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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
Pricing and availability is not currently available.

Quality Level

100

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

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Show Differences

1 of 4

This Item
711292736775711284
2-Bromo-1-methyl-1H-imidazole 95%

639850

2-Bromo-1-methyl-1H-imidazole

4-Bromo-1-methyl-1H-imidazole 95%

711292

4-Bromo-1-methyl-1H-imidazole

4-Methyl-1H-imidazole-2-carboxaldehyde 95%

736775

4-Methyl-1H-imidazole-2-carboxaldehyde

4-Bromo-1-methyl-1H-imidazole-5-carboxaldehyde 95%

711284

4-Bromo-1-methyl-1H-imidazole-5-carboxaldehyde

assay

95%

assay

95%

assay

95%

assay

95%

Quality Level

100

Quality Level

100

Quality Level

100

Quality Level

100

bp

172 °C (lit.)

bp

-

bp

-

bp

-

refractive index

n20/D 1.5440 (lit.)

refractive index

n20/D 1.545

refractive index

-

refractive index

-

form

solid

form

liquid

form

solid

form

solid

density

1.649 g/mL at 25 °C (lit.)

density

1.614 g/mL at 25 °C

density

-

density

-

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.[1][2] It provides protection from numerous carcinogens.[3] Oltipraz functions as a schistosomicide.[1]

Biochem/physiol Actions

Oltipraz is an activator of Nrf2.
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

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    Certificates of Analysis (COA)

    Lot/Batch Number
    080M4742V
    080M4742
    078K47163
    078K47162
    078K47161

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    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
    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)
    Seong Hwan Hwahng et al.
    Hepatology (Baltimore, Md.), 49(6), 1913-1925 (2009-04-21)
    Dithiolethiones, a novel class of adenosine monophosphate-activated protein kinase (AMPK) activators, prevent insulin resistance through AMPK-dependent p70 ribosomal S6 kinase-1 (S6K1) inhibition. There is no known effect of S6K1 for liver X receptor-alpha (LXRalpha)-mediated lipogenic gene expression and steatosis, a
    Nrf2 is essential for the chemopreventive efficacy of oltipraz against urinary bladder carcinogenesis
    Iida K, et al.
    Cancer Research, 64(18), 6424-6431 (2004)
    View All Related Papers

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