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Merck
CN

SML2872

EIDD-1931

≥98% (HPLC), ribonucleoside analog, powder

Synonym(s):

(oh)4Cyd, 1-((2R,3R,4S,5R)-3,4-Dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-4-(hydroxyamino)pyrimidin-2(1H)-one, 4-N-HO-Cyd, BHC, EIDD 1931, EIDD 2801 metabolite, EIDD-2801 metabolite, EIDD1931, EIDD2801 metabolite, N4-Hydroxycytidine, N4-OHcyd, N4OHcyd, NHC, beta-D-N4-Hydroxycytidine

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About This Item

Empirical Formula (Hill Notation):
C9H13N3O6
CAS Number:
3258-02-4
Molecular Weight:
259.22
UNSPSC Code:
12352200
NACRES:
NA.77

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Product Name

EIDD-1931, ≥98% (HPLC)

SMILES string

[n]2([c](nc(cc2)NO)=O)[C@@H]1O[C@@H]([C@H]([C@H]1O)O)CO

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

InChI key

XCUAIINAJCDIPM-XVFCMESISA-N

assay

≥98% (HPLC)

form

powder

color

white to beige

solubility

DMSO: 2 mg/mL, clear

storage temp.

−20°C

Quality Level

100

Related Categories

Biochem/physiol Actions

Orally available ribonucleoside analog with broad anti-viral activity (SARS-CoV-2, RSV, IAV, IBV, HCV, pestivirus, EBOV, CHIKV) in cultures and in vivo.
Originally recognized as a powerful mutagen that preferentially induces AT-to-GC transition in microorganisms, EIDD-1931 (NHC, N4-hydroxycytidine) is an orally available ribonucleoside analog with known anti-viral activity against SARS-CoV, SARS-CoV-2, respiratory syncytial virus (RSV), influenza A & B viruses (IAV & IBV), HCV, pestivirus, bovine viral diarrhoea virus (BVDV), Ebola virus (EBOV), Chikungunya virus (CHIKV), venezuelan equine encephalitis virus (VEEV). NHC effectively reduces RSV and IAVs replication in mice, and exhibts efficacy in a guinea pig IAV transmission model in vivo (100 & 400 mg/kg b.i.d. p.o.). Metabolic studies reveal species-dependent plasma stability.

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
0000191106
0000191107
0000166785
0000164788
0000164787

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George R Painter et al.
Antiviral research, 171, 104597-104597 (2019-09-09)
The New World alphaviruses Venezuelan, Eastern, and Western equine encephalitis viruses (VEEV, EEEV and WEEV, respectively) commonly cause a febrile disease that can progress to meningoencephalitis, resulting in significant morbidity and mortality. To address the need for a therapeutic agent
Dale L Barnard et al.
Antiviral chemistry & chemotherapy, 17(5), 275-284 (2006-12-21)
Compounds approved for therapeutic use and in vitro inhibitors of severe acute respiratory syndrome coronavirus (SARS-CoV) were evaluated for inhibition in the mouse SARS-CoV replication model. A hybrid interferon, interferon alpha (IFN-alpha) B/D, and a mismatched double-stranded (ds) RNA interferon
Zachary M Sticher et al.
Antimicrobial agents and chemotherapy, 64(2) (2019-11-27)
N4-Hydroxycytidine (NHC) is an antiviral ribonucleoside analog that acts as a competitive alternative substrate for virally encoded RNA-dependent RNA polymerases. It exhibits measurable levels of cytotoxicity, with 50% cytotoxic concentration values ranging from 7.5 μM in CEM cells and up
E Sledziewska et al.
Mutation research, 70(1), 11-16 (1980-03-01)
The mutagenic specificty of (oh)4Cyd was examined with T4rII phage mutants which allow for discrimination between AT yields GC and GC yields AT base transitions. AT yields GC transitions were induced with a frequency 1-2 orders of magnitude higher than
Maryam Ehteshami et al.
Antimicrobial agents and chemotherapy, 61(4) (2017-02-01)
Chikungunya virus (CHIKV) represents a reemerging global threat to human health. Recent outbreaks across Asia, Europe, Africa, and the Caribbean have prompted renewed scientific interest in this mosquito-borne alphavirus. There are currently no vaccines against CHIKV, and treatment has been
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