Glafenine | CAS# 3820-67-5

MedKoo Cat#: 591066 | Name: Glafenine

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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Glafenine is an anthranilic acid derivative with analgesic properties used for the relief of all types of pain.

Chemical Structure

Glafenine

CAS#3820-67-5

Theoretical Analysis

MedKoo Cat#: 591066

Name: Glafenine

CAS#: 3820-67-5

Chemical Formula: C18H17ClN2O4

Exact Mass: 372.0877

Molecular Weight: 372.81

Elemental Analysis: C, 61.21; H, 4.60; Cl, 9.51; N, 7.51; O, 17.17

Price and Availability

Size	Price	Availability
250mg	USD 250.00	2 Weeks
1g	USD 550.00	2 Weeks
5g	USD 950.00	2 Weeks

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Synonym

Glafenine; Glafenin; Glafenina; Glaphenine; Glycerylaminophenaquine; Glaphenin; R 1707; R1707; R-1707; NSC 757808; NSC757808; NSC 757808

IUPAC/Chemical Name

2,3-Dihydroxypropyl N-(7-chloro-4-quinolyl) anthranilate

InChi Key

GWOFUCIGLDBNKM-UHFFFAOYSA-N

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)

SMILES Code

O=C(OCC(O)CO)C1=CC=CC=C1NC2=CC=NC3=CC(Cl)=CC=C23

Appearance

Solid powder

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO

Shelf Life

>2 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.9001

More Info

Product Data

Product Data

Instruction

View handling instruction

Biological target:

Glafenine is a non-steroidal anti-inflammatory drug (NSAID), is a non-narcotic analgesic agent, widely used for the treatment of pains of various origins.

In vitro activity:

The experimental rationale is that if COX inhibition by glafenine reduces PGH2 production and promotes CFTR rescue, providing exogenous PGH2 should counteract this and reduce glafenine correction. To test this hypothesis, this study treated BHK cells expressing F508del-CFTR with glafenine (10 µM) or Trikafta in the presence or absence of PGH2 (1 µM) for 24 h and then assessed F508del-CFTR rescue by measuring CFTR surface expression in this study’s HTS assay (n = 4) (Fig. 5B). As shown in Fig. 5B, glafenine alone rescued CFTR, and this correction was abolished in the presence of PGH2; in contrast, PGH2 had no effect on the Trikafta mediated correction. These results suggest that a decrease in PGH2 is essential for glafenine-mediated F508del-CFTR correction. Reference: Sci Rep. 2022 Mar 17;12(1):4595. https://pubmed.ncbi.nlm.nih.gov/35302062/

In vivo activity:

This study next tested if serial Glafenine exposure resulted in intestinal inflammation. Gene-expression analysis of dissected digestive tracts revealed marked induction of mRNAs encoding proinflammatory effectors (il1b, saa, duox, mmp9, mmp13a, and tnfa) and regulators of innate immune signaling (stat3, socs3a, socs3b, and nfkbiaa) (Fig. 2A) in Glafenine-treated larvae. Moreover, this study observed intestinal leukocyte infiltration, with increased numbers of intestine-associated lyz+ polymorphonuclear cells (PMNs) and mpeg1+ macrophages at 48 h into the treatment regimen. By 72 h, PMN numbers typically returned to control levels (although in some experiments we observed significant PMN infiltration at this time point) (Fig. 2B and SI Appendix, Fig. S8A), while macrophage numbers remained elevated (Fig. 2C and SI Appendix, Fig. S8B). Together, these findings demonstrate Glafenine induces intestinal inflammation concomitant with IEC loss. Reference: Proc Natl Acad Sci U S A. 2019 Aug 20;116(34):16961-16970. https://pubmed.ncbi.nlm.nih.gov/31391308/

	Solvent	mg/mL	mM
Solubility
	DMSO	100.0	268.24

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 372.81 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:

1. Carlile GW, Yang Q, Matthes E, Liao J, Birault V, Sneddon HF, Poole DL, Hall CJ, Hanrahan JW, Thomas DY. 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. doi: 10.1038/s41598-022-08661-8. PMID: 35302062; PMCID: PMC8930988. 2. Espenschied ST, Cronan MR, Matty MA, Mueller O, Redinbo MR, Tobin DM, Rawls JF. Epithelial delamination is protective during pharmaceutical-induced enteropathy. Proc Natl Acad Sci U S A. 2019 Aug 20;116(34):16961-16970. doi: 10.1073/pnas.1902596116. Epub 2019 Aug 7. PMID: 31391308; PMCID: PMC6708343.

In vitro protocol:

In vivo protocol:

1. Espenschied ST, Cronan MR, Matty MA, Mueller O, Redinbo MR, Tobin DM, Rawls JF. Epithelial delamination is protective during pharmaceutical-induced enteropathy. Proc Natl Acad Sci U S A. 2019 Aug 20;116(34):16961-16970. doi: 10.1073/pnas.1902596116. Epub 2019 Aug 7. PMID: 31391308; PMCID: PMC6708343.

1: Alka K, Casey JR. Molecular phenotype of SLC4A11 missense mutants: Setting the stage for personalized medicine in corneal dystrophies. Hum Mutat. 2018 May;39(5):676-690. doi: 10.1002/humu.23401. Epub 2018 Feb 2. PubMed PMID: 29327391. 2: Burckhardt BC, Henjakovic M, Hagos Y, Burckhardt G. Differential Interaction of Dantrolene, Glafenine, Nalidixic Acid, and Prazosin with Human Organic Anion Transporters 1 and 3. J Pharmacol Exp Ther. 2017 Sep;362(3):450-458. doi: 10.1124/jpet.117.241406. Epub 2017 Jun 19. PubMed PMID: 28630284. 3: Goldsmith JR, Tomkovich S, Jobin C. A Rapid Screenable Assay for Compounds That Protect Against Intestinal Injury in Zebrafish Larva. Methods Mol Biol. 2016;1422:281-93. doi: 10.1007/978-1-4939-3603-8_25. PubMed PMID: 27246041. 4: Sen S, An H, Menezes P, Oakes J, Eron J, Lin W, Robertson K, Powers W. Increased Cortical Cerebral Blood Flow in Asymptomatic Human Immunodeficiency Virus-Infected Subjects. J Stroke Cerebrovasc Dis. 2016 Aug;25(8):1891-5. doi: 10.1016/j.jstrokecerebrovasdis.2016.03.045. Epub 2016 May 5. PubMed PMID: 27160382; PubMed Central PMCID: PMC5302846. 5: Chiu AM, Mandziuk JJ, Loganathan SK, Alka K, Casey JR. 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. doi: 10.1167/iovs.15-17802. PubMed PMID: 26641551. 6: Cheung L, Yu DM, Neiron Z, Failes TW, Arndt GM, Fletcher JI. Identification of new MRP4 inhibitors from a library of FDA approved drugs using a high-throughput bioluminescence screen. Biochem Pharmacol. 2015 Feb 1;93(3):380-8. doi: 10.1016/j.bcp.2014.11.006. Epub 2014 Nov 22. PubMed PMID: 25462817. 7: Goldsmith JR, Cocchiaro JL, Rawls JF, Jobin C. 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. doi: 10.1242/dmm.009852. Epub 2012 Aug 23. PubMed PMID: 22917923; PubMed Central PMCID: PMC3529347. 8: Wen B, Moore DJ. Bioactivation of glafenine by human liver microsomes and peroxidases: identification of electrophilic iminoquinone species and GSH conjugates. Drug Metab Dispos. 2011 Sep;39(9):1511-21. doi: 10.1124/dmd.111.039396. Epub 2011 May 31. PubMed PMID: 21628497. 9: Selver OB, Barash A, Ahmed M, Wolosin JM. ABCG2-dependent dye exclusion activity and clonal potential in epithelial cells continuously growing for 1 month from limbal explants. Invest Ophthalmol Vis Sci. 2011 Jun 17;52(7):4330-7. doi: 10.1167/iovs.10-5897. PubMed PMID: 21421882; PubMed Central PMCID: PMC3175974. 10: Walash M, Belal F, Eid M, el-Abass SA. Simultaneous HPLC determination of thiocolchicoside and glafenine as well as thiocolchicoside and floctafenine in their combined dosage forms. J Chromatogr Sci. 2011 Feb;49(2):159-64. PubMed PMID: 21223643. 11: Robert R, Carlile GW, Liao J, Balghi H, Lesimple P, Liu N, Kus B, Rotin D, Wilke M, de Jonge HR, Scholte BJ, Thomas DY, Hanrahan JW. 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. doi: 10.1124/mol.109.062679. Epub 2010 Mar 3. PubMed PMID: 20200141. 12: Zhang Y, Byun Y, Ren YR, Liu JO, Laterra J, Pomper MG. Identification of inhibitors of ABCG2 by a bioluminescence imaging-based high-throughput assay. Cancer Res. 2009 Jul 15;69(14):5867-75. doi: 10.1158/0008-5472.CAN-08-4866. Epub 2009 Jun 30. PubMed PMID: 19567678; PubMed Central PMCID: PMC2711991. 13: Sabry SM, Khamis EF. Application of H-point standard additions method to spectrophotometric and spectrofluorimetric determinations of glafenine and glafenic acid in mixtures. Talanta. 2000 May 5;51(6):1219-31. PubMed PMID: 18967954. 14: Hassan EM, Gazy AA, Abdel-Hay MH, Belal TS. High-performance liquid chromatographic determination of proquazone and its m-hydroxy metabolite in spiked human plasma and urine. J AOAC Int. 2007 Jul-Aug;90(4):971-6. PubMed PMID: 17760334. 15: Abadi AH, Hegazy GH, El-Zaher AA. Synthesis of novel 4-substituted-7-trifluoromethylquinoline derivatives with nitric oxide releasing properties and their evaluation as analgesic and anti-inflammatory agents. Bioorg Med Chem. 2005 Oct 15;13(20):5759-65. PubMed PMID: 16002298. 16: Jansen R, Lachatre G, Marquet P. LC-MS/MS systematic toxicological analysis: comparison of MS/MS spectra obtained with different instruments and settings. Clin Biochem. 2005 Apr;38(4):362-72. Review. PubMed PMID: 15766737. 17: Schöber W, Tran QB, Muringaseril M, Wiskirchen J, Kehlbach R, Rodegerdts E, Wiesinger B, Claussen CD, Duda SH. 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. PubMed PMID: 14642530. 18: El-Ragehy NA, Ellaithy MM, El-Ghobashy MA. Determination of thiocolchicoside in its binary mixtures (thiocolchicoside-glafenine and thiocolchicoside-floctafenine) by TLC-densitometry. Farmaco. 2003 Jun;58(6):463-8. PubMed PMID: 12767387. 19: Venisse N, Marquet P, Duchoslav E, Dupuy JL, Lachâtre G. A general unknown screening procedure for drugs and toxic compounds in serum using liquid chromatography-electrospray-single quadrupole mass spectrometry. J Anal Toxicol. 2003 Jan-Feb;27(1):7-14. PubMed PMID: 12587676. 20: Swiader M, Borowicz KK, Porebiak J, Kleinrok Z, Czuczwar SJ. Influence of agents affecting voltage-dependent calcium channels and dantrolene on the anticonvulsant action of the AMPA/kainate receptor antagonist LY 300164 in mice. Eur Neuropsychopharmacol. 2002 Aug;12(4):311-9. PubMed PMID: 12126870.