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| OLTIPRAZ Basic information |
| Product Name: | OLTIPRAZ | | Synonyms: | NSC 347901;3H-1,2-Dithiole-3-thione,4-methyl-5-(2-pyrazinyl)-;OLTIPRAZ;4-methyl-5-pyrazinyl-3h-1,2-dithiole-3-thione;4-methyl-5-pyrazinyl-3h-2-dithiole-3-thione;5-(2-pyrazinyl)-4-methyl-1,2-dithiole-3-thione;4-Methyl-5-(2-pyrazinyl)-3H-1,2-dithiole-3-thione;4-Methyl-5-(pyrazin-2-yl)-3H-1,2-dithiole-3-thione | | CAS: | 64224-21-1 | | MF: | C8H6N2S3 | | MW: | 226.34 | | EINECS: | 264-736-6 | | Product Categories: | | Mol File: | 64224-21-1.mol |
| OLTIPRAZ Chemical Properties |
| Melting point | 165-166 | | Boiling point | 408.1±55.0 °C(Predicted) | | density | 1.51±0.1 g/cm3(Predicted) | | RTECS | JP1293000 | | storage temp. | 2-8°C | | solubility | DMSO: >20mg/mL | | pka | 0.18±0.10(Predicted) | | form | Solid | | color | red | | Sensitive | Light Sensitive | | Stability: | Stable for 2 years from date of purchase as supplied. Solutions in DMSO may be stored at -20° for up to 1 month. | | InChIKey | CKNAQFVBEHDJQV-UHFFFAOYSA-N |
| OLTIPRAZ Usage And Synthesis |
| Description | Oltipraz (64224-21-1) upregulates the transcription factor NRF2 and prevents insulin resistance and obesity induced by high fat diet in C57BL/6J mice.1 Attenuates the progression of fibrosis in a rat model of nonalcoholic steatohepatitis.2 Oltipaz attenuates chronic hypoxia-induced cardiopulmonary alterations in mice.3 Promotes liver regeneration after partial hepatectomy.4 Off target effects: Activates constitutive androstane receptor (CAR).5 | | Chemical Properties | Dark Red Solid | | Uses | Oltipraz is a synthetic, substituted 1,2-dithiole-3-thione previously used in humans as an antischistosomal agent. Animal studies have demonstrated that oltipraz is a potent inducer of Phase II detoxi
fication enzymes, most notably glutathione-S-transferase (GST). Oltipraz is now known to be used for tumor prevention purposes. | | Uses | Oltipraz is a synthetic, substituted 1,2-dithiole-3-thione previously used in humans as an antischistosomal agent. Animal studies have demonstrated that oltipraz is a potent inducer of Phase II detoxification enzymes, most notably glutathione-S-transferase (GST). Oltipraz is now known to be used for tumor prevention purposes. | | Uses | schistosomicide, antineoplastic | | Definition | ChEBI: A 1,2-dithiole that is 3H-1,2-dithiole-3-thione substituted at positions 4 and 5 by methyl and pyrazin-2-yl groups respectively. | | General Description | Oltipraz, a dithiol derivative, is a member of dithiolethiones class of organosulfur compounds. It has anti-tumor, antioxidative, anti- inflammatory and radioprotective properties. It provides protection from numerous carcinogens. Oltipraz functions as a schistosomicide. | | Biochem/physiol Actions | Oltipraz is an activator of Nrf2. Nrf2 (NF-E2-related factor 2) is a transcription factor that binds to antioxidant response elements (AREs) and activates these genes. Oltipraz activates Nrf2 and subsequently elevates expression of the detoxification genes encoding anti-oxidant and multidrug resistance-associated proteins to mediate its chemopreventive efficacy. | | References | 1) Yu?et al. (2011),?Oltipraz upregulates the nuclear factor (erythroid-derived 2)-like 2 (NRF2) antioxidant system and prevents insulin resistance and obesity induced by a high-fat diet in C57BL/6J mice; Diabetologia,?54?922
2) Shimozono?et al. (2013),?Nrf2 activators attenuate the progression of nonalcoholic steatohepatitis-related fibrosis in a dietary rat model; Mol. Pharmacol,?84?62
3) Eba?et al. (2013),?The nuclear factor erythroid 2-related factor 2 activator oltipraz attenuates chronic hypoxia-induced cardiopulmonary alterations in mice; Am. J. Respir. Cell. Mol. Biol.,?49?324
4) Cho?et al. (2009), Oltipraz promotion of liver regeneration after partial hepatectomy: the role of PI3-kinase dependent C/EBPbeta and cyclin E regulation; Arch. Pharm. Res.,?32?625
5) Merrell?et al. (2008),?The Nrf2 activator oltipraz also activates the constitutive androstane receptor; Drug Metab. Dispos.,?36?1716 |
| OLTIPRAZ Preparation Products And Raw materials |
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