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SML1824

Sigma-Aldrich

GSK983

≥98% (HPLC)

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Synonym(s):
GSK260983, N-[(1R)-6-Chloro-2,3,4,9-tetrahydro-1H-carbazol-1-yl]-2-pyridinecarboxamide
Empirical Formula (Hill Notation):
C18H16ClN3O
CAS Number:
827591-02-6
Molecular Weight:
325.79
MDL number:
MFCD28978021
UNSPSC Code:
12352200
PubChem Substance ID:
329826082
NACRES:
NA.77

Quality Level

100

Assay

≥98% (HPLC)

form

powder

optical activity

[α]/D +175 to +195°, c = 1 in methylene chloride

storage condition

protect from light

color

white to beige

solubility

DMSO: 10 mg/mL, clear

storage temp.

2-8°C

SMILES string

ClC1=CC=C(NC2=C3CCC[C@H]2NC(C4=NC=CC=C4)=O)C3=C1

InChI

1S/C18H16ClN3O/c19-11-7-8-14-13(10-11)12-4-3-6-15(17(12)21-14)22-18(23)16-5-1-2-9-20-16/h1-2,5,7-10,15,21H,3-4,6H2,(H,22,23)

InChI key

WJQBOBGVBBZLJU-UHFFFAOYSA-N

Biochem/physiol Actions

GSK983 blocks RNA virus replication with EC50 values of 10–40 nM, and also blocks cell proliferation. GSK983 acts by inhibition of dihydroorotate dehydrogenase (DHODH), necesssary for pyrimidine biosynthesis. Exogenous deoxycytidine was able to reduce GSK983 cytotoxicity, allowing cells to synthesize DNA, but still preventing RNA virus replication. GSK983 was active against dengue fever and Venezuelan equine encephalitis viruses.
GSK983 is a tetrahydrocarbazole or a broad spectrum antiviral lead compound. GSK983 acts by stimulating a subset of interferon-stimulated genes.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H302,H315,H319

Hazard Classifications

Acute Tox. 4 Oral - Eye Irrit. 2 - Skin Irrit. 2

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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Kristjan S Gudmundsson et al.
Bioorganic & medicinal chemistry letters, 19(15), 4110-4114 (2009-06-27)
Synthesis of a series of tetrahydrocarbazole amides with potent activity against human papillomaviruses is described. Synthetic approaches allowing for variation of the substitution pattern of the tetrahydrocarbazole and the amide are outlined and resulting changes in antiviral activity and certain
GSK983: a novel compound with broad-spectrum antiviral activity.
Harvey R, et al.
Antiviral Research, 82(1), 1-11 (2009)
Richard M Deans et al.
Nature chemical biology, 12(5), 361-366 (2016-03-29)
Broad-spectrum antiviral drugs targeting host processes could potentially treat a wide range of viruses while reducing the likelihood of emergent resistance. Despite great promise as therapeutics, such drugs remain largely elusive. Here we used parallel genome-wide high-coverage short hairpin RNA
Yajie Yu et al.
Cell death & disease, 12(9), 821-821 (2021-09-01)
Metabolic reprogramming is an integral part of the growth-promoting program driven by the MYC family of oncogenes. However, this reprogramming also imposes metabolic dependencies that could be exploited therapeutically. Here we report that the pyrimidine biosynthetic enzyme dihydroorotate dehydrogenase (DHODH)
Parallel shRNA and CRISPR-Cas9 screens enable antiviral drug target identification.
Deans RM, et al.
Nature Chemical Biology, 12(5), 361-366 (2016)
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