N(4)-hydroxycytidine Chemical Properties

Melting point:

169-172 °C(Solv: methanol (67-56-1))

Density 

1.93±0.1 g/cm3(Predicted)

storage temp. 

Inert atmosphere,Store in freezer, under -20°C

solubility 

Soluble in DMSO (up to 25 mg/ml) or in Water (up to 15 mg/ml with warming).

pka

8.19±0.20(Predicted)

form 

solid

color 

White

Stability:

Stable for 1 year from date of purchase as supplied. Solutions in DMSO or distilled water may be stored at -20° for up to 3 months.

N(4)-hydroxycytidine Usage And Synthesis

Description

EIDD-1931 is a ribonucleoside analog with antiviral activity. It inhibits replication of severe acute respiratory syndrome coronavirus (SARS-CoV) in Vero 76 cells, Middle East respiratory syndrome coronavirus (MERS-CoV) in Calu-3 2B4 cells, and SARS-CoV-2 in Vero cells (IC₅₀s =0.1, 0.15 and 0.3 μM, respectively). It also reduces viral titers of Venezuelan equine encephalitis virus (VEEV) TC-83 in infected Vero cells (EC₅₀ = 0.426 μM) and wild-type and remdesivir-resistant strains of the model CoV mouse hepatitis virus (MHV) in infected DBT cells. EIDD-1931 (100 and 400 mg/kg twice per day) reduces lung viral titers in mouse models of respiratory syncytial virus (RSV) and H1N1 influenza A virus infection.

Uses

EIDD 1931 is an orally bioavailable broad-spectrum antiviral that inhibits SARS-CoV-2 and other multiple endemic, epidemic and bat coronavirus and has the potential for seasonal and pandemic influenza treatment. A broad-spectrum ribonucleoside analog inhibitor of influenza and respiratory syncytial viruses.

Definition

ChEBI: N(4)-hydroxycytidine is a nucleoside analogue that is cytidine which carries a hydroxy group at the N(4)-positon. It has broad-spectrum antiviral activity against influenza, SARS-CoV , SARS-CoV-2 and MERS-CoV. It has a role as a drug metabolite, a human xenobiotic metabolite, an anticoronaviral agent and an antiviral agent. It is a nucleoside analogue and a ketoxime. It is functionally related to a cytidine.

storage

Store at -20°C

References

1) Janion and Glickman (1980),?N4-hydroxycytidine: a mutagen specific for AT to GC transitions;?Mutat. Res.,?72?43 2) Stuyver?et al.?(2003),?Ribonucleotide analogue that blocks replication of bovine viral diarrhea and hepatitis C viruses in culture; Antimicrob. Agents Chemother.,?47?244 3) Costantini?et al.?(2012),?Antiviral activity of nucleoside analogues against norovirus; Antivir. Ther.,?17?981 4) Reynard?et al.?(2015),?Identification of a New Ribonucleoside Inhibitor of Ebola Virus Replication; Viruses,?7?6233 5) Ehteshami?et al.?(2017),?Characterization of ?-D-N4-Hydroxycytidine as a Novel Inhibitor of Chikungunya Virus; Antimicrob. Agents Chemother.,?61?e02395-16 6) Yoon?et al.?(2018),?Orally efficacious broad-spectrum ribonucleoside analog inhibitor of influenza and respiratory syncytial viruses; Antimicrob. Agents Chemother.,?62?e00766-18 7) Barnard?et al.?(2004),?Inhibition of severe acute respiratory syndrome-associated coronavirus (SARSCoV) by calpain inhibitors and beta-D-N4-hydroxycytidine; Antivir. Chem. Chemother., 15 15 8) Pyrc et al. (2006),?Inhibition of human coronavirus NL63 infection at early stages of the replication cycle; Antimicrob. Agents Chemother.,?50?2000 9) Toots et al. (2019),?Characterization of orally efficacious influenza drug with high resistance barrier in ferrets and human airway epithelia; Sci. Transl. Med.,?11?eaax5866

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