| Identification | Back Directory | [Name]
N(4)-hydroxycytidine | [CAS]
3258-02-4 | [Synonyms]
EIDD-1931
Uridine, 4-oxime
N-Hydroxycytidine
N(4)-hydroxycytidine
β-D-N4-Hydroxycytidine
Beta-d-N4-hydroxycytidine
EIDD2801 ,β-D-N4-hydroxycytidine
Beta-d-N4-hydroxycytidine
(NHC)
3,4-Dihydro-1-β-D-ribofuranosyl-4-(hydroxyimino)pyrimidin-2(1H)-one
1-[(2R)-3α,4α-Dihydroxy-5β-(hydroxymethyl)oxolane-2β-yl]-4-(hydroxyamino)pyrimidine-2(1H)-one | [Molecular Formula]
C9H13N3O6 | [MDL Number]
MFCD01675695 | [MOL File]
3258-02-4.mol | [Molecular Weight]
259.22 |
| Chemical Properties | Back Directory | [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). | [form ]
solid | [pka]
8.19±0.20(Predicted) | [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. |
| Hazard Information | Back Directory | [Description]
EIDD-1931 is a ribonucleoside analog with antiviral activity.1,2,3,4 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).3,4 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.2,4 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.1 | [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,unstable in solution, ready to use. | [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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