Oltipraz

Oltipraz
Clinical data
ATC code
  • none
Identifiers
IUPAC name
  • 4-methyl-5-(2-pyrazinyl)-3-dithiolethione
CAS Number
PubChem CID
ChemSpider
UNII
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.058.833
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Chemical and physical data
FormulaC8H6N2S3
Molar mass226.33 g·mol−1
3D model (JSmol)
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 ☒N
  • Key:CKNAQFVBEHDJQV-UHFFFAOYSA-N ☒N
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Oltipraz is an organosulfur compound belonging to the dithiolethione class.[1][2] 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.[3][4] Clinical trials of oltipraz have failed to demonstrate efficacy and have shown significant side effects, including neurotoxicity and gastrointestinal toxicity.[3] Oltipraz has also been shown to generate superoxide radical, which can be toxic.[5]

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. ↑ Ansari, Mohd Imran; Khan, Mohd M.; Saquib, Mohammad; Khatoon, Shahnaaz; Hussain, Mohd Kamil (2018-05-01). "Dithiolethiones: a privileged pharmacophore for anticancer therapy and chemoprevention". Future Medicinal Chemistry. 10 (10): 1241–1260. doi:10.4155/fmc-2017-0281. ISSN 1756-8927. PMID 29749746.
  3. 1 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.
  4. ↑ 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.
  5. ↑ 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.


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