oltipraz

{{Short description|Chemical compound}}

{{Drugbox

| Verifiedfields = changed

| verifiedrevid = 449559107

| IUPAC_name = 4-methyl-5-(2-pyrazinyl)-3-dithiolethione

| image = Oltipraz.png

| tradename =

| pregnancy_AU =

| pregnancy_US =

| pregnancy_category =

| legal_AU =

| legal_CA =

| legal_UK =

| legal_US =

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| routes_of_administration =

| bioavailability =

| protein_bound =

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| 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_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.{{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 }}{{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 }} 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.{{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 }}{{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 }} Clinical trials of oltipraz have failed to demonstrate efficacy and have shown significant side effects, including neurotoxicity and gastrointestinal toxicity. Oltipraz has also been shown to generate superoxide radicals, which can be toxic.{{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 }}