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C0424

Sigma-Aldrich

PK 11195

peripheral benzodiazepine antagonist, powder

Synonym(s):

1-(2-Chlorophenyl)-N-methyl-N-(1-methylpropyl)-3-isoquinolinecarboxamide

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About This Item

Empirical Formula (Hill Notation):
C21H21ClN2O
CAS Number:
85532-75-8
Molecular Weight:
352.86
MDL number:
MFCD00069334
UNSPSC Code:
12352200
PubChem Substance ID:
24278822
NACRES:
NA.77

Key Documents

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Product Name

PK 11195,

form

powder

Quality Level

200

SMILES string

CCC(C)N(C)C(=O)c1cc2ccccc2c(n1)-c3ccccc3Cl

InChI

1S/C21H21ClN2O/c1-4-14(2)24(3)21(25)19-13-15-9-5-6-10-16(15)20(23-19)17-11-7-8-12-18(17)22/h5-14H,4H2,1-3H3

InChI key

RAVIZVQZGXBOQO-UHFFFAOYSA-N

Gene Information

human ... BZRAP1(9256), TSPO(706)
rat ... Gabra2(29706), Tspo(24230)

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Application

PK 11195 has been used as an inhibitor of peripheral benzodiazepine receptor (PBR) homologs in primitive erythrocytes of embryos and in osteosarcoma cytoplasmic hydrids. It has also been used as an unlabelled competitive binder in in vitro autoradiography experiments in cardiac tissue sections.

Biochem/physiol Actions

PK 11195 is a peripheral benzodiazepine antagonist. It is also an antagonist for human constitutive androstane receptor (hCAR) and human pregnane X receptor (PXR). In human primary hepatocytes, PK 11195 upon demethylation elicits agonist functionality towards the receptor hCAR. PK 11195 also antagonise B-cell lymphoma 2 (Bcl-2) and may serve as a potential compound for mitochondrial targeting therapies and in the treatment of cholangiocarcinoma.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
057M4049V
13190107
079M4143V
078M4050V
13160719

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Eryn L Werry et al.
European journal of pharmaceutical sciences : official journal of the European Federation for Pharmaceutical Sciences, 96, 186-192 (2016-10-28)
The 18kDa translocator protein (TSPO) is a target for novel glioblastoma therapies due to its upregulation in this cancer and relatively low levels of expression in the healthy cortex. The pyrazolo[1,5-a]pyrimidine acetamides, exemplified by DPA-713 and DPA-714, are a class
Molecular basis of metabolism-mediated conversion of PK11195 from an antagonist to an agonist of the constitutive androstane receptor
Mackowiak B, et al.
Molecular Pharmacology, 92(1), 75-87 (2017)
Ségolène Hescot et al.
Oncotarget, 8(66), 109924-109940 (2018-01-05)
Mitotane (o,p'DDD), the most effective drug in adrenocortical carcinoma, concentrates into the mitochondria and impacts mitochondrial functions. To address the molecular mechanisms of mitotane action and to identify its potential target, metabolomic and lipidomic approaches as well as imaging analyses
A Klegeris et al.
Biochemical pharmacology, 59(10), 1305-1314 (2000-03-29)
Peripheral benzodiazepine receptors (PBRs) are widely distributed throughout the body, but their functions are unknown. They are found on mononuclear phagocytes, and they are up-regulated in a number of neurological and other disease states. We explored the functional consequences of
Soria Iatmanen-Harbi et al.
International journal of molecular sciences, 20(6) (2019-03-25)
The optimization of translocator protein (TSPO) ligands for Positron Emission Tomography as well as for the modulation of neurosteroids is a critical necessity for the development of TSPO-based diagnostics and therapeutics of neuropsychiatrics and neurodegenerative disorders. Structural hints on the
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