Product Name

Remdesivir

CAS Number

1809249-37-3

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Product Name:
Remdesivir
CAS Number:
1809249-37-3
Mode of Action:

Remdesivir is a nucleoside analog that is expected to inhibit the action of RNA polymerase.3 By incorporating into RNA, additional nucleotides cannot be added, terminating RNA transcription.3 Viruses with mutations in RNA polymerase to develop partial resistance to remdesivir have been shown to be less infective.

Pharmacodynamics:

Dosing was predicted to be twice daily to maintain therapeutic concentrations required for treatment of CoV infections.2 However, current clinical trials will use a regimen of 200mg once daily on the first day, followed by 100mg once daily for another 9 days.6,7,8

Metabolism:

Remdesivir is predominantly metabolized to a triphosphate metabolite.

Toxicity:

Data regarding overdoses of remdesivir are not readily available. Overdoses of other nucleoside analogs like acyclovir can be managed with symptomatic and supportive treatment.

IUPAC:
2-ethylbutyl (2S)-2-{[(S)-{[(2R,3S,4R,5R)-5-{4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl}-5-cyano-3,4-dihydroxyoxolan-2-yl]methoxy}(phenoxy)phosphoryl]amino}propanoate
DrugBank:
DB14761
Formula:
C27H35N6O8P
Molecular Mass:
602.585
Synonyms:
Remdesivir, Remdésivir, Remdesivirum
SMILES:
CCC(CC)COC(=O)[C@H](C)N[P@](=O)(OC[C@H]1O[C@](C#N)([C@H](O)[C@@H]1O)C1=CC=C2N1N=CN=C2N)OC1=CC=CC=C1
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
General Reference:
General Reference:

1. Warren TK, Jordan R, Lo MK, Ray AS, Mackman RL, Soloveva V, Siegel D, Perron M, Bannister R, Hui HC, Larson N, Strickley R, Wells J, Stuthman KS, Van Tongeren SA, Garza NL, Donnelly G, Shurtleff AC, Retterer CJ, Gharaibeh D, Zamani R, Kenny T, Eaton BP, Grimes E, Welch LS, Gomba L, Wilhelmsen CL, Nichols DK, Nuss JE, Nagle ER, Kugelman JR, Palacios G, Doerffler E, Neville S, Carra E, Clarke MO, Zhang L, Lew W, Ross B, Wang Q, Chun K, Wolfe L, Babusis D, Park Y, Stray KM, Trancheva I, Feng JY, Barauskas O, Xu Y, Wong P, Braun MR, Flint M, McMullan LK, Chen SS, Fearns R, Swaminathan S, Mayers DL, Spiropoulou CF, Lee WA, Nichol ST, Cihlar T, Bavari S: Therapeutic efficacy of the small molecule GS-5734 against Ebola virus in rhesus monkeys. Nature. 2016 Mar 17;531(7594):381-5. doi: 10.1038/nature17180. Epub 2016 Mar 2. [PubMed:26934220 http://www.ncbi.nlm.nih.gov/pubmed/26934220]
2. Sheahan TP, Sims AC, Graham RL, Menachery VD, Gralinski LE, Case JB, Leist SR, Pyrc K, Feng JY, Trantcheva I, Bannister R, Park Y, Babusis D, Clarke MO, Mackman RL, Spahn JE, Palmiotti CA, Siegel D, Ray AS, Cihlar T, Jordan R, Denison MR, Baric RS: Broad-spectrum antiviral GS-5734 inhibits both epidemic and zoonotic coronaviruses. Sci Transl Med. 2017 Jun 28;9(396). pii: 9/396/eaal3653. doi: 10.1126/scitranslmed.aal3653. [PubMed:28659436 http://www.ncbi.nlm.nih.gov/pubmed/28659436]
3. Agostini ML, Andres EL, Sims AC, Graham RL, Sheahan TP, Lu X, Smith EC, Case JB, Feng JY, Jordan R, Ray AS, Cihlar T, Siegel D, Mackman RL, Clarke MO, Baric RS, Denison MR: Coronavirus Susceptibility to the Antiviral Remdesivir (GS-5734) Is Mediated by the Viral Polymerase and the Proofreading Exoribonuclease. mBio. 2018 Mar 6;9(2). pii: mBio.00221-18. doi: 10.1128/mBio.00221-18. [PubMed:29511076 http://www.ncbi.nlm.nih.gov/pubmed/29511076]
4. de Wit E, Feldmann F, Cronin J, Jordan R, Okumura A, Thomas T, Scott D, Cihlar T, Feldmann H: Prophylactic and therapeutic remdesivir (GS-5734) treatment in the rhesus macaque model of MERS-CoV infection. Proc Natl Acad Sci U S A. 2020 Feb 13. pii: 1922083117. doi: 10.1073/pnas.1922083117. [PubMed:32054787 http://www.ncbi.nlm.nih.gov/pubmed/32054787]
5. Vander T, Medvedovsky M, Herishanu Y: Encephalopathy induced by oral acyclovir in a patient with normal renal function. J Infect. 2003 May;46(4):286. doi: 10.1053/jinf.2002.1119. [PubMed:12799156 http://www.ncbi.nlm.nih.gov/pubmed/12799156]
6. Ko WC, Rolain JM, Lee NY, Chen PL, Huang CT, Lee PI, Hsueh PR: Arguments in favor of remdesivir for treating SARS-CoV-2 infections. Int J Antimicrob Agents. 2020 Mar 5:105933. doi: 10.1016/j.ijantimicag.2020.105933. [PubMed:32147516 http://www.ncbi.nlm.nih.gov/pubmed/32147516]
7. NIH: Clinical Trial NCT04252664 [https://clinicaltrials.gov/ct2/show/NCT04252664]
8. NIH: Clinical Trial NCT04257656 [https://clinicaltrials.gov/ct2/show/NCT04257656]

Product Description:

Remdesivir, or GS-5734, is an adenosine triphosphate analog first described in the literature in 2016 as a potential treatment for Ebola.1 In 2017, its activity against the coronavirus family of viruses was also demonstrated.2 Remdesivir is also being researched as a potential treatment to SARS-CoV2, the coronavirus responsible for COVID-19.4

Products currently covered by valid US Patents are offered for R&D use in accordance with 35 USC 271(e)+A13(1). Any patent infringement and resulting liability is solely at buyer risk.

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