View source for Oltipraz

{{Short description|Chemical compound}}
{{Drugbox
| Verifiedfields = changed
| verifiedrevid = 449559107
| IUPAC_name = 4-methyl-5-(2-pyrazinyl)-3-dithiolethione
| image = Oltipraz.png
<!--Clinical data-->
| tradename =
| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X -->
| pregnancy_US = <!-- A / B            / C / D / X -->
| pregnancy_category =
| legal_AU = <!-- S2, S3, S4, S5, S6, S7, S8, S9 or Unscheduled-->
| legal_CA = <!-- Schedule I, II, III, IV, V, VI, VII, VIII -->
| legal_UK = <!-- GSL, P, POM, CD, or Class A, B, C -->
| legal_US = <!-- OTC / Rx-only / Schedule I, II, III, IV, V -->
| legal_status =
| routes_of_administration =
<!--Pharmacokinetic data-->
| bioavailability =
| protein_bound =
| metabolism =
| elimination_half-life =
| excretion =
<!--Identifiers-->
| CAS_number_Ref = {{cascite|correct|??}}
| CAS_number = 64224-21-1
| ATC_prefix = none
| ATC_suffix =
| PubChem = 47318
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank =
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 6N510JUL1Y
| ChEBI_Ref = {{ebicite|changed|EBI}}
| ChEBI = 77319
| ChEMBL_Ref = {{ebicite|changed|EBI}}
| ChEMBL = 178459
| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
| ChemSpiderID = 43066
<!--Chemical data-->
| chemical_formula =
| C=8 | H=6 | N=2 | S=3
| smiles = CC1=C(SSC1=S)C2=NC=CN=C2
| StdInChI_Ref = {{stdinchicite|changed|chemspider}}
| StdInChI = 1S/C8H6N2S3/c1-5-7(12-13-8(5)11)6-4-9-2-3-10-6/h2-4H,1H3
| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}
| StdInChIKey = CKNAQFVBEHDJQV-UHFFFAOYSA-N
}}
'''Oltipraz''' is an organosulfur compound belonging to the [[dithiolethione]] class.<ref name="pmid19150646">{{cite journal | vauthors = Prince M, Li Y, Childers A, Itoh K, Yamamoto M, Kleiner HE | title = Comparison of citrus coumarins on carcinogen-detoxifying enzymes in Nrf2 knockout mice | journal = Toxicology Letters | volume = 185 | issue = 3 | pages = 180–186 | date = March 2009 | pmid = 19150646 | pmc = 2676710 | doi = 10.1016/j.toxlet.2008.12.014 }}</ref><ref>{{cite journal | vauthors = Ansari MI, Khan MM, Saquib M, Khatoon S, Hussain MK | title = Dithiolethiones: a privileged pharmacophore for anticancer therapy and chemoprevention | journal = Future Medicinal Chemistry | volume = 10 | issue = 10 | pages = 1241–1260 | date = May 2018 | pmid = 29749746 | doi = 10.4155/fmc-2017-0281 }}</ref> 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.<ref name="pmid15252150">{{cite journal | vauthors = Zhang Y, Gordon GB | title = A strategy for cancer prevention: stimulation of the Nrf2-ARE signaling pathway | journal = Molecular Cancer Therapeutics | volume = 3 | issue = 7 | pages = 885–893 | date = July 2004 | pmid = 15252150 | doi = 10.1158/1535-7163.885.3.7 | doi-access = free }}</ref><ref name="pmid15374950">{{cite journal | vauthors = Iida K, Itoh K, Kumagai Y, Oyasu R, Hattori K, Kawai K, Shimazui T, Akaza H, Yamamoto M | display-authors = 6 | title = Nrf2 is essential for the chemopreventive efficacy of oltipraz against urinary bladder carcinogenesis | journal = Cancer Research | volume = 64 | issue = 18 | pages = 6424–6431 | date = September 2004 | pmid = 15374950 | doi = 10.1158/0008-5472.CAN-04-1906 | doi-access = free }}</ref> Clinical trials of oltipraz have failed to demonstrate efficacy and have shown significant side effects, including [[neurotoxicity]] and gastrointestinal toxicity.<ref name="pmid15252150"/> Oltipraz has also been shown to generate [[superoxide radical]]s, which can be toxic.<ref name="pmid15680910">{{cite journal | vauthors = Velayutham M, Villamena FA, Fishbein JC, Zweier JL | title = Cancer chemopreventive oltipraz generates superoxide anion radical | journal = Archives of Biochemistry and Biophysics | volume = 435 | issue = 1 | pages = 83–88 | date = March 2005 | pmid = 15680910 | doi = 10.1016/j.abb.2004.11.028 }}</ref>
== References ==
{{reflist}}
[[Category:Antiparasitic agents]]
[[Category:Pyrazines]]
[[Category:Dithioles]]
[[Category:Thiocarbonyl compounds]]
[[Category:Antineoplastic drugs]]
{{antiinfective-drug-stub}}