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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:
Molecular Weight:
226.34
EC Number:
MDL number:
UNSPSC Code:
12352200
PubChem Substance ID:
NACRES:
NA.77

Quality Level

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

Signal Word

Warning

Hazard Statements

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

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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
Nicholas T Longford
Statistics in medicine, 31(26), 3133-3146 (2012-04-26)
A general method of estimation with a variable observed subject to a limit of detection is introduced. It is based on extrapolation of the estimates obtained by increasing the limit of detection. Theoretical arguments support the method in some special
Min Kyung Kang et al.
Journal of pharmacy & pharmaceutical sciences : a publication of the Canadian Society for Pharmaceutical Sciences, Societe canadienne des sciences pharmaceutiques, 12(1), 1-16 (2009-05-28)
To evaluate the pharmacokinetic interaction between oltipraz and silymarin after intravenous and oral administration of both drugs to male Sprague-Dawley rats. Oltipraz (single doses of 10 and 30 mg/kg for intravenous and oral administration, respectively), silymarin (single doses of 50
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
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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