remdesivir (CHEBI:145994)

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CHEBI:145994 - remdesivir

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ChEBI ID	CHEBI:145994
ChEBI Name	remdesivir
Stars
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.
Last Modified	23 April 2020
Submitter	yingtliu
Downloads	Molfile

Formula	C27H35N6O8P
Net Charge	0
Average Mass	602.585
Monoisotopic Mass	602.22540
SMILES	CCC(CC)COC(=O)[C@H](C)N[P@](=O)(OC[C@H]1O[C@@](C#N)(c2ccc3c(N)ncnn23)[C@H](O)[C@@H]1O)Oc1ccccc1
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

Wikipedia

Roles Classification

Chemical Role:	Bronsted base A molecular entity capable of accepting a hydron from a donor (Brønsted acid).
Biological Roles:	anticoronaviral agent Any antiviral agent which inhibits the activity of coronaviruses. antiviral drug A substance used in the prophylaxis or therapy of virus diseases.
Applications:	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. antiviral drug A substance used in the prophylaxis or therapy of virus diseases.

ChEBI Ontology

Outgoing Relation(s)
	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	Source
remdesivir	WHO MedNet
remdesivir	WHO MedNet
remdesivirum	WHO MedNet
remdésivir	WHO MedNet

Synonyms	Source
GS-5734	ChemIDplus
GS5734	ChEBI
GS 5734	DrugBank
(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

Manual Xrefs	Databases
DB14761	DrugBank
D11472	KEGG DRUG
Remdesivir	Wikipedia

Registry Numbers	Sources
CAS:1809249-37-3	ChemIDplus

Citations