Oltipraz

Base Information

• Chemical Name: Oltipraz
• CAS No.: 64224-21-1
• Molecular Formula: C8H6N2S3
• Molecular Weight: 226.347
• Hs Code.: 2933990090
• European Community (EC) Number: 264-736-6
• NSC Number: 759840,347901
• UNII: 6N510JUL1Y
• DSSTox Substance ID: DTXSID7021079
• Nikkaji Number: J19.580D
• Wikipedia: Oltipraz
• Wikidata: Q7088765
• NCI Thesaurus Code: C1177
• Metabolomics Workbench ID: 49666
• ChEMBL ID: CHEMBL178459
• Mol file: 64224-21-1.mol

Synonyms:35 972 R.P.;4-methyl-5-pyrazinyl-3H-1,2-dithiole-3-thione;4-methyl-PDT;5-(2-pyrazinyl)-4-methyl-1,2-dithiol-3-thione;oltipraz;RP 35972

Chemical Property of Oltipraz

Chemical Property:

• Vapor Pressure: 1.69E-06mmHg at 25°C
• Melting Point: 165-166 °C
• Refractive Index: 1.76
• Boiling Point: 408.124 °C at 760 mmHg
• PKA: 0.18±0.10(Predicted)
• Flash Point: 200.627 °C
• PSA: 114.35000
• Density: 1.517 g/cm³
• LogP: 3.30450
• Storage Temp.: 2-8°C
• Sensitive.: Light Sensitive
• Solubility.: DMSO: >20mg/mL
• XLogP3: 1.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 1
• Exact Mass: 225.96931172
• Heavy Atom Count: 13
• Complexity: 262

Purity/Quality:

99% ^*data from raw suppliers

Oltipraz ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36/37/39-36/37

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC1=C(SSC1=S)C2=NC=CN=C2
• Recent ClinicalTrials: Oltipraz for Liver Fat Reduction in Patients With Non-alcoholic Fatty Liver Disease Except for Liver Cirrhosis
• Description: Oltipraz (64224-21-1) upregulates the transcription factor NRF2 and prevents insulin resistance and obesity induced by high fat diet in C57BL/6J mice.1 Attenuates the progression of fibrosis in a rat model of nonalcoholic steatohepatitis.2 Oltipaz attenuates chronic hypoxia-induced cardiopulmonary alterations in mice.3 Promotes liver regeneration after partial hepatectomy.4 Off target effects: Activates constitutive androstane receptor (CAR).5
• Uses: Oltipraz is a synthetic, substituted 1,2-dithiole-3-thione previously used in humans as an antischistosomal agent. Animal studies have demonstrated that oltipraz is a potent inducer of Phase II detoxi fication enzymes, most notably glutathione-S-transferase (GST). Oltipraz is now known to be used for tumor prevention purposes. Oltipraz is a synthetic, substituted 1,2-dithiole-3-thione previously used in humans as an antischistosomal agent. Animal studies have demonstrated that oltipraz is a potent inducer of Phase II detoxification enzymes, most notably glutathione-S-transferase (GST). Oltipraz is now known to be used for tumor prevention purposes. schistosomicide, antineoplastic

Technology Process of Oltipraz

There total 7 articles about Oltipraz which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 14.0%

methyl 2-methyl-3-(pyrazin-2-yl)-3-oxopropionate (324737-10-2) → Oltipraz (64224-21-1)

Guidance literature:

With tetraphosphorus decasulfide; In 5,5-dimethyl-1,3-cyclohexadiene; toluene; at 135 ℃; for 4h;

DOI:10.1016/j.bmc.2016.04.054

Reference yield:

ethyl 2-methyl-3-oxo-3-(pyrazin-2-yl)propanoate (64223-90-1) → Oltipraz (64224-21-1)

Guidance literature:

With diphosphorus pentasulfide; In toluene;

Reference yield:

pyrographite (7440-44-0) + methyl 2-methyl-3-(pyrazin-2-yl)-3-oxopropionate (324737-10-2) → Oltipraz (64224-21-1)

Guidance literature:

With P₂S₅; conc. ammonia; In methanol; water; toluene; acetonitrile;

upstream raw materials:

methyl 2-methyl-3-(pyrazin-2-yl)-3-oxopropionate

ethyl 2-methyl-3-oxo-3-(pyrazin-2-yl)propanoate

pyrographite

2-pyrazylcarboxylic acid

Downstream raw materials:

7-methyl-6,8-bis(methylthio)pyrrolo<1,2-a>pyrazine

6-Ethyldisulfanyl-7-methyl-8-methylsulfanyl-pyrrolo[1,2-a]pyrazine

7-methyl-6 (or 8-)-methylthio-pyrrolo<1,2-a>pyrazine disulphide

6,8-dimethylthio-7-formylpyrrolo <1,2-a> pyrazine

Refernces

• 1、 -. "METHODS FOR PREPARING OLTIPRAZ". Page/Page column 4; 16; 17. . Retrieved 2017/01/09.
• 2、 -. "METHOD FOR PREPARING OLTIPRAZ". Page 9-10. . Retrieved 2010/02/07.