Skip to main page content
U.S. flag

An official website of the United States government

Dot gov

The .gov means it’s official.
Federal government websites often end in .gov or .mil. Before sharing sensitive information, make sure you’re on a federal government site.

Https

The site is secure.
The https:// ensures that you are connecting to the official website and that any information you provide is encrypted and transmitted securely.

Access keys NCBI Homepage MyNCBI Homepage Main Content Main Navigation
. 2011 Sep;5(9):e1260.
doi: 10.1371/journal.pntd.0001260. Epub 2011 Sep 20.

Resolution of praziquantel

Michael Woelfle  1 , Jean-Paul Seerden, Jesse de Gooijer, Kees Pouwer, Piero Olliaro, Matthew H Todd
Affiliations

Resolution of praziquantel

Michael Woelfle et al. PLoS Negl Trop Dis. 2011 Sep.

Abstract

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.

PubMed Disclaimer

Conflict of interest statement

The authors have declared that no competing interests exist.

Figures

Figure 1
Figure 1. General approaches to the preparation of enantiopure praziquantel (PZQ).
Figure 2
Figure 2. Two resolution approaches to enantiopure PZQ discovered through A) open science and B) contract research.
See this image and copyright information in PMC

References

    1. Ross AGP, Bartley PB, Sleigh AC, Olds GR, Li Y, et al. Schistosomiasis. N Engl J Med. 2002;346:1212–1220. (DOI: 10.1056/NEJMra012396) - PubMed
    1. Chitsulo L, Engels D, Montresor A, Savioli L. The global status of schistosomiasis and its control. Acta Trop. 2000;77:41–51. (DOI: 10.1016/S0001-706X(00)00122-4) - PMC - PubMed
    1. King CH, Dickman K, Tisch DJ. Reassessment of the cost of chronic helmintic infection: a meta-analysis of disability-related outcomes in endemic schistosomiasis. Lancet. 2005;365:1561–1569. (DOI: 10.1016/S0140-6736(05)66457-4) - PubMed
    1. Caffrey CR. Chemotherapy of schistosomiasis: present and future. Curr Opin Chem Biol. 2007;11:433–439. (DOI: 10.1016/j.cbpa.2007.05.031) - PubMed
    1. Caffrey CR, Williams DL, Todd MH, Nelson DL, Keiser J, et al. Chemotherapeutic development strategies for schistosomiasis. In: Selzer PM, editor. Antiparasitic and antibacterial drug discovery from molecular targets to drug candidates. Weinheim, Germany: Wiley-VCH Verlag GmbH & Co. KGaA; 2009. (DOI: 10.1002/9783527626816.ch16)

Publication types

MeSH terms