| Identification | Back Directory | [Name]
Liproxstatin-1 | [CAS]
950455-15-9 | [Synonyms]
CS-1656
Liproxstatin-1
Liproxstatin-1 USP/EP/BP
LIPROXSTATIN-1;LIPROXSTATIN1
N-(3-Chlorobenzyl)-1'H-spiro[piperidine-4,2'-quinoxalin]-3'-amine
N-[(3-chlorophenyl)methyl]spiro[4H-quinoxaline-3,4'-piperidine]-2-amine
N-[(3-chlorophenyl)methyl]-spiro[piperidine-4,2'(1'H)-quinoxalin]-3'-amine
N-[(3-chlorophenyl)methyl]-1'H-spiro[piperidine-4,2'-quinoxaline]-3'-amine | [Molecular Formula]
C19H21ClN4 | [MDL Number]
MFCD14948691 | [MOL File]
950455-15-9.mol | [Molecular Weight]
340.85 |
| Chemical Properties | Back Directory | [Boiling point ]
581.4±50.0 °C(Predicted) | [density ]
1.32±0.1 g/cm3(Predicted) | [storage temp. ]
-20°C | [solubility ]
Soluble in DMSO (15 mg/ml) | [form ]
powder | [pka]
9.45±0.40(Predicted) | [color ]
white to light brown | [Stability:]
Stable for 1 year from date of purchase as supplied. Solutions in DMSO may be stored at -20°C for up to 2 month. | [InChI]
InChI=1S/C19H21ClN4/c20-15-5-3-4-14(12-15)13-22-18-19(8-10-21-11-9-19)24-17-7-2-1-6-16(17)23-18/h1-7,12,21,24H,8-11,13H2,(H,22,23) | [InChIKey]
YAFQFNOUYXZVPZ-UHFFFAOYSA-N | [SMILES]
N1CCC2(C(NCC3=CC=CC(Cl)=C3)=NC3=C(N2)C=CC=C3)CC1 |
| Hazard Information | Back Directory | [Description]
Liproxstatin-1 is a ferroptosis inhibitor.1 It inhibits ferroptotic cell death (IC50 = 22 nM) and lipid peroxidation in mouse embryonic fibroblasts (MEFs) with an inducible knockdown of glutathione peroxidase 4 (Gpx4-/- MEFs) when used at a concentration of 50 nM. Liproxstatin-1 also inhibits ferroptosis induced by the ferroptosis-inducing agents L-buthionine sulphoximine (BSO), erastin (Item No. 17754), and (1S,3R)-RSL3 (Item No. 19288) in a concentration-dependent manner in MEFs, but does not inhibit necroptosis, apoptosis, or necrosis. It inhibits cell death and lipid peroxidation induced by (1S,3R)-RSL3 in human renal proximal tubule epithelial cells. Liproxstatin-1 (10 mg/kg) increases survival and decreases TUNEL+ kidney cells in inducible Gpx4-/- mice and reduces tissue injury in a mouse model of hepatic ischemia/reperfusion injury. It is also an antioxidant that inhibits autooxidation of lipids by trapping peroxyl radicals.2 | [Uses]
Liproxstatin-1 has been used as a cell death inhibitor in the cell viability assay and for the determination of lipid peroxidation. | [Definition]
ChEBI: Liproxstatin-1 is an azaspiro compound that is 1'H-spiro[piperidine-4,2'-quinoxaline] in which the hydrogen at position 3' is replaced by a (3-chlorobenzyl)amino group. It is a potent inhibitor of ferroptosis. It has a role as a ferroptosis inhibitor, a radical scavenger, an antioxidant and a cardioprotective agent. It is a member of monochlorobenzenes, a secondary amino compound, an azaspiro compound and an organic heterotricyclic compound. | [Biochem/physiol Actions]
Liproxstatin-1 is a potent inhibitor of ferroptosis, a non-apoptotic form of cell death characterized by iron-dependent accumulation of lethal lipid reactive oxygen species (ROS). Liproxstatin-1 suppressed ferroptosis in human cells and in an ischaemia/reperfusion-induced tissue injury model in mice. Knockout of glutathione peroxidase 4 (Gpx4) Has been shown to cause cell death by ferroptosis. Liproxstatin-1 was able to suppress ferroptosis in Gpx4 knock-out mice. | [in vivo]
Liproxstatin-1 (10 mg/kg, i.p.) suppresses ferroptosis in human cells, Gpx4 / kidney and in an ischaemia/reperfusion-induced tissue injury model[1]. | [storage]
Store at -20°C | [References]
Angeli et al. (2014), Inactivation of the ferroptosis regulator Gpx4 triggers acute renal failure in mice; Nat. Chem. Biol. 16 1180
Feng et al. (2019), Liproxstatin-1 protects the mouse myocardium against ischemia/reperfusion injury by decreasing VDAC1 levels and restoring GPX4 levels; Biochem. Biophys. Res. Commun. 520 606
Zilka et al. (2017), On the mechanism of Cytoprotection by Ferrostatin-1 and Liproxstatin-1 and the Role of Lipid Peroxidation in Ferroptotic Cell Death; ACS Cent. Sci. 3 232 |
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