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Merck
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Key Documents

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SML2468

Sigma-Aldrich

CINPA1

≥98%

Sinónimos:

CAR Inhibitor not PXR Activator 1, Ethyl 5-(2-(diethylamino)acetyl)-10,11-dihydro-5H-dibenzo[b,f]azepin-3-ylcarbamate, [5-[(Diethylamino)acetyl]-10,11-dihydro-5H-dibenz[b,f]azepin-3-yl]carbamic acid ethyl ester

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About This Item

Fórmula empírica (notación de Hill):
C23H29N3O3
Número de CAS:
102636-74-8
Peso molecular:
395.49
MDL number:
MFCD00288296
UNSPSC Code:
12352200
NACRES:
NA.77

assay

≥98%

form

powder

color

white to beige

solubility

DMSO: 2 mg/mL, clear

storage temp.

−20°C

SMILES string

O=C(CN(CC)CC)N1C2=C(C=CC=C2)CCC3=C1C=C(NC(OCC)=O)C=C3

Biochem/physiol Actions

CINPA1 is a ligand-binding domain (LBD)-targeting constitutive androstane receptor (CAR) inhibitor that prevents CAR recruitment to promoter regions of regulated genes (by >85%; 1 μM CINPA1 against 0.1 μM CITCO-induced CAR recruitment to CYP2B6 or CYP3A4 promoters; human hepatocytes) by altering CAR-coregulator interactions. CINPA1 inhibits CAR-mediated transcription in a potent (IC50 = 70 nM; HepG2-hCAR1 CYP2B6-luc reporter cells) and selective manner with only weak PXR antagonist potency (68% inhibition by 18 μM CINPA1 against 5 μM rifampicin; HepG2-PXR reporter cells) and no cytotoxicity or agonist/antagonist activity toward FXR, GR, LXRα/β, PPARγ, RXRα/β, VDR.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Wenwei Lin et al.
European journal of medicinal chemistry, 108, 505-528 (2015-12-31)
Constitutive androstane receptor (CAR, NR1I3) and pregnane X receptor (PXR, NR1I2) are master regulators of endobiotic and xenobiotic metabolism and disposition. Because CAR is constitutively active in certain cellular contexts, inhibiting CAR might reduce drug-induced hepatotoxicity and resensitize drug-resistant cancer
Milu T Cherian et al.
Biochemical pharmacology, 152, 211-223 (2018-04-03)
The constitutive androstane receptor (CAR) and pregnane X receptor (PXR) are xenobiotic sensors that regulate the expression of drug-metabolizing enzymes and efflux transporters. CAR activation promotes drug elimination, thereby reducing therapeutic effectiveness, or causes adverse drug effects via toxic metabolites.
Baddreddine Boussadia et al.
Experimental neurology, 283(Pt A), 39-48 (2016-06-01)
Nuclear receptors (NRs) are a group of transcription factors emerging as players in normal and pathological CNS development. Clinically, an association between the constitutive androstane NR (CAR) and cognitive impairment was proposed, however never experimentally investigated. We wished to test
Milu T Cherian et al.
Drug metabolism and disposition: the biological fate of chemicals, 44(11), 1759-1770 (2016-08-16)
The constitutive androstane receptor (CAR) regulates the expression of genes involved in drug metabolism and other processes. A specific inhibitor of CAR is critical for modulating constitutive CAR activity. We recently described a specific small-molecule inhibitor of CAR, CINPA1 (ethyl
Judith Jeske et al.
Archives of toxicology, 91(6), 2375-2390 (2017-03-16)
Unintentional activation of xenosensing nuclear receptors pregnane X receptor (PXR) and/or constitutive androstane receptor (CAR) by clinical drug use is known to produce severe side effects in patients, which may be overcome by co-administering antagonists. However, especially antagonizing CAR is
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