Skip to main content
SpringerLink
Log in

Pyrazole: An Important Core in Many Marketed and Clinical Drugs

  • REVIEW
  • Published:
Russian Journal of Bioorganic Chemistry Aims and scope Submit manuscript

Abstract

In recent years, increasing research attention has been directed to structurally diverse pyrazole derivatives, many of which have become commercially available drugs with antispasmodic, anti-inflammatory, antibacterial, analgesis, antihyperglycemic, hypoglycemic, antineoplastic, antidepressive activities, etc. Due to their wide range of biological activities, pyrazole derivatives can be used to treat a range of diseases, such as cancers, respiratory diseases, infections, and neurological diseases. This review summarizes recent advances in the use of the pyrazole scaffold and provides pharmacologists with a road map for developing novel preclinical and clinical pyrazole-based drugs.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Fig. 1.
Fig. 2.
Fig. 3.
Fig. 4.
Fig. 5.
Fig. 6.
Fig. 7.

Similar content being viewed by others

REFERENCES

  1. Datusalia, A.K. and Khatik, G.L., Current Drug Dis. Technol., 2018, vol. 15, p. 162. https://doi.org/10.2174/157016381503180620153423

    Article  CAS  Google Scholar 

  2. Wang, R., Chen, Y., Yang, B., Yu, S., Zhao, X., Zhang, C., Hao, C., Zhao, D., and Cheng, M., Bioorg. Chem., 2020, vol. 94, p. 103474. https://doi.org/10.1016/j.bioorg.2019.103474

    Article  CAS  Google Scholar 

  3. Corte, J.R., Pinto, D.J.P., Fang, T., Osuna, H., Yang, W., Wang, Y., Lai, A., Clark, C.G., Sun, J.-H., Rampulla, R., Mathur, A., Kaspady, M., Neithnadka, P.R., Li, Y.-X.C., Rossi, K.A., Myers, J.E., Jr., Sheriff, S., Lou, Z., Harper, T.W., Huang, C., Zheng, J.J., Bozarth, J.M., Wu, Y., Wong, P.C., Crain, E.J., Seiffert, D.A., Luettgen, J.M., Lam, P.Y.S., Wexler, R.R., and Ewing, W.R., J. Med. Chem., 2020, vol. 63, pp. 784–803. https://doi.org/10.1021/acs.jmedchem.9b01768

    Article  CAS  Google Scholar 

  4. Gaba, M. and Mohan, C., J. Med.Chem. Res., 2016, vol. 25, pp. 173–210. https://doi.org/10.1007/s00044-015-1495-5

    Article  CAS  Google Scholar 

  5. Hussein, E.M., Al-Rooqi, M.M., Elkhawaga, A.A., and Ahmed, S.A., Arabian J. Chem., 2020, vol. 13, pp. 5345–5362. https://doi.org/10.1016/j.arabjc.2020.03.014

    Article  CAS  Google Scholar 

  6. Cao, Y., Luo, C., Yang, P., Li, P., and Wu, C., J. Med. Chem. Res., 2021, vol. 30, pp. 501–518. https://doi.org/10.1007/s00044-020-02665-7

    Article  CAS  Google Scholar 

  7. Luo, C., Ampomah-Wireko, M., Wang, H., Wu, C., Wang, Q, Zhang, H., and Cao, Yaquan, Anticancer Agents Med. Chem., 2021, vol. 21, pp. 811–824. https://doi.org/10.2174/1871520620666200424132248

    Article  CAS  Google Scholar 

  8. Singh, M., Kaur, M., and Silakari, U., Eur. J. Med. Chem., 2014, vol. 84, pp. 206–239. https://doi.org/10.1016/j.ejmech.2014.07.013

    Article  CAS  Google Scholar 

  9. Sissi, C. and Palumbo, M., Curr. Med. Chem. Anticancer Agents, 2003, vol. 3, pp. 439–450. https://doi.org/10.2174/1568011033482279

    Article  CAS  Google Scholar 

  10. Singh, T.P. and Singh, O.M., Mini-Rev. Med. Chem., 2018, vol. 18, pp. 9–25. https://doi.org/10.2174/1389557517666170807123201

    Article  CAS  Google Scholar 

  11. Ali, N.A.S., Dar, B.A., Pradhan, V., and Farooqui, M., Mini-Rev. Med. Chem., 2013, vol. 13, pp. 1792–1800. https://doi.org/10.2174/1389557511313120009

    Article  CAS  Google Scholar 

  12. Chen, A., Wu, D.-L., Shi, J., Narva, S., Zhao, X.-Y., Wu, Y.-L., and Zhang, W., Bioorg. Med. Chem. Lett., 2020, vol. 30, p. 127328. https://doi.org/10.1016/j.bmcl.2020.127328

    Article  CAS  Google Scholar 

  13. Shu, S., Dai, A., Wang, J., Wang, B., Feng, Y., Li, J., Cai, X., Yang, D., Ma, D., Wang, M.-W., and Liu, H., Bioorg. Med. Chem., 2018, vol. 26, pp. 1896–1908. https://doi.org/10.1016/j.bmc.2018.02.036

    Article  CAS  Google Scholar 

  14. Penning, T.D., Talley, J.J., Bertenshaw, S.R., Carter, J.S., Collins, P.W., Docter, S., Graneto, M.J., Lee, L.F., Malecha, J.W., Miyashiro, J.M., Rogers, R.S., Rogier, D.J., Yu, S.S., Anderson, G.D., Burton, E.G., Cogburn, J.N., Gregory, S.A., Koboldt, C.M., Perkins, W.E., Seibert, K., Veenhuizen, A.W., Zhang, Y.Y., and Isakson, P.C., J. Med. Chem., 1997, vol. 40, pp. 1347–1365. https://doi.org/10.1021/jm960803q

    Article  CAS  Google Scholar 

  15. Ramalingam, K., Thyvelikakath, G.X., Berlin, K.D., Chesnut, R.W., Brown, R.A., Durham, N.N., Ealick, S.E., and van der Helm, D., J. Med. Chem., 1977, vol. 20, pp. 847–850. https://doi.org/10.1021/jm00216a024

    Article  CAS  Google Scholar 

  16. Sousa, D. and Silva, S.J.P., Pharmaceuticals, 2012, vol. 5, pp. 317–324. https://doi.org/10.3390/ph5030317

    Article  CAS  Google Scholar 

  17. Evans, E.K., Gardino, A.K., Kim, J.L., Hodous, B.L., Shutes, A., Davis, A., Zhu, X.J., Schmidt-Kittler, O., Wilson, D., Wilson, K., DiPietro, L., Zhang, Y., Brooijmans, N., LaBranche, T.P., Wozniak, A., Gebreyohannes, Y.K., Schoffski, P., Heinrich, M.C., DeAngelo, D.J., Miller, S., Wolf, B., Kohl, N., Guzi, T., Lydon, N., Boral, A, and Lengauer, C., Sci. Transl. Med., 2017, vol. 9 (414), article no. eaao1690. https://doi.org/10.1126/scitranslmed.aao1690

  18. Wu, C.-P., Lusvarghi, S., Wang, J.-C., Hsiao, S.-H., Huang, Y.-H., Hung, T.-H., and Ambudkar, S.V., Mol. Pharm., 2019, vol. 16, pp. 3040–3052. https://doi.org/10.1021/acs.molpharmaceut.9b00274

    Article  CAS  Google Scholar 

  19. Lübke, J., Naumann, N., Kluger, S., Schwaab, J., Metzgeroth, G., Evans, E., Gardino, A.K., Lengauer, C., Hofmann, W.-K., Fabarius, A., Cross, N.C.P., Reiter, A., and Jawhar, M., Leukemia, 2019, vol. 33, pp. 1195–1205. https://doi.org/10.1038/s41375-019-0450-8

    Article  CAS  Google Scholar 

  20. Deutsch, A. and McLellan, B.N., JAAD Case Rep., 2020, vol. 6, pp. 569–571. https://doi.org/10.1016/j.jdcr.2020.04.013

    Article  Google Scholar 

  21. Arudra, K., Patel, R., Tetzlaff, M.T., Hymes, S., Subbiah, V., Meric-Bernstam, F., Torres-Cabala, C., Aung, P.P., Nagarajan, P., Diab, A., Prieto, V.G., Nelson, K., and Curry, J.L., J. Cutaneous Pathol., 2018, vol. 45, pp. 786–790. https://doi.org/10.1111/cup.13319

    Article  Google Scholar 

  22. Elawady, T., Khedr, A., El-Enany, N., and Belal, F., Microchem. J., 2020, vol. 154, p. 104555. https://doi.org/10.1016/j.microc.2019.104555

    Article  CAS  Google Scholar 

  23. Marandino, L., Raggi, D., Giannatempo, P., Fare, E., and Necchi, A., Exp. Rev. Anticancer Ther., 2019, vol. 19, pp. 835–846. https://doi.org/10.1080/14737140.2019.1671190

    Article  CAS  Google Scholar 

  24. Wu, C.-P., Hung, T.-H., Hsiao, S.-H., Huang, Y.-H., Hung, L.-C., Yu, Y.-J., Chang, Y.-T., Wang, S.-P, and Wu, Y.-S., Cancers, 2020, vol. 12, p. 1366. https://doi.org/10.3390/cancers12061366

    Article  CAS  Google Scholar 

  25. Chan, D.L. and Singh, S., Ther. Clin. Risk Manag., 2018, vol. 14, pp. 323–329. https://doi.org/10.2147/tcrm.S126143

    Article  CAS  Google Scholar 

  26. Christensen, J.G., Zou, H.Y., Arango, M.E., Li, Q., Lee, J.H., McDonnell, S.R., Yamazaki, S., Alton, G.R., Mroczkowski, B., and Los, G., Mol. Cancer Ther., 2007, vol. 6, pp. 3314–3322. https://doi.org/10.1158/1535-7163.Mct-07-0365

    Article  CAS  Google Scholar 

  27. La Madrid, A.M., Campbell, N., Smith, S., Cohn, S.L., and Salgia, R., Targeted Oncol., 2012, vol. 7, pp. 199–210. https://doi.org/10.1007/s11523-012-0227-8

    Article  Google Scholar 

  28. Shaw, A.T., Ou, S.-H.I., Bang, Y.-J., Camidge, D.R., Solomon, B.J., Salgia, R., Riely, G.J., Varella-Garcia, M., Shapiro, G.I., Costa, D.B., Doebele, R.C., Long Phi, L., Zheng, Z., Tan, W., Stephenson, P., Shreeve, S.M., Tye, L.M., Christensen, J.G., Wilner, K.D., Clark, J.W., and Iafrate, A.J., N. Engl. J. Med., 2014, vol. 371, pp. 1963–1971. https://doi.org/10.1056/NEJMoa1406766

    Article  CAS  Google Scholar 

  29. Dikopf, A., Wood, K., and Salgia, R., Exp. Opin. Drug Safety, 2015, vol. 14, pp. 485–493. https://doi.org/10.1517/14740338.2015.1007040

    Article  CAS  Google Scholar 

  30. Gravbrot, N. and Sundararajan, S., Case Rep. Oncol. Med., 2019, vol. 2019, p. 3051945. https://doi.org/10.1155/2019/3051945

    Article  Google Scholar 

  31. Gogas, H.J., Flaherty, K.T., Dummer, R., Ascierto, P.A., Arance, A., Mandala, M., Liszkay, G., Garbe, C., Schadendorf, D., Krajsova, I., Gutzmer, R., Sileni, V.C., Dutriaux, C., de Groot, J.W.B., Yamazaki, N., Loquai, C., Gollerkeri, A., Pickard, M.D, and Robert, C., Eur. J. Cancer, 2019, vol. 119, pp. 97–106. https://doi.org/10.1016/j.ejca.2019.07.016

    Article  CAS  Google Scholar 

  32. Delord, J.-P., Robert, C., Nyakas, M., McArthur, G.A., Kudchakar, R., Mahipal, A., Yamada, Y., Sullivan, R., Arance, A., Kefford, R.F., Carlino, M.S., Hidalgo, M., Gomez-Roca, C., Michel, D., Seroutou, A., Aslanis, V., Caponigro, G., Stuart, D.D., Moutouh-de Parseval, L., Demuth, T., and Dummer, R., Clinical Cancer Res., 2017, vol. 23, pp. 5339–5348. https://doi.org/10.1158/1078-0432.Ccr-16-2923

    Article  CAS  Google Scholar 

  33. Jagodzinska-Mucha, P. and Rutkowski, P., Oncol. Clin. Pract., 2020, vol. 16, pp. 75–82. https://doi.org/10.5603/ocp.2019.0038

    Article  CAS  Google Scholar 

  34. Schroer, K. and Nitschmann, S., Internist, 2017, vol. 58, pp. 863–865. https://doi.org/10.1007/s00108-017-0260-x

    Article  Google Scholar 

  35. Zhong, Y. and Xing, W., Foreign Med. (Antibiotics), 2000, vol. 02, pp. 75–78.

    Google Scholar 

  36. Yuan, J. and Li, G., Chinese J. Infect. Chemother., 2011, vol. 11, pp. 308–313.

    Google Scholar 

  37. Fu, K.P., Foleno, B.D., Lafredo, S.C., LoCoco, J.M., and Isaacson, D.M., Antimicrob. Agents Chemother., 1993, vol. 37, pp. 301–307. https://doi.org/10.1128/aac.37.2.301

    Article  CAS  Google Scholar 

  38. King, A., Bethune, L., and Phillips, I., Clin. Microbiol. Infect., 1995, vol. 1, pp. 13–17. https://doi.org/10.1111/j.1469-0691.1995.tb00018.x

    Article  CAS  Google Scholar 

  39. Grill, M.F. and Maganti, R., Ann. Pharm., 2008, vol. 42, pp. 1843–1850. https://doi.org/10.1345/aph.1L307

    Article  CAS  Google Scholar 

  40. Fujimori, Y., Katsuno, K., Nakashima, I., Ishikawa-Takemura, Y., Fujikura, H., and Isaji, M., J. Pharm. Exp. Ther., 2008, vol. 327, pp. 268–276. https://doi.org/10.1124/jpet.108.140210

    Article  CAS  Google Scholar 

  41. O'Connor-Semmes, R., Walker, S., Kapur, A., Hussey, E.K., Ye, J., Wang-Smith, L., Tao, W., Dobbins, R.L., Cheatham, B., and Wilkison, W.O., Drug Metabol. Disposit., 2015, vol. 43, pp. 1077–1083. https://doi.org/10.1124/dmd.114.062828

    Article  CAS  Google Scholar 

  42. Dharmalingam, M., Aravind, S.R., Thacker, H., Paramesh, S., Mohan, B., Chawla, M., Asirvatham, A., Goyal, R., Shembalkar, J., Balamurugan, R., Kadam, P., Alva, H., Kodgule, R., Tandon, M., Vaidyanathan, S., Pendse, A., Gaikwad, R., Katare, S., Suryawanshi, S., and Barkate, H., Drugs, 2020, vol. 80, pp. 587–600. https://doi.org/10.1007/s40265-020-01285-0

    Article  CAS  Google Scholar 

  43. Gupta, S., Pungsrinont, T., Ženata, O., Neubert, L., Vrzal, R., and Baniahmad, A., Hormon. Cancer, 2020, vol. 11, pp. 182–190. https://doi.org/10.1007/s12672-020-00391-5

    Article  CAS  Google Scholar 

  44. Baumgart, S.J., Nevedomskaya, E., Lesche, R., Newman, R., Mumberg, D., and Haendler, B., Mol. Oncol., 2020, vol. 14, pp. 2022–2039. https://doi.org/10.1002/1878-0261.12693

    Article  CAS  Google Scholar 

  45. Sugawara, T., Baumgart, S.J., Nevedomskaya, E., Reichert, K., Steuber, H., Lejeune, P., Mumberg, D., and Haendler, B., Int. J. Cancer, 2019, vol. 145, pp. 1382–1394. https://doi.org/10.1002/ijc.32242

    Article  CAS  Google Scholar 

  46. Matsubara, N., Mukai, H., Hosono, A., Onomura, M., Sasaki, M., Yajima, Y., Hashizume, K., Yasuda, M., Uemura, M., and Zurth, C., Cancer Chemother. Pharm., 2017, vol. 80, pp. 1063–1072. https://doi.org/10.1007/s00280-017-3417-3

    Article  CAS  Google Scholar 

  47. Mohan, V., Mithal, A., Joshi, S.R., Aravind, S.R., and Chowdhury, S., Drug Des. Develop. Ther., 2020, vol. 14, pp. 2487–2501. https://doi.org/10.2147/dddt.S221093

    Article  CAS  Google Scholar 

  48. Mann, K., in Peer-Reviewed Highlights from the European Association for the Study of Diabetes Annual Meeting, 2014, pp. 26–27. https://doi.org/10.1177/155989771432019

  49. Otsuki, H., Kosaka, T., Nakamura, K., Shimomura, F., Kuwahara, Y., and Tsukamoto, T., Int. Urol. Nephrol., 2014, vol. 46, pp. 427–432. https://doi.org/10.1007/s11255-013-0552-6

    Article  CAS  Google Scholar 

  50. Hoy, S.M., Drugs, 2019, vol. 79, pp. 2001–2007. https://doi.org/10.1007/s40265-019-01233-7

    Article  Google Scholar 

  51. US FDA. FDA approves new breakthrough therapy for cystic fibrosis. 2019. https://www.fda.gov/news-events/ press-announcements/fda-approves-new-breAkthrough-therapy-cystic-fibrosis. Accessed Oct. 23, 2019.

  52. Cheung, J.C. and Deber, C.M., Biochemistry, 2008, vol. 47, pp. 1465–1473. https://doi.org/10.1021/bi702209s

    Article  CAS  Google Scholar 

  53. Cappuzzo, F., Moro-Sibilot, D., Gautschi, O., Boleti, E., Felip, E., Groen, H.J.M., Germonpre, P., Meldgaard, P., Arriola, E., Steele, N., Fox, J., Schnell, P., Engelsberg, A., and Wolf, J., Lung Cancer, 2015, vol. 87, pp. 89–95. https://doi.org/10.1016/j.lungcan.2014.12.010

    Article  Google Scholar 

  54. Ostojic, A., Vrhovac, R., and Verstovsek, S., Ther. Clinical Risk Management, 2012, vol. 8, pp. 95–103. https://doi.org/10.2147/tcrm.S23277

    Article  CAS  Google Scholar 

  55. Higgins, J.P.T., Thompson, S.G., Deeks, J.J., and Altman, D.G., British Med. J., 2003, vol. 327, pp. 557–560. https://doi.org/10.1136/bmj.327.7414.557

    Article  Google Scholar 

  56. Verstovsek, S., Mesa, R.A., Gotlib, J., Levy, R.S., Gupta, V., DiPersio, J.F., Catalano, J.V., Deininger, M., Miller, C., Silver, R.T., Talpaz, M., Winton, E.F., Harvey, J.H., Jr., Arcasoy, M.O., Hexner, E., Lyons, R.M., Paquette, R., Raza, A., Vaddi, K., Erickson-Viitanen, S., Koumenis, I.L., Sun, W., Sandor, V., and Kantarjian, H.M., New England J. Med., 2012, vol. 366, pp. 799–807. https://doi.org/10.1056/NEJMoa1110557

    Article  CAS  Google Scholar 

  57. Conaghan, P.G., Rheumatol. Int., 2012, vol. 32, pp. 1491–1502. https://doi.org/10.1007/s00296-011-2263-6

    Article  CAS  Google Scholar 

  58. Krasselt, M. and Baerwald, C., Exp. Opin. Pharm., 2019, vol. 20, pp. 1689–1702. https://doi.org/10.1080/14656566.2019.1645123

    Article  CAS  Google Scholar 

  59. McGettigan, P. and Henry, D., PLoS Med., 2011, vol. 8. https://doi.org/10.1371/journal.pmed.1001098

  60. Stypinski, D., Fostvedt, L., Lam, J.L., Vaz, A., Johnson, T.R., Boerma, J.S., and Pithavala, Y.K., J. Clinical Pharm., 2020, vol. 60, pp. 1254–1267. https://doi.org/10.1002/jcph.1621

    Article  CAS  Google Scholar 

  61. Nagasaka, M., Ge, Y., Sukari, A., Kukreja, G., and Ou, S.-H.I., Crit. Rev. Oncol. Hematol., 2020, vol. 151, p. 102969. https://doi.org/10.1016/j.critrevonc.2020.102969

    Article  Google Scholar 

  62. Reed, M., Rosales, A.-L.S., Chioda, M.D., Parker, L., Devgan, G., and Kettle, J., Adv. Ther., 2020, vol. 37, pp. 3019–3030. https://doi.org/10.1007/s12325-020-01365-3

    Article  Google Scholar 

  63. Shaw, A.T., Felip, E., Bauer, T.M., Besse, B., Navarro, A., Postel-Vinay, S., Gainor, J.F., Johnson, M., Dietrich, J., and James, L.P., Lancet Oncol., 2017, vol. 18, pp. 1590–1599. https://doi.org/10.1016/S1470-2045(17)30680-0

    Article  CAS  Google Scholar 

  64. Zou, H.Y., Li, Q., Engstrom, L.D., West, M., Appleman, V., Wong, K.A., McTigue, M., Deng, Y.-L., Liu, W., Brooun, A., Timofeevski, S., McDonnell, S.R.P., Jiang, P., Falk, M.D., Lappin, P.B., Affolter, T., Nichols, T., Hu, W., Lam, J., Johnson, T.W., Smeal, T., Charest, A., and Fantin, V.R., Proceed. Nat. Acad. Sci. U.S.A., 2015, vol. 112, pp. 3493–3498. https://doi.org/10.1073/pnas.1420785112

    Article  CAS  Google Scholar 

  65. Zou, H.Y., Friboulet, L., Kodack, D.P., Engstrom, L.D., Li, Q., West, M., Tang, R.W., Wang, H., Tsaparikos, K., Wang, J., Timofeevski, S., Katayama, R., Dinh, D.M., Lam, H., Lam, J.L., Yamazaki, S., Hu, W., Patel, B., Bezwada, D., Frias, R.L., Lifshits, E., Mahmood, S., Gainor, J.F., Affolter, T., Lappin, P.B., Gukasyan, H., Lee, N., Deng, S., Jain, R.K., Johnson, T.W., Shaw, A.T., Fantin, V.R., and Smeal, T., Cancer Cell, 2015, vol. 28, pp. 70–81. https://doi.org/10.1016/j.ccell.2015.05.010

    Article  CAS  Google Scholar 

  66. Gelhorn, H.L., Kulke, M.H., O’Dorisio, T., Yang, Q.M., Jackson, J., Jackson, S., Boehm, K.A., Law, L., Kostelec, J., Auguste, P., and Lapuerta, P., Clin. Ther., 2016, vol. 38, pp. 759–768. https://doi.org/10.1016/j.clinthera.2016.03.002

    Article  CAS  Google Scholar 

  67. Kim, J.J., Wang, H., Terc, J.D., Zambrowicz, B., Yang, Q.M., and Khan, W.I., Am. J. Physiol.-Gastrointest. Liver Physiol., 2015, vol. 309, pp. G455–G465. https://doi.org/10.1152/ajpgi.00299.2014

    Article  CAS  Google Scholar 

  68. Biftu, T., Sinha-Roy, R., Chen, P., Qian, X., Feng, D., Kuethe, J.T., Scapin, G., Gao, Y.D., Tan, Y., Krueger, D., Bak, A., Eiermann, G., He, J., Cox, J., Hicks, J., Lyons, K., He, H., Salituro, G., Tong, S., Patel, S., Doss, G., Petrov, A., Wu, J., Xu, S.S., Sewall, C., Zhang, X., Zhang, B., Thornberry, N.A., and Weber, A.E., J. Med. Chem., 2014, vol. 57, pp. 3205–3212. https://doi.org/10.1021/jm401992e

    Article  CAS  Google Scholar 

  69. Kadowaki, T., Haneda, M., Ito, H., Ueno, M., Matsukawa, M., Yamakura, T., Sasaki, K., Kimura, M., and Iijima, H., Exp. Opin. Pharm., 2018, vol. 19, pp. 83–91. https://doi.org/10.1080/14656566.2017.1420165

    Article  CAS  Google Scholar 

  70. Investi Farma SA. Teneglucon (teneligliptin) via oral: Argentina prescribing information. 2015. http://investi.e-tradeconsult.com/teneglucon/art-234/es/. Accessed Aug. 10, 2015.

  71. Scott, L.J., Drugs, 2017, vol. 77, pp. 209–224. https://doi.org/10.1007/s40265-016-0686-9

    Article  CAS  Google Scholar 

  72. Heijerman, H.G.M., McKone, E.F., Downey, D.G., Van Braeckel, E., Rowe, S.M., Tullis, E., Mall, M.A., Welter, J.J., Ramsey, B.W., McKee, C.M., Marigowda, G., Moskowitz, S.M., Waltz, D., Sosnay, P.R., Simard, C., Ahluwalia, N., Xuan, F., Zhang, Y., Taylor-Cousar, J.L., and McCoy, K.S., Lancet, 2019, vol. 394, pp. 1940–1948. https://doi.org/10.1016/s0140-6736(19)32597-8

    Article  CAS  Google Scholar 

  73. Zhao, M., J. Comm. Med., 2006, vol. 14, pp. 26–27. https://doi.org/10.3969/j.issn.1672-4208.2006.16.017

    Article  Google Scholar 

  74. Wang, X. and Ding J., Chin. Pharm. Bull., 1995, vol. 01, pp. 79–79.

    Google Scholar 

  75. Xie, H., Chin. Rural Med., 1991, pp. 37–39.

    Google Scholar 

  76. Sardak, A. and Qian, S., People’s Military Medicine, 1954, vol. 4.

  77. Volz, M. and Kellner, H.M., Br. J. Clin. Pharmacol., 1980, vol. 10 Suppl 2, pp. 299S–308S. https://doi.org/10.1111/j.1365-2125.1980.tb01813.x

    Article  Google Scholar 

  78. Arellano, F. and Sacristan, J.A., Eur. J. Clinical Pharm., 1990, vol. 38, pp. 617–619. https://doi.org/10.1007/bf00278592

    Article  CAS  Google Scholar 

  79. Bakke, O.M., Wardell, W.M., and Lasagna, L.J., Clin. Pharmacol. Ther., 1984, vol. 35(5), pp. 559–567. https://doi.org/10.1038/clpt.1984.78

    Article  CAS  Google Scholar 

  80. Vesell, E.S., Clin. Pharm. Ther., 1979, vol. 26, pp. 275–286. https://doi.org/10.1002/cpt1979263275

    Article  CAS  Google Scholar 

  81. Hartleb, M., Biopharm. Drug Disp., 1991, vol. 12, pp. 559–570. https://doi.org/10.1002/bdd.2510120802

    Article  CAS  Google Scholar 

  82. Al-Salama, Z.T. and Keam, S.J., Drugs, 2019, vol. 79, pp. 1477–1483. https://doi.org/10.1007/s40265-019-01177-y

    Article  Google Scholar 

  83. Roche Group. Japan becomes the first country to approve Roche’s personalised medicine Rozlytrek. June 18, 2019 Media Release. https://www.roche.com/media/releases/med-cor-2019-06-18.htm. Accessed August 13, 2022.

  84. Liu, D., Offin, M., Harnicar, S., Li, B.T., and Drilon, A., Ther. Clin. Risk Manag., 2018, vol. 14, pp. 1247–1252. https://doi.org/10.2147/tcrm.S147381

    Article  CAS  Google Scholar 

  85. Rolfo, C., Ruiz, R., Giovannetti, E., Gil-Bazo, I., Russo, A., Passiglia, F., Giallombardo, M., Peeters, M., and Raez, L., Expert Opin. Investig. Drugs, 2015, vol. 24, pp. 1493–1500. https://doi.org/10.1517/13543784.2015.1096344

    Article  CAS  Google Scholar 

  86. Qi, W.-X., He, A.-N., Shen, Z., and Yao, Y., Br. J. Clin. Pharmacol., 2013, vol. 76, pp. 348–357. https://doi.org/10.1111/bcp.12149

    Article  CAS  Google Scholar 

  87. Yang, L.P.H. and McKeage, K., Drugs, 2012, vol. 72, pp. 2375–2384. https://doi.org/10.2165/11209230-000000000-00000

    Article  CAS  Google Scholar 

  88. Rixe, O., Bukowski, R.M., Michaelson, M.D., Wilding, G., Hudes, G.R., Bolte, O., Motzer, R.J., Bycott, P., Liou, K.F., Freddo, J., Trask, P.C., Kim, S., and Rini, B.I., Lancet Oncol., 2007, vol. 8, pp. 975–984. https://doi.org/10.1016/s1470-2045(07)70285-1

    Article  Google Scholar 

  89. Rugo, H.S., Herbst, R.S., Liu, G., Park, J.W., Kies, M.S., Steinfeldt, H.M., Pithavala, Y.K., Reich, S.D., Freddo, J.L., and Wilding, G., J. Clin. Oncol., 2005, vol. 23, pp. 5474–5483. https://doi.org/10.1200/jco.2005.04.192

    Article  CAS  Google Scholar 

  90. Epstein, J.B., Silverman, S., Paggiarino, D.A., Crockett, S., Schubert, M.M., Senzer, N.N., Lockhart, P.B., Gallagher, M.J., Peterson, D.E., and Leveque, F.G., Cancer, 2001, vol. 92, pp. 875–885. https://doi.org/10.1002/1097-0142(20010815)92:4<875::Aid-cncr1396>3.0.Co;2-1

    Article  CAS  Google Scholar 

  91. Huang, Y.-S., Hung, N.-K., Lee, M.-S., Kuo, C.-P., Yu, J.-C., Huang, G.-S., Cherng, C.-H., Wong, C.-S., Chu, C.-H., and Wu, C.-T., Anesth. Analg., 2010, vol. 111, pp. 887–891. https://doi.org/10.1213/ANE.0b013e3181e6d82a

    Article  CAS  Google Scholar 

  92. Quane, P.A., Graham, G.G., and Ziegler, J.B., Inflammopharmacology, 1998, vol. 6, pp. 95–107. https://doi.org/10.1007/s10787-998-0026-0

    Article  CAS  Google Scholar 

  93. Turnbull, R.S., J. Can. Dent. Assoc., 1995, vol. 61, pp. 127–134. PMID: 7600413

    CAS  Google Scholar 

  94. Plosker, G.L. and Goa, K.L., J.D., 1991, vol. 42, pp. 805–824. https://doi.org/10.2165/00003495-199142050-00007

    Article  CAS  Google Scholar 

  95. Hsu, E.S., Am. J. Ther., 2010, vol. 17, pp. 476–486. https://doi.org/10.1097/MJT.0b013e3181ea7821

    Article  Google Scholar 

  96. Fake, C.S., King, F., and Sanger, G.J., Br. J. Pharmacol., 1987, vol. 91 (S1), p. 335P. https://doi.org/10.1111/j.1476-5381.1987.tb16271.x

    Article  Google Scholar 

  97. Dilly, S., Semin. Oncol., 1994, vol. 21, pp. 10–14. PMID: 8042031

    CAS  Google Scholar 

  98. Yarker, Y.E. and McTavish, D., Drugs, 1994, vol. 48, pp. 761–793. https://doi.org/10.2165/00003495-199448050-00008

    Article  CAS  Google Scholar 

  99. Moore, K.N., Mirza, M.R., and Matulonis, U.A., Gynecol. Oncol., 2018, vol. 149, pp. 214–220. https://doi.org/10.1016/j.ygyno.2018.01.011

    Article  CAS  Google Scholar 

  100. Hughes, D.L., Org. Process Res. Develop., 2017, vol. 21, pp. 1227–1244. https://doi.org/10.1021/acs.oprd.7b00235

    Article  CAS  Google Scholar 

  101. Sisay, M. and Edessa, D., Gynecol. Oncol. Res. Pract., 2017, vol. 4, pp. 18. https://doi.org/10.1186/s40661-017-0055-8

    Article  Google Scholar 

  102. Caruso, D., Papa, A., Tomao, S., Vici, P., Panici, P.B., and Tomao, F., Ther. Adv. Med. Oncol., 2017, vol. 9, pp. 579–588. https://doi.org/10.1177/1758834017718775

    Article  CAS  Google Scholar 

  103. Bornstein, E. and Jimeno, A., Drugs Today, 2016, vol. 52, pp. 17–28. https://doi.org/10.1358/dot.2016.52.1.2440714

    Article  CAS  Google Scholar 

  104. Balfour, J.A. and Clissold, S.P., Drugs, 1990, vol. 39, pp. 575–596. https://doi.org/10.2165/00003495-199039040-00007

    Article  CAS  Google Scholar 

  105. Guglielmotti, A., Capezzone De Joannon, A., Cazzolla, N., Marchetti, M., Soldo, L., Cavallo, G., and Pinza, M., Pharm. Res., 1995, vol. 32, pp. 369–373. https://doi.org/10.1016/s1043-6618(05)80042-8

    Article  CAS  Google Scholar 

  106. Silvestrini, B., Tanese, B.C., Barillari, G., Iorio, E., and Valeri, P., Int. J. Tissue React., 1983, vol. 5, pp. 217–225. https://doi.org/10.1007/BF00916303

    Article  CAS  Google Scholar 

  107. Testa, M., Iuliano, G., Marino, E., Buongiovanni, C., Paolercio, F., Trapanese, A., and Mortow, P.J., J. Ocular Pharmacol. Ther., 1986, vol. 2, pp. 251. https://doi.org/10.1089/jop.1986.2.251

    Article  CAS  Google Scholar 

  108. Kim, S.T., Jang, H.-L., Lee, S.J., Lee, J., Choi, Y.-L., Kim, K.-M., Cho, J., Park, S.H., Park, Y.S., Lim, H.Y., Yashiro, M., Kang, W.K., and Park, J.O., Mol. Cancer Ther., 2014, vol. 13, pp. 2527–2536. https://doi.org/10.1158/1535-7163.Mct-14-0255

    Article  CAS  Google Scholar 

  109. Sloan, B. and Scheinfeld, N.S., Curr. Opin. Investig. Drugs, 2008, vol. 9, pp. 1324–1335.

    CAS  Google Scholar 

  110. Keisner, S.V. and Shah, S.R., Drugs, 2011, vol. 71, pp. 443–454. https://doi.org/10.2165/11588960-000000000-00000

    Article  CAS  Google Scholar 

  111. Liu, J. and Feng, G., World Biotechnol. Congress J., 2013, p. 74.

  112. Shao, F., Wang, L., and Chu, X., J. South. Med. Univer., 2015, vol. 00. https://doi.org/10.3969/j.issn.1673-4254.2015.06.021

  113. Floridi, A., Paggi, M.G., Marcante, M.L., Silvestrini, B., and Martino, C.D.J., J. Nat. Cancer Inst., 1981, vol. 66, p. 497. https://doi.org/10.1093/jnci/66.3.497

    Article  CAS  Google Scholar 

  114. Scott, L.J., Drugs, 2019, vol. 79, pp. 201–206. https://doi.org/10.1007/s40265-018-1044-x

    Article  CAS  Google Scholar 

  115. Loxo Oncology. Loxo Oncology announces EMA Orphan Drug Designation granted to LOXO-101 for treatment of soft tissue sarcoma. 2016 Media Release. http://www.loxooncology.com. Accessed Dec. 6, 2018.

  116. Drilon, A., Laetsch, T.W., Kummar, S., DuBois, S.G., Lassen, U.N., Demetri, G.D., Nathenson, M., Doebele, R.C., Farago, A.F., Pappo, A.S., Turpin, B., Dowlati, A., Brose, M.S., Mascarenhas, L., Federman, N., Berlin, J., El-Deiry, W.S., Baik, C., Deeken, J., Boni, V., Nagasubramanian, R., Taylor, M., Rudzinski, E.R., Meric-Bernstam, F., Sohal, D.P.S., Ma, P.C., Raez, L.E., Hechtman, J.F., Benayed, R., Ladanyi, M., Tuch, B.B., Ebata, K., Cruickshank, S., Ku, N.C., Cox, M.C., Hawkins, D.S., Hong, D.S., and Hyman, D.M., N. Eng. J. Med., 2018, vol. 378, pp. 731–739. https://doi.org/10.1056/NEJMoa1714448

    Article  CAS  Google Scholar 

  117. Laetsch, T.W., DuBois, S.G., Mascarenhas, L., Turpin, B., Federman, N., Albert, C.M., Nagasubramanian, R., Davis, J.L., Rudzinski, E., Feraco, A.M., Tuch, B.B., Ebata, K.T., Reynolds, M., Smith, S., Cruickshank, S., Cox, M.C., Pappo, A.S., and Hawkins, D.S., Lancet Oncol., 2018, vol. 19, pp. 705–714. https://doi.org/10.1016/s1470-2045(18)30119-0

    Article  CAS  Google Scholar 

  118. Nishio, S., Abe, M., and Ito, H., Diabetes Metab. Syndr. Obes., 2015, vol. 8, pp. 163–171. https://doi.org/10.2147/dmso.S54679

    Article  Google Scholar 

  119. Uchino, H. and Kaku, K.J., Japanese Pharmacol. Ther., 2012, vol. 40, pp. 859–869.

    CAS  Google Scholar 

  120. Weitzel, K.W., Wickman, J.M., Augustin, S.G., and Strom, J.G., Clin. Ther., 2000, vol. 22, pp. 1254–1267. https://doi.org/10.1016/s0149-2918(00)83024-6

    Article  CAS  Google Scholar 

  121. Walsh, J.K. and Engelhardt, C.L., Sleep, 1999, vol. 22, p. S386–S393.

    Google Scholar 

  122. Ebbens, M.M. and Verster, J.C., Nat. Sci. Sleep, 2010, vol. 2, pp. 115–126. https://doi.org/10.2147/nss.s6853

    Article  Google Scholar 

  123. Conole, D. and Scott, L.J., Drugs, 2013, vol. 73, pp. 1967–1975. https://doi.org/10.1007/s40265-013-0149-5

    Article  CAS  Google Scholar 

  124. Boutou, A.K. and Pitsiou, G., Exp. Opin. Pharm., 2020, vol. 21, pp. 1145–1155. https://doi.org/10.1080/14656566.2020.1727446

    Article  CAS  Google Scholar 

  125. Pichl, A., Sommer, N., Bednorz, M., Seimetz, M., Hadzic, S., Kuhnert, S., Kraut, S., Roxlau, E.T., Kojonazarov, B., Wilhelm, J., Gredic, M., Gall, H., Tello, K., Richter, M.J., Pak, O., Petrovic, A., Hecker, M., Schermuly, R.T., Grimminger, F., Seeger, W., Ghofrani, H.A., Weissmann, N., Eur. Respiratory J., 2019, vol. 53, p. 1802445. https://doi.org/10.1183/13993003.02445-2018

    Article  CAS  Google Scholar 

  126. Binder, C., Zotter-Tufaro, C., and Bonderman, D., Exp. Opin. Drug Safety, 2016, vol. 15, pp. 1671–1677. https://doi.org/10.1080/14740338.2016.1248400

    Article  CAS  Google Scholar 

  127. Ghofrani, H.-A., Humbert, M., Langleben, D., Schermuly, R., Stasch, J.-P., Wilkins, M.R., and Klinger, J.R., Chest, 2017, vol. 151, pp. 468–480. https://doi.org/10.1016/j.chest.2016.05.024

    Article  Google Scholar 

  128. Langtry, H.D. and Markham, A., Drugs, 1999, vol. 57, pp. 967–989. https://doi.org/10.2165/00003495-199957060-00015

    Article  CAS  Google Scholar 

  129. Gresser, U. and Gleiter, C.H., Eur. J. Med. Res., 2002, vol. 7, pp. 435–446. PMID: 12435622

    CAS  Google Scholar 

  130. Boolell, M., Allen, M.J., Ballard, S.A., Gepi-Attee, S., Muirhead, G.J., Naylor, A.M., Osterloh, I.H., and Gingell, C., Int. J. Imp. Res., 1996, vol. 8, pp. 47–52. PMID: 8858389

    CAS  Google Scholar 

  131. Wagner, G.J.I., Int. J. Impotence Res., 1998, vol. 10. https://doi.org/10.1038/sj.ijir.3900335

  132. Davids, M.S. and Brown, J.R., Future Oncol., 2014, vol. 10, pp. 957–967. https://doi.org/10.2217/fon.14.51

    Article  CAS  Google Scholar 

  133. Akinleye, A., Chen, Y., Mukhi, N., Song, Y., and Liu, D., J. Hematol. Oncol., 2013, vol. 6. https://doi.org/10.1186/1756-8722-6-59

  134. Novero, A., Ravella, P.M., Chen, Y., Dous, G., and Liu, D., Exp. Hematol. Oncol., 2014, vol. 3, p. 4. https://doi.org/10.1186/2162-3619-3-4

    Article  CAS  Google Scholar 

  135. Honigberg, L.A., Smith, A.M., Sirisawad, M., Verner, E., Loury, D., Chang, B., Li, S., Pan, Z., Thamm, D.H., Miller, R.A., and Buggy, J.J., Proceed. Nat. Acad. Sci. U.S.A., 2010, vol. 107, pp. 13075–13080. https://doi.org/10.1073/pnas.1004594107

    Article  Google Scholar 

  136. Burger, J.A. and Buggy, J.J., Leuk. Lymphoma, 2013, vol. 54, pp. 2385–2391. https://doi.org/10.3109/10428194.2013.777837

    Article  CAS  Google Scholar 

  137. Leong, D.P., Caron, F., Hillis, C., Duan, A., Healey, J.S., Fraser, G., and Siegal, D., Blood, 2016, vol. 128, pp. 138–140. https://doi.org/10.1182/blood-2016-05-712828

    Article  CAS  Google Scholar 

  138. Bradford, D., Larkins, E., Mushti, S.L., Rodriguez, L., Skinner, A.M., Helms, W.S., Price, L.S.L., Zirkelbach, J.F., Li, Y., Liu, J., Charlab, R., Turcu, F.R., Liang, D., Ghosh, S., Roscoe, D., Philip, R., Zack-Taylor, A., Tang, S., Kluetz, P.G., Beaver, J.A., Pazdur, R., Theoret, M.R., and Singh, H., Clin. Cancer Res., 2021, vol. 27, pp. 2130–2135. https://doi.org/10.1158/1078-0432.Ccr-20-3558

    Article  CAS  Google Scholar 

  139. Markham, A., Drugs, 2020, vol. 80, pp. 1119–1124. https://doi.org/10.1007/s40265-020-01343-7

    Article  CAS  Google Scholar 

  140. Drilon, A., Oxnard, G.R., Tan, D.S.W., Loong, H.H.F., Johnson, M., Gainor, J., McCoach, C.E., Gautschi, O., Besse, B., Cho, B.C., Peled, N., Weiss, J., Kim, Y.J., Ohe, Y., Nishio, M., Park, K., Patel, J., Seto, T., Sakamoto, T., Rosen, E., Shah, M.H., Barlesi, F., Cassier, P.A., Bazhenova, L., De Braud, F., Garralda, E., Velcheti, V., Satouchi, M., Ohashi, K., Pennell, N.A., Reckamp, K.L., Dy, G.K., Wolf, J., Solomon, B., Falchook, G., Ebata, K., Nguyen, M., Nair, B., Zhu, E.Y., Yang, L., Huang, X., Olek, E., Rothenberg, S.M., Goto, K., and Subbiah, V., N. Engl. J. Med., 2020, vol. 383, pp. 813–824. https://doi.org/10.1056/NEJMoa2005653

    Article  CAS  Google Scholar 

  141. Kishi, Y., Ohta, S., Kasuya, N., Sakita, S., Ashikaga, T., and Isobe, M., Cardiovasc. Drug Rev., 2001, vol. 19, pp. 215–225. https://doi.org/10.1111/j.1527-3466.2001.tb00066.x

    Article  CAS  Google Scholar 

  142. Ledeboer, A., Hutchinson, M.R., Watkins, L.R., and Johnson, K.W., Exp.Opin. Investig. Drugs, 2007, vol. 16, pp. 935–950. https://doi.org/10.1517/13543784.16.7.935

    Article  CAS  Google Scholar 

  143. Goodman, A.D., Gyang, T., and Smith, A.D., III, Exp.Opin. Investig. Drugs, 2016, vol. 25, pp. 1231–1237. https://doi.org/10.1080/13543784.2016.1221924

    Article  CAS  Google Scholar 

  144. Barkhof, F., Hulst, H.E., Drulovic, J., Uitdehaag, B.M.J., Matsuda, K., and Landin, R., Neurology, 2010, vol. 74, pp. 1033–1040. https://doi.org/10.1212/WNL.0b013e3181d7d651

    Article  CAS  Google Scholar 

  145. Rolan, P., Hutchinson, M.R., and Johnson, K.W., Exp. Opin. Pharmacother., 2009, vol. 10, pp. 2897–2904. https://doi.org/10.1517/14656560903426189

    Article  CAS  Google Scholar 

Download references

Funding

This work was supported by National Key Technologies R&D Program of China (Grant no. 2017YFD0501401).

Author information

Authors and Affiliations

  1. School of Pharmaceutical Sciences, Zhengzhou University, 450001, Zhengzhou, China

    Hongjin Zhai, Shuo Zhang, Maxwell Ampomah-Wireko, Huanhuan Wang, Yaquan Cao, Pu Yang, Yingxue Yang, Firas Obald Arhema Frejat, Lihong Wang, Bingbing Zhao & Chunli Wu

  2. Key Laboratory of Technology of Drug Preparation (Zhengzhou University), Ministry of Education of China, 450001, Zhengzhou, China

    Hongjin Zhai, Shuo Zhang, Maxwell Ampomah-Wireko, Huanhuan Wang, Yaquan Cao, Pu Yang, Yingxue Yang, Firas Obald Arhema Frejat, Lihong Wang, Bingbing Zhao & Chunli Wu

  3. Zhengzhou Key Laboratory of New Veterinary Drug Preparation Innovation, 450001, Zhengzhou, China

    Hongjin Zhai, Shuo Zhang, Maxwell Ampomah-Wireko, Huanhuan Wang, Yaquan Cao, Pu Yang, Yingxue Yang, Firas Obald Arhema Frejat, Lihong Wang, Bingbing Zhao & Chunli Wu

  4. Henan Qunbo Pharmaceutical Research Institute Co. LTD, Zhengzhou, China

    Changzhong Ren & Chunli Wu

Authors
  1. Hongjin Zhai
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Shuo Zhang
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Maxwell Ampomah-Wireko
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Huanhuan Wang
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Yaquan Cao
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. Pu Yang
    View author publications

    You can also search for this author in PubMed Google Scholar

  7. Yingxue Yang
    View author publications

    You can also search for this author in PubMed Google Scholar

  8. Firas Obald Arhema Frejat
    View author publications

    You can also search for this author in PubMed Google Scholar

  9. Lihong Wang
    View author publications

    You can also search for this author in PubMed Google Scholar

  10. Bingbing Zhao
    View author publications

    You can also search for this author in PubMed Google Scholar

  11. Changzhong Ren
    View author publications

    You can also search for this author in PubMed Google Scholar

  12. Chunli Wu
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Chunli Wu.

Ethics declarations

COMPLIANCE WITH ETHICAL STANDARDS

This article does not contain any studies involving humans and animals as research subjects.

Conflict of Interests

The authors declare that they have no conflicts of interest.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Hongjin Zhai, Zhang, S., Ampomah-Wireko, M. et al. Pyrazole: An Important Core in Many Marketed and Clinical Drugs. Russ J Bioorg Chem 48, 1175–1189 (2022). https://doi.org/10.1134/S1068162022060280

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1068162022060280

Keywords:

Search

Navigation