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Also known as: N4-hydroxycytidine, 3258-02-4, Beta-d-n4-hydroxycytidine, Eidd-1931, Uridine, 4-oxime, N-hydroxycytidine
Molecular Formula
C9H13N3O6
Molecular Weight
259.22  g/mol
InChI Key
XCUAIINAJCDIPM-XVFCMESISA-N
FDA UNII
C3D11PV2O4

BDBM430624
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.
1 2D Structure

BDBM430624

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-4-(hydroxyamino)pyrimidin-2-one
2.1.2 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
2.1.3 InChI Key
XCUAIINAJCDIPM-XVFCMESISA-N
2.1.4 Canonical SMILES
C1=CN(C(=O)N=C1NO)C2C(C(C(O2)CO)O)O
2.1.5 Isomeric SMILES
C1=CN(C(=O)N=C1NO)[C@H]2[C@@H]([C@@H]([C@H](O2)CO)O)O
2.2 Other Identifiers
2.2.1 UNII
C3D11PV2O4
2.3 Synonyms
2.3.1 MeSH Synonyms

1. 4-oxime Uridine

2. Beta-d-n4-hydroxycytidine

3. Eidd-1931

4. N4-hydroxycytidine

2.3.2 Depositor-Supplied Synonyms

1. N4-hydroxycytidine

2. 3258-02-4

3. Beta-d-n4-hydroxycytidine

4. Eidd-1931

5. Uridine, 4-oxime

6. N-hydroxycytidine

7. 4-n-hydroxycytidine

8. Eidd1931

9. C3d11pv2o4

10. 1-[(2r,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-4-(hydroxyamino)pyrimidin-2-one

11. 1-((2r,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-4-(hydroxyimino)-3,4-dihydropyrimidin-2(1h)-one

12. 4-oxime Uridine

13. 1-[(2r,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-4-(hydroxyamino)-1,2-dihydropyrimidin-2-one

14. N-4-hydroxycytidine

15. Cytidine, N-hydroxy-

16. Ccris 1074

17. 1-[(2r,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]-4-(hydroxyimino)-3,4-dihydropyrimidin-2(1h)-one

18. Unii-c3d11pv2o4

19. Beta-d-n(4)-hydroxycytidine

20. N-hydroxy-3,4-dihydrocytidine

21. Schembl5190819

22. Chembl2178720

23. Schembl24780346

24. Eidd 1931

25. Gtpl10735

26. Dtxsid20186274

27. Chebi:180654

28. Bdbm430624

29. Ex-a3655

30. Mfcd01675695

31. At13085

32. Bs-47105

33. Hy-125033

34. Cs-0088698

35. En300-7534996

36. Z4171362498

37. 1-((2r,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-4-(hydroxyamino)pyrimidin-2(1h)-one

38. 1-((2r,3r,4s,5r)-3,4-dihydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-4-hydroxyamino-1h-pyrimidin-2-one

39. 1-[(2r,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-4-(hydroxyimino)-1,2,3,4-tetrahydropyrimidin-2-one

40. 1-[(2r,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]-4-(hydroxyamino)pyrimidin-2-one

2.3.3 Other Synonyms

1. Uridine, 4-oxime

2.4 Create Date
2005-08-01
3 Chemical and Physical Properties
Molecular Weight 259.22 g/mol
Molecular Formula C9H13N3O6
XLogP3-2.2
Hydrogen Bond Donor Count5
Hydrogen Bond Acceptor Count6
Rotatable Bond Count3
Exact Mass g/mol
Monoisotopic Mass g/mol
Topological Polar Surface Area135
Heavy Atom Count18
Formal Charge0
Complexity398
Isotope Atom Count0
Defined Atom Stereocenter Count4
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Drug and Medication Information
4.1 Drug Indication

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.


5 Pharmacology and Biochemistry
5.1 Absorption, Distribution and Excretion

Absorption

N4-hydroxycytidine is orally bioavailable in mice but poorly bioavailable in non-human primates.


5.2 Metabolism/Metabolites

N4-hydroxycytidine distributes into tissues where it is is phosphorylated to the 5'-triphosphate form.


5.3 Mechanism of Action

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.


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