1-(2-Chlorophenyl)-N-methyl-N-(1-methylpropyl)-3-isoquinolinecarboxamide
- CAS No.
- 85532-75-8
- Chemical Name:
- 1-(2-Chlorophenyl)-N-methyl-N-(1-methylpropyl)-3-isoquinolinecarboxamide
- Synonyms
- pk11995;PK 11195;PK 11195(RP 52028);PK 11195 PERIPHERAL BENZODIAZE;PK11195, benzodiazepine receptor antagonist;1-(2-chlorophenyl)-N-methyl-*N-(1-methylpropyl)-3;chlorophenylmethyl(1-methylpropyl)isoquinolinecarboxamide;1-(2-Chlorophenyl)-N-(1-methylpropyl)-3-isoquinolinecarboxamide;1-(2-chlorophenyl)-n-methyl-n-(1-methylpropyl)-3-isoquinolinecarboxamid;N-Methyl-N-(1-methylpropyl)-1-(2-chlorophenyl)-3-isoquinolinecarboxamide
- CBNumber:
- CB6102434
- Molecular Formula:
- C21H21ClN2O
- Molecular Weight:
- 352.86
- MDL Number:
- MFCD00069334
- MOL File:
- 85532-75-8.mol
- MSDS File:
- SDS
- TDS File:
- TDS
| Boiling point | 511.7±45.0 °C(Predicted) |
|---|---|
| Density | 1.179±0.06 g/cm3(Predicted) |
| storage temp. | Store at RT |
| solubility | Soluble in DMSO (up to 25 mg/ml) or in Ethanol (up to 15 mg/ml). |
| form | White crystalline powder. |
| pka | 1.76±0.50(Predicted) |
| color | White |
| Stability | Stable for 1 year from date of purchase as supplied. Solutions in DMSO may be stored under nitrogen or argon at -20° for up to 1 month. |
| 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 |
| InChIKey | RAVIZVQZGXBOQO-UHFFFAOYSA-N |
| SMILES | Clc1c(cccc1)c2nc(cc3c2cccc3)C(=O)N(C(CC)C)C |
| CAS DataBase Reference | 85532-75-8(CAS DataBase Reference) |
| FDA UNII | YNF83VN1RL |
| UNSPSC Code | 12352200 |
| NACRES | NA.77 |
SAFETY
Risk and Safety Statements
| WGK Germany | 3 |
|---|---|
| RTECS | NW6987000 |
| Storage Class | 11 - Combustible Solids |
1-(2-Chlorophenyl)-N-methyl-N-(1-methylpropyl)-3-isoquinolinecarboxamide price More Price(47)
| Manufacturer | Product number | Product description | CAS number | Packaging | Price | Updated | Buy |
|---|---|---|---|---|---|---|---|
| Sigma-Aldrich | C0424 | PK 11195 | 85532-75-8 | 10mg | $153 | 2026-04-30 | Buy |
| Sigma-Aldrich | C0424 | PK 11195 | 85532-75-8 | 50mg | $528 | 2026-04-30 | Buy |
| Sigma-Aldrich | 5.05981 | PK11195 - CAS 85532-75-8 - Calbiochem | 85532-75-8 | 10mg | $97.5 | 2026-04-30 | Buy |
| Cayman Chemical | 10525 | PK11195 ≥98% | 85532-75-8 | 10mg | $90 | 2026-04-30 | Buy |
| Cayman Chemical | 10525 | PK11195 ≥98% | 85532-75-8 | 50mg | $306 | 2026-04-30 | Buy |
1-(2-Chlorophenyl)-N-methyl-N-(1-methylpropyl)-3-isoquinolinecarboxamide Chemical Properties, Uses, Production
Description
PK-11195 (85532-75-8) is a selective and potent peripheral benzodiazepine receptor, PBR (or TSPO, translocator protein) antagonist.1,2 It has been shown to chemosensitize tumor cells to a variety of chemotherapeutic agents via PBR-independent pathways.3,4 PK-11195 is also able to induce apoptosis in a variety of cell lines.5-7
Uses
PK 11195 is a high affinity peripheral benzodiazepine receptor (PBR) ligand. PK 11195 has been shown to regulate protein phosphorylation in rat brain mitochondria under control of Ca2+. PK11195 promotes mitochondrial apoptosis and blocks P-glycoprotein (Pgp)-mediated drug efflux to chemosensitize cancer cells.
Definition
ChEBI: A monocarboxylic acid amide obtained by formal condensation of the carboxy group of 1-(2-chlorophenyl)isoquinoline-3-carboxylic acid with the amino group of sec-butylmethylamine
Biological Activity
Possesses high affinity for the MDR (peripheral benzodiazepine receptor) without binding to other known neurotransmitter receptors.
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
Room temperature
References
[1] Peripheral benzodiazepine binding sites: effect of PK 11195, 1-(2-chlorophenyl)-N-methyl-N-(1-methylpropyl)-3-isoquinolinecarboxamide. I. In vitro studies
[2] Peripheral benzodiazepine binding sites: effect of PK 11195, 1-(2-chlorophenyl)-N-methyl-N-(1-methylpropyl)-3-isoquinolinecarboxamide. II. In vivo studies
[3] ROSA-ANA GONZALEZ-POLO. PK11195 potently sensitizes to apoptosis induction independently from the peripheral benzodiazepin receptor[J]. Oncogene, 2005, 24 51: 7503-7513. DOI:10.1038/sj.onc.1208907
[4] ROLAND B WALTER. PK11195, a peripheral benzodiazepine receptor (pBR) ligand, broadly blocks drug efflux to chemosensitize leukemia and myeloma cells by a pBR-independent, direct transporter-modulating mechanism.[J]. Blood, 2005, 106 10: 3584-3593. DOI:10.1182/blood-2005-02-0711
[5] BEATRICE CHELLI . Peripheral benzodiazepine receptor ligands: mitochondrial transmembrane potential depolarization and apoptosis induction in rat C6 glioma cells[J]. Biochemical pharmacology, 2004, 68 1: Pages 125-134. DOI:10.1016/j.bcp.2004.03.008
[6] ANDREAS P. SUTTER . Peripheral benzodiazepine receptor ligands induce apoptosis and cell cycle arrest in human hepatocellular carcinoma cells and enhance chemosensitivity to paclitaxel, docetaxel, doxorubicin and the Bcl-2 inhibitor HA14-1[J]. Journal of Hepatology, 2004, 41 5: Pages 799-807. DOI:10.1016/j.jhep.2004.07.015
[7] K MAASER. Specific ligands of the peripheral benzodiazepine receptor induce apoptosis and cell cycle arrest in human colorectal cancer cells[J]. British Journal of Cancer, 2001, 85 11: 1771-1780. DOI:10.1054/bjoc.2001.2181
1-(2-Chlorophenyl)-N-methyl-N-(1-methylpropyl)-3-isoquinolinecarboxamide Preparation Products And Raw materials
Raw materials
Preparation Products
1-(2-Chlorophenyl)-N-methyl-N-(1-methylpropyl)-3-isoquinolinecarboxamide Suppliers
| Supplier | Tel | Country | ProdList | Advantage | |
|---|---|---|---|---|---|
| CHAUNGZERUI | 15301951213 | aolinaijiao@sina.com | China | 34 | 58 |
| J & K SCIENTIFIC LTD. | 18210857532 18210857532 | jkinfo@jkchemical.com | China | 96815 | 76 |
| 3B Pharmachem (Wuhan) International Co.,Ltd. | 18930552037 | 3bsc@sina.com | China | 15813 | 69 |
| BOC Sciences | 1-631-485-4226; 16314854226 | info@bocsci.com | United States | 9920 | 65 |
| Shanghai Tauto Biotech Co., Ltd. | 021-51320588 | tauto@tautobiotech.com | China | 3984 | 66 |
| Sigma-Aldrich | 021-61415566 800-8193336 | orderCN@merckgroup.com | China | 51389 | 80 |
| EMMX Biotechnology LLC | 888-539-0666 | info@emmx.com | United States | 8435 | 60 |
| Shanghai EFE Biological Technology Co., Ltd. | 021-65675885 18964387627 | info@efebio.com | China | 9799 | 58 |
| Shanghai Chaolan Chemical Technology Center | QQ：65489617 13301690235 | Sales@ATKchemical.com | China | 9729 | 58 |
| Tianjin heowns Biochemical Technology Co., Ltd. | 400-6387771-6039 18920764717 | sales@heowns.com | China | 24650 | 60 |
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