CAS 19983-44-9 Stattic (HCID 2779853)

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Basic information

CAS: 19983-44-9
Standard SMILES: O=[N+]([O-])c1ccc2c(c1)S(=O)(=O)C=C2
InChIKey: ZRRGOUHITGRLBA-UHFFFAOYSA-N
Molecular formula: C8H5NO4S
Average molar mass: 211.2 g/mol
Monoisotopic mass: 210.99392864

Overview

Stattic is a member of the class of 1-benzothiophenes that is 1-benzothiophene-1,1-dioxide substituted at position 6 by a nitro group. Used as a radiosensitising agent for esophageal squamous cell carcinoma. It has a role as a radiosensitizing agent, an antineoplastic agent and a STAT3 inhibitor. It is a C-nitro compound, a sulfone and a member of 1-benzothiophenes.

Names & identifiers

Preferred name: Stattic
IUPAC: 6-nitro-1-benzothiophene 1,1-dioxide
English name: Stattic
Molecular formula: C8H5NO4S
Molecular weight: 211.19

Names & synonyms

Stattic19983-44-9CHEBI:86989RefChem:1853806-Nitrobenzo[b]thiophene 1,1-dioxide6-nitro-1-benzothiophene 1,1-dioxideBenzo[b]thiophene, 6-nitro-, 1,1-dioxide6-nitro-16-Nitrobenzo[b]thiophene-1,1-dioxideC8H5NO4SMFCD001737991,1-DIOXIDE-6-NITRO-BENZO[B]THIOPHENE

Show more names

CS-1523AKOS 100115-Methyl-PGF2αBUTTPARK 97\04-73STAT3 Inhibitor VStattic USP/EP/BPStattic, 10 mM in DMSOStattic, STAT3 inhibitorStat3 inhibitor V, stattic

CHEMBL1337170Maybridge1_0051486-nitro-1lambda6-benzothiophene-1,1-dioneHMS556B22DTXSID70381575HMS3263A18CCG-222352CS-5879

Database identifiers

CAS: 19983-44-9
PubChem CID: 2779853
DTXSID: DTXSID70381575
ChEMBL

Properties

Computed structural properties

XLogP: 0.7
Topological polar surface area: 88.3 Å²
Hydrogen bond donors: 0
Hydrogen bond acceptors: 4
Rotatable bonds: 0
Heavy atoms: 14
Formal charge: 0
Complexity: 375

Physicochemical properties

Melting point: 187 · 187-188 °C
Boiling point: 461.1 · 461.1±45.0 °C(Predicted)
Density: 1.621 · 1.621±0.06 g/cm3(Predicted)
storage temp.: 2 · Sealed in dry,2-8°C
solubility: 20 mg/mL · DMSO: >20mg/mL
form: powder
color: white to beige
Stability: 2 years · Stable for 2 years from date of purchase as supplied. Solutions in DMSO or ethanol may be stored at -20° for up to 3 months.
InChI: InChI=1S/C8H5NO4S/c10-9(11)7-2-1-6-3-4-14(12,13)8(6)5-7/h1-5H
InChIKey: ZRRGOUHITGRLBA-UHFFFAOYSA-N
SMILES: C12=CC([N+]([O-])=O)=CC=C1C=CS2(=O)=O
UNSPSC Code: 12352200 · 12352200
NACRES: 77 · NA.77
Symbol(GHS): 7 · GHS07
Signal word: Warning

Safety & regulation

GHS classification

GHS Classification · 4 items

Warning

H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]

P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 40 reports by companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

Hazard Classes and CategoriesAcute Tox. 4 (100%)

Safety data

PPE: dust mask type N95 (US), Eyeshields, Gloves
wgk: 3
hs_code: 2934999090
risk_code: 20/21/22-36/37/38-22
Signal word: Warning
Symbol(GHS): GHS07
hazard_code: Xi,Xn
hazard_note: Irritant
safety_code: 26-36/37/39
Storage Class: 11 - Combustible Solids
target organs: Respiratory system
Hazard statements: H302-H315-H319-H335
Hazard Classifications: Acute Tox. 4 OralEye Irrit. 2Skin Irrit. 2STOT SE 3
Precautionary statements: P261-P264-P270-P301+P312-P302+P352-P305+P351+P338

Chemistry & industry

Applications · 3 items

DescriptionStattic (19983-44-9) is a STAT3 inhibitor that inhibits binding of tyrosine-phosphorylated peptides to STAT3 SH2 domain and inhibiting STAT3 activation, dimerization and nuclear translocation.1 Displays selectivity over STAT1, STAT5, c-Myc/Max, Jun/Jun and Lck. Induces apoptosis in STAT3-dependent cancer cell lines. Alkyates four cysteine residues on STAT3.2 Exhibits potent antitumor activity.3 Protects against angiotensin II-induced vascular dysfunction and hypertension.4Stattic is an extremely useful tool to probe involvement of STAT3 in cellular signaling.

UsesStattic is a Stat3 inhibitor which exhibited potent anti-tumor and induced chemo- and radio-sensitivity in nasopharyngeal carcinoma.

UsesStattic was used to study Stat3-mediated cell signaling in human lung carcinoma cells.5