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C6240

Sigma-Aldrich

CITCO

≥98% (HPLC), solid

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Synonym(s):
6-(4-Chlorophenyl)imidazo[2,1-b][1,3]thiazole-5-carbaldehyde O-(3,4-dichlorobenzyl)oxime
Empirical Formula (Hill Notation):
C19H12N3OCl3S
CAS Number:
338404-52-7
Molecular Weight:
436.74
MDL number:
MFCD00139608
UNSPSC Code:
12352203
PubChem Substance ID:
24724448
NACRES:
NA.77

Assay

≥98% (HPLC)

form

solid

storage condition

desiccated

solubility

DMSO: soluble 28 mg/mL
H2O: insoluble

storage temp.

−20°C

SMILES string

Clc1ccc(cc1)-c2nc3sccn3c2\C=N\OCc4ccc(Cl)c(Cl)c4

InChI

1S/C19H12Cl3N3OS/c20-14-4-2-13(3-5-14)18-17(25-7-8-27-19(25)24-18)10-23-26-11-12-1-6-15(21)16(22)9-12/h1-10H,11H2/b23-10+

InChI key

ZQWBOKJVVYNKTL-AUEPDCJTSA-N

General description

CITCO is an imidazothiazole derivative. It stimulates human constitutive androstane receptor (CAR) nuclear translocation.

Application

CITCO has been used for the activation of mouse constitutive androstane receptor (CAR) and human CAR.

Biochem/physiol Actions

CITCO is a constitutive androstane receptor (CAR) agonist; nuclear receptor NR113 agonist.

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

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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Identification of a novel human constitutive androstane receptor (CAR) agonist and its use in the identification of CAR target genes
Maglich JM, et al.
The Journal of Biological Chemistry, 278(19), 17277-17283 (2003)
Tadeja Režen et al.
Drug metabolism and disposition: the biological fate of chemicals, 45(8), 974-976 (2017-05-26)
Statins are well known lipid lowering agents that inhibit the enzyme 3-hydroxy-3-methylglutaryl-CoA (HMG-CoA) reductase. They also activate drug metabolism but their exact receptor-mediated action has not been proven so far. We tested whether atorvastatin and rosuvastatin are direct ligands of
Constitutive androstane receptor agonist CITCO inhibits growth and expansion of brain tumour stem cells
Chakraborty S , et al.
British Journal of Cancer, 104(3), 448-448 (2011)
Constitutive androstane receptor (Car)-driven regeneration protects liver from failure following tissue loss
Tschuor C, et l.
Journal of Hepatology, 65(1), 66-74 (2016)
Cristina Saez-Lopez et al.
Scientific reports, 7(1), 12284-12284 (2017-09-28)
Sex hormone-binding globulin (SHBG) carries sex steroids in blood regulating their bioavailability. Red wine consumption increases plasma SHBG levels, and we have discovered that resveratrol, a polyphenol enriched in red wine, acts specifically through the human constitutive androstane receptor (CAR)
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