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Glafenine (Standard)

CAT: 0804-HY-B1153R-01Size: 5 mgDry Ice: NoHazardous: No
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CAT#:0804-HY-B1153R-01Size:5 mg
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24/48H Stock Items & 2 to 6 Weeks non Stock Items.
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Description
Glafenine (Standard) is the analytical standard of Glafenine. This product is intended for research and analytical applications. Glafenine (Glafenin) is a non-selective, non-steroidal anti-inflammatory drug-based COX-1/COX-2 inhibitor. Glafenine exerts anti-inflammatory, anti-proliferative and anti-cell migration effects by inhibiting the arachidonic acid metabolic pathway and reducing prostaglandin synthesis. Glafenine can induce cell cycle arrest in vascular smooth muscle cells and endothelial cells and reduce the synthesis of the extracellular matrix protein Tenascin. Glafenine can be used in the research of inflammatory-related diseases, vascular restenosis and cystic fibrosis (CF) [1][2][3][4].
CAS Number
3820-67-5
UNSPSC
12352100
Hazard Statement
H315, H319, H335
Target
Apoptosis; CFTR; COX; Endoplasmic Reticulum Oxidoreductase 1 (ERO1) ; Reference Standards
Related Pathways
Anti-infection; Apoptosis; Immunology/Inflammation; Membrane Transporter/Ion Channel; Others
Field of Research
Metabolic Disease; Inflammation/Immunology
Purity
98.59
Smiles
O=C(OCC(O)CO)C1=CC=CC=C1NC2=CC=NC3=CC(Cl)=CC=C23
Molecular Formula
C19H17ClN2O4
Molecular Weight
372.80
Precautions
H315, H319, H335
References & Citations
[1]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|[2]Carlile GW, et al. The NSAID glafenine rescues class 2 CFTR mutants via cyclooxygenase 2 inhibition of the arachidonic acid pathway. Sci Rep. 2022 Mar 17;12 (1) :4595|[3]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.|[4]Chiu AM, et al. High Throughput Assay Identifies Glafenine as a Corrector for the Folding Defect in Corneal Dystrophy-Causing Mutants of SLC4A11. Invest Ophthalmol Vis Sci. 2015 Dec;56 (13) :7739-53.
Shipping Conditions
Blue Ice
Storage Conditions
-20°C, sealed storage, away from light and moisture
Scientific Category
Reference Standards
Clinical Information
Launched

Chemical Information

Glafenine

Glafenine is a carboxylic ester that is 2,3-dihydroxypropyl anthranilate in which the amino group is substituted by a 7-chloroquinolin-4-yl group. A non-steroidal anti-inflammatory drug, glafenine and its hydrochloride salt were used for the relief of all types of pain, but high incidence of anaphylactic reactions resulted in their withdrawal from the market. It has a role as an inhibitor, a non-steroidal anti-inflammatory drug and a non-narcotic analgesic. It is a glycol, a carboxylic ester, an organochlorine compound, an aminoquinoline and a secondary amino compound. It is functionally related to a glycerol and an anthranilic acid.

CAS Number3820-67-5
PubChem CID3474
IUPAC Name2,3-dihydroxypropyl 2-[(7-chloroquinolin-4-yl)amino]benzoate
Molecular FormulaC19H17ClN2O4
Molecular Weight372.8
XLogP3.5
Topological Polar Surface Area91.7
Hydrogen Bond Donor Count3
Hydrogen Bond Acceptor Count6
Rotatable Bond Count7
Heavy Atom Count26
Formal Charge0
Complexity467
SMILES
C1=CC=C(C(=C1)C(=O)OCC(CO)O)NC2=C3C=CC(=CC3=NC=C2)Cl
InChI
InChI=1S/C19H17ClN2O4/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)
InChIKey
GWOFUCIGLDBNKM-UHFFFAOYSA-N
Chemical Structure
2D Structure
2D structure of Glafenine
CAS: 3820-67-5
CID: 3474
Formula: C19H17ClN2O4
MW: 372.8
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight372.8
XLogP33.5
Hydrogen Bond Donor Count3
Hydrogen Bond Acceptor Count6
Rotatable Bond Count7
Exact Mass372.0876847
Monoisotopic Mass372.0876847
Topological Polar Surface Area91.7 Ų
Heavy Atom Count26
Formal Charge0
Complexity467
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count1
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

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Alternative Products

CatalogName
T0055-01Glafenine
MBS3605489-01Glafenine Hydrochloride
A24321-500Glafenine 500mg
A24321-100Glafenine 100mg
sc-495725Glafenine-d4
sc-495670Glafenine N-Oxide

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