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.

InChI

InChI=1S/C9H13N3O6/c13-3-4-6(14)7(15)8(18-4)12-2-1-5(11-17)10-9(12)16/h1-2,4,6-8,13-15,17H,3H2,(H,10,11,16)/t4-,6-,7-,8-/m1/s1

InChIKey

XCUAIINAJCDIPM-XVFCMESISA-N

SMILES

OC[C@H]1O[C@@H](N2C=CC(=NO)NC2=O)[C@H](O)[C@@H]1O

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] CELINA JANION  Barry W G. N4-hydroxycytidine: A mutagen specific for at to GC transitions[J]. Mutation Research-Fundamental and Molecular Mechanisms of Mutagenesis, 1980, 72 1: Pages 43-47. DOI:10.1016/0027-5107(80)90218-3
[2] LIEVEN J STUYVER. Ribonucleoside analogue that blocks replication of bovine viral diarrhea and hepatitis C viruses in culture.[J]. Antimicrobial Agents and Chemotherapy, 2003, 47 1: 244-254. DOI:10.1128/aac.47.1.244-254.2003
[3] VERÓNICA P COSTANTINI. Antiviral activity of nucleoside analogues against norovirus.[J]. Antiviral Therapy, 2012, 17 6: 981-991. DOI:10.3851/imp2229
[4] O. REYNARD. Identification of a New Ribonucleoside Inhibitor of Ebola Virus Replication[J]. Viruses-Basel, 2015, 7 1: 6233-6240. DOI:10.3390/v7122934
[5] M. EHTESHAMI. Characterization of β-d-N4-Hydroxycytidine as a Novel Inhibitor of Chikungunya Virus[J]. Antimicrobial Agents and Chemotherapy, 2017. DOI:10.1128/aac.02395-16
[6] JEONG-JOONG YOON. Orally Efficacious Broad-Spectrum Ribonucleoside Analog Inhibitor of Influenza and Respiratory Syncytial Viruses.[J]. Antimicrobial Agents and Chemotherapy, 2018, 62 8. DOI:10.1128/aac.00766-18
[7] DALE L BARNARD. Inhibition of severe acute respiratory syndrome-associated coronavirus (SARSCoV) by calpain inhibitors and beta-D-N4-hydroxycytidine.[J]. Antiviral Chemistry and Chemotherapy, 2004, 15 1: 15-22. DOI:10.1177/095632020401500102
[8] KRZYSZTOF PYRC. Inhibition of human coronavirus NL63 infection at early stages of the replication cycle.[J]. Antimicrobial Agents and Chemotherapy, 2006: 2000-2008. DOI:10.1128/aac.01598-05
[9] MART TOOTS. Characterization of orally efficacious influenza drug with high resistance barrier in ferrets and human airway epithelia[J]. Science Translational Medicine, 2019, 11 515. DOI:10.1126/scitranslmed.aax5866

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