| Identification | Back Directory | [Name]
Ferrostatin-1 (Fer-1) | [CAS]
347174-05-4 | [Synonyms]
Fer1
Fer-1
Fer 1
3-amino-4-(cycL
Ferrostatin-1 (Fer-1)
Ferrostatin-1 (Fer-1) USP/EP/BP
Ethyl 3-amino-4-(cyclohexylamino)benzoate
3-Amino-4-cyclohexylaminobenzoic acid ethyl ester
Benzoic acid, 3-amino-4-(cyclohexylamino)-, ethyl ester
FER-1;FER 1;FER1;FERROSTATIN-1;FERROSTATIN 1;FERROSTATIN1
(Ferrostatin-1 (Fer-1))3-Amino-4-cyclohexylamino benzoic acid ethyl ester | [Molecular Formula]
C15H22N2O2 | [MDL Number]
MFCD08072959 | [MOL File]
347174-05-4.mol | [Molecular Weight]
262.347 |
| Chemical Properties | Back Directory | [Boiling point ]
437.3±35.0 °C(Predicted) | [density ]
1.150±0.06 g/cm3(Predicted) | [storage temp. ]
2-8°C | [solubility ]
DMSO: soluble10mg/mL, clear | [form ]
powder | [pka]
4.78±0.11(Predicted) | [color ]
purple to brown | [Stability:]
Stable for 2 years from date of purchase as supplied. Solutions in DMSO or ethanol may be stored at -20° for up to 1 month. | [InChI]
InChI=1S/C15H22N2O2/c1-2-19-15(18)11-8-9-14(13(16)10-11)17-12-6-4-3-5-7-12/h8-10,12,17H,2-7,16H2,1H3 | [InChIKey]
UJHBVMHOBZBWMX-UHFFFAOYSA-N | [SMILES]
C(OCC)(=O)C1=CC=C(NC2CCCCC2)C(N)=C1 |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
36/37/38 | [Safety Statements ]
26 | [WGK Germany ]
3 | [HazardClass ]
IRRITANT | [HS Code ]
2922498590 | [Storage Class]
11 - Combustible Solids | [Hazard Classifications]
Eye Irrit. 2
Skin Irrit. 2
STOT SE 3 |
| Hazard Information | Back Directory | [Description]
Ferrostatin-1 (347174-05-4) inhibits ferroptosis (EC50=60 nM), an iron-dependent form of nonapoptotic cell death.1?Potent inhibitor of ferroptosis in cancer cells and glutamate-induced cell death in organotypic rat brain slices.1?Blocks the cytotoxic effects of sorafenib in hepatocellular carcinoma cells.2?Ferrostatin-1 inhibits oxidative lipid damage and cell death in diverse disease models3 and prevents apoptosis of renal proximal tubular cells induced by reactive oxygen species4. | [Uses]
Ferrostatin-1 (Fer-1) is a potent and selective inhibitor of ferroptosis. | [Definition]
ChEBI: Ferrostatin-1 is an ethyl ester resulting from the formal condensation of the carboxy group of 3-amino-4-(cyclohexylamino)benzoic acid with ethanol. It is a potent inhibitor of ferroptosis, a distinct non-apoptotic form of cell death caused by lipid peroxidation. It is also a radical-trapping antioxidant and has the ability to reduce the accumulation of lipid peroxides and chain-carrying peroxyl radicals. It has a role as a ferroptosis inhibitor, a radiation protective agent, an antioxidant, a radical scavenger, an antifungal agent and a neuroprotective agent. It is a substituted aniline, an ethyl ester and a primary arylamine. | [Biochem/physiol Actions]
Ferrostatin-1 is an active radical-trapping antioxidant that traps peroxyl radicals, and thus serves as a potential inhibitor of ferroptosis. Ferroptosis is considered as regulated necrosis, which differs from apoptosis and autophagy. Ferrostatin-1 is known to show protective effects against Huntington′s disease and also prevents neurotoxicity induced by glutamate in cellular models. | [Synthesis]
General procedure for the synthesis of ethyl 3-amino-4-(cyclohexylamino)benzoate from ethyl 4-(cyclohexylamino)-3-nitrobenzoate: the nitro derivative (24.28 g, 83 mmol) was dissolved in methanol (150 mL) and 20% Pd(OH)2/carbon catalyst (200 mg) was added. The hydrogenation reaction was carried out under hydrogen atmosphere at 1 atmosphere for 3 days. Upon completion of the reaction, the catalyst was removed by filtration followed by evaporation of the solvent under reduced pressure to afford the target product ethyl 3-amino-4-(cyclohexylamino)benzoate (21.72 g, 100% yield) as a dark purple solid. | [storage]
4°C, protect from light | [References]
1) Dixon et al. (2012), Ferroptosis: an iron-dependent form of nonapoptotic cell death; Cell, 149 1060
2) Louandre et al. (2013), Iron-dependent cell death of hepatocellular carcinoma cells exposed to sorafenib; Int. J. Cancer, 133 1732
3) Skouta et al. (2014), Ferrostatins inhibit oxidative lipid damage and cell death in diverse disease models; J. Am. Chem. Soc., 136 4551
4) Nowak et al. (2013), Protein kinase C-α interaction with iHSP70 in mitochondria promotes recovery of mitochondrial function after injury in renal proximal tubular cells; Am. J. Physiol. Renal. Physiol., 305 F764 |
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Energy Chemical
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| Telephone: |
400-0056266 |
| Website: |
www.energy-chemical.com |
| Company Name: |
Sigma-Aldrich
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021-61415566 800-8193336 |
| Website: |
https://www.sigmaaldrich.cn |
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