Vol. 22 No. 2 (2023): Mapana Journal of Sciences
Review Articles

A Comprehensive Review on the Therapeutic Applications and Synthetic Approaches of Buparvaquone

PDF
  • Sanjay Sukumar Saralaya,
  • Shashiprabha,
  • Shridhara Kanakamajalu
Sanjay Sukumar Saralaya
Sri Dharmasthala Manjunatheshwara Institute of Technology (SDM IT), Ujire - 574240, Karnataka, India.
Shashiprabha
PG Department of Chemistry, Sri Dharmasthala Manjunatheshwara College (Autonomous), Ujire - 574 240, Karnataka, India
Shridhara Kanakamajalu
Arkgen Pharma Private Limited, Peenya Industrial Area, Bangalore - 560 058, Karnataka, India
DOI: https://doi.org/10.12723/mjs.65.10

Published 2023-07-14

Keywords

  • Buparvaquone,
  • Therapeutic application,
  • Synthesis,
  • Isomer,
  • Epimerization,
  • Recrystallization
    • ...More
    Less

Copyright (c) 2023

Creative Commons License

This work is licensed under a Creative Commons Attribution-ShareAlike 4.0 International License.

Abstract

Buparvaquone 1a is a predominant anti-protozoal drug, it belongs to the pharmacologically active class of hydroxy-naphthoquinones. There are numerous publications on the wide therapeutic applications of 1a, but only a few approaches were reported towards its synthesis. Most of the prior arts report the synthesis from expensive raw materials with low yield, whereas only a few involves the use of readily available and less expensive raw materials with moderate to better yield. The present review work covers the developments on therapeutic applications of 1a along with the synthetic approaches disclosed till date.

PDF

References

  1. . Hudson, A. T., & Randall, A. W. (1983). 1.4-Naphthoquinones, methods for their preparation, pharmaceutical and veterinary formulations thereof. European Patent Application, EP 0077551 A2.
  2. . Latter, V. S., Hudson, A. T., Richards, W. H. G., & Randall, A. W. (1984). Antiprotozoal agents containing naphthoquinones and 4-pyridinol derivatives. European Patent Application, EP 123239 A2.
  3. . McHardy, N., Wekesa, L. S., Hudson, A. T., & Randall, A. W. (1985). Antitheilerial activity of BW720C (buparvaquone): a comparison with parvaquone. Research in Veterinary Science, 39(1), 29–33.
  4. . Dhar, S., Malhotra, D. V., Bhushan, C., & Gautam, O. P. (1986). Chemotherapy of Theileria annulata infection with buparvaquone. The Veterinary Record, 119(25–26), 635–636.
  5. . Dhar, S., Malhotra, D. V., Bhushan, C., & Gautam, O. P. (1987). Chemoimmunoprophylaxis with buparvaquone against theileriosis in calves. The Veterinary Record, 120(15), 375.
  6. . Mutugi, J. J., Young, A. S., Maritim, A. C., Linyonyi, A., Mbogo, S. K., & Leitch, B. L. (1988). Immunization of cattle using varying infective doses of Theileria parva lawrencei sporozoites derived from an African buffalo (Syncerus caffer) and treatment with buparvaquone. Parasitology, 96(2), 391–402.
  7. . Dhar, S., Malhotra, D. V., Bhushan, C., & Gautam, O. P. (1988). Treatment of experimentally induced Theileria annulata infection in cross-bred calves with buparvaquone. Veterinary Parasitology, 27(3–4), 267–275.
  8. . Zaugg, J. L., & Lane, V. M. (1989). Evaluations of buparvaquone as a treatment for equine babesiosis (Babesia equi). American Journal of Veterinary Research, 50(5), 782–785.
  9. . Michael, S. A., el Refaii, A. H., McHardy, N., & Rae, D. G. (1989). Effect of treatment of chronic theileriosis with buparvaquone on milk yields. Tropical Animal Health and Production, 21(4), 218–222.
  10. . Bansal, G. C., & Sharma, N. N. (1989). Prophylactic efficacy of buparvaquone in experimentally induced Theileria annulata infection in calves. Veterinary Parasitology, 33(3–4), 219–224.
  11. . Sharma, N. N., & Mishra, A. K. (1990). Treatment of bovine tropical theileriosis with buparvaquone. Tropical Animal Health and Production, 22(1), 63–65.
  12. . Dhar, S., Malhotra, D. V., Bhushan, C., & Gautam, O. P. (1990). Chemoimmunoprophylaxis against bovine tropical theileriosis in young calves: a comparison between buparvaquone and long-acting oxytetracycline. Research in Veterinary Science, 49(1), 110–112.
  13. . Rintelen, M., Schein, E., & Ahmed, J. S. (1990). Buparvaquone but not cyclosporin A prevents Theileria annulata-infected bovine lymphoblastoid cells from stimulating uninfected lymphocytes. Tropical Medicine and Parasitology, 41(2), 203–207.
  14. . Motzel, S. L., & Wagner, J. E. (1990). Treatment of experimentally induced cytauxzoonosis in cats with parvaquone and buparvaquone. Veterinary Parasitology, 35(1–2), 131–138.
  15. . Stewart, N. P., de Vos, A. J., McHardy, N., & Standfast, N. F. (1990). Elimination of Theileria buffeli infections from cattle by concurrent treatment with buparvaquone and primaquine phosphate. Tropical Animal Health and Production, 22(2), 116–122.
  16. . Hashemi-Fesharki, R. (1991). Chemotherapeutic value of parvaquone and buparvaquone against Theileria annulata infection of cattle. Research in Veterinary Science, 50(2), 204–207.
  17. . McHardy, N. (1991). Integrated strategy to control East Coast fever. The Veterinary Record, 129(21), 475.
  18. . Mutugi, J. J., Young, A. S., Kariuki, D. P., Tameno, J. M., & Morzaria, S. P. (1991). Epidemiological observations on theileriosis following field immunisation using infection and treatment. Tropical Animal Health and Production, 23(2), 75–82.
  19. . Mitema, E. S., Kocan, A. A., Mukolwe, S. W., Sangiah, S., & Sherban, D. (1991). Activity of buparvaquone against Theileria cervi in white-tailed deer. Veterinary Parasitology, 38(1), 49–53.
  20. . Croft, S. L., Hogg, J., Gutteridge, W. E., Hudson, A. T., & Randall, A. W. (1992). The activity of hydroxynaphthoquinones against Leishmania donovani. The Journal of Antimicrobial Chemotherapy, 30(6), 827–832.
  21. . Zaugg, J. L., & Lane, V. M. (1992). Efficacy of buparvaquone as a therapeutic and clearing agent of Babesia equi of European origin in horses. American Journal of Veterinary Research, 53(8), 1396–1399.
  22. . Dolan, T. T., Injairu, R., Gisemba, F., Maina, J. N., Mbadi, G., Mbwiria, S. K., Mulela, G. H., and Othieno, D. A. (1992). A clinical trial of buparvaquone in the treatment of East Coast fever. The Veterinary Record, 130(24), 536–538.
  23. . Ngumi, P. N., Young, A. S., Lampard, D., Mining, S. K., Ndungu, S. G., Lesan, A. C., Linyonyi, S. M., and Kariuki, D. P. (1992). Further evaluation of the use of buparvaquone in the infection and treatment method of immunizing cattle against Theileria parva derived from African buffalo (Syncerus caffer). Veterinary Parasitology, 43(1–2), 15–24.
  24. . Ahmed, J. S., Rintelen, M., Schein, E., Williams, R. O., & Dobbelaere, D. (1992). Effect of buparvaquone on the expression of interleukin 2 receptors in Theileria annulata-infected cells. Parasitology Research, 78(4), 285–290.
  25. . Singh, D. K., Thakur, M., Raghav, P. R., & Varshney, B. C. (1993). Chemotherapeutic trials with four drugs in crossbred calves experimentally infected with Theileria annulata. Research in Veterinary Science, 54(1), 68–71.
  26. . Singh, J., Gill, J. S., Kwatra, M. S., & Sharma, K. K. (1993). Treatment of theileriosis in crossbred cattle in the Punjab. Tropical Animal Health and Production, 25(2), 75–78.
  27. . Mishra, A. K., Sharma, N. N., & Viswanathan, C. B. (1993). Efficacy of Butalex in field cases of bovine theileriosis—short communication. Acta Veterinaria Hungarica, 41(3–4), 361–363.
  28. . Mbogo, S. K., Kariuki, D. P., Ngumi, P. N., & McHardy, N. (1996). A mild Theileria parva parasite with potential for immunisation against East Coast fever. Veterinary Parasitology, 61(1–2), 41–47.
  29. . Vexenat, J. A., Croft, S. L., Furtado Campos, J. H., & Miles, M. A. (1998). Failure of buparvaquone (Butalex) in the treatment of canine visceral leishmaniosis. Veterinary Parasitology, 77(1), 71–73.
  30. . Wilkie, G. M., Brown, C. G., Kirvar, B. E., Thomas, M., Williamson, S. M., Bell-Sakyi, L. J., & Sparagano, O. (1998). Chemoprophylaxis of Theileria annulata and Theileria parva infections of calves with buparvaquone. Veterinary Parasitology, 78(1), 1–12.
  31. . Wilkie, G. M., Kirvar, E., Thomas, E. M., Sparagano, O., & Brown, C. G. (1998). Stage-specific activity in vitro on the Theileria infection process of serum from calves treated prophylactically with buparvaquone. Veterinary Parasitology, 80(2), 127–136.
  32. . Muraguri, G. R., Kiara, H. K., & McHardy, N. (1999). Treatment of East Coast fever: a comparison of parvaquone and buparvaquone. Veterinary Parasitology, 87(1), 25–37.
  33. . El-Metenawy, T. M. (1999). Therapeutic effects of some antihaematozoal drugs against Haemoproteus columbae in domestic pigeons. DTW. Deutsche Tierarztliche Wochenschrift, 106(2), 72.
  34. . Naziroğlu, M., Saki, C. E., & Sevgili, M. (1999). The effect of buparvaquone treatment on the levels of some antioxidant vitamins, lipid peroxidation and glutathione peroxidase in cattle with theileriosis. Zentralblatt Für Veterinarmedizin. Reihe B. Journal of Veterinary Medicine. Series B, 46(4), 233–239.
  35. . Müller, J., Aguado-Martínez, A., Ortega-Mora, L.-M., Moreno-Gonzalo, J., Ferre, I., Hulverson, M. A., … Hemphill, A. (2017). Development of a murine vertical transmission model for Toxoplasma gondii oocyst infection and studies on the efficacy of bumped kinase inhibitor (BKI)-1294 and the naphthoquinone buparvaquone against congenital toxoplasmosis. The Journal of Antimicrobial Chemotherapy, 72(8), 2334–2341.
  36. . Penzhorn, B. L., Lewis, B. D., López-Rebollar, L. M., & Swan, G. E. (2000). Screening of five drugs for efficacy against Babesia felis in experimentally infected cats. Journal of the South African Veterinary Association, 71(1), 53–57.
  37. . Kumar, S., Gupta, A. K., Pal, Y., & Dwivedi, S. K. (2003). In-vivo therapeutic efficacy trial with artemisinin derivative, buparvaquone and imidocarb dipropionate against Babesia equi infection in donkeys. The Journal of Veterinary Medical Science, 65(11), 1171–1177.
  38. . Gwamaka, M., Matovelo, J. A., Mtambo, M. M. A., Mbassa, G. K., Maselle, R. M., & Boniphace, S. (2004). The effect of dexamethasone and promethazine in combination with buparvaquone in the management of East Coast fever. The Onderstepoort Journal of Veterinary Research, 71(2), 119–128.
  39. . Mbwambo, H. A., Magwisha, H. B., & Mfinanga, J. M. (2006). Evaluation of buparvaquone (BUTA-Kel KELA, Belgium) as a treatment of East Coast fever in cattle, in the peri-urban of Dar Es Salaam city, Tanzania. Veterinary Parasitology, 139(1–3), 67–73.
  40. . Osman, S. A., & Al-Gaabary, M. H. (2007). Clinical, haematological and therapeutic studies on tropical theileriosis in water buffaloes (Bubalus bubalis) in Egypt. Veterinary Parasitology, 146(3–4), 337–340.
  41. . Mhadhbi, M., Naouach, A., Boumiza, A., Chaabani, M. F., BenAbderazzak, S., & Darghouth, M. A. (2010). In vivo evidence for the resistance of Theileria annulata to buparvaquone. Veterinary Parasitology, 169(3–4), 241–247.
  42. . Mchardy, N., Smith, R., & Brady, P. D. (2013). Use of buparvaquone for controlling mites parasitising honeybees, EP Patent No. 2433624:B1.
  43. . Müller, J., Aguado-Martinez, A., Manser, V., Balmer, V., Winzer, P., Ritler, D., … Hemphill, A. (2015). Buparvaquone is active against Neospora caninum in vitro and in experimentally infected mice. International Journal for Parasitology, Drugs and Drug Resistance, 5(1), 16–25.
  44. . Müller, J., Aguado-Martínez, A., Manser, V., Wong, H. N., Haynes, R. K., & Hemphill, A. (2016). Repurposing of antiparasitic drugs: the hydroxy-naphthoquinone buparvaquone inhibits vertical transmission in the pregnant neosporosis mouse model. Veterinary Research, 47(1), 32.
  45. . Checa, R., Montoya, A., Ortega, N., González-Fraga, J. L., Bartolomé, A., Gálvez, R., … Miró, G. (2017). Efficacy, safety and tolerance of imidocarb dipropionate versus atovaquone or buparvaquone plus azithromycin used to treat sick dogs naturally infected with the Babesia microti-like piroplasm. Parasites & Vectors, 10(1), 145.
  46. . Rufener, R., Dick, L., D’Ascoli, L., Ritler, D., Hizem, A., Wells, T. N. C., … Lundström-Stadelmann, B. (2018). Repurposing of an old drug: In vitro and in vivo efficacies of buparvaquone against Echinococcus multilocularis. International Journal for Parasitology, Drugs and Drug Resistance, 8(3), 440–450.
  47. . Müller, J., Manser, V., & Hemphill, A. (2019). In vitro treatment of Besnoitia besnoiti with the naphto-quinone buparvaquone results in marked inhibition of tachyzoite proliferation, mitochondrial alterations and rapid adaptation of tachyzoites to increased drug concentrations. Parasitology, 146(1), 112–120.
  48. . Goud, K. S., & Vijayakumar, K. (2020). Molecular diagnosis and treatment of oriental theileriosis in calves. The Pharma Innovation, 9(9), 568–571.
  49. . Borba-Santos, L. P., Barreto, T. L., Vila, T., Chi, K. D., Dos Santos Monti, F., de Farias, M. R., … Rozental, S. (2021). In vitro and in vivo antifungal activity of buparvaquone against Sporothrix brasiliensis. Antimicrobial Agents and Chemotherapy, 65(9), e0069921.
  50. . Ferreira, V. F., de Carvalho, A. S., Ferreira, P. G., Lima, C. G. S., & de C da Silva, F. (2021). Quinone-based drugs: An important class of molecules in medicinal chemistry. Medicinal Chemistry {Shariqah (United Arab Emirates)}, 17(10), 1073–1085.
  51. . Nixon, G. L., Moss, D. M., Shone, A. E., Lalloo, D. G., Fisher, N., O’Neill, P. M., … Biagini, G. A. (2013). Antimalarial pharmacology and therapeutics of atovaquone. The Journal of Antimicrobial Chemotherapy, 68(5), 977–985.
  52. . Hudson, A. T., & Randall, A. W. (1984). Antiprotozoal compounds. United States Patent, US 4485117 A.
  53. . Wang, Y., Tan, W., Ding, D., & Ma, J. (2008). Technique for synthesizing buparvaquone. Chinese Patent Application, CN 101265172 A.
  54. . Lv, Y. (2016). Buparvaquone synthesis process, Chinese Patent Application, CN 105646175 A.
  55. . Arulmoli, T., Balaya, L., Adithya, S, V, R., Pallikere, V, M., Kunder, K., & Udupa, K, V. (2012). A process for preparation of 2-((4-tert-butylcyclohexyl)methyl)-3- hydroxy-1,4-naphthoquinone. Indian Patent Application, IN 2012MU00356 A.
  56. . Balaya, L., Udupa, K, V., Arulmoli, T., Das, G, K., Adithya, S, V, R., Kunder, K., Shet, K., & Shettipal, A, B. (2014). A process for preparation of 2-((4-tert-butylcyclohexyl)methyl)-3- hydroxy-1,4-naphthoquinone. Indian Patent Application, IN 2012MU03303 A.
  57. . Ma, H., Guo, Q., Yan, B., Dong, K., Peng, X., & Sang, Y. (2013). Benzopyranone compound, as well as preparation method and application thereof. Chinese Patent Application, CN 103450141 A.
  58. . Ma, H., Guo, Q., Yan, B., Dong, K., Peng, X., & Sang, Y. (2014). Preparation method of buparvaquone. Chinese Patent Application, CN 103483176 A.
  59. . Shen, N., Han, L., Li, W., Guo, M., Liu, H., Zhou, Y., & Dong, H. (2015). Preparation method for buparvaquone. Chinese Patent Application, CN 105198718 A.
  60. . Cui, Q., Wang, B., Zhang, M., & Xu, X. (2020). Preparation method of buparvaquone. Chinese Patent Application, CN 110734368 A.
  61. . Saralaya, S. S., Shashikumar, H. S., Shashiprabha, Kanakamajalu, S., Ranganathan, K. R., Veeraswamy, A., Govindaraju, J., Kothapalli, S. R., & Nagarajan, K. (2012). Preparation of naphthoquinone compounds using 2,3-dihalonaphthoquinone. United States Patent, US 8283499 B2.
  62. . Saralaya, S. S., Shashiprabha, Kanakamajalu, S., Nagarajan, K., & Ranganathan, K. R. (2022). A systematic study towards the synthesis, isolation, and recrystallization of atovaquone, an antimalarial drug: A sustainable synthetic pathway. Mapana Journal of Sciences, 21(1), 19–37.
  63. . Saralaya, S. S., Shashiprabha, Kanakamajalu, S., Nagarajan, K., & Ranganathan, K. R. (2022). A Novel and Sustainable Method for the Synthesis of 2-chloro-3-[trans-4-(4-chlorophenyl) cyclohexyl]-1,4-naphthoquinone, accomplished by systematic process development studies - Trans-Cl synthesis. Mapana Journal of Sciences, 21(3).

Most read articles by the same author(s)