Imd-0354
IMD 0354 ，S2864 · IMD 0354 · IMD-0354 · IMD-0354 USP/EP/BP · IMD-0354, 10 mM in DMSO · IMD 0354, IKKbeta inhibitor · IKK-2 INHIBITOR V · IMD0354
Identifiers & Physical Properties
| CAS No. | 978-62-1 |
|---|---|
| Molecular formula | C15H8ClF6NO2 |
| Average molar mass | 383.67 g/mol |
| Monoisotopic mass | 383.0147752 g/mol |
| SMILES | O=C(Nc1cc(C(F)(F)F)cc(C(F)(F)F)c1)c1cc(Cl)ccc1O |
| InChIKey | CHILCFMQWMQVAL-UHFFFAOYSA-N |
| PubChem CID | 5081913 |
| ChEMBL | CHEMBL536151 |
| ChEBI | CHEBI:93310 |
| EC No. | 635-542-2 |
| DTXSID | DTXSID50243248 |
Chemical & Physical Properties
| XLogP | 6.2 |
|---|---|
| Topological polar surface area | 49.3 |
| Hydrogen bond donors | 2 |
| Hydrogen bond acceptors | 8 |
| Rotatable bonds | 2 |
| Heavy atoms | 25 |
| Formal charge | 0 |
| Complexity | 462 |
| Boiling point | 323.1±42.0 °C(Predicted) |
| Density | 1.561 |
| Storage conditions | -20°C |
| Solubility | DMSO (5 mg/ml) or Ethanol (1 mg/ml). |
| pKa (acidity coefficient) | 7.61±0.43(Predicted) |
| Physical state | White solid |
| Color | White to off-white |
| Sensitivity | Light Sensitive |
| InChI | 1S/C15H8ClF6NO2/c16-9-1-2-12(24)11(6-9)13(25)23-10-4-7(14(17,18)19)3-8(5-10)15(20,21)22/h1-6,24H,(H,23,25) |
| InChIKey | CHILCFMQWMQVAL-UHFFFAOYSA-N |
| SMILES | Oc1ccc(Cl)cc1C(=O)Nc2cc(cc(c2)C(F)(F)F)C(F)(F)F |
| CAS DataBase Reference | 978-62-1 |
| FDA UNII | 76145IS906 |
| UNSPSC Code | 12352200 |
| NACRES | NA.77 |
| GHS pictogram | GHS07 |
| Signal word | Warning |
| GHS hazard statements | H315-H319-H335 |
| GHS precautionary statements | P261-P280a-P304+P340-P305+P351+P338-P405-P501a |
| Personal protective equipment (PPE) | dust mask type N95 (US), Eyeshields, Gloves |
| Hazard symbols | Xi |
| Risk statements (R) | 36/37/38 |
| Safety statements (S) | 26-36 |
| Water hazard class (WGK) | 3 |
| Customs code | 29242990 |
| Storage class | 11 - Combustible Solids |
Safety & Regulations
| GHS classification | WarningH315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]H319 (100%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]H335 (100%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposureRespiratory tract irritation]P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 38 reports by companies from 1 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website. |
|---|---|
| Hazard Classes and Categories | Skin Irrit. 2 (100%)Eye Irrit. 2 (100%)STOT SE 3 (100%) |
| Personal protective equipment (PPE) | dust mask type N95 (US), Eyeshields, Gloves |
| Water hazard class (WGK) | 3 |
| Customs code | 29242990 |
| Risk statements (R) | 36/37/38 |
| Signal word | Warning |
| GHS pictogram | GHS07 |
| Hazard symbols | Xi |
| Safety statements (S) | 26-36 |
| Storage class | 11 - Combustible Solids |
| GHS hazard statements | H315-H319-H335 |
| GHS precautionary statements | P261-P280a-P304+P340-P305+P351+P338-P405-P501a |
Applications & Uses
Uses
IMD 0354 is an IKKβ (IKK2) inhibitor that blocks NF-κB phosphorylation (IC50 = ~250 nM) and subsequent NF-κB p65 nuclear translocation. It exhibits cardioprotective properties by decreasing expression of P-selectin and ICAM-1 in the vasculature and blocking cardiomyocyte IL-1β and MCP-1 production, resulting in suppressed neutrophil accumulation in a rat model of ischemia/reperfusion injury. IMD 0354, suppresses the growth of human breast cancer cells by inducing cell cycle arrest and apoptosis. It induces apoptosis of chronic lymphocytic leukemia cells at 1-10 μM by directly targeting the NF-κB pathway, decreasing expression of anti-apoptotic genes and increasing expression of proapoptotic genes.
Uses
IMD-0354 has been used to study the effect of NF-κB (nuclear factor) inhibition on differentially expressed in chondrocytes 2. It has also been used to study the role of NF-κB signaling in tumor necrosis factor-induced certain transcription factors expression using human primary fibroblasts.