182
Views
3
CrossRef citations to date
0
Altmetric
Review

Synthesis and therapeutic delivery approaches for praziquantel: a patent review (2010-present)

, ORCID Icon, ORCID Icon, ORCID Icon & ORCID Icon
Pages 851-865 | Received 18 Nov 2020, Accepted 07 Apr 2021, Published online: 19 Apr 2021

References

  • Aruleba RT, Adekiya TA, Oyinloye BE, et al. PZQ therapy: how close are we in the development of effective alternative anti-schistosomal drugs? Infect Disor Drug Targets (Formerly Curr Drug Targets Infect Disor). 2019;19(4):337–349.
  • Utzinger J, N’goran EK, N’dri A, et al. Efficacy of praziquantel against Schistosoma mansoni with particular consideration for intensity of infection. Trop Med Int Health. 2000;5(11):771–778.
  • Friis H, Byskov J. The effect of praziquantel against Schistosoma mansoni-infections in Botswana. Trop Geo Med. 1989;41(1):49–51.
  • Adekiya TA, Kondiah PP, Choonara YE, et al. A review of nanotechnology for targeted anti-schistosomal therapy. Front Bioengine Biotechnol. 2020;2020:8.
  • Malhotra G, Raut P, Pharmaceutical compositions. WO2015071668A1; 2015
  • Gryseels B, Nkulikyinka L, Coosemans MH. Field trials of praziquantel and oxamniquine for the treatment of schistosomiasis mansoni in Burundi. T Roy Soc Trop Med H. 1987;81(4):641–644.
  • Magnussen P. Treatment and re-treatment strategies for schistosomiasis control in different epidemiological settings: a review of 10 years’ experiences. Acta Trop. 2003;86(2–3):243–254.
  • Cioli D, Pica-Mattoccia L, Basso A, et al. Schistosomiasis control: praziquantel forever? Mol Biochem Parasitol. 2014;195(1):23–29.
  • Zingone G, Albertini B, Passerini N, et al., Praziquantel coground with mesoporous silica: solid state characterization and antihelmintic Activity. In 3rd European Conference on Pharmaceutics. 2019. Bologna, Italy.
  • Perissutti B, Passerini N, Trastullo R, et al. An explorative analysis of process and formulation variables affecting comilling in a vibrational mill: the case of praziquantel. Int J Pharmaceut. 2017;533(2):402–412. .
  • Trr T, De Melo CG, De Alencar Danda LJ, et al. Layered double hydroxides of CaAl: a promising drug delivery system for increased dissolution rate and thermal stability of praziquantel. Appl Clay Sci. 2019;180:105197.
  • Trainor-Moss S, Mutapi F, Schistosomiasis therapeutics: whats in the pipeline? 2016.
  • Lago EM, Xavier RP, Teixeira TR, et al. Antischistosomal agents: state of art and perspectives. Fut Med Chem. 2018;10(1):89–120.
  • Bergquist R, Utzinger J, Keiser J. Controlling schistosomiasis with praziquantel: how much longer without a viable alternative? Infect Dis Poverty. 2017;6(1):1–10.
  • Mafud AC, Ferreira LG, Mascarenhas YP, et al. Discovery of novel antischistosomal agents by molecular modeling approaches. Trends Parasitol. 2016;32(11):874–886.
  • Pax R, Bennett JL, Fetterer R. A benzodiazepine derivative and praziquantel: effects on musculature of Schistosoma mansoni and Schistosoma japonicum. Naunyn-Schmiedebergs Arch Pharmacol. 1987;304(3):309–315.
  • Kohn AB, Anderson PA, Roberts-Misterly JM, et al. Schistosome calcium channel β subunits unusual modulatory effects and potential role in the action of the antischistosomal drug praziquantel. J Biol Chem. 2001;276(40):36873–36876.
  • Doenhoff MJ, Cioli D, Utzinger J. Praziquantel: mechanisms of action, resistance and new derivatives for schistosomiasis. Curr Opin Infect Dis. 2008;21(6):659–667.
  • Doenhoff MJ, Sabah AAA, Fletcher C, et al. Evidence for an immune-dependent action of praziquantel on Schistosoma mansoni in mice. T Roy Soc Tro Med H. 1978;81(6):947–951.
  • Harnett W, Kusel JR. Increased exposure of parasite antigens at the surface of adult male Schistosoma mansoni exposed to praziquantel in vitro. Parasitol. 1986;93(2):401–405.
  • Brindley PJ, Strand M, Norden AP, et al. Role of host antibody in the chemotherapeutic action of praziquantel against Schistosoma mansoni: identification of target antigens. Mol Biochem Parasitol. 1989;34(2):99–108.
  • Balaya L, Manjathuru M, Derambala Y, et al., Process for the preparation of praziquantel. U.S. Patent 8,754,215; 2014
  • Qian M, Tongli Biomedical Co., Ltd. R-praziquantel preparation method. U.S. Patent 9,175,321; 2015.
  • Qian M, Tongli Biomedical Co., Ltd. Method for preparing (R)-praziquantel. U.S. Patent 9,068,214; 2015.
  • Qian M, Tongli Biomedical Co., Ltd. Method for preparing (R)-praziquantel. U.S. Patent 9,139,859; 2015.
  • Qian M, Tongli Biomedical Co., Ltd. Process for the synthesis of (R)-praziquantel. U.S. Patent 9,802,934; 2017.
  • Qian M, Tongli Biomedical Co., LTD. Praziquantel crystal B substance, its preparation method and its applications in medicines and healthcare products. CN102786519A and CN102786519B; 2017
  • Qian M, Ho RJ, Qiao C et al., Crystal form of (R)-praziquantel and preparation method and application thereof. U.S. Patent 9,657,017; 2017.
  • Zhang F, Yang Z, Bao R, et al., Shanghai Institute of Pharmaceutical Industry and Zhejiang Hisun Pharmaceutical Co Ltd, Preparation method for praziquantel and intermediate compounds thereof. U.S. Patent 10,035,798; 2018.
  • Shanghai Institute of Pharmaceutical Industry Zhejiang Hisun Pharmaceutical Co Ltd. Preparation method for praziquantel and intermediate compounds thereof. WO2016127350A1; 2020
  • Eberhardt L, Waechtler A, Maillard D, et al., Method for the production of praziquantel and precursors thereof. WO2017036577A1; 2018
  • Eberhardt L, Waechtler A, Maillard D, et al., Method for the production of praziquantel and precursors thereof. U.S. Patent 10,273,213; 2019.
  • Maillard D, Waechtler A, Maurin J, et al., Method for the production of praziquantel and its precursors. ES2706314T3; 2019
  • Maillard D, Waechtler A, Maurin J, et al., Method for the production of Praziquantel and precursors thereof. U.S. Patent 9,932,337; 2018.
  • Waechtler A, Saleh-kassim H, Jasper C, et al., Method for the production of praziquantel. U.S. Patent 10,160,758; 2018.
  • Waechtler A, Saleh-kassim H, Jasper C, et al., Method for the production of praziquantel. WO2016078758A1; 2016
  • Qian M, Suzhou CN. United States Suzhou Tongli Biomedical Co., Ltd. method for preparing (r)-praziquantel. 20140370555; 2014
  • Lavet Gyogyszergyarto es Szolgaltato Kft. Taste masking compositions of praziquantel. EP2662075A1; 2013
  • Sabnis SS, Hayes J, Zupan JA, Endoparasiticidal gel composition. US8241669B2; 2012
  • Sabnis SS, Hayes J, Zupan JA, et al. Endoparasiticidal gel composition. U.S. Patent 6,893,652; 2005.
  • Dadak A, Franz S, Liebhart A, Oral gel comprising praziquantel. EP2594258A1; 2020
  • Isele U. Palatable ductile chewable veterinary composition. US8541019B2; 2013
  • Praziquantel emulsion injection and preparation technology thereof. CN103432074A; 2015
  • CN103381141A, Praziquantel long-circulating nanoparticle injection and preparation method thereof. CN103381141A; 2013
  • CN102697729A, Preparation method of praziquantel lipid lyophilized preparation. CN102697729A; 2012.
  • CN103316005A, Praziquantel-mebendazole nanoemulsion oral liquid and preparation method thereof. CN103316005A; 2013.
  • CN105816421A, Praziquantel nanoemulsion in situ gel for preventing and treating bilharziasis and preparation method and application thereof. CN105816421A; 2016.
  • CN106361758A, Compound ivermectin praziquantel bi-continuous phase emulsion and preparation method thereof. CN106361758A; 2016.
  • Qin L, Niu Y, Wang Y, et al. Combination of phospholipid complex and submicron emulsion techniques for improving Oral bioavailability and therapeutic efficacy of water-insoluble drug. Mol Pharm. 2018;15(3):1238–1247.
  • Bell IR, Schwartz GE, Boyer NN, et al. Advances in integrative nanomedicine for improving infectious disease treatment in public health. Eur J Integr Med. 2013;5(2):126–140.
  • Coelho JF, Ferreira PC, Alves P, et al. Drug delivery systems: advanced technologies potentially applicable in personalized treatments. Epma J. 2010;1(1):164–209.
  • Torres ES, Holban AM, Gestal MC. Applications of nanodiamonds in the detection and therapy of infectious diseases. Materials (Basel). 2019;12:10.
  • Qasim M, Lim DJ, Park H, et al. Nanotechnology for diagnosis and treatment of infectious diseases. J Nanosci Nanotechnol. 2014;14(10):7374–7387.
  • Ranghar S, Sirohi P, Verma P, et al. Nanoparticle-based drug delivery systems: promising approaches against infections. Braz Arch Biol Technol. 2014;57(2):209–222.
  • Amara RO, Ramadan AA, El-Moslemany RM, et al. Praziquantel–lipid nanocapsules: an oral nanotherapeutic with potential Schistosoma mansoni tegumental targeting. Int J Nanomed. 2018;13:4493.
  • Frezza TF, Mpd G, Zanotti-Magalhães EM, et al. Liposomal-praziquantel: efficacy against Schistosoma mansoni in a preclinical assay. Acta Trop. 2013;128(1):70–75.
  • Mourão SC, Costa PI, Salgado HR, et al. Improvement of antischistosomal activity of praziquantel by incorporation into phosphatidylcholine-containing liposomes. Int J Pharm. 2005;295(1–2):157–162.
  • Aeml EG, Mohammed FA, Abdel-Rahman SA, et al. Effect of nanoparticles on the therapeutic efficacy of praziquantel against Schistosoma mansoni infection in murine models. J Parasit Dis. 2019;43(3):416–425.
  • Frezza TF, Alr DS, Prado CCR, et al. Effectiveness of hyperbaric oxygen for experimental treatment of schistosomiasis mansoni using praziquantel-free and encapsulated into liposomes: assay in adult worms and oviposition. Acta trop. 2015;150:182–189.
  • Radwan A, El-Lakkany NM, William S, et al. A novel praziquantel solid lipid nanoparticle formulation shows enhanced bioavailability and antischistosomal efficacy against murine S. mansoni infection. Parasite vector. 2019; 12(1): 304.
  • Dkhil MA, Khalil MF, Bauomy AA, et al. Efficacy of gold nanoparticles against nephrotoxicity induced by Schistosoma mansoni Infection in mice. Biomed Environ Sci. 2016;29(11):773–781.
  • Tawfeek GM, Baki MHA, Ibrahim AN, et al. Enhancement of the therapeutic efficacy of praziquantel in murine Schistosomiasis mansoni using silica nanocarrier. Parasitol Res. 2019;118(12):3519–3533.
  • El-Feky GS, Mohamed WS, Nasr HE, et al. Praziquantel in a clay nanoformulation shows more bioavailability and higher efficacy against murine Schistosoma mansoni infection. Antimicrob Agents Chemother. 2015;59(6):3501–3508.
  • Adekiya TA, Aruleba RT, Oyinloye BE, et al. The effect of climate change and the snail-schistosome cycle in transmission and bio-control of schistosomiasis in sub-saharan Africa. Int J Environ Res Public Health. 2020;17(1):181.
  • Adekiya TA, Kappo AP, Okosun KO. Temperature and rainfall impact on schistosomiasis. Glob J Pure Appl Math. 2017;13:8453–8469.
  • Adekiya TA, Theoretical modelling of temperature and rainfall influence on Schistosoma species population dynamics (Doctoral dissertation, University of Zululand). 2018.
  • Adekiya TA, Aruleba RT, Klein A, et al. In silico inhibition of SGTP4 as a therapeutic target for the treatment of schistosomiasis. J Biomol Struc Dyn. 2020; 1–9.
  • WHO Fact Sheets, 2020. https://www.who.int/health-topics/schistosomiasis#tab=tab_1 Accessed on 28/10/2020.
  • Pearce EJ, Freitas TC. Reverse genetics and the study of the immune response to schistosomes. Parasite Immunol. 2008;30(4):215–221.
  • Aruleba RT, Carter KC, Brombacher F, et al. Can we harness immune responses to improve drug treatment in leishmaniasis? Microorganisms. 2020;8(7):1069.
  • Sundar S, Lockwood DN, Agrawal G, et al. Treatment of Indian visceral leishmaniasis with single or daily infusions of low dose liposomal amphotericin B: randomised trialCommentary: cost and resistance remain issues. Bmj. 2001;323(7310):419–422.
  • Van Griensven J, Carrillo E, Lopez-Velez R, et al. Leishmaniasis in immunosuppressed individuals. Clin Microbiol Infect. 2014;20(4):286–299.

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.