GS-441524

Key facts

CAS number

1191237-69-0

Purity

>98%

Form

Solid

form

Molecular weight

291.26 Da

Molecular formula

C₁₂H₁₃N₅O₄

PubChem

44468216

Nature

Synthetic

Solubility

~10 mg/ml in DMSO

~10 mg/ml in DMF

Biochemical name

(2R,3R,4S,5R)-2-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-carbonitrile

Biological description

The predominant metabolite of remdesivir in blood and is the nucleoside of the prodrug remdesivir. It is phosphorylated to the active triphosphate metabolite which incorporates into RNA. It shows broad spectrum activity in cell based assays against HCV, YFV, DENV-2, Influenza A, Parainfluenza 3 and SARS-CoV viruses with EC₅₀ values ranging from 1.7 μM-27.9 μM. It inhibits SARS-CoV and MERS-CoV infected human airway epithelial cell cultures with EC₅₀ values of 0.18 μM and 0.86 μM respectively. GS-441524 is suggested for the treatment of COVID-19 due to lower toxicity and simpler synthesis when compared to remdesivir.

Canonical smiles

C1=C2C(=NC=NN2C(=C1)C3(C(C(C(O3)CO)O)O)C#N)N

Isomeric smiles

C1=C2C(=NC=NN2C(=C1)[C@]3([C@@H]([C@@H]([C@H](O3)CO)O)O)C#N)N

InChi

InChI=1S/C12H13N5O4/c13-4-12(10(20)9(19)7(3-18)21-12)8-2-1-6-11(14)15-5-16-17(6)8/h1-2,5,7,9-10,18-20H,3H2,(H2,14,15,16)/t7-,9-,10-,12+/m1/s1

InChiKey

BRDWIEOJOWJCLU-LTGWCKQJSA-N

IUPAC Name

(2R,3R,4S,5R)-2-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)-3,4-dihydroxy-5-(hydroxymethyl)oxolane-2-carbonitrile