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SML2872

Sigma-Aldrich

EIDD-1931

≥98% (HPLC)

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

Quality Level

100

Assay

≥98% (HPLC)

form

powder

color

white to beige

solubility

DMSO: 2 mg/mL, clear

storage temp.

−20°C

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

Biochem/physiol Actions

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 Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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
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
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
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
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
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