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SML0777

Sigma-Aldrich

Oltipraz metabolite M2

≥98% (HPLC)

Synonym(s):

7-Methyl-6,8-bis(methylthio)-pyrrolo[1,2-a]pyrazine

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About This Item

Empirical Formula (Hill Notation):
C10H12N2S2
CAS Number:
84201-40-1
Molecular Weight:
224.35
UNSPSC Code:
12352200
NACRES:
NA.77

Quality Level

100

Assay

≥98% (HPLC)

form

powder

storage condition

protect from light

color

white to light brown

solubility

DMSO: 10 mg/mL, clear

storage temp.

2-8°C

InChI

1S/C10H12N2S2/c1-7-9(13-2)8-6-11-4-5-12(8)10(7)14-3/h4-6H,1-3H3

InChI key

MYLBTCQBKAKUTJ-UHFFFAOYSA-N

Biochem/physiol Actions

M2 is a metabolite of the chemopreventive agent oltipraz. Oltipraz metabolite M2 has been shown to inhibit liver steatosis by inhibiting lipogenesis and enhancing mitochondrial function, including fuel oxidation. Oltipraz metabolite M2 acts as a potent inhibitor of LXRa transcriptional activity, and also AMPK activator inducing the phosphorylation of AMPK.

Features and Benefits

This compound is featured on the AMPKs page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

Other Notes

Light sensitive and air sensitive.

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

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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H J Prochaska et al.
Molecular pharmacology, 48(1), 15-20 (1995-07-01)
Oltipraz, an inhibitor of human immunodeficiency virus type 1 replication in vitro (ED50 approximately 10 microM), undergoes extensive metabolism in vivo. Most of the orally administered drug undergoes opening of the dithiolethione ring, reduction, recyclization, and methylation to form 7-methyl-6,8-bis(methylthio)pyrrolo[1,2-a]pyrazine
S G Kim et al.
Clinical pharmacology and therapeutics, 88(3), 360-368 (2010-07-29)
Oltipraz is a potential candidate drug for the treatment of liver fibrosis (LF) and liver cirrhosis (LC). The pharmacokinetics of oltipraz and its major rearranged metabolite (7-methyl-6,8-bis(methylthio)H-pyrrolo[1,2-a]pyrazine (RM)) were evaluated after single-dose (30-90 mg) and multiple-dose (60 mg b.i.d. or

Articles

AMPKs

The AMP-activated protein kinase (AMPK) acts as a sensor of cellular energy status. AMPK exists as heterotrimeric complexes comprising a catalytic α subunit and regulatory β and γ subunits.

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