Remdesivir

Remdesivir
Clinical data
Trade names	GS-5734
Legal status
Legal status	US: Investigational New Drug ;
Identifiers
	IUPAC name (2S)-2-{(2R,3R,4S,5R)-[5-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)-5-cyano-3,4-dihydroxy-tetrahydro-furan-2-ylmethoxy]phenoxy-(S)-phosphorylamino}propionic acid 2-ethyl-butyl ester;
CAS Number	1809249-37-3 ;
ChemSpider	58827832;
Chemical and physical data
Formula	C27H35N6O8P
Molar mass	602.575
3D model (JSmol)	Interactive image;
	SMILES Nc3ncnn2c3ccc2C(C#N)(C1O)OC(C1O)CO[P](=O)(NC(C)C(=O)OCC(CC)CC)Oc4ccccc4;
	InChI InChI=1S/C27H35N6O8P/c1-4-18(5-2)13-38-26(36)17(3)32-42(37,41-19-9-7-6-8-10-19)39-14-21-23(34)24(35)27(15-28,40-21)22-12-11-20-25(29)30-16-31-33(20)22/h6-12,16-18,21,23-24,34-35H,4-5,13-14H2,1-3H3,(H,32,37)(H2,29,30,31)/t17-,21+,23+,24+,27-,42-/m0/s1; Key:RWWYLEGWBNMMLJ-YSOARWBDSA-N;

Remdesivir (GS-5734) is an antiviral drug, a novel nucleotide analog prodrug. It was developed by Gilead Sciences as a treatment for filovirus infections such as Ebola virus disease and Marburg virus, though it has subsequently also been found to show reasonable antiviral activity against more distantly related viruses such as respiratory syncytial virus, Junin virus, Lassa fever virus, and MERS-coronavirus.^[1] GS-5734 was rapidly pushed through clinical trials due to the 2013–2016 West African Ebola virus epidemic crisis, eventually being used in at least one human patient despite its early development stage at the time. Preliminary results have been promising, and further clinical trials are planned.^[2]^[3]^[4]^[5]

References

↑ Agostini ML, et al. Coronavirus Susceptibility to the Antiviral Remdesivir (GS-5734) Is Mediated by the Viral Polymerase and the Proofreading Exoribonuclease. mBio, 2018; 9 (2): e00221-18 Agostini, Maria L; Andres, Erica L; Sims, Amy C; Graham, Rachel L; Sheahan, Timothy P; Lu, Xiaotao; Smith, Everett Clinton; Case, James Brett; Feng, Joy Y; Jordan, Robert; Ray, Adrian S; Cihlar, Tomas; Siegel, Dustin; MacKman, Richard L; Clarke, Michael O; Baric, Ralph S; Denison, Mark R (2018). "Coronavirus Susceptibility to the Antiviral Remdesivir (GS-5734) is Mediated by the Viral Polymerase and the Proofreading Exoribonuclease". Mbio. 9 (2). doi:10.1128/mBio.00221-18. PMC 5844999. PMID 29511076.
↑ Investigators also found that the drug was effective against SARS in mice, according to the study in the June 28 issue of the journal Science Translational Medicine. https://medlineplus.gov/news/fullstory_166953.html Tomas Cihlar, Gilead Sciences. Discovery and Development of GS-5734, a Novel Nucleotide Prodrug with Broad Spectrum Anti-Filovirus Activity. FANG-WHO Workshop, Fort Detrick, MD. 20 October 2015
↑ Warren, Travis; Jordan, Robert; Lo, Michale; Soloveva, Veronica; Ray, Adrian; Bannister, Roy; MacKman, Richard; Perron, Michel; Stray, Kirsten; Feng, Joy; Xu, Yili; Wells, Jay; Stuthman, Kelly; Welch, Lisa; Doerffler, Edward; Zhang, Lijun; Chun, Kwon; Hui, Hon; Neville, Sean; Lew, Willard; Park, Yeojin; Babusis, Darius; Strickley, Robert; Wong, Pamela; Swaminathan, Swami; Lee, William; Mayers, Douglas; Cihlar, Tomas; Bavari, Sina (Fall 2015). "Nucleotide Prodrug GS-5734 Is a Broad-Spectrum Filovirus Inhibitor That Provides Complete Therapeutic Protection Against the Development of Ebola Virus Disease (EVD) in Infected Non-human Primates". Open Forum Infect Dis. 2. doi:10.1093/ofid/ofv130.02.
↑ Warren, T. K.; Jordan, R; Lo, M. K.; Ray, A. S.; MacKman, R. L.; Soloveva, V; Siegel, D; Perron, M; Bannister, R; Hui, H. C.; Larson, N; Strickley, R; Wells, J; Stuthman, K. S.; Van Tongeren, S. A.; Garza, N. L.; Donnelly, G; Shurtleff, A. C.; Retterer, C. J.; Gharaibeh, D; Zamani, R; Kenny, T; Eaton, B. P.; Grimes, E; Welch, L. S.; Gomba, L; Wilhelmsen, C. L.; Nichols, D. K.; Nuss, J. E.; et al. (2016). "Therapeutic efficacy of the small molecule GS-5734 against Ebola virus in rhesus monkeys". Nature. 531 (7594): 381–5. Bibcode:2016Natur.531..381W. doi:10.1038/nature17180. PMC 5551389. PMID 26934220.
↑ Jacobs, M; Rodger, A; Bell, D. J.; Bhagani, S; Cropley, I; Filipe, A; Gifford, R. J.; Hopkins, S; Hughes, J; Jabeen, F; Johannessen, I; Karageorgopoulos, D; Lackenby, A; Lester, R; Liu, R. S.; MacConnachie, A; Mahungu, T; Martin, D; Marshall, N; Mepham, S; Orton, R; Palmarini, M; Patel, M; Perry, C; Peters, S. E.; Porter, D; Ritchie, D; Ritchie, N. D.; Seaton, R. A.; et al. (2016). "Late Ebola virus relapse causing meningoencephalitis: a case report". Lancet. 388 (10043): 498–503. doi:10.1016/S0140-6736(16)30386-5. PMC 4967715. PMID 27209148.

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[1] Agostini ML, et al. Coronavirus Susceptibility to the Antiviral Remdesivir (GS-5734) Is Mediated by the Viral Polymerase and the Proofreading Exoribonuclease. mBio, 2018; 9 (2): e00221-18 Agostini, Maria L; Andres, Erica L; Sims, Amy C; Graham, Rachel L; Sheahan, Timothy P; Lu, Xiaotao; Smith, Everett Clinton; Case, James Brett; Feng, Joy Y; Jordan, Robert; Ray, Adrian S; Cihlar, Tomas; Siegel, Dustin; MacKman, Richard L; Clarke, Michael O; Baric, Ralph S; Denison, Mark R (2018). "Coronavirus Susceptibility to the Antiviral Remdesivir (GS-5734) is Mediated by the Viral Polymerase and the Proofreading Exoribonuclease". Mbio. 9 (2). doi:10.1128/mBio.00221-18. PMC 5844999. PMID 29511076.

[2] Investigators also found that the drug was effective against SARS in mice, according to the study in the June 28 issue of the journal Science Translational Medicine. https://medlineplus.gov/news/fullstory_166953.html Tomas Cihlar, Gilead Sciences. Discovery and Development of GS-5734, a Novel Nucleotide Prodrug with Broad Spectrum Anti-Filovirus Activity. FANG-WHO Workshop, Fort Detrick, MD. 20 October 2015

[3] Warren, Travis; Jordan, Robert; Lo, Michale; Soloveva, Veronica; Ray, Adrian; Bannister, Roy; MacKman, Richard; Perron, Michel; Stray, Kirsten; Feng, Joy; Xu, Yili; Wells, Jay; Stuthman, Kelly; Welch, Lisa; Doerffler, Edward; Zhang, Lijun; Chun, Kwon; Hui, Hon; Neville, Sean; Lew, Willard; Park, Yeojin; Babusis, Darius; Strickley, Robert; Wong, Pamela; Swaminathan, Swami; Lee, William; Mayers, Douglas; Cihlar, Tomas; Bavari, Sina (Fall 2015). "Nucleotide Prodrug GS-5734 Is a Broad-Spectrum Filovirus Inhibitor That Provides Complete Therapeutic Protection Against the Development of Ebola Virus Disease (EVD) in Infected Non-human Primates". Open Forum Infect Dis. 2. doi:10.1093/ofid/ofv130.02.

[4] Warren, T. K.; Jordan, R; Lo, M. K.; Ray, A. S.; MacKman, R. L.; Soloveva, V; Siegel, D; Perron, M; Bannister, R; Hui, H. C.; Larson, N; Strickley, R; Wells, J; Stuthman, K. S.; Van Tongeren, S. A.; Garza, N. L.; Donnelly, G; Shurtleff, A. C.; Retterer, C. J.; Gharaibeh, D; Zamani, R; Kenny, T; Eaton, B. P.; Grimes, E; Welch, L. S.; Gomba, L; Wilhelmsen, C. L.; Nichols, D. K.; Nuss, J. E.; et al. (2016). "Therapeutic efficacy of the small molecule GS-5734 against Ebola virus in rhesus monkeys". Nature. 531 (7594): 381–5. Bibcode:2016Natur.531..381W. doi:10.1038/nature17180. PMC 5551389. PMID 26934220.

[5] Jacobs, M; Rodger, A; Bell, D. J.; Bhagani, S; Cropley, I; Filipe, A; Gifford, R. J.; Hopkins, S; Hughes, J; Jabeen, F; Johannessen, I; Karageorgopoulos, D; Lackenby, A; Lester, R; Liu, R. S.; MacConnachie, A; Mahungu, T; Martin, D; Marshall, N; Mepham, S; Orton, R; Palmarini, M; Patel, M; Perry, C; Peters, S. E.; Porter, D; Ritchie, D; Ritchie, N. D.; Seaton, R. A.; et al. (2016). "Late Ebola virus relapse causing meningoencephalitis: a case report". Lancet. 388 (10043): 498–503. doi:10.1016/S0140-6736(16)30386-5. PMC 4967715. PMID 27209148.

Remdesivir

See also

References