CHEBI:145994 - remdesivir

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ChEBI Name remdesivir
ChEBI ID CHEBI:145994
Definition A carboxylic ester resulting from the formal condensation of the carboxy group of N-[(S)-{[(2R,3S,4R,5R)-5-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)-5-cyano-3,4-dihydroxytetrahydrofuran-2-yl]methoxy}(phenoxy)phosphoryl]-L-alanine with the hydroxy group of 2-ethylbutan-1-ol. A broad-spectrum antiviral prodrug with potent in vitro antiviral activity against a diverse panel of RNA viruses such as Ebola virus, MERS-CoV and SARS-CoV. It is currently in Phase III clinical trials for the treatment of Covid-19 in adults.
Stars This entity has been manually annotated by the ChEBI Team.
Submitter Yingtong Liu
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Formula C27H35N6O8P
Net Charge 0
Average Mass 602.585
Monoisotopic Mass 602.22540
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
InChIKey RWWYLEGWBNMMLJ-YSOARWBDSA-N
SMILES [C@]1(O[C@@H]([C@H]([C@H]1O)O)CO[P@@](N[C@H](C(OCC(CC)CC)=O)C)(OC=2C=CC=CC2)=O)(C#N)C=3N4N=CN=C(C4=CC3)N
Roles Classification
Chemical Role(s): Bronsted base
A molecular entity capable of accepting a hydron from a donor (Bronsted acid).
(via organic amino compound )
Biological Role(s): anticoronaviral agent
Any antiviral agent which inhibits the activity of coronaviruses.
antiviral drug
A substance used in the prophylaxis or therapy of virus diseases.
Application(s): antiviral drug
A substance used in the prophylaxis or therapy of virus diseases.
prodrug
A compound that, on administration, must undergo chemical conversion by metabolic processes before becoming the pharmacologically active drug for which it is a prodrug.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing remdesivir (CHEBI:145994) has functional parent GS-441524 (CHEBI:147281)
remdesivir (CHEBI:145994) has role anticoronaviral agent (CHEBI:149553)
remdesivir (CHEBI:145994) has role antiviral drug (CHEBI:36044)
remdesivir (CHEBI:145994) has role prodrug (CHEBI:50266)
remdesivir (CHEBI:145994) is a C-nucleoside (CHEBI:37086)
remdesivir (CHEBI:145994) is a aromatic amine (CHEBI:33860)
remdesivir (CHEBI:145994) is a carboxylic ester (CHEBI:33308)
remdesivir (CHEBI:145994) is a nitrile (CHEBI:18379)
remdesivir (CHEBI:145994) is a phosphoramidate ester (CHEBI:27577)
remdesivir (CHEBI:145994) is a pyrrolotriazine (CHEBI:88341)
IUPAC Name
2-ethylbutyl N-[(S)-{[(2R,3S,4R,5R)-5-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)-5-cyano-3,4-dihydroxytetrahydrofuran-2-yl]methoxy}(phenoxy)phosphoryl]-L-alaninate
INNs Sources
remdésivir WHO MedNet
remdesivir WHO MedNet
remdesivir WHO MedNet
remdesivirum WHO MedNet
Synonyms Sources
(2S)-2-{(2R,3S,4R,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 ChEBI
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-dihydroxytetrahydrofuran-2-yl]methoxy}(phenoxy)phosphoryl]amino}propanoate ChEBI
GS 5734 DrugBank
GS-5734 ChemIDplus
GS5734 ChEBI
Manual Xrefs Databases
D11472 KEGG DRUG
DB14761 DrugBank
Remdesivir Wikipedia
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Registry Number Type Source
1809249-37-3 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
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PMC5630887 PubMed Central citation Europe PMC
Last Modified
23 April 2020