Oltipraz

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Oltipraz
Clinical data
ATC code
  • none
Identifiers
  • 4-methyl-5-(2-pyrazinyl)-3-dithiolethione
CAS Number
PubChem CID
ChemSpider
UNII
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.058.833 Edit this at Wikidata
Chemical and physical data
FormulaC8H6N2S3
Molar mass226.33 g·mol−1
3D model (JSmol)
  • CC1=C(SSC1=S)C2=NC=CN=C2
  • 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
 ☒NcheckY (what is this?)  (verify)

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 radicals, 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". Toxicology Letters. 185 (3): 180–186. doi:10.1016/j.toxlet.2008.12.014. PMC 2676710. PMID 19150646.
  2. ^ Ansari MI, Khan MM, Saquib M, Khatoon S, Hussain MK (May 2018). "Dithiolethiones: a privileged pharmacophore for anticancer therapy and chemoprevention". Future Medicinal Chemistry. 10 (10): 1241–1260. doi:10.4155/fmc-2017-0281. PMID 29749746.
  3. ^ a b Zhang Y, Gordon GB (July 2004). "A strategy for cancer prevention: stimulation of the Nrf2-ARE signaling pathway". Molecular Cancer Therapeutics. 3 (7): 885–893. doi:10.1158/1535-7163.885.3.7. PMID 15252150.
  4. ^ Iida K, Itoh K, Kumagai Y, Oyasu R, Hattori K, Kawai K, et al. (September 2004). "Nrf2 is essential for the chemopreventive efficacy of oltipraz against urinary bladder carcinogenesis". Cancer Research. 64 (18): 6424–6431. 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". Archives of Biochemistry and Biophysics. 435 (1): 83–88. doi:10.1016/j.abb.2004.11.028. PMID 15680910.
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