Resolution of praziquantel.
BACKGROUND:Praziquantel remains the drug of choice for the worldwide treatment and control of schistosomiasis. The drug is synthesized and administered as a racemate. Use of the pure active enantiomer would be desirable since the inactive enantiomer is associated with side effects and is responsible...
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ftdoajarticles:oai:doaj.org/article:a5bed4afb49441778740fdeba107627c 2023-05-15T15:05:22+02:00 Resolution of praziquantel. Michael Woelfle Jean-Paul Seerden Jesse de Gooijer Kees Pouwer Piero Olliaro Matthew H Todd 2011-09-01T00:00:00Z https://doi.org/10.1371/journal.pntd.0001260 https://doaj.org/article/a5bed4afb49441778740fdeba107627c EN eng Public Library of Science (PLoS) http://europepmc.org/articles/PMC3176743?pdf=render https://doaj.org/toc/1935-2727 https://doaj.org/toc/1935-2735 1935-2727 1935-2735 doi:10.1371/journal.pntd.0001260 https://doaj.org/article/a5bed4afb49441778740fdeba107627c PLoS Neglected Tropical Diseases, Vol 5, Iss 9, p e1260 (2011) Arctic medicine. Tropical medicine RC955-962 Public aspects of medicine RA1-1270 article 2011 ftdoajarticles https://doi.org/10.1371/journal.pntd.0001260 2022-12-31T08:57:13Z BACKGROUND:Praziquantel remains the drug of choice for the worldwide treatment and control of schistosomiasis. The drug is synthesized and administered as a racemate. Use of the pure active enantiomer would be desirable since the inactive enantiomer is associated with side effects and is responsible for the extremely bitter taste of the pill. METHODOLOGY/PRINCIPAL FINDINGS:We have identified two resolution approaches toward the production of praziquantel as a single enantiomer. One approach starts with commercially available praziquantel and involves a hydrolysis to an intermediate amine, which is resolved with a derivative of tartaric acid. This method was discovered through an open collaboration on the internet. The second method, identified by a contract research organisation, employs a different intermediate that may be resolved with tartaric acid itself. CONCLUSIONS/SIGNIFICANCE:Both resolution procedures identified show promise for the large-scale, economically viable production of praziquantel as a single enantiomer for a low price. Additionally, they may be employed by laboratories for the production of smaller amounts of enantiopure drug for research purposes that should be useful in, for example, elucidation of the drug's mechanism of action. Article in Journal/Newspaper Arctic Directory of Open Access Journals: DOAJ Articles Arctic PLoS Neglected Tropical Diseases 5 9 e1260 |
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Open Polar |
collection |
Directory of Open Access Journals: DOAJ Articles |
op_collection_id |
ftdoajarticles |
language |
English |
topic |
Arctic medicine. Tropical medicine RC955-962 Public aspects of medicine RA1-1270 |
spellingShingle |
Arctic medicine. Tropical medicine RC955-962 Public aspects of medicine RA1-1270 Michael Woelfle Jean-Paul Seerden Jesse de Gooijer Kees Pouwer Piero Olliaro Matthew H Todd Resolution of praziquantel. |
topic_facet |
Arctic medicine. Tropical medicine RC955-962 Public aspects of medicine RA1-1270 |
description |
BACKGROUND:Praziquantel remains the drug of choice for the worldwide treatment and control of schistosomiasis. The drug is synthesized and administered as a racemate. Use of the pure active enantiomer would be desirable since the inactive enantiomer is associated with side effects and is responsible for the extremely bitter taste of the pill. METHODOLOGY/PRINCIPAL FINDINGS:We have identified two resolution approaches toward the production of praziquantel as a single enantiomer. One approach starts with commercially available praziquantel and involves a hydrolysis to an intermediate amine, which is resolved with a derivative of tartaric acid. This method was discovered through an open collaboration on the internet. The second method, identified by a contract research organisation, employs a different intermediate that may be resolved with tartaric acid itself. CONCLUSIONS/SIGNIFICANCE:Both resolution procedures identified show promise for the large-scale, economically viable production of praziquantel as a single enantiomer for a low price. Additionally, they may be employed by laboratories for the production of smaller amounts of enantiopure drug for research purposes that should be useful in, for example, elucidation of the drug's mechanism of action. |
format |
Article in Journal/Newspaper |
author |
Michael Woelfle Jean-Paul Seerden Jesse de Gooijer Kees Pouwer Piero Olliaro Matthew H Todd |
author_facet |
Michael Woelfle Jean-Paul Seerden Jesse de Gooijer Kees Pouwer Piero Olliaro Matthew H Todd |
author_sort |
Michael Woelfle |
title |
Resolution of praziquantel. |
title_short |
Resolution of praziquantel. |
title_full |
Resolution of praziquantel. |
title_fullStr |
Resolution of praziquantel. |
title_full_unstemmed |
Resolution of praziquantel. |
title_sort |
resolution of praziquantel. |
publisher |
Public Library of Science (PLoS) |
publishDate |
2011 |
url |
https://doi.org/10.1371/journal.pntd.0001260 https://doaj.org/article/a5bed4afb49441778740fdeba107627c |
geographic |
Arctic |
geographic_facet |
Arctic |
genre |
Arctic |
genre_facet |
Arctic |
op_source |
PLoS Neglected Tropical Diseases, Vol 5, Iss 9, p e1260 (2011) |
op_relation |
http://europepmc.org/articles/PMC3176743?pdf=render https://doaj.org/toc/1935-2727 https://doaj.org/toc/1935-2735 1935-2727 1935-2735 doi:10.1371/journal.pntd.0001260 https://doaj.org/article/a5bed4afb49441778740fdeba107627c |
op_doi |
https://doi.org/10.1371/journal.pntd.0001260 |
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PLoS Neglected Tropical Diseases |
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5 |
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9 |
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e1260 |
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1766337081892667392 |