CAS 65513-72-6|Glafenine Hydrochloride
| Common Name | Glafenine Hydrochloride | ||
|---|---|---|---|
| CAS Number | 65513-72-6 | Molecular Weight | 409.26300 |
| Density | / | Boiling Point | 618ºC at 760 mmHg |
| Molecular Formula | C19H18Cl2N2O4 | Melting Point | / |
| MSDS | ChineseUSA | Flash Point | 327.6ºC |
Names
| Name | 2,3-dihydroxypropyl 2-[(7-chloroquinolin-4-yl)amino]benzoate,hydrochloride |
|---|---|
| Synonym | More Synonyms |
Glafenine Hydrochloride BiologicalActivity
| Description | Glafenine hydrochloride is a non-narcotic analgesic and non-steroidal anti-inflammatory drug. It is an ABCG2 inhibitor with an IC50 of 3.2 μM. |
|---|---|
| Related Catalog | Signaling Pathways >>Others >>OthersResearch Areas >>Inflammation/Immunology |
| Target | IC50: 3.2 μM (ABCG2)[1] |
| In Vitro | Glafenine increases the surface expressionof mutant CFTR in baby hamster kidney (BHK) cells to 40% of that observed for wild-type CFTR[2]. Glafenine hydrochloride inhibits the proliferation and clonogenic activity of haSMCs and ECs in a dose-dependent manner. A block in the G2/M phase and a reduction in the G1 phase occurr. The migratory ability of haSMCs is impaired in a dose-dependent manner and the extracellular matrix protein tenascin is reduced[3]. |
| In Vivo | Glafenine injection (25 mg/kg i.v.) shows enhanced BLI signal in mice with an average of 2.9-fold signal enhancement over the control. Glafenine causes increases in BLI signal of up to 11.6- and 17.4-fold in two separate HEK293/ABCG2/fLuc xenografts in the same mouse compared to the signals generated by those xenografts immediately before injection[1]. Incubating polarized CFBE41o- monolayers and intestines isolated from mutant CFTR mice with glafenine increases the short-circuit current response to forskolin and genistein. Treatment with glafenine also partially restores total salivary secretion[2]. Glafenine-treated zebrafish shows evidence of endoplasmic reticulum and mitochondrial stress, with disrupted intestinal architecture and halted cell stress responses, alongside accumulation of apoptotic intestinal epithelial cells in the lumen[4]. |
| Cell Assay | Glafenine hydrochloride is added to the culture medium of the smooth muscle cells at three concentrations (10 μM, 50 μM, 100 μM). After 4 days of treatment, cells are harvested and the absolute cell number is counted[3]. |
| Animal Admin | Mice: HEK293/empty/fLuc and HEK293/ABCG2/fLuc cells are implanted subcutaneously into opposite flanks of female nude mice. Five mice are implanted to generate 10 ABCG2-overexpressing xenografts and five controls. Animals are imaged after D-luciferin administration, which is followed by a bolus injection of a single dose of glafenine (25 mg/kg) and continued imaging[1]. |
| References | [1]. Zhang Y, et al. Identification of inhibitors of ABCG2 by a bioluminescence imaging-based high-throughput assay. Cancer Res. 2009 Jul 15;69(14):5867-75. [2]. Robert R, et al. Correction of the Delta phe508 cystic fibrosis transmembrane conductance regulator trafficking defect by the bioavailable compound glafenine. Mol Pharmacol. 2010 Jun;77(6):922-30. [3]. Schöber W, et al. Impact of glafenine hydrochloride on human endothelial cells and human vascular smooth muscle cells: a substance reducing proliferation, migration and extracellular matrix synthesis. Cell Biol Int. 2003;27(12):987-96. [4]. Goldsmith JR, et al. Glafenine-induced intestinal injury in zebrafish is ameliorated by μ-opioid signaling via enhancement of Atf6-dependent cellular stress responses. Dis Model Mech. 2013 Jan;6(1):146-59. |
Chemical & Physical Properties
| Boiling Point | 618ºC at 760 mmHg |
|---|---|
| Molecular Formula | C19H18Cl2N2O4 |
| Molecular Weight | 409.26300 |
| Flash Point | 327.6ºC |
| Exact Mass | 408.06400 |
| PSA | 91.68000 |
| LogP | 4.01680 |
| InChIKey | CEUMONXVSJOJIH-UHFFFAOYSA-N |
| SMILES | Cl.O=C(OCC(O)CO)c1ccccc1Nc1ccnc2cc(Cl)ccc12 |
| Storage condition | 2-8℃ |
Safety Information
| Personal Protective Equipment | Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter |
|---|---|
| Hazard Codes | Xn |
| Risk Phrases | 22 |
| Safety Phrases | 36 |
| RIDADR | NONH for all modes of transport |
| WGK Germany | 3 |
| RTECS | CB2687000 |
Articles1
More Articles| Identification of new MRP4 inhibitors from a library of FDA approved drugs using a high-throughput bioluminescence screen. Biochem. Pharmacol. 93(3) , 380-8, (2015) Multidrug resistance protein 4 (MRP4) effluxes a wide variety of drugs and endogenous signaling molecules from cells and has been proposed as an attractive therapeutic target in several solid tumors, ... |
Synonyms
| Glafenine hydrochloride |
| Prestwick_628 |
| Glafenine (hydrochloride) |
