remdesivir   

GtoPdb Ligand ID: 10715

Synonyms: compound 4b [PMID: 28124907] | GS5734
Compound class: Synthetic organic
Comment: Remdesivir (GS-5734) is a nucleotide analogue drug that was developed by Gilead Sciences for antiviral potential, in particular for anti-Ebola and anti-Marburg virus activity [5]. It is a prodrug whose active metabolite is GS-441524 (PubChem CID: 44468216). The compound's 1'-CN group and C-linked nucleobase ensure optimal anti-Ebola potency and selectivity against host polymerase enzymes. Remdesivir has broad-spectrum activity against other RNA viruses, including the SARS and MERS coronaviruses (CoVs) and endemic circulating human CoVs, and possibly against newly emerging CoVs such as SARS-CoV-2 [1,4]. The first patient to test positive for SARS-CoV-2 in the US was treated with i.v. remdesivir (using compassionate use of an investigational therapy prescribing) and his clinical condition improved significantly within the next 24h without observation of adverse effects [3].
2D Structure
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Physico-chemical Properties
Hydrogen bond acceptors 12
Hydrogen bond donors 4
Rotatable bonds 14
Topological polar surface area 213.36
Molecular weight 602.23
XLogP 1.93
No. Lipinski's rules broken 2
SMILES / InChI / InChIKey
Canonical SMILES CCC(COC(=O)[C@@H](N[P@@](=O)(Oc1ccccc1)OC[C@H]1O[C@@]([C@@H]([C@@H]1O)O)(C#N)c1ccc2n1ncnc2N)C)CC
Isomeric SMILES CCC(COC(=O)[C@@H](N[P@@](=O)(Oc1ccccc1)OC[C@H]1O[C@@]([C@@H]([C@@H]1O)O)(C#N)c1ccc2n1ncnc2N)C)CC
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
InChI Key RWWYLEGWBNMMLJ-YSOARWBDSA-N
Classification
Compound class Synthetic organic
IUPAC Name
2-ethylbutyl (2S)-2-[[[(2R,3S,4R,5R)-5-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)-5-cyano-3,4-dihydroxyoxolan-2-yl]methoxy-phenoxyphosphoryl]amino]propanoate
International Nonproprietary Names
INN number INN
10478 remdesivir
Synonyms
compound 4b [PMID: 28124907] | GS5734
Database Links
CAS Registry No. 1809249-37-3 (source: WHO INN record)
ChEMBL Ligand CHEMBL4065616
DrugCentral Ligand 5376
GtoPdb PubChem SID 404859162
PubChem CID 121304016
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