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Merck
CN

SML1824

GSK983

≥98% (HPLC)

Synonym(s):

GSK260983, N-[(1R)-6-Chloro-2,3,4,9-tetrahydro-1H-carbazol-1-yl]-2-pyridinecarboxamide

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About This Item

Empirical Formula (Hill Notation):
C18H16ClN3O
CAS Number:
827591-02-6
Molecular Weight:
325.79
NACRES:
NA.77
PubChem Substance ID:
329826082
UNSPSC Code:
51111800
MDL number:
MFCD28978021

Key Documents

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Product Name

GSK983, ≥98% (HPLC)

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)

SMILES string

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

InChI key

WJQBOBGVBBZLJU-UHFFFAOYSA-N

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

Quality Level

100

Related Categories

Biochem/physiol Actions

GSK983 blocks RNA virus replication with EC50 values of 10–40 nM, and also blocks cell proliferation.
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

signalword

Warning

Hazard Classifications

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

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
0000481501
0000298907
0000298907
0000148791
0000148791

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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
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
GSK983: a novel compound with broad-spectrum antiviral activity.
Harvey R, et al.
Antiviral Research, 82(1), 1-11 (2009)
Robert Harvey et al.
Antiviral research, 82(1), 1-11 (2009-02-04)
GSK983, a novel tetrahydrocarbazole, inhibits the replication of a variety of unrelated viruses in vitro with EC(50) values of 5-20 nM. Both replication of the adenovirus Ad-5 and the polyoma virus SV-40, and episomal maintenance of human papillomaviruses (HPV) and
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)
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