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Beta-D-N4-hydroxycytidine

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Also known as: N4-hydroxycytidine, Eidd-1931, Beta-d-n4-hydroxycytidine, N-hydroxycytidine, 3258-02-4, 4-n-hydroxycytidine

Molecular Formula

C₉H₁₃N₃O₆

Molecular Weight

259.22 g/mol

InChI Key

XCUAIINAJCDIPM-XVFCMESISA-N

FDA UNII

C3D11PV2O4

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

Beta-D-N4-hydroxycytidine

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. Eidd-1931

3. Beta-d-n4-hydroxycytidine

4. N-hydroxycytidine

5. 3258-02-4

6. 4-n-hydroxycytidine

7. C3d11pv2o4

8. 1-[(2r,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-4-(hydroxyamino)pyrimidin-2-one

9. 1-((2r,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-4-(hydroxyimino)-3,4-dihydropyrimidin-2(1h)-one

10. 4-oxime Uridine

11. N-4-hydroxycytidine

12. Cytidine, N-hydroxy-

13. Ccris 1074

14. 1-[(2r,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]-4-(hydroxyimino)-3,4-dihydropyrimidin-2(1h)-one

15. Unii-c3d11pv2o4

16. Eidd1931

17. Beta-d-n(4)-hydroxycytidine

18. N-hydroxy-3,4-dihydrocytidine

19. Schembl5190819

20. Chembl2178720

21. Eidd 1931

22. Gtpl10735

23. Dtxsid20186274

24. Chebi:180654

25. Ex-a3655

26. Mfcd01675695

27. At13085

28. Bs-47105

29. Hy-125033

30. Cs-0088698

31. 1-((2r,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-4-(hydroxyamino)pyrimidin-2(1h)-one

32. 1-((2r,3r,4s,5r)-3,4-dihydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-4-hydroxyamino-1h-pyrimidin-2-one

33. 1-[(2r,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-4-(hydroxyamino)-1,2-dihydropyrimidin-2-one

34. 1-[(2r,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]-4-(hydroxyamino)pyrimidin-2-one

2.4 Create Date

2005-08-01

3 Chemical and Physical Properties

Molecular Formula	C₉H₁₃N₃O₆
Molecular Weight	259.22 g/mol
XLogP3	-2.2
Hydrogen Bond Donor Count	5
Hydrogen Bond Acceptor Count	6
Rotatable Bond Count	3
Exact Mass	259.08043514 g/mol
Monoisotopic Mass	259.08043514 g/mol
Topological Polar Surface Area	135 Å²
Heavy Atom Count	18
Formal Charge	0
Complexity	398
Isotope Atom Count	0
Defined Atom Stereocenter Count	4
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

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.