N4-Hydroxycytidine
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N4-Hydroxycytidine
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CAS No:
3258-02-4
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Formula:
C9H13N3O6
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Chemical Name:
N4-Hydroxycytidine
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Synonyms:
Uridine,4-oxime;Cytidine,N-hydroxy-;N4-Hydroxycytidine;N-Hydroxycytidine;EIDD 1931;NHC;85373-26-8
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CAS No:
Description
N4-Hydroxyctidine, or EIDD-1931, is a ribonucleoside analog which induces mutations in RNA virions. N4-hydroxycytidine was first described in the literature in 1980 as a potent mutagen of bacteria and phage. It has shown antiviral activity against Venezuelan equine encephalitis virus, and the human coronavirus HCoV-NL63 in vitro. N4-hydroxycytodine has been shown to inhibit SARS-CoV-2 as well as other human and bat coronaviruses in mice and human airway epithelial cells. It is orally bioavailable in mice and distributes into tissue before becoming the active 5’-triphosphate form, which is incorporated into the genome of new virions, resulting in the accumulation of inactivating mutations. In non-human primates, N4-hydroxycytidine was poorly orally bioavailable. A [remdesivir] resistant mutant mouse hepatitis virus has also been shown to have increased sensitivity to N4-hydroxycytidine. The prodrug of N4-hydroxycytidine, [EIDD-2801], is also being investigated for its broad spectrum activity against the coronavirus family of viruses.
Toxicity
Data regarding overdose of N4-hydroxycytidine is not readily available. The therapeutic index of N4-hydroxycytidine against a clinical isolate of SARS-CoV-2 is expected to be >100, with an _in vitro_ IC50 of 0.3µM and a CC50 of >10µM.
Drug Information
N4-hydroxycytidine and its prodrug [EIDD-2801] is being studied for its activity against a number of viral infections including influenza, MERS-CoV, and SARS-CoV-2.
N4-hydroxycytidine is orally bioavailable in mice but poorly bioavailable in non-human primates.
N4-hydroxycytidine distributes into tissues where it is is phosphorylated to the 5'-triphosphate form.
N4-hydroxycytidine is phosphorylated in tissue to the active 5’-triphosphate form, which is incorporated into the genome of new virions, resulting in the accumulation of inactivating mutations, known as viral error catastrophe. A [remdesivir] resistant mutant mouse hepatitis virus has also been shown to have increased sensitivity to N4-hydroxycytidine.
4-oxime uridine
Computed Properties
Molecular Weight:259.22
XLogP3:-2.2
Hydrogen Bond Donor Count:5
Hydrogen Bond Acceptor Count:6
Rotatable Bond Count:3
Exact Mass:259.08043514
Monoisotopic Mass:259.08043514
Topological Polar Surface Area:135
Heavy Atom Count:18
Complexity:398
Defined Atom Stereocenter Count:4
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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