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| 25mg |
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| 100mg |
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| 250mg |
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| 500mg |
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| 1g |
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Purity: ≥98%
Oltipraz (RP 35972; NSC 347901), a potential anticancer agent, is a potent Nrf2 activator and an inducer of Phase II detoxification enzymes such as glutathione-S-transferase (GST). Originally used in humans as an anti-schistosomal agent, oltipraz is a synthetic, substituted 1,2-dithiole-3-thione. Since Oltipraz favorably increases Phase II detoxification enzymes while only marginally changing the expression of Phase I "activating" enzymes, it has been categorized as a monofunctional inducer.
| Targets |
Nrf2; HIF-1α (IC50 = 10 μM)
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|---|---|
| ln Vitro |
Oltipraz acts as a chemoprotective agent and, in an Nrf2-dependent manner, stimulates the activity of Phase II detoxification enzymes. [1] Oltipraz inhibits the induction of HIF-1α by insulin, hypoxia, or CoCl2 in human HT29 colon cancer cells by markedly accelerating the protein's breakdown. [2]
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| ln Vivo |
Oltipraz (500 mg/kg, p.o.) has no effect on tumor burden in nrf2-deficient mice but significantly reduces the multiplicity of gastric neoplasia by 55% in wild-type mice. [1] Oltipraz (200 mg/kg, p.o.) inhibits tumor growth and angiogenesis in BALB/c nude mice transplanted with HCT116 cells by blocking HIF-1. [2] Oltipraz slowed the development of non-alcoholic steatohepatitis-related fibrosis in rats on a CDAA diet. [3]
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| Cell Assay |
Oltipraz has been classified as a monofunctional inducer since it advantageously elevates Phase II detoxification enzymes, while only slightly altering the expression of the Phase I “activating” enzymes. Oltipraz effectively induced quinone reductase in Hepa 1c1c7 cells defective in the aryl hydrocarbon receptor function required by bifunctional inducers
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| Animal Protocol |
Female wild-type and nrf2-disrupted mice
500 mg/kg p.o. |
| References | |
| Additional Infomation |
Oltipraz is a 1,2-dithiole that is 3H-1,2-dithiole-3-thione substituted at positions 4 and 5 by methyl and pyrazin-2-yl groups respectively. It has a role as an antineoplastic agent, an antimutagen, a protective agent, an antioxidant, an EC 3.1.3.48 (protein-tyrosine-phosphatase) inhibitor, a schistosomicide drug, a neurotoxin and an angiogenesis modulating agent. It is a 1,2-dithiole and a member of pyrazines.
Oltipraz has been used in trials studying the treatment and prevention of Lung Cancer, Liver Fibrosis, Liver Cirrhosis, and Non-alcoholic Fatty Liver Disease. Oltipraz is a synthetic dithiolethione with potential chemopreventive and anti-angiogenic properties. Oltipraz induces phase II detoxification enzymes, such as glutathione S transferase (GST) and NAD(P)H:quinone oxidoreductase 1 (NQO1). The induction of detoxification enzymes enhances the detoxification of certain cancer-causing agents, thereby enhancing their elimination and preventing carcinogen-induced DNA damages. Although the exact mechanism through which the anti-angiogenesis effect remains to be fully elucidated, oltipraz maybe able to modulate the expression of a number of angiogenic factors, thereby blocking the sustained and focal neovascularization in multiple tumor cell types. |
| Molecular Formula |
C8H6N2S3
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|---|---|---|
| Molecular Weight |
226.34
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| Exact Mass |
225.969
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| Elemental Analysis |
C, 42.45; H, 2.67; N, 12.38; S, 42.50
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| CAS # |
64224-21-1
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| Related CAS # |
Oltipraz-d3;2012598-51-3
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| PubChem CID |
47318
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| Appearance |
Solid powder
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| Density |
1.5±0.1 g/cm3
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| Boiling Point |
408.1±55.0 °C at 760 mmHg
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| Melting Point |
165-166ºC
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| Flash Point |
200.6±31.5 °C
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| Vapour Pressure |
0.0±0.9 mmHg at 25°C
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| Index of Refraction |
1.760
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| LogP |
1.92
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| Hydrogen Bond Donor Count |
0
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| Hydrogen Bond Acceptor Count |
5
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| Rotatable Bond Count |
1
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| Heavy Atom Count |
13
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| Complexity |
262
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| Defined Atom Stereocenter Count |
0
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| SMILES |
S1C(C2C([H])=NC([H])=C([H])N=2)=C(C(=S)S1)C([H])([H])[H]
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| InChi Key |
CKNAQFVBEHDJQV-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C8H6N2S3/c1-5-7(12-13-8(5)11)6-4-9-2-3-10-6/h2-4H,1H3
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| Chemical Name |
4-methyl-5-pyrazin-2-yldithiole-3-thione
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| Synonyms |
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| HS Tariff Code |
2934.99.9001
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| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month |
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| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
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| Solubility (In Vitro) |
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| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 1 mg/mL (4.42 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 10.0 mg/mL clear DMSO stock solution to 400 μL of PEG300 and mix evenly; then add 50 μL of Tween-80 to the above solution and mix evenly; then add 450 μL of normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 1 mg/mL (4.42 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 10.0 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly. (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 4.4181 mL | 22.0907 mL | 44.1813 mL | |
| 5 mM | 0.8836 mL | 4.4181 mL | 8.8363 mL | |
| 10 mM | 0.4418 mL | 2.2091 mL | 4.4181 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
| NCT Number | Recruitment | interventions | Conditions | Sponsor/Collaborators | Start Date | Phases |
| NCT00006457 | Completed | Drug: oltipraz | Lung Cancer | Northwestern University | August 2000 | Phase 1 |
| NCT00956098 | Completed | Drug: oltipraz Drug: placebo |
Liver Fibrosis Liver Cirrhosis |
HK inno.N Corporation | February 2006 | Phase 2 |
| NCT01373554 | Completed | Drug: Placebo Drug: Oltipraz |
Non-alcoholic Fatty Liver Disease |
PharmaKing | May 2011 | Phase 2 |
| NCT04142749 | Completed | Drug: Oltipraz Drug: Placebos |
Non-Alcoholic Fatty Liver Disease |
PharmaKing | November 15, 2019 | Phase 3 |
| NCT02068339 | Completed | Drug: Oltipraz 1 (90mg) Drug: Oltipraz 2 (120mg) |
Non-alcholic Fatty Liver Disease |
PharmaKing | February 2014 | Phase 3 |
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