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Oltipraz

January 24, 2023

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]

Oltipraz
Clinical data
ATC code
  • none
Identifiers
  • 4-methyl-5-(2-pyrazinyl)-3-dithiolethione
CAS Number
  • 64224-21-1 Y
PubChem CID
  • 47318
ChemSpider
  • 43066 N
UNII
  • 6N510JUL1Y
ChEBI
  • CHEBI:77319 N
ChEMBL
  • ChEMBL178459 N
CompTox Dashboard (EPA)
  • DTXSID7021079
ECHA InfoCard100.058.833
Chemical and physical data
FormulaC8H6N2S3
Molar mass226.33 g·mol−1
3D model (JSmol)
  • Interactive image
  • 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
 NY (what is this?)  (verify)

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. ^ a b 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. doi:10.1158/1535-7163.885.3.7. 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.


 

This antiinfective drug article is a stub. You can help Wikipedia by expanding it.

January 24, 2023
oltipraz, organosulfur, compound, belonging, dithiolethione, class, acts, schistosomicide, been, shown, rodent, models, inhibit, formation, cancers, bladder, blood, colon, kidney, liver, lung, pancreas, stomach, trachea, skin, mammary, tissue, clinical, trials. 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 OltiprazClinical dataATC codenoneIdentifiersIUPAC name 4 methyl 5 2 pyrazinyl 3 dithiolethioneCAS Number64224 21 1 YPubChem CID47318ChemSpider43066 NUNII6N510JUL1YChEBICHEBI 77319 NChEMBLChEMBL178459 NCompTox Dashboard EPA DTXSID7021079ECHA InfoCard100 058 833Chemical and physical dataFormulaC 8H 6N 2S 3Molar mass226 33 g mol 13D model JSmol Interactive imageSMILES CC1 C SSC1 S C2 NC CN C2InChI InChI 1S C8H6N2S3 c1 5 7 12 13 8 5 11 6 4 9 2 3 10 6 h2 4H 1H3 NKey CKNAQFVBEHDJQV UHFFFAOYSA N N N Y what is this verify References Edit 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 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 a b 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 doi 10 1158 1535 7163 885 3 7 PMID 15252150 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 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 This antiinfective drug article is a stub You can help Wikipedia by expanding it vte Retrieved from https en wikipedia org w index php title Oltipraz amp oldid 1133099781, wikipedia, wiki, book, books, library,

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