title: Resolution of praziquantel.
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.
  
  
  RESULTS
  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
  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.
authors.affiliation: School of Chemistry, The University of Sydney, Sydney, New South Wales, Australia.
authors.forename: Michael
authors.initials: M
authors.lastname: Woelfle
authors.forename: Jean-Paul
authors.initials: JP
authors.lastname: Seerden
authors.forename: Jesse
authors.initials: J
authors.lastname: de Gooijer
authors.forename: Kees
authors.initials: K
authors.lastname: Pouwer
authors.forename: Piero
authors.initials: P
authors.lastname: Olliaro
authors.forename: Matthew H
authors.initials: MH
authors.lastname: Todd
mesh_terms: D000871:Anthelmintics / Q000009:adverse effects / Q000737:chemistry* / Q000302:isolation & purification* / Q000494:pharmacology; D002626:Chemistry, Pharmaceutical / Q000191:economics / Q000379:methods*; D006801:Humans; D007391:International Cooperation; D011223:Praziquantel / Q000009:adverse effects / Q000737:chemistry* / Q000302:isolation & purification* / Q000494:pharmacology; D012552:Schistosomiasis / Q000188:drug therapy; D013237:Stereoisomerism; D013678:Technology, Pharmaceutical / Q000191:economics / Q000379:methods*
chemical_list: D000871:Anthelmintics; D011223:Praziquantel