| Size | Price | Stock | Qty |
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| 100mg |
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| 250mg |
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| 500mg |
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| Other Sizes |
| Targets |
Glafenine's primary mechanism of action involves the non-selective inhibition of cyclooxygenase (COX)-1 and COX-2 enzymes. By inhibiting these enzymes, it blocks the arachidonic acid metabolic pathway and reduces prostaglandin synthesis, which are key mediators of pain and inflammatory responses. Additionally, glafenine acts as a corrector of class 2 CFTR mutants, such as F508del-CFTR, via cyclooxygenase 2 inhibition of the arachidonic acid pathway. It also targets apoptosis pathways and endoplasmic reticulum oxidoreductase 1 (ERO1).
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| ln Vitro |
In vitro, glafenine exerts anti-inflammatory, anti-proliferative, and anti-cell migration effects by inhibiting the arachidonic acid metabolic pathway and reducing prostaglandin synthesis. It can induce cell cycle arrest in vascular smooth muscle cells and endothelial cells and reduce the synthesis of the extracellular matrix protein Tenascin. Glafenine inhibits COX-2 in the arachidonic acid pathway and rescues class 2 CFTR mutants. It has been used in research related to inflammatory diseases, vascular restenosis, and cystic fibrosis.
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| ln Vivo |
In vivo, glafenine produces analgesic and anti-inflammatory effects by reducing the production of prostaglandins. Its pharmacological activity is consistent with its mechanism of action as a non-steroidal anti-inflammatory drug. Glafenine-induced intestinal injury in zebrafish has been shown to be ameliorated by μ-opioid signaling via enhancement of Atf6-dependent cellular stress responses. It has also been identified as a corrector for the folding defect in corneal dystrophy-causing mutants of SLC4A11.
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| Enzyme Assay |
In vitro enzyme assays for glafenine typically measure its ability to inhibit COX-1 and COX-2 activity. The enzyme is incubated with arachidonic acid in the presence of increasing concentrations of the compound. Prostaglandin formation is measured by ELISA or radioimmunoassay. IC50 values are calculated from dose-response curves. Glafenine exhibits COX-2 inhibition in the arachidonic acid pathway.
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| Cell Assay |
Cell-based assays for glafenine involve treating various cell lines with the compound and measuring cell proliferation, migration, and prostaglandin production. Its effects on vascular smooth muscle cells and endothelial cells are assessed by measuring cell cycle arrest. The compound's ability to rescue F508del-CFTR mutants can be evaluated in CFTR-expressing cell lines. High throughput assays have identified glafenine as a corrector for the folding defect in corneal dystrophy-causing mutants of SLC4A11.
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| Animal Protocol |
In vivo animal studies for glafenine typically involve administration to animal models of pain and inflammation. The compound's efficacy and safety profile are evaluated. Glafenine-induced intestinal injury in zebrafish has been studied, and it was found to be ameliorated by μ-opioid signaling via enhancement of Atf6-dependent cellular stress responses.
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| ADME/Pharmacokinetics |
Glafenine is soluble in DMSO at 75 mg/mL and in ethanol at 4 mg/mL, but is insoluble in water. For in vivo oral administration, it can be prepared as a homogeneous suspension in CMC-Na at ≥5 mg/mL. For injection, it can be formulated as a clear solution using 5% DMSO, 40% PEG300, 5% Tween 80, and 50% ddH2O.
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| Toxicity/Toxicokinetics |
Glafenine has been associated with adverse effects, including hypersensitivity reactions and anaphylactic shock. It has been withdrawn from the market in several countries due to safety concerns, including the risk of anaphylactic shock and renal toxicity. It should be handled with caution in research settings.
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| Additional Infomation |
Glafenine is a carboxylic acid ester, specifically 2,3-dihydroxypropyl anthranilate, in which the amino group is substituted with a 7-chloroquinoline-4-yl group. Glafenine and its hydrochloride salt were once used as nonsteroidal anti-inflammatory drugs (NSAIDs) to relieve various types of pain, but were eventually withdrawn from the market due to a high incidence of allergic reactions. It has a dual role as a non-narcotic analgesic, NSAID, and inhibitor. It is an organochlorine compound, a secondary amino compound, a diol, a carboxylic acid ester, and an aminoquinoline compound. Its structure is related to glycerol and anthranilic acid. Glafenine is an analgesic anthranilic acid derivative that was once used to relieve various types of pain. Glafenine has been withdrawn from the US market.
Glafenine (Glafenin) is a non-selective COX-1/COX-2 inhibitor with additional activity as a CFTR corrector. Its dual mechanism of action makes it a valuable research tool for studying inflammation, pain, and cystic fibrosis. It is not approved for clinical use in many countries. It is also known to induce cell cycle arrest in vascular smooth muscle cells and endothelial cells. |
| Molecular Formula |
C18H17CLN2O4
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|---|---|
| Molecular Weight |
372.81
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| Exact Mass |
372.088
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| CAS # |
3820-67-5
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| Related CAS # |
Glafenine hydrochloride;65513-72-6
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| PubChem CID |
3474
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| Appearance |
Light yellow to yellow solid powder
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| Density |
1.428g/cm3
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| Boiling Point |
618ºC at 760 mmHg
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| Melting Point |
170℃
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| Flash Point |
327.6ºC
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| Index of Refraction |
1.696
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| LogP |
3.214
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| Hydrogen Bond Donor Count |
3
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| Hydrogen Bond Acceptor Count |
6
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| Rotatable Bond Count |
7
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| Heavy Atom Count |
26
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| Complexity |
467
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| Defined Atom Stereocenter Count |
0
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| InChi Key |
GWOFUCIGLDBNKM-UHFFFAOYSA-N
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| InChi Code |
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)
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| Chemical Name |
2,3-dihydroxypropyl 2-[(7-chloroquinolin-4-yl)amino]benzoate
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| Synonyms |
Glafenina; Glafenin; Glafenine
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| HS Tariff Code |
2934.99.9001
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| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
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| Solubility (In Vitro) |
DMSO : ~100 mg/mL (~268.24 mM)
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|---|---|
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.08 mg/mL (5.58 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: 2.08 mg/mL (5.58 mM) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), suspension solution; with ultrasonication. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. View More
Solubility in Formulation 3: ≥ 2.08 mg/mL (5.58 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 2.6823 mL | 13.4117 mL | 26.8233 mL | |
| 5 mM | 0.5365 mL | 2.6823 mL | 5.3647 mL | |
| 10 mM | 0.2682 mL | 1.3412 mL | 2.6823 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
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