remdesivir   Click here for help

GtoPdb Ligand ID: 10715

Synonyms: compound 4b [PMID: 28124907] | GS-5734 | GS5734 | Veklury®
Approved drug
remdesivir is an approved drug (FDA & EMA (2020))
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 [7]. It acts is an inhibitor of the viral RNA-dependent RNA polymerase (RdRP) that functions as a chain terminator during viral RNA synthesis. Remdesivir is a prodrug whose major active metabolite is GS-441524. Its 1'-CN group and C-linked nucleobase ensure optimal anti-Ebola potency and selectivity against host polymerase enzymes. Remdesivir has broad-spectrum activity against several viral families such as filoviruses, paramyxoviruses, and coronaviruses, and including the SARS and MERS coronaviruses (CoVs), endemic circulating human CoVs, and against SARS-CoV-2 [1-2,6]. 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 [4].

remdesivir is commercially available from our sponsors

2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/). All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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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

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

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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

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes (FDA & EMA (2020))
Approved drug? Yes. EMA (2020)  |  FDA (2020)
Is prodrug? Yes
Active form GS-441524
IUPAC Name Click here for help
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 Click here for help
INN number INN
10478 remdesivir
Synonyms Click here for help
compound 4b [PMID: 28124907] | GS-5734 | GS5734 | Veklury®
Database Links Click here for help
Specialist databases
Reactome Drug Reactome logo R-ALL-9680278
Reactome Reaction Reactome logo R-HSA-9687384, R-HSA-9687388, R-HSA-9680262, R-HSA-9694665, R-HSA-9694541, R-HSA-9694419
Other databases
CAS Registry No. 1809249-37-3 (source: WHO INN record)
ChEMBL Ligand CHEMBL4065616
DrugCentral Ligand 5376
GtoPdb PubChem SID 404859162
PubChem CID 121304016
Search Google for chemical match using the InChIKey RWWYLEGWBNMMLJ-YSOARWBDSA-N
Search Google for chemicals with the same backbone RWWYLEGWBNMMLJ
Search PubMed clinical trials remdesivir
Search PubMed titles remdesivir
Search PubMed titles/abstracts remdesivir
UniChem Compound Search for chemical match using the InChIKey RWWYLEGWBNMMLJ-YSOARWBDSA-N
UniChem Connectivity Search for chemical match using the InChIKey RWWYLEGWBNMMLJ-YSOARWBDSA-N

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MedChemExpress
Remdesivir (links to external site)
Cat. No. HY-104077