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SML1225

Sigma-Aldrich

Indisulam

≥98% (HPLC)

Synonym(s):

N-(3-chloro-1H-indol-7-yl)-4-sulfamoylbenzenesulfonamide, N1-(3-Chloro-1H-indol-7-yl)-1,4-benzenedisulfonamide

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About This Item

Empirical Formula (Hill Notation):
C14H12ClN3O4S2
CAS Number:
165668-41-7
Molecular Weight:
385.85
MDL number:
MFCD00945325
UNSPSC Code:
12352200
PubChem Substance ID:
329825730
NACRES:
NA.77

Quality Level

100

Assay

≥98% (HPLC)

form

powder

color

white to pink

solubility

DMSO: 20 mg/mL, clear

storage temp.

−20°C

SMILES string

ClC1=CNC2=C1C=CC=C2NS(C3=CC=C(S(=O)(N)=O)C=C3)(=O)=O

InChI

1S/C14H12ClN3O4S2/c15-12-8-17-14-11(12)2-1-3-13(14)18-24(21,22)10-6-4-9(5-7-10)23(16,19)20/h1-8,17-18H,(H2,16,19,20)

InChI key

SETFNECMODOHTO-UHFFFAOYSA-N

Biochem/physiol Actions

Indisulam is a carbonic anhydrase inibitor and Antitumor CDK inhibitor. Indisulam targets the G1 phase of the cell cycle by depleting cyclin E. inducing p53 and p21, and inhibiting CDK2, causing a blockade in the G1/S transition.
Indisulam is synthetic sulfonamide compound. In vitro and in vivo studies point out that indisulam prevents retinoblastoma protein phosphorylation. Also, it inhibits cyclins A and B1 activity. Indisulam is known to promote apoptosis. Indisulam is a potent inhibitor of cellular dehydrogenases and thus, is likely to interfere with metabolic pathways such as malate-aspartate shuttle, glycolysis and gluconeogenesis.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319

Hazard Classifications

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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Semi-physiological model describing the hematological toxicity of the anti-cancer agent indisulam.
van Kesteren C, et al.
Investigational New Drugs, 23(3), 225-234 (2005)
Sung Ah Kim et al.
Molecules and cells, 43(11), 935-944 (2020-11-11)
Aryl hydrocarbon receptor nuclear translocator (ARNT) plays an essential role in maintaining cellular homeostasis in response to environmental stress. Under conditions of hypoxia or xenobiotic exposure, ARNT regulates the subset of genes involved in adaptive responses, by forming heterodimers with
Cristina Mayor-Ruiz et al.
Nature chemical biology, 16(11), 1199-1207 (2020-08-05)
Targeted protein degradation is a new therapeutic modality based on drugs that destabilize proteins by inducing their proximity to E3 ubiquitin ligases. Of particular interest are molecular glues that can degrade otherwise unligandable proteins by orchestrating direct interactions between target

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