Oltipraz | CAS#64224-21-1 | chemopreventive agent

MedKoo Cat#: 205913 | Name: Oltipraz

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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Oltipraz, a promising cancer chemopreventive agent, is a bifunctional inducer, modulating both phase I and II drug-metabolizing enzymes to enhance carcinogen detoxification. Oltipraz is an NRF2 activator which is seen to also promote the degradation of HIF-2alpha.

Chemical Structure

Oltipraz

CAS#64224-21-1

Theoretical Analysis

MedKoo Cat#: 205913

Name: Oltipraz

CAS#: 64224-21-1

Chemical Formula: C8H6N2S3

Exact Mass: 225.9693

Molecular Weight: 226.33

Elemental Analysis: C, 42.45; H, 2.67; N, 12.38; S, 42.50

Price and Availability

Size	Price	Availability	Quantity
100mg	USD 450.00
250mg	USD 575.00
500mg	USD 840.00

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Synonym

Oltipraz; CD1400; CD-1400; CD 1400;

IUPAC/Chemical Name

4-methyl-5-(pyrazin-2-yl)-3H-1,2-dithiole-3-thione

InChi Key

CKNAQFVBEHDJQV-UHFFFAOYSA-N

InChi Code

InChI=1S/C8H6N2S3/c1-5-7(12-13-8(5)11)6-4-9-2-3-10-6/h2-4H,1H3

SMILES Code

S=C1SSC(C2=NC=CN=C2)=C1C

Appearance

Solid powder

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO, not in water

Shelf Life

>5 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.9001

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Product Data

Product Data

Instruction

View handling instruction

Biological target:

Oltipraz has an inhibitory effect on HIF-1α activation in a time-dependent manner, completely abrogating HIF-1α induction at ≥10 μM concentrations, the IC50 of Oltipraz for HIF-1α inhibition is 10 μM. Oltipraz is a potent Nrf2 activator.

In vitro activity:

Oltipraz significantly inhibited MTB-induced death and apoptosis in human macrophages. MTB-induced reactive oxygen species production, mitochondrial depolarization and programmed necrosis were attenuated by oltipraz in macrophages. Oltipraz activated Nrf2 signaling, causing Keap1-Nrf2 disassociation, Nrf2 protein stabilization and nuclear translocation, simultaneously promoting expression of Nrf2-dependent genes (HO1, NQO1 and GST) in human macrophages. Reference: Biochem Biophys Res Commun. 2020 Oct 20;531(3):312-319. https://pubmed.ncbi.nlm.nih.gov/32800560/

In vivo activity:

Oltipraz treatment abrogated insulin-induced H(2)O(2) production, thereby preventing H(2)O(2)-enhanced HIF-1alpha expression and promoting its ubiquitination and degradation. In an animal model, tumor regression by oltipraz was accompanied by decreases in microvessel density and vascular endothelial growth factor induction. Oltipraz inhibits HIF-1alpha activity and HIF-1alpha-dependent tumor growth, which may result from a decrease in HIF-1alpha stability through S6K1 inhibition in combination with an H(2)O(2)-scavenging effect. Reference: Mol Cancer Ther. 2009 Oct;8(10):2791-802. https://pubmed.ncbi.nlm.nih.gov/19789218/

	Solvent	mg/mL	mM
Solubility
	DMSO	11.1	49.07

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 226.33 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:

1. Sun Q, Shen X, Ma J, Lou H, Zhang Q. Activation of Nrf2 signaling by oltipraz inhibits death of human macrophages with mycobacterium tuberculosis infection. Biochem Biophys Res Commun. 2020 Oct 20;531(3):312-319. doi: 10.1016/j.bbrc.2020.07.026. Epub 2020 Aug 14. PMID: 32800560. 2. Jiang Z, Bian M, Wu J, Li D, Ding L, Zeng Q. Oltipraz Prevents High Glucose-Induced Oxidative Stress and Apoptosis in RSC96 Cells through the Nrf2/NQO1 Signalling Pathway. Biomed Res Int. 2020 Jun 23;2020:5939815. doi: 10.1155/2020/5939815. PMID: 32685505; PMCID: PMC7333049. 3. Lee WH, Kim YW, Choi JH, Brooks SC 3rd, Lee MO, Kim SG. Oltipraz and dithiolethione congeners inhibit hypoxia-inducible factor-1alpha activity through p70 ribosomal S6 kinase-1 inhibition and H2O2-scavenging effect. Mol Cancer Ther. 2009 Oct;8(10):2791-802. doi: 10.1158/1535-7163.MCT-09-0420. Epub 2009 Sep 29. PMID: 19789218. 4. Ramos-Gomez M, Kwak MK, Dolan PM, Itoh K, Yamamoto M, Talalay P, Kensler TW. Sensitivity to carcinogenesis is increased and chemoprotective efficacy of enzyme inducers is lost in nrf2 transcription factor-deficient mice. Proc Natl Acad Sci U S A. 2001 Mar 13;98(6):3410-5. doi: 10.1073/pnas.051618798. PMID: 11248092; PMCID: PMC30667.

In vitro protocol:

In vivo protocol:

1. Lee WH, Kim YW, Choi JH, Brooks SC 3rd, Lee MO, Kim SG. Oltipraz and dithiolethione congeners inhibit hypoxia-inducible factor-1alpha activity through p70 ribosomal S6 kinase-1 inhibition and H2O2-scavenging effect. Mol Cancer Ther. 2009 Oct;8(10):2791-802. doi: 10.1158/1535-7163.MCT-09-0420. Epub 2009 Sep 29. PMID: 19789218. 2. Ramos-Gomez M, Kwak MK, Dolan PM, Itoh K, Yamamoto M, Talalay P, Kensler TW. Sensitivity to carcinogenesis is increased and chemoprotective efficacy of enzyme inducers is lost in nrf2 transcription factor-deficient mice. Proc Natl Acad Sci U S A. 2001 Mar 13;98(6):3410-5. doi: 10.1073/pnas.051618798. PMID: 11248092; PMCID: PMC30667.

1: Shen J, Lai Y, Lu Y, Liu Y, Zhang J, Wu Y, Pan Y, Chen H, Gao Q, Wei Q, Chen Y, Ye J, Lin Y, Liu B, Jiang J, Nan J. NRF2-HIF2α Signaling Attenuates Endothelial Cell Senescence and Maintains Intercellular Junctions in Diabetes. Int J Biol Sci. 2024 Jul 22;20(10):4055-4073. doi: 10.7150/ijbs.96719. PMID: 39113713; PMCID: PMC11302875. 2: Jian W, Ma H, Hu Y, Zhang Q, Xu J, Jiang J, Zhu G, Gong Y. Oltipraz attenuated cerebral ischemia-reperfusion injury through inhibiting the oxidative stress and ferroptosis in mice. Int Immunopharmacol. 2024 Aug 2;140:112800. doi: 10.1016/j.intimp.2024.112800. Epub ahead of print. PMID: 39096875. 3: He W, Zhang S, Qi Z, Liu W. Unveiling the potential of estrogen: Exploring its role in neuropsychiatric disorders and exercise intervention. Pharmacol Res. 2024 Jun;204:107201. doi: 10.1016/j.phrs.2024.107201. Epub 2024 May 3. PMID: 38704108. 4: Francis S, Kortei NK, Sackey M, Richard SA. Aflatoxin B1 induces infertility, fetal deformities, and potential therapies. Open Med (Wars). 2024 Jan 26;19(1):20240907. doi: 10.1515/med-2024-0907. PMID: 38283584; PMCID: PMC10818061. 5: Zeng D, Yin C, Wei H, Li Y, Yang Y, Nie H, Pan Y, Xu R, Tai Y, Du J, Liu J, Wang P, Liu B, Liu B. Activation of Nrf2 antioxidant signaling alleviates gout arthritis pain and inflammation. Biomed Pharmacother. 2024 Jan;170:115957. doi: 10.1016/j.biopha.2023.115957. Epub 2023 Dec 1. PMID: 38042115. 6: Jie P, Wu Y, Song C, Cheng Y, Liu Y, Chen K. Mechanism of Nrf2/miR338-3p/TRAP-1 pathway involved in hyperactivation of synovial fibroblasts in patients with osteoarthritis. Heliyon. 2023 Oct 21;9(11):e21412. doi: 10.1016/j.heliyon.2023.e21412. PMID: 37920489; PMCID: PMC10618819. 7: Su K, Zhao SL, Yang WX, Lo CS, Chenier I, Liao MC, Pang YC, Peng JZ, Miyata KN, Cailhier JF, Ethier J, Lattouf JB, Filep JG, Ingelfinger JR, Zhang SL, Chan JSD. NRF2 Deficiency Attenuates Diabetic Kidney Disease in Db/Db Mice via Down- Regulation of Angiotensinogen, SGLT2, CD36, and FABP4 Expression and Lipid Accumulation in Renal Proximal Tubular Cells. Antioxidants (Basel). 2023 Sep 4;12(9):1715. doi: 10.3390/antiox12091715. PMID: 37760019; PMCID: PMC10525648. 8: Masubuchi Y, Mikami K. Efficacy of oltipraz in preventing acetaminophen- induced liver injury in mice. Naunyn Schmiedebergs Arch Pharmacol. 2024 Feb;397(2):923-930. doi: 10.1007/s00210-023-02649-5. Epub 2023 Aug 3. PMID: 37535075. 9: Polat EC, Bozkurt M, Ozcan L, Sonmez K, Ozturk Gurgen H, Danis E, Otunctemur A. Effect of Oltipraz on urethral healing: An experimental study. Prog Urol. 2023 Sep;33(11):555-561. doi: 10.1016/j.purol.2023.06.001. Epub 2023 Jun 27. PMID: 37385830. 10: Cao Y, Li Y, Wang X, Liu S, Zhang Y, Liu G, Ye S, Zheng Y, Zhao J, Zhu X, Chen Y, Xu H, Feng D, Chen D, Chen L, Liu W, Zhou W, Zhang Z, Zhou P, Deng K, Ye L, Yu Y, Yao Z, Liu Q, Xu H, Zhou J. Dopamine inhibits group 2 innate lymphoid cell-driven allergic lung inflammation by dampening mitochondrial activity. Immunity. 2023 Feb 14;56(2):320-335.e9. doi: 10.1016/j.immuni.2022.12.017. Epub 2023 Jan 23. Erratum in: Immunity. 2023 May 9;56(5):1148-1151. doi: 10.1016/j.immuni.2023.03.019. PMID: 36693372. 11: Yang R, Li J, Zhang J, Xue Q, Qin R, Wang R, Goltzman D, Miao D. 17β-estradiol plays the anti-osteoporosis role via a novel ESR1-Keap1-Nrf2 axis- mediated stress response activation and Tmem119 upregulation. Free Radic Biol Med. 2023 Feb 1;195:231-244. doi: 10.1016/j.freeradbiomed.2022.12.102. Epub 2022 Dec 30. PMID: 36592659. 12: Dai YQ, Bai Y, Gu J, Fan BY. Stanniocalcin1 knockdown induces ferroptosis and suppresses glycolysis in prostate cancer via the Nrf2 pathway. Neoplasma. 2022 Dec;69(6):1396-1405. doi: 10.4149/neo_2022_220626N665. PMID: 36591803. 13: Wang D, Wu J, Le S, Wang H, Luo J, Li R, Chen X, Song Y, Wu L, Ye P, Du X, Huang X. Oltipraz, the activator of nuclear factor erythroid 2-related factor 2 (Nrf2), protects against the formation of BAPN-induced aneurysms and dissection of the thoracic aorta in mice by inhibiting activation of the ROS-mediated NLRP3 inflammasome. Eur J Pharmacol. 2022 Dec 5;936:175361. doi: 10.1016/j.ejphar.2022.175361. Epub 2022 Nov 3. PMID: 36336010. 14: Kapoor-Narula U, Lenka N. Elucidating the Anti-Tumorigenic Efficacy of Oltipraz, a Dithiolethione, in Glioblastoma. Cells. 2022 Sep 29;11(19):3057. doi: 10.3390/cells11193057. PMID: 36231019; PMCID: PMC9562012. 15: Jiang Z, Wang H, Zhang Z, Pan J, Yuan H. Cartilage targeting therapy with reactive oxygen species-responsive nanocarrier for osteoarthritis. J Nanobiotechnology. 2022 Sep 19;20(1):419. doi: 10.1186/s12951-022-01629-w. PMID: 36123746; PMCID: PMC9484188. 16: Kamisako T, Tanaka Y. Oltipraz ameliorates the progression of steatohepatitis in Nrf2-null mice fed a high-fat diet. J Clin Biochem Nutr. 2022 Mar;70(2):147-153. doi: 10.3164/jcbn.21-58. Epub 2021 Nov 5. PMID: 35400824; PMCID: PMC8921722. 17: Wen JJ, Mobli K, Rontoyanni VG, Cummins CB, Radhakrishnan GL, Murton A, Radhakrishnan RS. Nuclear Factor Erythroid 2-Related Factor 2 Activation and Burn-Induced Cardiac Dysfunction. J Am Coll Surg. 2022 Apr 1;234(4):660-671. doi: 10.1097/XCS.0000000000000119. PMID: 35290286; PMCID: PMC9634710. 18: Yang R, Zhang J, Li J, Qin R, Chen J, Wang R, Goltzman D, Miao D. Inhibition of Nrf2 degradation alleviates age-related osteoporosis induced by 1,25-Dihydroxyvitamin D deficiency. Free Radic Biol Med. 2022 Jan;178:246-261. doi: 10.1016/j.freeradbiomed.2021.12.010. Epub 2021 Dec 8. PMID: 34890768. 19: Lin J, Zhang L, Wang Z, Guan Q, Bao K, Wu L. G2/M cell cycle arrest and apoptosis induced by COH-203 in human promyelocytic leukemia HL-60 cells. Oncol Lett. 2021 Dec;22(6):815. doi: 10.3892/ol.2021.13076. Epub 2021 Sep 28. PMID: 34671429; PMCID: PMC8503807. 20: Xu Y, Sang W, Zhong Y, Xue S, Yang M, Wang C, Lu H, Huan R, Mao X, Zhu L, He C, Ma J. CoCrMo-Nanoparticles induced peri-implant osteolysis by promoting osteoblast ferroptosis via regulating Nrf2-ARE signalling pathway. Cell Prolif. 2021 Dec;54(12):e13142. doi: 10.1111/cpr.13142. Epub 2021 Oct 11. PMID: 34632658; PMCID: PMC8666286.