| Identification | Back Directory | [Name]
OLTIPRAZ | [CAS]
64224-21-1 | [Synonyms]
OLTIPRAZ
RP-35972
CCRIS 4048
NSC 347901
BRN 0978110
OLTIPRAZ USP/EP/BP
Oltipraz (RP 35972
Oltipraz (NSC-347901)
4-methyl-5-pyrazin-2-yldithiole-3-thione
4-methyl-5-pyrazin-2-yl-dithiole-3-thione
4-methyl-5-pyrazinyl-3h-2-dithiole-3-thione
4-methyl-5-pyrazinyl-3h-1,2-dithiole-3-thione
4-methyl-5-pyrazin-2-yl-1,2-dithiole-3-thione
4-Methyl-5-(2-pyrazinyl)-1,2-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
3H-1,2-Dithiole-3-thione,4-methyl-5-(2-pyrazinyl)- | [EINECS(EC#)]
264-736-6 | [Molecular Formula]
C8H6N2S3 | [MDL Number]
MFCD00868499 | [MOL File]
64224-21-1.mol | [Molecular Weight]
226.34 |
| Chemical Properties | Back Directory | [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 | [form ]
Solid | [pka]
0.18±0.10(Predicted) | [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 |
| Hazard Information | Back Directory | [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]
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. | [Enzyme inhibitor]
This schistosomicide (FW = 226.35 g/mol; CAS 64224-21-1), also known
as 5- (2-pyrazinyl) -4-methyl-1,2-dithiole-3-thione, is used to treat disease
caused by parasitic flatworms and is also a potent cancer chemopreventive
agent. Oltipraz was found to protect against chemically induced carcinogens
within the lung, stomach, colon, and urinary bladder. The anti-HIV activity
of the pharmaceutical is believed to be due to its ability to irreversibly
inhibit HIV reverse transcriptase. Target (s) : CYP1A2 (1-3); CYP3A4;
HIV I reverse transcriptase; RNA-directed DNA polymerase. 1.
Sofowora, Choo, Mayo, Shyr & Wilkinson Cancer Chemother.
Pharmaco | [storage]
Store at -20°C | [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 |
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