Oltipraz

Oltipraz
Clinical data
ATC code	none;
Identifiers
	IUPAC name 4-methyl-5-(2-pyrazinyl)-3-dithiolethione;
CAS Number	64224-21-1 ;
PubChem CID	47318;
ChemSpider	43066 ;
UNII	6N510JUL1Y;
ChEBI	CHEBI:77319 ;
ChEMBL	ChEMBL178459 ;
CompTox Dashboard (EPA)	DTXSID7021079 ;
ECHA InfoCard	100.058.833
Chemical and physical data
Formula	C8H6N2S3
Molar mass	226.33 g·mol−1
3D model (JSmol)	Interactive image;
	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]^[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

^ 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.
^ 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.
^ ^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.
^ 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.
^ 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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[pmid19150646-1] 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.

[pmid15252150-3] 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.

[pmid15374950-4] 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.

[pmid15680910-5] 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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Clinical data

ATC code	none
Identifiers
IUPAC name 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 InfoCard	100.058.833
Chemical and physical data
Formula	C₈H₆N₂S₃
Molar mass	226.33 g·mol⁻¹
3D model (JSmol)	Interactive image
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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