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

• ChemBase ID: 154437
• Molecular Formular: C8H6N2S3
• Molecular Mass: 226.34164
• Monoisotopic Mass: 225.9693112
• SMILES: Cc1c(ssc1=S)c1cnccn1
• Canonical SMILES: S=c1ssc(c1C)c1cnccn1
• InChI: InChI=1S/C8H6N2S3/c1-5-7(12-13-8(5)11)6-4-9-2-3-10-6/h2-4H,1H3
• InChIKey: CKNAQFVBEHDJQV-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-methyl-5-(pyrazin-2-yl)-3H-1,2-dithiole-3-thione
• IUPAC Traditional name: oltipraz
• Synonyms: Oltipraz; 4-Methyl-5-(2-pyrazinyl)-1,2-dithiole-3-thione; 4-Methyl-5-(2-pyrazinyl)-1,2-dithiole-3-thione; BRN 0978110; CCRIS 4048; NSC 347901; RP 35972; Oltipraz

Database IDs

• CAS Number: 64224-21-1
• EC Number: 264-736-6
• MDL Number: MFCD00868499
• PubChem SID: 162248576
• PubChem CID: 47318

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 1.790329
• LogD (pH = 7.4): 1.790331
• Log P: 1.7903311
• Molar Refractivity: 63.359 cm^3
• Polarizability: 24.64723 Å^3
• Polar Surface Area: 25.78 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO: >20 mg/mL
• Apperance: red powder

Safety Information

• Storage Condition: protect from light
• Storage Warning: Light Sensitive
• RTECS: JP1293000
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36/37; 26-37-60
• TSCA Listed: 否
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338; P261-P305+P351+P338-P302+P352-P321-P405-P501
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C8H6N2S3

DETAILS

Sigma Aldrich - O9389

Biochem/physiol Actions
Oltipraz is an activator of Nrf2. Nrf2 (NF-E2-related factor 2) is a transcription factor that binds to antioxidant response elements (AREs) and activates these genes. Oltipraz activates Nrf2 and subsequently elevates expression of the detoxification genes encoding anti-oxidant and multidrug resistance-associated proteins to mediate its chemopreventive efficacy.