''Tafenoquine''' (also called '''WR 238605''' or '''SB-252263''') is an [[8-aminoquinoline]] drug manufactured by [[GlaxoSmithKline]] that is currently being investigated as a potential treatment for malaria, as well as for malaria prevention.<ref name="Shanks2001">{{cite journal | title=A New Primaquine Analogue, Tafenoquine (WR 238605), for prophylaxis against ''Plasmodium falciparum'' malaria. | author=Shanks GD, Oloo AJ, Aleman GM, ''et al.'' | journal=Clin Infect Dis | year=2001 | volume=33 | pages=1968&ndash;74 | url=http://www.jstor.org/pss/4482936 | doi=10.1086/324081 | pmid=11700577 | issue=12 }}</ref><ref>{{cite journal | author=Lell B, Faucher JF, Missinou MA, ''et al.'' | title=Malaria chemoprophylaxis with tafenoquine: a randomised study. | journal=Lancet | year=2000 | volume=355 | issue=9220 | pages=2041&ndash;5 | pmid=10885356 | doi=10.1016/S0140-6736(00)02352-7 }}</ref>
'''Tafenoquine''' (also called '''WR 238605''' or '''SB-252263''') is an [[8-aminoquinoline]] drug manufactured by [[GlaxoSmithKline]] that is currently being investigated as a potential treatment for malaria, as well as for malaria prevention.<ref name="Shanks2001">{{cite journal | title=A New Primaquine Analogue, Tafenoquine (WR 238605), for prophylaxis against ''Plasmodium falciparum'' malaria. | author=Shanks GD, Oloo AJ, Aleman GM, ''et al.'' | journal=Clin Infect Dis | year=2001 | volume=33 | pages=1968&ndash;74 | url=http://www.jstor.org/pss/4482936 | doi=10.1086/324081 | pmid=11700577 | issue=12 }}</ref><ref>{{cite journal | author=Lell B, Faucher JF, Missinou MA, ''et al.'' | title=Malaria chemoprophylaxis with tafenoquine: a randomised study. | journal=Lancet | year=2000 | volume=355 | issue=9220 | pages=2041&ndash;5 | pmid=10885356 | doi=10.1016/S0140-6736(00)02352-7 }}</ref>

Revision as of 20:58, 31 August 2011

Tafenoquine
Clinical data
ATC code
  • none
Identifiers
  • N-[2,6-dimethoxy-4-methyl-5-[3-(trifluoromethyl)
    phenoxy]quinolin-8-yl]pentane-1,4-diamine
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC24H28F3N3O3
Molar mass463.493 g/mol g·mol−1
3D model (JSmol)
  • FC(F)(F)c3cc(Oc1c(OC)cc(NC(C)CCCN)c2nc(OC)cc(c12)C)ccc3
  • 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 checkY
  • Key:LBHLFPGPEGDCJG-UHFFFAOYSA-N checkY
 ☒NcheckY (what is this?)  (verify)

Tafenoquine (also called WR 238605 or SB-252263) is an 8-aminoquinoline drug manufactured by GlaxoSmithKline that is currently being investigated as a potential treatment for malaria, as well as for malaria prevention.[1][2]

The main advantage of tafenoquine is that it has a long half-life and therefore does not need to be taken as frequently as primaquine. Like primaquine, tafenoquine causes haemolysis in people with G-6-PD deficiency.[1]

A shorter regimen has also been described as an advantage.[3]

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.[4]

References

  1. ^ 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. PMID 11700577. {{cite journal}}: Explicit use of et al. in: |author= (help)CS1 maint: multiple names: authors list (link)
  2. ^ 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. {{cite journal}}: Explicit use of et al. in: |author= (help)CS1 maint: multiple names: authors list (link)
  3. ^ Elmes NJ, Nasveld PE, Kitchener SJ, Kocisko DA, Edstein MD (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. {{cite journal}}: Unknown parameter |month= ignored (help)CS1 maint: multiple names: authors list (link)
  4. ^ 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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