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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

signalword

Warning

Hazard Classifications

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

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

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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Yoko Yagishita et al.
Antioxidants (Basel, Switzerland), 9(8) (2020-08-14)
The transcription factor NF-E2 p45-related factor 2 (NRF2; encoded by NFE2L2) plays a critical role in the maintenance of cellular redox and metabolic homeostasis, as well as the regulation of inflammation and cellular detoxication pathways. The contribution of the NRF2
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
Varsha Rani et al.
Chemico-biological interactions, 295, 84-92 (2017-10-13)
Dimethylnitrosamine (DMN) is a potent hepatotoxic, carcinogenic and mutagenic compound. It induces massive liver cell necrosis and death in experimental animals. Several drugs have been tested in the past for their protective behavior against DMN toxicity. However, it is for
Song Hwa Choi et al.
Expert opinion on drug metabolism & toxicology, 6(2), 213-224 (2010-01-26)
Comprehensive studies indicate that oltipraz exerts cancer chemopreventive effects. Oltipraz has other therapeutic potentials, which include anti-fibrotic effect, inhibition of insulin resistance, mitochondrial protection and cytoprotective effect against oxidative stress. Although antioxidant mechanisms may account for its cancer chemopreventive effect
The effects of oltipraz on tissue regeneration in the process of wound healing: a stereological study
Noorafshan A, et al.
Bulletin of emergency and trauma, 2(4), 161-161 (2014)
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