![1-GLYCERYL N-[7-CHLORO-4-QUINOLYL]ANTHRANILATE HYDROCHLORIDE structure, CAS 65513-72-6](/structures/180000/179302_3_65513_72_6.png)
| Chemical & Physical Properties | |
|---|---|
| CAS Number | 65513-72-6 |
| Catalog No. | 2A-2178627 |
| Chinese Name | 格拉非宁 盐酸盐 |
| Synonyms | Glafenine hydrochloride; Prestwick_628; Glafenine (hydrochloride) |
| Molecular Formula | C19H18Cl2N2O4 |
| Molecular Weight | 409.26300 |
| Boiling Point | 618ºC at 760 mmHg |
| Storage Condition | 2-8℃ |
| Application | Glafenine hydrochloride is a non-narcotic analgesic and non-steroidal anti-inflammatory drug. It is an ABCG2 inhibitor with an IC50 value of 3.2 μM. |
| SMILES | Cl.O=C(OCC(O)CO)c1ccccc1Nc1ccnc2cc(Cl)ccc12 |
| InChI | InChI=1S/C19H17ClN2O4.ClH/c20-12-5-6-14-17(7-8-21-18(14)9-12)22-16-4-2-1-3-15(16)19(25)26-11-13(24)10-23;/h1-9,13,23-24H,10-11H2,(H,21,22);1H |
| InChI Key | CEUMONXVSJOJIH-UHFFFAOYSA-N |
| Hazard Symbols | transportation |
| MSDS | msds/179302_2_65513_72_6.pdf |
| Bioactivity | 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 >> Others Research 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℃ |
| Use of | 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. Properties Name 2,3-dihydroxypropyl 2-[(7-chloroquinolin-4-yl)amino]benzoate,hydrochloride Synonym More Synonyms Glafenine Hydrochloride Biological Activity 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 >> Others Research Areas >> Inflammation/Immunology IC50: 3.2 μM (ABCG2)[1] 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]. 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. [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 Exact Mass 408.06400 PSA 91.68000 LogP 4.01680 InChIKey CEUMONXVSJOJIH-UHFFFAOYSA-N Storage condition 2-8℃ |
| Transport Info | Shipping Name: UN |
| MSDS Transport Info | Module 14. Shipping information European Land Transport Dangerous Regulations: -International Maritime Dangerous Regulations: -International Air Transport Dangerous Regulations: - 14.2 United Nations shipping name European Land Transport Dangerous Regulations: Non-dangerous goods IMDG Code: Non-dangerous goods International air transport dangerous goods regulations: non-dangerous goods 14.3 Transport hazard categories European Land Transport Dangerous Regulations: -International Maritime Dangerous Regulations: -International Air Transport Dangerous Regulations: - 14.4 Package group European Land Transport Dangerous Regulations: -International Maritime Dangerous Regulations: -International Air Transport Dangerous Regulations: - 14.5 Environmental hazards European Land Transport Danger Regulations: No International Maritime Danger Regulations International Air Transport Danger Regulations: No Marine pollutants (yes/no): No 14.6 Special reminder to users No data available |
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