Oltipraz | CAS#64224-21-1 | MedKoo Biosciences

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

MedKoo CAT#: 205913

CAS#: 64224-21-1

Description: Oltipraz, a promising cancer chemopreventive agent, is a bifunctional inducer, modulating both phase I and II drug-metabolizing enzymes to enhance carcinogen detoxification.

Chemical Structure

Oltipraz

CAS# 64224-21-1

Product data Instruction

Theoretical Analysis

MedKoo Cat#: 205913
Name: Oltipraz
CAS#: 64224-21-1
Chemical Formula: C8H6N2S3
Exact Mass: 225.97
Molecular Weight: 226.330
Elemental Analysis: C, 42.45; H, 2.67; N, 12.38; S, 42.50

Price and Availability

Size	Price	Availability	Quantity
100mg	USD 230
250mg	USD 370
500mg	USD 630
Bulk inquiry Welcome, Customer: Please do not inquire quote if your intended use is for a patient since our products are for research use and for chemical synthesis use, not for human use . For in-stock products, we listed price in the web page. You may inquire prices for which sizes were not listed. If no price is listed, this means the product is not in stock at the moment, which may be available via custom synthesis. For cost-effective reason, minimum order of 1g is requested (typically very expensive). The lead time is usually 2-4 months. Quote of less than 1g will not be provided. MedKoo may not offer quote for below reasons: (1) current available synthetic method appears to be extremely expensive which is obviously not affordable to most customers; (2) Key raw material to make the product is temporally not available; (3) DEA controlled substances; (4) the product is under patent protection in customer’s country.

Synonym: Oltipraz; CD1400

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:

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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/

Solubility Data

	Solvent	Max Conc. mg/mL	Max Conc. mM
Solubility
	DMSO	11.1	49.07

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:	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.
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.

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1: Kang SG, Lee WH, Lee YH, Lee YS, Kim SG. Hypoxia-inducible factor-1α inhibition by a pyrrolopyrazine metabolite of oltipraz as a consequence of microRNAs 199a-5p and 20a induction. Carcinogenesis. 2012 Mar;33(3):661-9. Epub 2012 Jan 4. PubMed PMID: 22223846.

2: Kim SG, Kim YM, Choi JY, Han JY, Jang JW, Cho SH, Um SH, Chon CY, Lee DH, Jang JJ, Yu E, Lee YS. Oltipraz therapy in patients with liver fibrosis or cirrhosis: a randomized, double-blind, placebo-controlled phase II trial. J Pharm Pharmacol. 2011 May;63(5):627-35. doi: 10.1111/j.2042-7158.2011.01259.x. Epub 2011 Mar 14. PubMed PMID: 21492164.

3: Bhattacharyya S, Zhou H, Seiner DR, Gates KS. Inactivation of protein tyrosine phosphatases by oltipraz and other cancer chemopreventive 1,2-dithiole-3-thiones. Bioorg Med Chem. 2010 Aug 15;18(16):5945-9. Epub 2010 Jun 30. PubMed PMID: 20655236; PubMed Central PMCID: PMC3253851.

4: Choi SH, Kim YM, Lee JM, Kim SG. Antioxidant and mitochondrial protective effects of oxidized metabolites of oltipraz. Expert Opin Drug Metab Toxicol. 2010 Feb;6(2):213-24. Review. PubMed PMID: 20095791.

5: Piton A, Rauch C, Langouet S, Guillouzo A, Morel F. Involvement of pregnane X receptor in the regulation of CYP2B6 gene expression by oltipraz in human hepatocytes. Toxicol In Vitro. 2010 Mar;24(2):452-9. Epub 2009 Oct 12. PubMed PMID: 19833192.

6: 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. Epub 2009 Sep 29. PubMed PMID: 19789218.

7: Cho IJ, Sung DK, Kang KW, Kim SG. Oltipraz promotion of liver regeneration after partial hepatectomy: The role of PI3-kinase-dependent C/EBPbeta and cyclin E regulation. Arch Pharm Res. 2009 Apr;32(4):625-35. Epub 2009 Apr 29. PubMed PMID: 19407981.

8: Shin SM, Kim SG. Inhibition of arachidonic acid and iron-induced mitochondrial dysfunction and apoptosis by oltipraz and novel 1,2-dithiole-3-thione congeners. Mol Pharmacol. 2009 Jan;75(1):242-53. Epub 2008 Oct 22. PubMed PMID: 18945820.

9: Velayutham M, Muthukumaran RB, Sostaric JZ, McCraken J, Fishbein JC, Zweier JL. Interactions of the major metabolite of the cancer chemopreventive drug oltipraz with cytochrome c: a novel pathway for cancer chemoprevention. Free Radic Biol Med. 2007 Oct 1;43(7):1076-85. Epub 2007 Jul 6. PubMed PMID: 17761303.

10: Glintborg B, Weimann A, Kensler TW, Poulsen HE. Oltipraz chemoprevention trial in Qidong, People's Republic of China: unaltered oxidative biomarkers. Free Radic Biol Med. 2006 Sep 15;41(6):1010-4. Epub 2006 Jul 4. PubMed PMID: 16934685.

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