Zafirlukast

Identification

Summary

Zafirlukast is a leukotriene receptor antagonist used for prophylaxis and chronic treatment of asthma.

Brand Names

Accolate

Generic Name

Zafirlukast

DrugBank Accession Number

DB00549

Background

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), which is usually taken just once daily.

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.

Type

Small Molecule

Groups

Approved, Investigational

Structure

Similar Structures

Weight: Average: 575.675
Monoisotopic: 575.209006493
Chemical Formula: C₃₁H₃₃N₃O₆S

Synonyms

4-(5-cyclopentyloxycarbonylamino-1-methyl-1H-indol-3-ylmethyl)-3-methoxy-N-o-tolylsulfonylbenzamide
cyclopentyl 3-(2-methoxy-4-((o-tolylsulfonyl)carbamoyl)benzyl)-1-methylindole-5-carbamate
Zafirlukast

External IDs

ICI 204,219
ICI-204,219
ICI-204219

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Pharmacology

Indication

For the prophylaxis and chronic treatment of asthma.

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Associated Conditions

Indication Type	Indication	Combined Product Details	Approval Level	Age Group	Patient Characteristics	Dose Form
Management of	Asthma		••••••••••••
Treatment of	Chronic urticaria		••• •••••

Contraindications & Blackbox Warnings

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Pharmacodynamics

Zafirlukast is a synthetic, selective peptide leukotriene receptor antagonist (LTRA) indicated for the prophylaxis and chronic treatment of asthma. Patients with asthma were found in one study to be 25-100 times more sensitive to the bronchoconstricting activity of inhaled LTD₄ than nonasthmatic subjects. In vitro studies demonstrated that zafirlukast antagonized the contractile activity of three leukotrienes (LTC₄, LTD₄ and LTE₄) in conducting airway smooth muscle from laboratory animals and humans. Zafirlukast prevented intradermal LTD₄-induced increases in cutaneous vascular permeability and inhibited inhaled LTD₄-induced influx of eosinophils into animal lungs.

Mechanism of action

Zafirlukast is a selective and competitive receptor antagonist of leukotriene D4 and E4 (LTD₄ and LTE4), components of slow-reacting substance of anaphylaxis (SRSA). Cysteinyl leukotriene production and receptor occupation have been correlated with the pathophysiology of asthma, including airway edema, smooth muscle constriction, and altered cellular activity associated with the inflammatory process, which contribute to the signs and symptoms of asthma.

Target	Actions	Organism
ACysteinyl leukotriene receptor 1	antagonist	Humans

Absorption

Rapidly absorbed following oral administration, reduced following a high-fat or high-protein meal.

Volume of distribution

70 L

Protein binding

99%

Metabolism

Hepatic

Hover over products below to view reaction partners

Zafirlukast

Route of elimination

The most common metabolic products are hydroxylated metabolites which are excreted in the feces.

Half-life

10 hours

Clearance

apparent oral CL=20 L/h
11.4 L/h [7-11 yrs]
9.2 L/h [5-6 yrs]

Adverse Effects

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Toxicity

Side effects include rash and upset stomach.

Pathways

Not Available

Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">

Not Available

Interactions

Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">

This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.

Drug	Interaction
Integrate drug-drug interactions in your software
Abatacept	The metabolism of Zafirlukast can be increased when combined with Abatacept.
Abemaciclib	The serum concentration of Abemaciclib can be increased when it is combined with Zafirlukast.
Abrocitinib	The metabolism of Abrocitinib can be decreased when combined with Zafirlukast.
Acalabrutinib	The serum concentration of Acalabrutinib can be increased when it is combined with Zafirlukast.
Acenocoumarol	The serum concentration of Acenocoumarol can be increased when it is combined with Zafirlukast.

Food Interactions

Take on an empty stomach. Take at least 1 hour before or 2 hours after meals.

Products

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Product Images

Brand Name Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End
Accolate	Tablet, film coated	20 mg/1	Oral	Par Pharmaceutical Inc.	2015-01-09	2017-09-30
Accolate	Tablet, film coated	10 mg/1	Oral	Astra Zeneca Lp	1996-10-01	2017-04-28
Accolate	Tablet, coated	20 mg/1	Oral	Par Pharmaceutical, Inc.	2015-11-01	2023-11-30
Accolate	Tablet, film coated	20 mg/1	Oral	Physicians Total Care, Inc.	1996-09-26	2011-09-30
Accolate	Tablet, film coated	10 mg/1	Oral	Par Pharmaceutical Inc.	2015-01-09	2019-04-30

Generic Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End
Zafirlukast	Tablet, film coated	10 mg/1	Oral	Aurobindo Pharma Limited	2023-11-27	Not applicable
Zafirlukast	Tablet, film coated	20 mg/1	Oral	Camber Pharmaceuticals, Inc.	2020-09-10	Not applicable
Zafirlukast	Tablet, film coated	20 mg/1	Oral	American Health Packaging	2013-05-22	Not applicable
Zafirlukast	Tablet, film coated	10 mg/1	Oral	Dr. Reddys Laboratories Limited	2010-11-18	Not applicable
Zafirlukast	Tablet	20 mg/1	Oral	Rising Pharmaceuticals, Inc.	2022-08-25	Not applicable

Chemical Identifiers

UNII: XZ629S5L50
CAS number: 107753-78-6
InChI Key: YEEZWCHGZNKEEK-UHFFFAOYSA-N
InChI: 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)
IUPAC Name: cyclopentyl N-[3-({2-methoxy-4-[(2-methylbenzenesulfonyl)carbamoyl]phenyl}methyl)-1-methyl-1H-indol-5-yl]carbamate
SMILES: COC1=CC(=CC=C1CC1=CN(C)C2=C1C=C(NC(=O)OC1CCCC1)C=C2)C(=O)NS(=O)(=O)C1=CC=CC=C1C

References

Synthesis Reference

Arie Gutman, "Process for the preparation of zafirlukast." U.S. Patent US20040186300, issued September 23, 2004.

US20040186300

General References

Not Available

External Links

Human Metabolome Database: HMDB0014689
KEGG Drug: D00411
KEGG Compound: C07206
PubChem Compound: 5717
PubChem Substance: 46506874
ChemSpider: 5515
BindingDB: 50009073
RxNav: 114970
ChEBI: 10100
ChEMBL: CHEMBL603
ZINC: ZINC000000896717
Therapeutic Targets Database: DAP000091
PharmGKB: PA451949
Guide to Pharmacology: GtP Drug Page
PDBe Ligand: ZLK
RxList: RxList Drug Page
Drugs.com: Drugs.com Drug Page
Wikipedia: Zafirlukast

PDB Entries

6rz5 / 7ypz

FDA label

Download (233 KB)

MSDS

Download (57.6 KB)

Clinical Trials

Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">

Phase	Status	Purpose	Conditions	Count
2	Not Yet Recruiting	Treatment	Allergy to Cats	1
2	Recruiting	Treatment	Ovarian Cancer	1
2	Terminated	Treatment	Breast Cancer	1
1	Completed	Treatment	Healthy Subjects (HS)	1

Pharmacoeconomics

Manufacturers

Astrazeneca uk ltd

Packagers

AstraZeneca Inc.
Cardinal Health
IPR Pharmaceuticals Inc.
Murfreesboro Pharmaceutical Nursing Supply
Physicians Total Care Inc.
Resource Optimization and Innovation LLC
Zeneca Pharma Inc.

Dosage Forms

Form	Route	Strength
Tablet, film coated	Oral	20 mg/1
Tablet	Oral	20 mg
Tablet, film coated	Oral
Tablet, film coated	Oral	10 mg
Tablet, film coated	Oral	20 mg
Tablet, coated	Oral	250 mg
Tablet	Oral	20.00 mg
Tablet	Oral	10 mg/1
Tablet	Oral	20 mg/1
Tablet, coated	Oral	10 mg/1
Tablet, coated	Oral	20 mg/1
Tablet, film coated	Oral	10 mg/1

Prices

Unit description	Cost	Unit
Accolate 10 mg tablet	1.92USD	tablet
Accolate 20 mg tablet	1.86USD	tablet

DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.

Patents

Patent Number	Pediatric Extension	Approved	Expires (estimated)
US5612367	No	1997-03-18	2014-03-18
US4859692	No	1989-08-22	2010-09-26
CA2056066	No	2002-04-02	2011-11-22
CA1340567	No	1999-06-01	2016-06-01

Properties

State

Solid

Experimental Properties

Property	Value	Source
melting point (°C)	139 °C	Not Available
logP	5.4	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.000962 mg/mL	ALOGPS
logP	4.84	ALOGPS
logP	6.4	Chemaxon
logS	-5.8	ALOGPS
pKa (Strongest Acidic)	4.29	Chemaxon
pKa (Strongest Basic)	-1.1	Chemaxon
Physiological Charge	-1	Chemaxon
Hydrogen Acceptor Count	6	Chemaxon
Hydrogen Donor Count	2	Chemaxon
Polar Surface Area	115.73 Å²	Chemaxon
Rotatable Bond Count	8	Chemaxon
Refractivity	158.58 m³·mol^-1	Chemaxon
Polarizability	62 Å³	Chemaxon
Number of Rings	5	Chemaxon
Bioavailability	0	Chemaxon
Rule of Five	No	Chemaxon
Ghose Filter	No	Chemaxon
Veber's Rule	No	Chemaxon
MDDR-like Rule	Yes	Chemaxon

Predicted ADMET Features

Property	Value	Probability
Human Intestinal Absorption	+	0.8849
Blood Brain Barrier	+	0.9153
Caco-2 permeable	-	0.6613
P-glycoprotein substrate	Non-substrate	0.7027
P-glycoprotein inhibitor I	Non-inhibitor	0.6249
P-glycoprotein inhibitor II	Inhibitor	0.8915
Renal organic cation transporter	Non-inhibitor	0.8475
CYP450 2C9 substrate	Non-substrate	0.5189
CYP450 2D6 substrate	Non-substrate	0.9116
CYP450 3A4 substrate	Substrate	0.5322
CYP450 1A2 substrate	Non-inhibitor	0.5261
CYP450 2C9 inhibitor	Inhibitor	0.646
CYP450 2D6 inhibitor	Non-inhibitor	0.8263
CYP450 2C19 inhibitor	Inhibitor	0.5826
CYP450 3A4 inhibitor	Inhibitor	0.7904
CYP450 inhibitory promiscuity	High CYP Inhibitory Promiscuity	0.9189
Ames test	Non AMES toxic	0.6072
Carcinogenicity	Non-carcinogens	0.7292
Biodegradation	Not ready biodegradable	0.9972
Rat acute toxicity	2.5723 LD50, mol/kg	Not applicable
hERG inhibition (predictor I)	Weak inhibitor	0.9216
hERG inhibition (predictor II)	Inhibitor	0.7693

ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)

Not Available

Spectra

Spectrum	Spectrum Type	Splash Key
Predicted GC-MS Spectrum - GC-MS	Predicted GC-MS	splash10-052f-9330620000-fc40738dd1a7e2c81dc5
LC-MS/MS Spectrum - LC-ESI-qTof , Positive	LC-MS/MS	splash10-00di-0001190000-27c5d161a5754e1434f4
LC-MS/MS Spectrum - LC-ESI-qTof , Positive	LC-MS/MS	splash10-00di-0001190000-27c5d161a5754e1434f4
LC-MS/MS Spectrum - LC-ESI-qTof , Positive	LC-MS/MS	splash10-0292-0940000000-f369442eba5344b3ecb4
LC-MS/MS Spectrum - LC-ESI-qTof , Positive	LC-MS/MS	splash10-0292-0940000000-f369442eba5344b3ecb4
MS/MS Spectrum - , positive	LC-MS/MS	splash10-0002-0003191000-ba3996913abfda3b22c4
MS/MS Spectrum - , positive	LC-MS/MS	splash10-0a4r-0259300000-1440474b4cb47824c9f2
MS/MS Spectrum - , positive	LC-MS/MS	splash10-0002-0001191000-58bcdb71b459847fc794
MS/MS Spectrum - , positive	LC-MS/MS	splash10-0ap0-0149300000-896e679131032968db95
Predicted MS/MS Spectrum - 10V, Positive (Annotated)	Predicted LC-MS/MS	splash10-0a4i-1900270000-06eb659c512cbfd08eed
Predicted MS/MS Spectrum - 10V, Negative (Annotated)	Predicted LC-MS/MS	splash10-00di-2900020000-2881801382cb9f5d5f9d
Predicted MS/MS Spectrum - 20V, Positive (Annotated)	Predicted LC-MS/MS	splash10-000i-3019330000-2acee3391d6ba1d5b9ef
Predicted MS/MS Spectrum - 20V, Negative (Annotated)	Predicted LC-MS/MS	splash10-006x-9500340000-478b152044ad573bc250
Predicted MS/MS Spectrum - 40V, Positive (Annotated)	Predicted LC-MS/MS	splash10-00mo-9014130000-40053ee7cf9a32e8de02
Predicted MS/MS Spectrum - 40V, Negative (Annotated)	Predicted LC-MS/MS	splash10-052o-9300230000-11fa70a9c7e58a3ecb35

Chromatographic Properties

Collision Cross Sections (CCS)

Adduct	CCS Value (Å²)	Source type	Source
[M-H]-	244.7834039	predicted	DarkChem Lite v0.1.0
[M-H]-	263.3453039	predicted	DarkChem Lite v0.1.0
[M-H]-	226.52211	predicted	DeepCCS 1.0 (2019)
[M+H]+	247.2436039	predicted	DarkChem Lite v0.1.0
[M+H]+	264.1508039	predicted	DarkChem Lite v0.1.0
[M+H]+	228.70529	predicted	DeepCCS 1.0 (2019)
[M+Na]+	247.2219039	predicted	DarkChem Lite v0.1.0
[M+Na]+	263.9610039	predicted	DarkChem Lite v0.1.0
[M+Na]+	234.6179	predicted	DeepCCS 1.0 (2019)

Targets

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insights and accelerate drug research.

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Property	Measurement	pH	Temperature (°C)	References
IC 50 (nM)	44	N/A	N/A	A28543
IC 50 (nM)	2	N/A	N/A	A28544
Ki (nM)	0.3	N/A	N/A	A28540 / A28541 / A28300
Ki (nM)	0.34	N/A	N/A	A28542
Ki (nM)	2	N/A	N/A	A28545 / A28546
Ki (nM)	0.26	N/A	N/A	A19817

Details1. Cysteinyl leukotriene receptor 1

Kind: Protein
Organism: Humans
Pharmacological action: Yes
Actions: Antagonist

General Function: Leukotriene receptor activity
Specific Function: Receptor for cysteinyl leukotrienes mediating bronchoconstriction of individuals with and without asthma. Stimulation by LTD4 results in the contraction and proliferation of smooth muscle, edema, e...
Gene Name: CYSLTR1
Uniprot ID: Q9Y271
Uniprot Name: Cysteinyl leukotriene receptor 1
Molecular Weight: 38540.55 Da

References

Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]
Cazzola M, Boveri B, Carlucci P, Santus P, DiMarco F, Centanni S, Allegra L: Lung function improvement in smokers suffering from COPD with zafirlukast, a CysLT(1)-receptor antagonist. Pulm Pharmacol Ther. 2000;13(6):301-5. [Article]
Murata Y, Sugimoto O: [Zafirlukast (Accolate): a review of its pharmacological and clinical profile]. Nihon Yakurigaku Zasshi. 2002 Apr;119(4):247-58. [Article]
Wang S, Gustafson E, Pang L, Qiao X, Behan J, Maguire M, Bayne M, Laz T: A novel hepatointestinal leukotriene B4 receptor. Cloning and functional characterization. J Biol Chem. 2000 Dec 29;275(52):40686-94. [Article]
O'Byrne PM: Leukotrienes in the pathogenesis of asthma. Chest. 1997 Feb;111(2 Suppl):27S-34S. [Article]
Heise CE, O'Dowd BF, Figueroa DJ, Sawyer N, Nguyen T, Im DS, Stocco R, Bellefeuille JN, Abramovitz M, Cheng R, Williams DL Jr, Zeng Z, Liu Q, Ma L, Clements MK, Coulombe N, Liu Y, Austin CP, George SR, O'Neill GP, Metters KM, Lynch KR, Evans JF: Characterization of the human cysteinyl leukotriene 2 receptor. J Biol Chem. 2000 Sep 29;275(39):30531-6. [Article]
Singh RK, Tandon R, Dastidar SG, Ray A: A review on leukotrienes and their receptors with reference to asthma. J Asthma. 2013 Nov;50(9):922-31. doi: 10.3109/02770903.2013.823447. Epub 2013 Aug 16. [Article]
McMahon B, Mitchell D, Shattock R, Martin F, Brady HR, Godson C: Lipoxin, leukotriene, and PDGF receptors cross-talk to regulate mesangial cell proliferation. FASEB J. 2002 Nov;16(13):1817-9. doi: 10.1096/fj.02-0416fje. Epub 2002 Sep 5. [Article]
Figueroa EE, Kramer M, Strange K, Denton JS: CysLT1 receptor antagonists pranlukast and zafirlukast inhibit LRRC8-mediated volume regulated anion channels independently of the receptor. Am J Physiol Cell Physiol. 2019 Oct 1;317(4):C857-C866. doi: 10.1152/ajpcell.00281.2019. Epub 2019 Aug 7. [Article]
Ruiz I, Nevers Q, Hernandez E, Ahnou N, Brillet R, Softic L, Donati F, Berry F, Hamadat S, Fourati S, Pawlotsky JM, Ahmed-Belkacem A: MK-571, a Cysteinyl Leukotriene Receptor 1 Antagonist, Inhibits Hepatitis C Virus Replication. Antimicrob Agents Chemother. 2020 May 21;64(6). pii: AAC.02078-19. doi: 10.1128/AAC.02078-19. Print 2020 May 21. [Article]
Reques FG, Rodriguez JL: Tolerability of leukotriene modifiers in asthma: a review of clinical experience. BioDrugs. 1999 Jun;11(6):385-94. doi: 10.2165/00063030-199911060-00003. [Article]

Enzymes

Property	Measurement	pH	Temperature (°C)	References
Ki (nM)	2500	N/A	N/A	A27342

Details1. Cytochrome P450 2C9

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Substrate
Inhibitor

General Function: Steroid hydroxylase activity
Specific Function: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name: CYP2C9
Uniprot ID: P11712
Uniprot Name: Cytochrome P450 2C9
Molecular Weight: 55627.365 Da

References

Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [Article]
Dekhuijzen PN, Koopmans PP: Pharmacokinetic profile of zafirlukast. Clin Pharmacokinet. 2002;41(2):105-14. doi: 10.2165/00003088-200241020-00003. [Article]
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. [Article]
Flockhart Table of Drug Interactions [Link]
Zafirlukast FDA label [File]

Details2. Cytochrome P450 2C8

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Inhibitor
Curator comments: The clinical significance of these enzyme actions in vivo are unknown, and these listed enzyme actions are based on the results of in vitro studies.

General Function: Steroid hydroxylase activity
Specific Function: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name: CYP2C8
Uniprot ID: P10632
Uniprot Name: Cytochrome P450 2C8
Molecular Weight: 55824.275 Da

References

Walsky RL, Gaman EA, Obach RS: Examination of 209 drugs for inhibition of cytochrome P450 2C8. J Clin Pharmacol. 2005 Jan;45(1):68-78. [Article]
Jaakkola T, Backman JT, Neuvonen M, Niemi M, Neuvonen PJ: Montelukast and zafirlukast do not affect the pharmacokinetics of the CYP2C8 substrate pioglitazone. Eur J Clin Pharmacol. 2006 Jul;62(7):503-9. doi: 10.1007/s00228-006-0136-9. Epub 2006 May 3. [Article]
Jaakkola T, Laitila J, Neuvonen PJ, Backman JT: Pioglitazone is metabolised by CYP2C8 and CYP3A4 in vitro: potential for interactions with CYP2C8 inhibitors. Basic Clin Pharmacol Toxicol. 2006 Jul;99(1):44-51. doi: 10.1111/j.1742-7843.2006.pto_437.x. [Article]

Details3. Prostaglandin G/H synthase 1

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Substrate

General Function: Prostaglandin-endoperoxide synthase activity
Specific Function: Converts arachidonate to prostaglandin H2 (PGH2), a committed step in prostanoid synthesis. Involved in the constitutive production of prostanoids in particular in the stomach and platelets. In gas...
Gene Name: PTGS1
Uniprot ID: P23219
Uniprot Name: Prostaglandin G/H synthase 1
Molecular Weight: 68685.82 Da

References

Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [Article]

Details4. Cytochrome P450 3A4

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Substrate
Inhibitor

General Function: Vitamin d3 25-hydroxylase activity
Specific Function: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
Gene Name: CYP3A4
Uniprot ID: P08684
Uniprot Name: Cytochrome P450 3A4
Molecular Weight: 57342.67 Da

References

Garey KW, Peloquin CA, Godo PG, Nafziger AN, Amsden GW: Lack of effect of zafirlukast on the pharmacokinetics of azithromycin, clarithromycin, and 14-hydroxyclarithromycin in healthy volunteers. Antimicrob Agents Chemother. 1999 May;43(5):1152-5. [Article]
Kassahun K, Skordos K, McIntosh I, Slaughter D, Doss GA, Baillie TA, Yost GS: Zafirlukast metabolism by cytochrome P450 3A4 produces an electrophilic alpha,beta-unsaturated iminium species that results in the selective mechanism-based inactivation of the enzyme. Chem Res Toxicol. 2005 Sep;18(9):1427-37. doi: 10.1021/tx050092b. [Article]
Karonen T, Laitila J, Niemi M, Neuvonen PJ, Backman JT: Fluconazole but not the CYP3A4 inhibitor, itraconazole, increases zafirlukast plasma concentrations. Eur J Clin Pharmacol. 2012 May;68(5):681-8. doi: 10.1007/s00228-011-1158-5. Epub 2011 Nov 23. [Article]
Liu KH, Lee YM, Shon JH, Kim MJ, Lee SS, Yoon YR, Cha IJ, Shin JG: Potential of pranlukast and zafirlukast in the inhibition of human liver cytochrome P450 enzymes. Xenobiotica. 2004 May;34(5):429-38. doi: 10.1080/00498250410001691253 . [Article]

Details5. Cytochrome P450 1A2

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Inhibitor
Curator comments: Data is limited to in vitro studies.

General Function: Oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen, reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygen
Specific Function: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name: CYP1A2
Uniprot ID: P05177
Uniprot Name: Cytochrome P450 1A2
Molecular Weight: 58293.76 Da

References

Shader RI, Granda BW, von Moltke LL, Giancarlo GM, Greenblatt DJ: Inhibition of human cytochrome P450 isoforms in vitro by zafirlukast. Biopharm Drug Dispos. 1999 Nov;20(8):385-8. [Article]

Details6. Cytochrome P450 2C19

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Inhibitor
Curator comments: Data supporting this enzyme inhibition is limited to one in vitro study.

General Function: Steroid hydroxylase activity
Specific Function: Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and im...
Gene Name: CYP2C19
Uniprot ID: P33261
Uniprot Name: Cytochrome P450 2C19
Molecular Weight: 55930.545 Da

References

Shader RI, Granda BW, von Moltke LL, Giancarlo GM, Greenblatt DJ: Inhibition of human cytochrome P450 isoforms in vitro by zafirlukast. Biopharm Drug Dispos. 1999 Nov;20(8):385-8. [Article]

Details7. Cytochrome P450 2D6

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Inhibitor

General Function: Steroid hydroxylase activity
Specific Function: Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic...
Gene Name: CYP2D6
Uniprot ID: P10635
Uniprot Name: Cytochrome P450 2D6
Molecular Weight: 55768.94 Da

References

Shader RI, Granda BW, von Moltke LL, Giancarlo GM, Greenblatt DJ: Inhibition of human cytochrome P450 isoforms in vitro by zafirlukast. Biopharm Drug Dispos. 1999 Nov;20(8):385-8. [Article]

Transporters

Details1. ATP-binding cassette sub-family G member 2

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Antagonist

General Function: Xenobiotic-transporting atpase activity
Specific Function: High-capacity urate exporter functioning in both renal and extrarenal urate excretion. Plays a role in porphyrin homeostasis as it is able to mediates the export of protoporhyrin IX (PPIX) both fro...
Gene Name: ABCG2
Uniprot ID: Q9UNQ0
Uniprot Name: ATP-binding cassette sub-family G member 2
Molecular Weight: 72313.47 Da

References

Sun YL, Kathawala RJ, Singh S, Zheng K, Talele TT, Jiang WQ, Chen ZS: Zafirlukast antagonizes ATP-binding cassette subfamily G member 2-mediated multidrug resistance. Anticancer Drugs. 2012 Sep;23(8):865-73. doi: 10.1097/CAD.0b013e328354a196. [Article]

Details2. Sodium/bile acid cotransporter

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Inhibitor

General Function: Virus receptor activity
Specific Function: The hepatic sodium/bile acid uptake system exhibits broad substrate specificity and transports various non-bile acid organic compounds as well. It is strictly dependent on the extracellular presenc...
Gene Name: SLC10A1
Uniprot ID: Q14973
Uniprot Name: Sodium/bile acid cotransporter
Molecular Weight: 38118.64 Da

References

Donkers JM, Zehnder B, van Westen GJP, Kwakkenbos MJ, IJzerman AP, Oude Elferink RPJ, Beuers U, Urban S, van de Graaf SFJ: Reduced hepatitis B and D viral entry using clinically applied drugs as novel inhibitors of the bile acid transporter NTCP. Sci Rep. 2017 Nov 10;7(1):15307. doi: 10.1038/s41598-017-15338-0. [Article]

Drug created at June 13, 2005 13:24 / Updated at February 20, 2024 23:55

Zafirlukast

Identification

Structure for Zafirlukast (DB00549)

Pharmacology

Interactions

Products

Categories

Chemical Identifiers

References

Clinical Trials

Pharmacoeconomics

Properties

Spectra

Collision Cross Sections (CCS)

Targets

References

Enzymes

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References

References

References

References

References

Transporters

References

References