Lodoxamide | CAS#53882-12-5 | Antiasthmatic

MedKoo Cat#: 599146 | Name: Lodoxamide

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Description:

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

Lodoxamide is a potent agonist of GPR35 with an EC50 value of 1.61 nM in a β-arrestin-2 interaction assay using CHO-K1 cells expressing the human receptor. It inhibits histamine release induced by compound 48/80 (Item No. 22173), anti-IgE, or A23187 (Item No. 11016) in isolated rat peritoneal mast cells (IC50s = 0.1-50 µM) and inhibits A23187-induced calcium influx in mast cells. It reduces antigen-induced histamine release from rat conjunctival tissue by 46% in vitro when used at a concentration of 10 µg/ml. Lodoxamine (0.1 and 10%, w/v) reduces the immediate hypersensitivity response in rat conjunctiva in vivo in a dose-dependent manner and reduces mast cell degranulation in a topical ovalbumin challenge. Formulations containing lodoxamide have been used in the treatment of vernal conjunctivitis and keratitis.

Chemical Structure

Lodoxamide

CAS#53882-12-5

Theoretical Analysis

MedKoo Cat#: 599146

Name: Lodoxamide

CAS#: 53882-12-5

Chemical Formula: C11H6ClN3O6

Exact Mass: 310.9945

Molecular Weight: 311.63

Elemental Analysis: C, 42.40; H, 1.94; Cl, 11.38; N, 13.48; O, 30.80

Price and Availability

Size	Price	Availability	Quantity
50mg	USD 350.00	2 weeks
100mg	USD 650.00	2 weeks

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Related CAS #

63610-09-3 (Tromethamide) 53882-12-5

Synonym

Lodoxamide; Lodoxamidum; Lodoxamida;

IUPAC/Chemical Name

2,2'-((2-chloro-5-cyano-1,3-phenylene)bis(azanediyl))bis(2-oxoacetic acid)

InChi Key

RVGLGHVJXCETIO-UHFFFAOYSA-N

InChi Code

InChI=1S/C11H6ClN3O6/c12-7-5(14-8(16)10(18)19)1-4(3-13)2-6(7)15-9(17)11(20)21/h1-2H,(H,14,16)(H,15,17)(H,18,19)(H,20,21)

SMILES Code

N#CC1=CC(NC(C(O)=O)=O)=C(Cl)C(NC(C(O)=O)=O)=C1

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

>3 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

2934.99.03.00

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Product Data

Product Data

Instruction

View handling instruction

Biological target:

Lodoxamide (U-42585E free acid) is an antiallergic compound acting as a mast-cell stabilizer for the treatment of asthma and allergic conjunctivitis.

In vitro activity:

Lodoxamide was also able to strongly inhibit the release of eosinophil peroxidase after IgA-dependent activation and, to a lesser extent, the release of eosinophil cationic protein and eosinophil-derived neurotoxin. Taken together, these results indicate that lodoxamide can exert potent inhibitory effects on eosinophil activation in vitro combined with a strong inhibition of eosinophil attraction, leading therefore to a reduction in their pathological potential in vivo. Reference: Int Arch Allergy Immunol. 1998 Jun;116(2):140-6. https://pubmed.ncbi.nlm.nih.gov/9652307/

In vivo activity:

This study hypothesized that adding an inhibitor of mast cell degranulation, lodoxamide tromethamine (10 micromol/L), to Euro-Collins and University of Wisconsin preservation solutions, would decrease lung preservation injury in rat lungs. After 12 hours of ischemic storage, lodoxamide tromethamine-enhanced Euro-Collins solution decreased alveolar-arterial oxygen difference from 588 to 485 (p < 0.001), increased oxygen tension from 100 to 161 mm Hg (p = 0.012), decreased capillary filtration coefficient from 6.2 to 2.6 (p < 0.001), and increased compliance from 0.12 to 0.21 (p < 0.001); lodoxamide tromethamine-enhanced University of Wisconsin solution decreased alveolar-arterial oxygen difference from 478 to 322 (p < 0.001), increased oxygen tension from 214 to 335 mm Hg (p < 0.001), decreased capillary filtration constant from 4.2 to 2.0 (p < 0.001), and increased compliance from 0.20 to 0.25 (p < 0.001). Reference: J Thorac Cardiovasc Surg. 1998 Mar;115(3):631-6; discussion 636-7. https://pubmed.ncbi.nlm.nih.gov/9535451/

	Solvent	mg/mL	mM
Solubility
	DMF	3.0	9.63
	PBS (pH 7.2)	2.0	6.42

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 311.63 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. Capron M, Loiseau S, Papin JP, Robertson S, Capron A. Inhibitory effects of lodoxamide on eosinophil activation. Int Arch Allergy Immunol. 1998 Jun;116(2):140-6. doi: 10.1159/000023937. PMID: 9652307. 2. Kim MJ, Park SJ, Nam SY, Im DS. Lodoxamide Attenuates Hepatic Fibrosis in Mice: Involvement of GPR35. Biomol Ther (Seoul). 2019 Jun 13;28(1):92-97. doi: 10.4062/biomolther.2018.227. Epub ahead of print. PMID: 31189299; PMCID: PMC6939691. 3. Barr ML, Carey JN, Nishanian GP, Roberts RF, Sakamaki Y, Darbinian SH, Starnes VA. Addition of a mast cell stabilizing compound to organ preservation solutions decreases lung reperfusion injury. J Thorac Cardiovasc Surg. 1998 Mar;115(3):631-6; discussion 636-7. doi: 10.1016/S0022-5223(98)70328-9. PMID: 9535451.

In vitro protocol:

In vivo protocol:

1. Kim MJ, Park SJ, Nam SY, Im DS. Lodoxamide Attenuates Hepatic Fibrosis in Mice: Involvement of GPR35. Biomol Ther (Seoul). 2019 Jun 13;28(1):92-97. doi: 10.4062/biomolther.2018.227. Epub ahead of print. PMID: 31189299; PMCID: PMC6939691. 2. Barr ML, Carey JN, Nishanian GP, Roberts RF, Sakamaki Y, Darbinian SH, Starnes VA. Addition of a mast cell stabilizing compound to organ preservation solutions decreases lung reperfusion injury. J Thorac Cardiovasc Surg. 1998 Mar;115(3):631-6; discussion 636-7. doi: 10.1016/S0022-5223(98)70328-9. PMID: 9535451.

1: MacKenzie AE, Caltabiano G, Kent TC, Jenkins L, McCallum JE, Hudson BD, Nicklin SA, Fawcett L, Markwick R, Charlton SJ, Milligan G. The antiallergic mast cell stabilizers lodoxamide and bufrolin as the first high and equipotent agonists of human and rat GPR35. Mol Pharmacol. 2014 Jan;85(1):91-104. doi: 10.1124/mol.113.089482. Epub 2013 Oct 10. PubMed PMID: 24113750; PubMed Central PMCID: PMC3868900. 2: Das D, Khan M, Gul A, Alam R. Safety and efficacy of lodoxamide in vernal keratoconjunctivitis. J Pak Med Assoc. 2011 Mar;61(3):239-41. PubMed PMID: 21465936. 3: Verin P, Allewaert R, Joyaux JC, Piozzi E, Koliopoulos J, Bloch-Michel E; Lodoxamide Study Group. Comparison of lodoxamide 0.1% ophthalmic solution and levocabastine 0.05% ophthalmic suspension in vernal keratoconjunctivitis. Eur J Ophthalmol. 2001 Apr-Jun;11(2):120-5. PubMed PMID: 11456011. 4: Ciprandi G, Buscaglia S, Catrullo A, Paolieri F, Riccio AM, Fiorino N, Canonica GW. Antiallergic activity of topical lodoxamide on in vivo and in vitro models. Allergy. 1996 Dec;51(12):946-51. PubMed PMID: 9020426. 5: Gündüz K, Uçakhan O, Budak K, Eryilmaz T, Ozkan M. Efficacy of lodoxamide 0.1% versus N-acetyl aspartyl glutamic acid 6% ophthalmic solutions in patients with vernal keratoconjunctivitis. Ophthalmic Res. 1996;28(2):80-7. PubMed PMID: 8792357. 6: Denis D, Bloch-Michel E, Verin P, Sebastiani A, Tazartes M, Helleboid L, Di Giovanni A, Lecorvec M. Treatment of common ocular allergic disorders; a comparison of lodoxamide and NAAGA. Br J Ophthalmol. 1998 Oct;82(10):1135-8. PubMed PMID: 9924299; PubMed Central PMCID: PMC1722390. 7: Santos CI, Huang AJ, Abelson MB, Foster CS, Friedlaender M, McCulley JP. Efficacy of lodoxamide 0.1% ophthalmic solution in resolving corneal epitheliopathy associated with vernal keratoconjunctivitis. Am J Ophthalmol. 1994 Apr 15;117(4):488-97. PubMed PMID: 8154531. 8: Cerqueti PM, Ricca V, Tosca MA, Buscaglia S, Ciprandi G. Lodoxamide treatment of allergic conjunctivitis. Int Arch Allergy Immunol. 1994 Oct;105(2):185-9. PubMed PMID: 7920019. 9: Capron M, Loiseau S, Papin JP, Robertson S, Capron A. Inhibitory effects of lodoxamide on eosinophil activation. Int Arch Allergy Immunol. 1998 Jun;116(2):140-6. PubMed PMID: 9652307. 10: Akman A, Irkeç M, Orhan M. Effects of lodoxamide, disodium cromoglycate and fluorometholone on tear leukotriene levels in vernal keratoconjunctivitis. Eye (Lond). 1998;12 ( Pt 2):291-5. PubMed PMID: 9683957. 11: Yanni JM, Weimer LK, Glaser RL, Lang LS, Robertson SM, Spellman JM. Effect of lodoxamide on in vitro and in vivo conjunctival immediate hypersensitivity responses in rats. Int Arch Allergy Immunol. 1993;101(1):102-6. PubMed PMID: 7684628. 12: Adefule-Ositelu AO, Onakoya AO, Olasimbo OO, Adefule AK. A clinicopathological analysis of the efficacy of lodoxamide 0.1% eye drops on the conjunctiva of patients with vernal keratoconjunctivitis seen at Guinness Eye Centre, Lagos University Teaching Hospital. Niger Postgrad Med J. 2006 Mar;13(1):35-40. PubMed PMID: 16633377. 13: Purello D'Ambrosio F, Gangemi S, Ricciardi L, Cuzzocrea S, Di Lorenzo G. Lodoxamide versus spaglumic acid: a comparative double-blind trial on patients suffering from seasonal allergic conjunctivitis induced by Parietaria pollen. Allergol Immunopathol (Madr). 1997 Sep-Oct;25(5):233-7. PubMed PMID: 9395007. 14: Richard C, Trinquand C, Bloch-Michel E. Comparison of topical 0.05% levocabastine and 0.1% lodoxamide in patients with allergic conjunctivitis. Study Group. Eur J Ophthalmol. 1998 Oct-Dec;8(4):207-16. PubMed PMID: 9891891. 15: Caldwell DR, Verin P, Hartwich-Young R, Meyer SM, Drake MM. Efficacy and safety of lodoxamide 0.1% vs cromolyn sodium 4% in patients with vernal keratoconjunctivitis. Am J Ophthalmol. 1992 Jun 15;113(6):632-7. PubMed PMID: 1598953. 16: Oguz H, Bitiren M, Aslan OS, Ozardali I. Efficacy of lodoxamide eye drops on tear fluid cytology of patients with vernal conjunctivitis. Acta Med Okayama. 1999 Jun;53(3):123-6. PubMed PMID: 10410789. 17: Ball TD, Lundy EF, Zelenock GB, D'Alecy LG. Effects of lodoxamide tromethamine on paraplegia that occurs after infrarenal aortic occlusion in the rabbit. J Vasc Surg. 1987 Dec;6(6):572-7. PubMed PMID: 3694755. 18: Schoch C. Effects of ketotifen 0.025% and lodoxamide 0.1% on eosinophil infiltration into the guinea pig conjunctiva in a model of allergic conjunctivitis. J Ocul Pharmacol Ther. 2003 Apr;19(2):153-9. PubMed PMID: 12804060. 19: Watt GD, Bui TC, Bewtra AK, Townley RG. Protective effect opf lodoxamide tromethamine on allergen inhalation challenge. J Allergy Clin Immunol. 1980 Oct;66(4):286-94. PubMed PMID: 7419830. 20: Zhang W, Lin Z. Contrast of the effect of alomide and sodium cromoglycate in the treatment of allergic eye diseases. Yan Ke Xue Bao. 2000 Sep;16(3):214-6. PubMed PMID: 12579651.

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