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| | 2-[1-[4-[2-(4-Chlorophenoxy)acetyl]-1-piperazinyl]ethyl]-3-(2-ethoxyphenyl)-4(3H)-Quinazolinone Basic information |
| Product Name: | 2-[1-[4-[2-(4-Chlorophenoxy)acetyl]-1-piperazinyl]ethyl]-3-(2-ethoxyphenyl)-4(3H)-Quinazolinone | | Synonyms: | 2-[1-[4-[2-(4-Chlorophenoxy)acetyl]-1-piperazinyl]ethyl]-3-(2-ethoxyphenyl)-4(3H)-Quinazolinone;4(3H)-Quinazolinone, 2-[1-[4-[2-(4-chlorophenoxy)acetyl]-1-piperazinyl]ethyl]-3-(2-ethoxyphenyl)-;2-[1-[4-[2-(4-Chlorophenoxy)acetyl]-1-piperazinyl]ethyl]-3-(2-ethoxyphenyl)-4(3H)-quinazolinone Erastin;Erastin;CS-1430;Erastin - CAS 571203-78-6 - Calbiochem;2-(1-(4-(2-(4-Chlorophenoxy)acetyl)piperazin-1-yl)ethyl)-3-(2-ethoxyphenyl)quinazolin-4(3H)-on;2-(1-(4-(2-(4-Chlorophenoxy)acetyl)piperazin-1-yl)ethyl)-3-(2-ethoxyphenyl)quinazolin-4(3H)-one | | CAS: | 571203-78-6 | | MF: | C30H31ClN4O4 | | MW: | 547.04 | | EINECS: | | | Product Categories: | API;Inhibitors | | Mol File: | 571203-78-6.mol | ![2-[1-[4-[2-(4-Chlorophenoxy)acetyl]-1-piperazinyl]ethyl]-3-(2-ethoxyphenyl)-4(3H)-Quinazolinone Structure](CAS/GIF/571203-78-6.gif) |
| | 2-[1-[4-[2-(4-Chlorophenoxy)acetyl]-1-piperazinyl]ethyl]-3-(2-ethoxyphenyl)-4(3H)-Quinazolinone Chemical Properties |
| Boiling point | 721.9±70.0 °C(Predicted) | | density | 1.28±0.1 g/cm3(Predicted) | | storage temp. | -20°C | | solubility | DMSO: soluble5mg/mL, clear (warmed) | | form | White solid | | pka | 5.54±0.10(Predicted) | | color | white to beige | | Stability: | Stable for 1 year from date of purchase as supplied. Solutions in DMSO may be stored at -20°C for up to 3 months. | | CAS DataBase Reference | 571203-78-6 |
| Hazard Codes | T | | Risk Statements | 25 | | Safety Statements | 45 | | RIDADR | UN 2811 6.1/PG 3 | | WGK Germany | 3 | | HS Code | 2933599590 |
| | 2-[1-[4-[2-(4-Chlorophenoxy)acetyl]-1-piperazinyl]ethyl]-3-(2-ethoxyphenyl)-4(3H)-Quinazolinone Usage And Synthesis |
| Description | Erastin, named for eradicator of RAS and small T (ST) antigen-expressing cells, is a ferroptosis inducer. It induces ferroptotic cell death in vitro, an effect that can be blocked by the ferroptosis inhibitors ciclopirox olamine, Trolox , ferrostatin-1 , U-0126 , cycloheximide , and β-mercaptoethanol. Erastin (5 μM) inhibits cystine uptake by the system xc- cystine-glutamate transporter in HT-1080 fibrosarcoma and Calu-1 lung carcinoma cells and inhibits glutamate release in an enzyme-coupled fluorescence assay (EC50 = 1.2 μM). It also selectively induces cell death in cells expressing the SV40 small T oncoprotein and oncogenic Ras (IC50s = 1.25-5 μg/ml). | | Uses | Erastin has been used:
- as a positive control for inducing ferroptosis in hepatic stellate cell (HSC)
- to induce ferroptosis and in transferrin internalization assay of human fibrosarcoma HT1080 cells
- to induce ferroptosis of muscle-derived cell lines
| | Uses | Erastin, named for eradicator of RAS and ST-expressing cells, is an irreversible antitumor agent that selectively kills cells expressing the small T oncoprotein and oncogenic Ras (IC50s = 1.25-5 μg/ml). It produces non-apoptotic tumor cell death by altering mitochondrial voltage-dependent anion channel gating, allowing cations to enter mitochondria and leading to release of oxidative species causing oxidative cell death.[Cayman Chemical] | | Definition | ChEBI: Erastin is a member of the class of quinazolines that is quinazolin-4(3H)-one in which the hydrogens at positions 2 and 3 are replaced by 1-{4-[(4-chlorophenoxy)acetyl]piperazin-1-yl}ethyl and 2-ethoxyphenyl groups, respectively. It is an inhibitor of voltage-dependent anion-selective channels (VDAC2 and VDAC3) and a potent ferroptosis inducer. It has a role as a ferroptosis inducer, an antineoplastic agent and a voltage-dependent anion channel inhibitor. It is a member of quinazolines, a member of monochlorobenzenes, an aromatic ether, a N-acylpiperazine, a N-alkylpiperazine, a diether and a tertiary carboxamide. | | General Description | Erastin is a cell-permeable piperazinyl-quinazolinone. It interacts with antiporter system Xc-. | | Biochem/physiol Actions | Erastin is an antitumor agent selective for tumor cells bearing oncogenic RAS (i.e. HRAS, KRAS). Erastin produces ferroptosis, a non-apoptotic tumor cell death, by altering mitochondrial voltage-dependent anion channel (VDAC) gating allowing cations to enter mitochondria and leading to release of oxidative species causing oxidative cell death. | | storage | Store at -20°C | | References | 1) Dolma et al. (2003), Identification of genotype-selective antitumor agents using synthetic lethal chemical screening in engineered human tumor cells; Cancer Cell, 3 285
2) Dixon et al. (2014), Pharmacological inhibition of cysteine-glutamate exchange induces endoplasmic reticulum stress and ferroptosis; Elife, 3 e02523
3) Sato et al. (2018), The ferroptosis inducer erastin irreversibly inhibits system xc-and synergizes with cisplatin to increase cisplatin’s cytotoxicity in cancer cells; Sci. Rep., 8 968
4) Yagoda et al. (2007), RAS-RAF-MEK-dependent oxidative cell death involving voltage-dependent anion channels; Nature, 447 864 |
| | 2-[1-[4-[2-(4-Chlorophenoxy)acetyl]-1-piperazinyl]ethyl]-3-(2-ethoxyphenyl)-4(3H)-Quinazolinone Preparation Products And Raw materials |
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