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O9389

Sigma-Aldrich

Oltipraz

≥98% (HPLC), powder

Synonym(s):

4-Methyl-5-(2-pyrazinyl)-1,2-dithiole-3-thione, BRN 0978110, CCRIS 4048, NSC 347901, RP 35972

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About This Item

Empirical Formula (Hill Notation):
C8H6N2S3
CAS Number:
64224-21-1
Molecular Weight:
226.34
EC Number:
264-736-6
MDL number:
MFCD00868499
UNSPSC Code:
12352200
PubChem Substance ID:
329818939
NACRES:
NA.77

Assay

≥98% (HPLC)

form

powder

storage condition

protect from light

color

red

solubility

DMSO: >20 mg/mL

storage temp.

2-8°C

SMILES string

CC1=C(SSC1=S)c2cnccn2

InChI

1S/C8H6N2S3/c1-5-7(12-13-8(5)11)6-4-9-2-3-10-6/h2-4H,1H3

InChI key

CKNAQFVBEHDJQV-UHFFFAOYSA-N

General description

Oltipraz, a dithiol derivative, is a member of dithiolethiones class of organosulfur compounds. It has anti-tumor, antioxidative, anti- inflammatory and radioprotective properties. It provides protection from numerous carcinogens. Oltipraz functions as a schistosomicide.

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.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Alberto Izzotti et al.
Cancer prevention research (Philadelphia, Pa.), 3(1), 62-72 (2010-01-07)
We previously showed that exposure to environmental cigarette smoke (ECS) for 28 days causes extensive downregulation of microRNA expression in the lungs of rats, resulting in the overexpression of multiple genes and proteins. In the present study, we evaluated by
A randomized phase IIb trial of anethole dithiolethione in smokers with bronchial dysplasia
Lam S, et al.
Journal of the National Cancer Institute, 94(13), 1001-1009 (2002)
Sang Geon Kim et al.
The Journal of pharmacy and pharmacology, 63(5), 627-635 (2011-04-16)
Oltipraz, a cancer chemopreventive agent, has an anticirrhotic effect in animals. A phase II trial was designed to investigate the preliminary efficacy of oltipraz therapy in liver fibrosis or cirrhosis. Of 83 patients who were randomized to receive placebo, oltipraz
Nrf2 is essential for the chemopreventive efficacy of oltipraz against urinary bladder carcinogenesis
Iida K, et al.
Cancer Research, 64(18), 6424-6431 (2004)
Ryan Holland et al.
Chemical research in toxicology, 22(8), 1427-1434 (2009-09-30)
The ability of three dithiolethione cancer chemopreventives, oltipraz 1, anetholedithione (ADT) 2, 1,2-dithiole-3-thione (D3T) 3, and the major metabolite, 4, of 1, to induce the cytoprotective enzyme NQO1 in Hepa 1c1c7 cells and the inhibition of this induction by catalase
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