| Revision as of 11:31, 5 December 2011 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{drugbox}} taken from revid 462379041 of page Pamaquine for the Chem/Drugbox validation project (updated: 'CAS_number'). |
Latest revision as of 22:55, 19 October 2020 edit Monkbot (talk | contribs)Bots3,695,952 editsm →History: Task 17: replace to-be-deprecated: |name-list-format= (1× replaced; usage: 1 of 1);Tag: AWB |
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{{Short description|A drug (of the 8-aminoquinoline class) formerly used to treat malaria}} |
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{{ambox | text = This page contains a copy of the infobox ({{tl|drugbox}}) taken from revid of page ] with values updated to verified values.}} |
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{{Drugbox |
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{{Drugbox |
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| Verifiedfields = changed |
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| verifiedrevid = 462272320 |
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| verifiedrevid = 464197136 |
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| IUPAC_name = ''N'',''N''-diethyl-''N'''-(6-methoxyquinolin-8-yl)pentane-<br>1,4-diamine |
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| IUPAC_name = ''N'',''N''-diethyl-''N'''-(6-methoxyquinolin-8-yl)pentane-<br>1,4-diamine |
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| image = Pamaquine.svg |
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| image = Pamaquine.svg |
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| legal_US = <!-- OTC / Rx-only / Schedule I, II, III, IV, V --> |
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| legal_US = <!-- OTC / Rx-only / Schedule I, II, III, IV, V --> |
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| legal_status = |
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| legal_status = |
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| routes_of_administration = |
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| routes_of_administration = |
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<!--Pharmacokinetic data--> |
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<!--Pharmacokinetic data--> |
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| metabolism = |
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| metabolism = |
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| elimination_half-life = |
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| elimination_half-life = |
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| excretion = |
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| excretion = |
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<!--Identifiers--> |
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<!--Identifiers--> |
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| CAS_number_Ref = {{cascite|changed|??}} |
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| CAS_number_Ref = {{cascite|changed|??}} |
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| CAS_number = <!-- blanked - oldvalue: 491-92-9 --> |
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| CAS_number = 491-92-9 |
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| ATC_prefix = none |
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| ATC_prefix = none |
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<!--Chemical data--> |
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<!--Chemical data--> |
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| C=19 | H=29 | N=3 | O=1 |
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| C=19 | H=29 | N=3 | O=1 |
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| molecular_weight = 315.453 g/mol |
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| smiles = O(c1cc(NC(C)CCCN(CC)CC)c2ncccc2c1)C |
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| smiles = O(c1cc(NC(C)CCCN(CC)CC)c2ncccc2c1)C |
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| InChI = 1/C19H29N3O/c1-5-22(6-2)12-8-9-15(3)21-18-14-17(23-4)13-16-10-7-11-20-19(16)18/h7,10-11,13-15,21H,5-6,8-9,12H2,1-4H3 |
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| InChIKey = QTQWMSOQOSJFBV-UHFFFAOYAS |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI = 1S/C19H29N3O/c1-5-22(6-2)12-8-9-15(3)21-18-14-17(23-4)13-16-10-7-11-20-19(16)18/h7,10-11,13-15,21H,5-6,8-9,12H2,1-4H3 |
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| StdInChI = 1S/C19H29N3O/c1-5-22(6-2)12-8-9-15(3)21-18-14-17(23-4)13-16-10-7-11-20-19(16)18/h7,10-11,13-15,21H,5-6,8-9,12H2,1-4H3 |
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| StdInChIKey = QTQWMSOQOSJFBV-UHFFFAOYSA-N |
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| StdInChIKey = QTQWMSOQOSJFBV-UHFFFAOYSA-N |
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}} |
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}} |
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'''Pamaquine''' is an ] drug formerly used for the treatment of ]. It is closely related to ]. |
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==Synonyms== |
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*Plasmochin |
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*Plasmoquine<ref name="Manifold1931"/><ref name="Ryan_1993"/> |
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*Plasmaquine |
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==Uses== |
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Pamaquine is effective against the hypnozoites of the relapsing malarias ('']'' and '']''); and unlike primaquine, it is also very effective against the erythrocytic stages of all four human malarias. One small clinical trial of pamaquine as a causal ] was disappointing<ref>{{cite journal | vauthors = Sweeney AW, Blackburn CR, Rieckmann KH | title = Short report: the activity of pamaquine, an 8-aminoquinoline drug, against sporozoite-induced infections of Plasmodium vivax (New Guinea strains) | journal = The American Journal of Tropical Medicine and Hygiene | volume = 71 | issue = 2 | pages = 187–9 | date = August 2004 | pmid = 15306708 | doi = 10.4269/ajtmh.2004.71.2.0700187 | url = http://www.ajtmh.org/cgi/content/full/71/2/187 | doi-access = free }}</ref> (whereas primaquine is an extremely effective causal prophylactic). |
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Pamaquine is more toxic and less efficacious than ]; therefore, pamaquine is no longer routinely used, and of the two, only primaquine is currently recommended by the ].<ref name="WHO-malaria-guideline"/> |
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==Adverse effects== |
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Like primaquine, pamaquine causes ] in patients with ]. Patients should therefore always be screened for G6PD deficiency prior to being prescribed pamaquine. |
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==History== |
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Pamaquine was the second synthetic antimalarial drug to be discovered (after ]). It was synthesised by Schulemann, Schoenhoeffer and Wingler in 1924. In 1926, Roehl demonstrated that pamaquine was effective in treating malaria in birds, and introduced it into use in humans.<ref>{{cite journal|author=Roehl W|year=1926|title=Die Wirkung of Plasmochins auf die Vogelmalaria|journal=Arch Schiffs-Tropenhyg|volume=30|issue=Suppl 3|pages=311–318|bibcode=1926NW.....14.1156R|doi=10.1007/BF01451737|s2cid=2535139}}</ref> Its development is of interest in the history of ] because it was one of the early victories in validating the potential of applying ] to the ] of chemicals that would fight infections with good specificity while presenting ] profiles small enough that ], relative to the contemporary alternative of little to no ] treatment for many debilitating diseases. In other words, it expanded the evidence that the hope for great potential of ] shown by ] and others was worth pursuing with more research<ref name="Ryan_1993">{{cite book | last = Ryan | first = Frank | name-list-style = vanc | year = 1993 | title = The forgotten plague: how the battle against tuberculosis was won—and lost | publisher = Little, Brown | location = Boston | isbn = 978-0316763806 | url-access = registration | url = https://archive.org/details/forgottenplagueh00ryan }}</ref>{{rp|88–91}}—and that early wins such as ] were more than just isolated ]. This was a time period when organic chemistry's largest economic applications included textile dyes, explosives, munitions, and chemical weapons but not yet pharmaceuticals. The fact that systematic, iterative experiments had eventually synthesized an antimalarial drug that was 30 times more effective than ]<ref name="Ryan_1993"/>{{rp|91}} while being safe enough to use (relative to the bleak alternatives of the era) supported the concept of modern pharmaceutical research laboratories as it would develop in coming decades. |
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A large trial of pamaquine performed by the ] and the British ] in 1929 showed for the first time that it was possible to prevent relapse of vivax malaria.<ref name="Manifold1931">{{cite journal|author=Manifold J|year=1931|title=Report on a trial of plasmoquine and quinine in the treatment of benign tertian malaria|journal=Journal of the Royal Army Medical Corps|volume=LVI|issue=5|pages=321–338,410–423}}</ref> Prior to this, it was understood that patients with vivax malaria would suffer from relapses, but there was no treatment that could prevent the relapses from occurring. |
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The relative weights of treatment benefit and harm change over decades as science advances. About a decade after pamaquine became available, ] arrived, and about a decade after that, ] arrived. Pamaquine is more toxic and less efficacious than ]; therefore, pamaquine is no longer routinely used, and of the two, only primaquine is currently recommended by the ].<ref name="WHO-malaria-guideline">{{cite book |author=World Health Organization |year=2015 |title=Guidelines for the treatment of malaria |edition=3rd |location=Geneva, Switzerland |publisher=WHO |isbn=9789241549127 |url=http://apps.who.int/iris/bitstream/handle/10665/162441/9789241549127_eng.pdf;jsessionid=D96EA87D8A27F566623293B450C9B9D4 |access-date=2018-08-31}}</ref> |
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== References == |
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{{reflist}} |
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{{Antimalarials}} |
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] |
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] |
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] |
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] |