PK11195

Names

[ Name ]:
PK11195

[Synonym ]:
N-sec-Butyl-1-(2-chlorophenyl)-N-methyl-3-isoquinolinecarboxamide
UNII:YNF83VN1RL
MFCD00069334
3-Isoquinolinecarboxamide, 1-(2-chlorophenyl)-N-methyl-N-(1-methylpropyl)-
N-sec-Butyl-1-(2-chlorophenyl)-N-methylisoquinoline-3-carboxamide

Biological Activity

[Description]:

PK-11195 is a ligand of translocator protein (TSPO), which targets Leishmania chemotherapy, with IC50s of 14.2 μM, 8.2 μM, 3.5 μM for L. amazonensis, L. major and L. braziliensis, respectively.

[Related Catalog]:

Signaling Pathways >> Anti-infection >> Parasite

Research Areas >> Infection

[Target]

IC50: 14.2 μM (L. amazonensis), 8.2 μM (L. major), 3.5 μM (L. braziliensis)[1].

[In Vitro]

Median IC50 values for PK-11195 are 14.2 μM for L. amazonensis, 8.2 μM for L. major, and 3.5 μM for L. braziliensis. The selective index value for L. amazonensis is 13.7, indicating the safety of PK-11195 for future testing in mammals. Time-and dose-dependent reductions in the percentage of infected macrophages, the number of parasites per infected macrophage, and the number of viable intracellular parasites are observed. Electron microscopy reveals some morphological alterations suggestive of autophagy. Interestingly, MCP-1 and superoxide levels are reduced in L. amazonensis-infected macrophages treated with PK-11195[1].

[References]

[1]. Guedes CES, et al. In vitro evaluation of the anti-leishmanial activity and toxicity of PK-11195. Mem Inst Oswaldo Cruz. 2018 Feb 5;113(4):e170345.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.2±0.1 g/cm3

[ Boiling Point ]:
511.7±45.0 °C at 760 mmHg

[ Melting Point ]:
74-75

[ Molecular Formula ]:
C₂₁H₂₁ClN₂O

[ Molecular Weight ]:
352.857

[ Flash Point ]:
263.3±28.7 °C

[ Exact Mass ]:
352.134247

[ PSA ]:
33.20000

[ LogP ]:
4.58

[ Vapour Pressure ]:
0.0±1.3 mmHg at 25°C

[ Index of Refraction ]:
1.611

[ Storage condition ]:
Store at RT

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: NW6987000

CHEMICAL NAME :: 3-Isoquinolinecarboxamide, 1-(2-chlorophenyl)-N-methyl-N-(1-methylpropyl)-

CAS REGISTRY NUMBER :: 85532-75-8

LAST UPDATED :: 199612

DATA ITEMS CITED :: 2

MOLECULAR FORMULA :: C21-H21-Cl-N2-O

MOLECULAR WEIGHT :: 352.89

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

MUTATION DATA

TYPE OF TEST :: Unscheduled DNA synthesis

TEST SYSTEM :: Rodent - mouse Fibroblast

DOSE/DURATION :: 1 nmol/L

REFERENCE :: CALEDQ Cancer Letters (Shannon, Ireland). (Elsevier Scientific Pub. Ireland Ltd., POB 85, Limerick, Ireland) V.1- 1975- Volume(issue)/page/year: 49,115,1990

Safety Information

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
3

[ RTECS ]:
NW6987000

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Articles

Inhibitory action of 1-(2-chlorophenyl)-N-methyl-N-(1-methylpropyl)-3-isoquinolinecarboxam ide (PK 11195) on some mononuclear phagocyte functions.

Biochem. Pharmacol. 59 , 1305-1314, (2000)

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 ...

Chronic exposure of rat primary astrocyte cultures to manganese results in increased binding sites for the 'peripheral-type' benzodiazepine receptor ligand 3H-PK 11195.

Neurosci. Lett. 271 , 5, (1999)

Alterations of 'peripheral-type' benzodiazepine receptors (PTBRs) in brain are a feature of hepatic encephalopathy (HE). Although ammonia toxicity has been implicated in the disorder, recent findings ...

Pharmacokinetics of the peripheral benzodiazepine receptor antagonist, PK 11195, in rats. The effect of dose and gender.

Pharmacol. Res. 41 , 461-468, (2000)

In spite of the extensive use of the peripheral benzodiazepine (BZ) receptor antagonist, PK 11195 (PK), in pharmacological studies, there is a lack of information of its pharmacokinetics in the rat. I...