Oltipraz

Oltipraz

Systematic (IUPAC) name
4-methyl-5-(2-pyrazinyl)-3-dithiolethione
Identifiers
CAS Number	64224-21-1
ATC code	None
PubChem	CID 47318
ChemSpider	43066
UNII	6N510JUL1Y
ChEBI	CHEBI:77319
ChEMBL	CHEMBL178459
Chemical data
Formula	C8H6N2S3
Molar mass	226.34 g/mol
SMILES CC1=C(SSC1=S)C2=NC=CN=C2
InChI InChI=1S/C8H6N2S3/c1-5-7(12-13-8(5)11)6-4-9-2-3-10-6/h2-4H,1H3 Key:CKNAQFVBEHDJQV-UHFFFAOYSA-N
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Oltipraz is an organosulfur compound belonging to the dithiolethione class.^[1] It acts as a schistosomicide and has been shown in rodent models to inhibit the formation of cancers in the bladder, blood, colon, kidney, liver, lung, pancreas, stomach, and trachea, skin, and mammary tissue.^[2][3] Clinical trials of oltipraz have failed to demonstrate efficacy and have shown significant side effects, including neurotoxicity and gastrointestinal toxicity.^[2] Oltipraz has also been shown to generate superoxide radical, which can be toxic.^[4]

References

1. Prince M, Li Y, Childers A, Itoh K, Yamamoto M, Kleiner HE (March 2009). "Comparison of citrus coumarins on carcinogen-detoxifying enzymes in Nrf2 knockout mice". Toxicol. Lett. 185 (3): 180–6. doi:10.1016/j.toxlet.2008.12.014. PMC 2676710. PMID 19150646.
2. Zhang Y, Gordon GB (July 2004). "A strategy for cancer prevention: stimulation of the Nrf2-ARE signaling pathway". Mol. Cancer Ther. 3 (7): 885–93. PMID 15252150.
3. Iida K, Itoh K, Kumagai Y, et al. (September 2004). "Nrf2 is essential for the chemopreventive efficacy of oltipraz against urinary bladder carcinogenesis". Cancer Res. 64 (18): 6424–31. doi:10.1158/0008-5472.CAN-04-1906. PMID 15374950.
4. Velayutham M, Villamena FA, Fishbein JC, Zweier JL (March 2005). "Cancer chemopreventive oltipraz generates superoxide anion radical". Arch. Biochem. Biophys. 435 (1): 83–8. doi:10.1016/j.abb.2004.11.028. PMID 15680910.