Zafirlukast

• CAT Number: A000661
• CAS Number: 107753-78-6
• Molecular Formula: C31H33N3O6S
• Molecular Weight: 575.7
• Purity: ≥95%
• Synonyms: 107753-78-6; Accolate; Olmoran; Aeronix; ICI-204219
• Target: Leukotriene Receptor
• Solubility: >23.9mg/mL in DMSO
• Storage: -20°C
• 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)
• InChIKey: YEEZWCHGZNKEEK-UHFFFAOYSA-N
• SMILES: CC1=CC=CC=C1S(=O)(=O)NC(=O)C2=CC(=C(C=C2)CC3=CN(C4=C3C=C(C=C4)NC(=O)OC5CCCC5)C)OC

Zafirlukast is an oral leukotriene receptor antagonist (LTRA) for the maintenance treatment of asthma, often used in conjunction with an inhaled steroid and/or long-acting bronchodilator. It is available as a tablet and is usually dosed twice daily. Another leukotriene receptor antagonist is montelukast (Singulair), taken once daily. Zileuton (Zyflo), also used in the treatment of asthma via its inhibition of 5-lipoxygenase, is taken four times per day. Zafirlukast blocks the action of the cysteinyl leukotrienes on the CysLT1 receptors, thus reducing constriction of the airways, build-up of mucus in the lungs and inflammation of the breathing passages.

Reference

1: Gerits E, Van der Massen I, Vandamme K, De Cremer K, De Brucker K, Thevissen
K, Cammue BPA, Beullens S, Fauvart M, Verstraeten N, Michiels J, Roberts M. In
vitro activity of the antiasthmatic drug zafirlukast against the oral pathogens
Porphyromonas gingivalis and Streptococcus mutans. FEMS Microbiol Lett. 2017 Jan
1;364(2). doi: 10.1093/femsle/fnx005. PubMed PMID: 28087617.

2: Generali JA, Cada DJ. Zafirlukast: Chronic Urticaria. Hosp Pharm. 2015
Nov;50(10):873-875. Epub 2015 Nov 19. PubMed PMID: 27729674; PubMed Central
PMCID: PMC5057193.

3: Lee HJ, Kim YH, Kim SH, Lee CM, Yang AY, Jang CG, Lee SY, Bae JW, Choi CI.
Effects of CYP2C9 genetic polymorphisms on the pharmacokinetics of zafirlukast.
Arch Pharm Res. 2016 Jul;39(7):1013-9. doi: 10.1007/s12272-016-0785-x. Epub 2016
Jul 4. PubMed PMID: 27377818.

4: Madsen CM, Boyd B, Rades T, Müllertz A. Supersaturation of zafirlukast in
fasted and fed state intestinal media with and without precipitation inhibitors.
Eur J Pharm Sci. 2016 Aug 25;91:31-9. doi: 10.1016/j.ejps.2016.05.026. Epub 2016
May 31. PubMed PMID: 27260089.

5: Oda S, Fujiwara R, Kutsuno Y, Fukami T, Itoh T, Yokoi T, Nakajima M. Targeted
screen for human UDP-glucuronosyltransferases inhibitors and the evaluation of
potential drug-drug interactions with zafirlukast. Drug Metab Dispos. 2015
Jun;43(6):812-8. doi: 10.1124/dmd.114.062141. Epub 2015 Apr 1. PubMed PMID:
25834030.

6: Kang SH, Shin KC, Kim WS, Bae TH, Kim HK, Kim MK. The preventive effect of
topical zafirlukast instillation for peri-implant capsule formation in rabbits.
Arch Plast Surg. 2015 Mar;42(2):179-85. doi: 10.5999/aps.2015.42.2.179. Epub 2015
Mar 16. PubMed PMID: 25798389; PubMed Central PMCID: PMC4366699.

7: Chen CF, Lv Y, Zhang HP, Wang G. Does zafirlukast reduce future risk of asthma
exacerbations in adults? Systematic review and meta-analysis. Multidiscip Respir
Med. 2014 May 28;9(1):30. doi: 10.1186/2049-6958-9-30. eCollection 2014. Review.
PubMed PMID: 24936302; PubMed Central PMCID: PMC4059702.

8: Iqbal M, Ezzeldin E, Al-Rashood KA, Al-Khamees KI, Khan RM, Raish M, Anwer T.
Simple and rapid determination of zafirlukast in plasma by ultra-performance
liquid chromatography tandem mass spectrometric method: application into
pharmacokinetic study in rabbits. Drug Res (Stuttg). 2014 Aug;64(8):412-9. doi:
10.1055/s-0033-1358748. Epub 2013 Nov 20. PubMed PMID: 24258705.

9: Moosavi SA, Raji H, Tasorian B, Mostafapour E, Shahabi S, Purfakharan M,
Fereshtehnejad SM. Effect of Zafirlukast on improving lung function in patients
with chronic obstructive pulmonary diseases. Med J Islam Repub Iran. 2013
May;27(2):57-61. PubMed PMID: 23741166; PubMed Central PMCID: PMC3610308.

10: Pinault L, Han JS, Kang CM, Franco J, Ronning DR. Zafirlukast inhibits
complexation of Lsr2 with DNA and growth of Mycobacterium tuberculosis.
Antimicrob Agents Chemother. 2013 May;57(5):2134-40. doi: 10.1128/AAC.02407-12.
Epub 2013 Feb 25. PubMed PMID: 23439641; PubMed Central PMCID: PMC3632936.