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Necrosulfonamide

CAT: 0804-HY-100573-01Size: 5 mgDry Ice: NoHazardous: No
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CAT#:0804-HY-100573-01Size:5 mg
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Description
Necrosulfonamide is a MLKL and Gasdermin D (GSDMD) inhibitor, capable of separately inhibiting necroptosis and pyroptosis of cells. Necrosulfonamide does not affect the activation of upstream signals, but specifically inhibits the downstream executor oligomerization step. Necrosulfonamide reduces the expression of the key kinases NLRP3 and caspase-1 involved in necroptosis and pyroptosis, activate the Nrf2 pathway and the downstream antioxidant enzymes, and also downregulates a variety of inflammatory factors. Necrosulfonamide plays significant roles in various diseases such as neurodegenerative diseases (such as Parkinson’s disease), tissue damage and ischemia-reperfusion injury, inflammatory bowel disease, osteoarthritis and fracture repair, and hair loss by regulating two important programmed necrosis pathways[1][2][3][4][5][6][7].
CAS Number
1360614-48-7
UNSPSC
12352005
Hazard Statement
H302, H315, H319, H335
Target
Caspase; Heme Oxygenase (HO) ; Interleukin Related; Keap1-Nrf2; Mixed Lineage Kinase; Necroptosis; NO Synthase; NOD-like Receptor (NLR) ; Pyroptosis; TNF Receptor
Type
Reference compound
Related Pathways
Apoptosis; Immunology/Inflammation; MAPK/ERK Pathway; Metabolic Enzyme/Protease; NF-κB
Applications
Cancer-Kinase/protease
Field of Research
Endocrinology; Metabolic Disease; Inflammation/Immunology; Neurological Disease; Cardiovascular Disease
Assay Protocol
https://www.medchemexpress.com/Necrosulfonamide.html
Concentration
10mM
Purity
99.47
Solubility
DMSO : ≥ 28 mg/mL
Smiles
O=C(NC1=CC=C(S(=O)(NC2=NC=CN=C2OC)=O)C=C1)/C=C/C3=CC=C([N+]([O-])=O)S3
Molecular Formula
C18H15N5O6S2
Molecular Weight
461.47
Precautions
H302, H315, H319, H335
References & Citations
[1]Sun L, et al. Mixed lineage kinase domain-like protein mediates necrosis signaling downstream of RIP3 kinase. Cell. 2012;148 (1-2) :213-227.|[2]Yang W, et al. Necrosulfonamide ameliorates intestinal inflammation via inhibiting GSDMD-medicated pyroptosis and MLKL-mediated necroptosis. Biochem Pharmacol. 2022 Dec;206:115338.|[3]Zhou XY, et al. The brain protection of MLKL inhibitor necrosulfonamide against focal ischemia/reperfusion injury associating with blocking the nucleus and nuclear envelope translocation of MLKL and RIP3K. Front Pharmacol. 2023 Oct 24;14:1157054. |[4]Zhang J, Wei K. Necrosulfonamide reverses pyroptosis-induced inhibition of proliferation and differentiation of osteoblasts through the NLRP3/caspase-1/GSDMD pathway. Exp Cell Res. 2021 Aug 15;405 (2) :112648. |[5]Liu Y, et al. Necrosulfonamide promotes hair growth and ameliorates DHT-induced hair growth inhibition. J Dermatol Sci. 2024 Aug;115 (2) :64-74.|[6]Wu YL, et al. Gasdermin D Inhibitor Necrosulfonamide Alleviates Lipopolysaccharide/D-galactosamine-induced Acute Liver Failure in Mice. J Clin Transl Hepatol. 2022 Dec 28;10 (6) :1148-1154. |[7]Kim DY, Leem YH, Kim HS. MLKL Inhibitor Reduces Oxidative Stress, Inflammation, and Dopaminergic Neuronal Cell Death in MPTP-Induced Parkinson's Disease Mouse Model. Biomol Ther (Seoul) . 2025 May 1;33 (3) :429-437.
Shipping Conditions
Room Temperature
Storage Conditions
-20°C, 3 years; 4°C, 2 years (Powder)
Scientific Category
Reference compound1
Clinical Information
No Development Reported
Isoform
Caspase 1; HO-1; IL-1; IL-6; iNOS; NLRP3

Chemical Information

Necrosulfonamide

Necrosulfonamide is a sulfonamide that is a 3-methoxypyrazin-2-yl derivative of (E)-N-(4-(N-(4,6-dimethylpyrimidin-2-yl)sulfamoyl)phenyl)-3-(5-nitrothiophene-2-yl)acrylamide. Necrosulfonamide specifically blocks necrosis downstream of the activation of RIP3 (the receptor-interacting serine-threonine kinase 3), a key signalling molecule in the programmed necrosis (necroptosis) pathway. It has a role as a necroptosis inhibitor and a neuroprotective agent. It is a member of thiophenes, a sulfonamide and a member of pyrazines.

CAS Number1360614-48-7
PubChem CID1566236
IUPAC Name(E)-N-[4-[(3-methoxypyrazin-2-yl)sulfamoyl]phenyl]-3-(5-nitrothiophen-2-yl)prop-2-enamide
Molecular FormulaC18H15N5O6S2
Molecular Weight461.5
XLogP2.5
Topological Polar Surface Area193
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count10
Rotatable Bond Count7
Heavy Atom Count31
Formal Charge0
Complexity760
SMILES
COC1=NC=CN=C1NS(=O)(=O)C2=CC=C(C=C2)NC(=O)/C=C/C3=CC=C(S3)[N+](=O)[O-]
InChI
InChI=1S/C18H15N5O6S2/c1-29-18-17(19-10-11-20-18)22-31(27,28)14-6-2-12(3-7-14)21-15(24)8-4-13-5-9-16(30-13)23(25)26/h2-11H,1H3,(H,19,22)(H,21,24)/b8-4+
InChIKey
FNPPHVLYVGMZMZ-XBXARRHUSA-N
Chemical Structure
2D Structure
2D structure of Necrosulfonamide
CAS: 1360614-48-7
CID: 1566236
Formula: C18H15N5O6S2
MW: 461.5
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight461.5
XLogP32.5
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count10
Rotatable Bond Count7
Exact Mass461.04637556
Monoisotopic Mass461.04637556
Topological Polar Surface Area193 Ų
Heavy Atom Count31
Formal Charge0
Complexity760
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count1
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

Alternative Products

CatalogName
B7731-10Necrosulfonamide

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