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
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About This Item
Empirical Formula (Hill Notation):
C31H33N3O6S
CAS Number:
Molecular Weight:
575.68
MDL number:
UNSPSC Code:
12352200
PubChem Substance ID:
NACRES:
NA.77
Recommended Products
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)
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.
Hazard Statements
Precautionary Statements
Hazard Classifications
Aquatic Chronic 4
Storage Class Code
11 - Combustible Solids
WGK
WGK 3
Flash Point(F)
Not applicable
Flash Point(C)
Not applicable
Certificates of Analysis (COA)
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J C Adkins et al.
Drugs, 55(1), 121-144 (1998-02-17)
Zafirlukast is a competitive and selective leukotriene receptor antagonist indicated for the prophylaxis and treatment of chronic asthma. The rationale for the development of leukotriene antagonists was based on in vitro and in vivo data demonstrating the extensive role of
F Wunder et al.
British journal of pharmacology, 160(2), 399-409 (2010-04-29)
Cysteinyl leukotrienes (CysLTs) have been implicated in the pathophysiology of inflammatory and cardiovascular disorders. Their actions are mediated by CysLT(1) and CysLT(2) receptors. Here we report the discovery of 3-({[(1S,3S)-3-carboxycyclohexyl]amino}carbonyl)-4-(3-{4-[4-(cyclo-hexyloxy)butoxy]phenyl}propoxy) benzoic acid (HAMI3379), the first potent and selective CysLT(2) receptor
Lucile Pinault et al.
Antimicrobial agents and chemotherapy, 57(5), 2134-2140 (2013-02-27)
The mycobacterial nucleoid-associated protein Lsr2 is a DNA-bridging protein that plays a role in condensation and structural organization of the genome and acts as a global repressor of gene transcription. Here we describe experiments demonstrating that zafirlukast inhibits the complexation
Tiina Karonen et al.
European journal of clinical pharmacology, 67(2), 151-155 (2010-10-12)
Gemfibrozil, a strong inhibitor of cytochrome P450 (CYP) 2C8 in vivo, was recently found to markedly increase the plasma concentrations of montelukast in humans. Like montelukast, zafirlukast is a substrate of CYP2C9 and CYP3A4 and a potent inhibitor of CYP2C8
James Mann et al.
Molecular pharmaceutics, 14(12), 4192-4201 (2017-07-25)
Dissolution testing with biorelevant media has become widespread in the pharmaceutical industry as a means of better understanding how drugs and formulations behave in the gastrointestinal tract. Until now, however, there have been few attempts to gauge the reproducibility of
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