Oltipraz
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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

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Oltipraz
CAS# 64224-21-1

Theoretical Analysis

MedKoo Cat#: 205913
Name: Oltipraz
CAS#: 64224-21-1
Chemical Formula: C8H6N2S3
Exact Mass: 225.96931
Molecular Weight: 226.34
Elemental Analysis: C, 42.45; H, 2.67; N, 12.38; S, 42.50

Price and Availability

Size Price Availability Quantity
100.0mg USD 230.0 2 Weeks
250.0mg USD 370.0 2 Weeks
500.0mg USD 630.0 2 Weeks
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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

Preparing Stock Solutions

The following data is based on the product molecular weight 226.34 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.

Recalculate based on batch purity %
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

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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.

Oltipraz

100.0mg / USD 230.0


Additional Information