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Merck

SML2872

Sigma-Aldrich

EIDD-1931

≥98% (HPLC)

Synonym(e):

(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

Empirische Formel (Hill-System):
C9H13N3O6
CAS-Nummer:
Molekulargewicht:
259.22
UNSPSC-Code:
12352200
NACRES:
NA.77

Qualitätsniveau

Assay

≥98% (HPLC)

Form

powder

Farbe

white to beige

Löslichkeit

DMSO: 2 mg/mL, clear

Lagertemp.

−20°C

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

InChIKey

XCUAIINAJCDIPM-XVFCMESISA-N

Biochem./physiol. Wirkung

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.

Lagerklassenschlüssel

11 - Combustible Solids

WGK

WGK 3

Flammpunkt (°F)

Not applicable

Flammpunkt (°C)

Not applicable


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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
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
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
Maria L Agostini et al.
Journal of virology, 93(24) (2019-10-04)
Coronaviruses (CoVs) have emerged from animal reservoirs to cause severe and lethal disease in humans, but there are currently no FDA-approved antivirals to treat the infections. One class of antiviral compounds, nucleoside analogues, mimics naturally occurring nucleosides to inhibit viral

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