Z4152

Zafirlukast

≥98% (HPLC)

• Synonym(s): N-[3-[[2-Methoxy-4-[[[(2-methylphenyl)sulfonyl]amino]carbonyl]phenyl]methyl]-1-methyl-1H-indol-5-yl]carbamic acid cyclopentyl ester
• Empirical Formula (Hill Notation): C₃₁H₃₃N₃O₆S
• CAS Number: 107753-78-6
• Molecular Weight: 575.68
• MDL number: MFCD00864775
• UNSPSC Code: 12352200
• PubChem Substance ID: 329831612
• NACRES: NA.77

Properties

• assay: ≥98% (HPLC)
• form: solid
• solubility: DMSO: ≥28 mg/mL
• originator: AstraZeneca
• storage temp.: room temp
• SMILES string: COc1cc(ccc1Cc2cn(C)c3ccc(NC(=O)OC4CCCC4)cc23)C(=O)NS(=O)(=O)c5ccccc5C
• InChI: 1S/C31H33N3O6S/c1-20-8-4-7-11-29(20)41(37,38)33-30(35)22-13-12-21(28(17-22)39-3)16-23-19-34(2)27-15-14-24(18-26(23)27)32-31(36)40-25-9-5-6-10-25/h4,7-8,11-15,17-19,25H,5-6,9-10,16H2,1-3H3,(H,32,36)(H,33,35)
• InChI key: YEEZWCHGZNKEEK-UHFFFAOYSA-N
• Gene Information: human ... CYSLTR1(10800)

Description

Application

Zafirlukast has been used to stimulate pancreatic β cell line (MIN6) and pancreatic islets for insulin secretion assay. It may be used as an adenosine triphosphate-binding cassette transporter (ABCG2) inhibitor in MTT [3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide] cytotoxicity assay in human embryonic kidney cells (HEK293) and in Kirby-Bauer disc diffusion assays, bactericidal activity and minimal inhibitory concentration (mIC) assay against M. smegmatis

Biochem/physiol Actions

Zafirlukast is a potent subtype specific cysteinyl leukotriene type 1 receptor (CysLT1) antagonist; antiasthmatic. Zafirlukast has over 1000-fold selectivity for CysLT1, one of two receptors for cysteinyl leukotrienes LTC4, LTD4, and LTE4, which are important mediators of human bronchial asthma.

Zafirlukast plays a key role in alleviating mucus and airway constriction in asthma based inflammatory response. It regulates pancreatic β cells for the secretion of insulin and this functionality is interlinked to the calcium based phosphorylation of the Ca²⁺/calmodulin-dependent protein kinase II (CaMKII) and protein kinase B (AKT). Zafirlukast has inhibitory potential on ATP-binding cassette (ABC) transporters and reverses the multidrug resistance function of ATP-binding cassette super-family G member 2 (ABCG2). Zafirlukast inhibits mycobacterial nucleoid-associated protein Lsr2 and halts the growth of Mycobacteria.

Features and Benefits

This compound is featured on the Leukotriene Receptors page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

This compound was developed by AstraZeneca. To browse the list of other pharma-developed compounds and Approved Drugs/Drug Candidates, click here.

Safety Information

• hcodes: H413
• pcodes: P273 - P501
• Hazard Classifications: Aquatic Chronic 4
• Storage Class: 11 - Combustible Solids
• wgk_germany: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable