Cinalukast
Explore a selection of our essential drug information below, or:
Identification
- Generic Name
- Cinalukast
- DrugBank Accession Number
- DB00587
- Background
Used in the treatment of asthma, cinalukast selectively antagonizes leukotriene D4 (LTD4) at the cysteinyl leukotriene receptor, CysLT1, in the human airway. Cinalukast inhibits the actions of LTD4 at the CysLT1 receptor, preventing airway edema, smooth muscle contraction, and enhanced secretion of thick, viscous mucus.
- Type
- Small Molecule
- Groups
- Experimental
- Structure
- Weight
- Average: 412.545
Monoisotopic: 412.182063462 - Chemical Formula
- C23H28N2O3S
- Synonyms
- 3'-((E)-2-(4-cyclobutyl-2-thiazolyl)vinyl)-2,2-diethylsuccinanilic acid
- Cinalukast
- External IDs
- RO 24-5913
- RO-24-5913
Pharmacology
- Indication
For Protection against second- phase inflamation in exercise-induced bronchoconstriction and Asthma.
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- Pharmacodynamics
Used in the treatment of asthma, cinalukast selectively antagonizes leukotriene D4 (LTD4) at the cysteinyl leukotriene receptor, CysLT1, in the human airway. Cinalukast inhibits the actions of LTD4 at the CysLT1 receptor, preventing airway edema, smooth muscle contraction, and enhanced secretion of thick, viscous mucus.
- Mechanism of action
Binds to the cysteinyl leukotriene receptor. The cysteinyl leukotrienes (LTC4, LTD4, LTE4) are products of arachidonic acid metabolism and are released from various cells, including mast cells and eosinophils. These eicosanoids bind to cysteinyl leukotriene receptors (CysLT) found in the human airway. Cysteinyl leukotrienes and leukotriene receptor occupation have been correlated with the pathophysiology of asthma, including airway edema, smooth muscle contraction, 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 antagonistHumans - Absorption
Not Available
- Volume of distribution
Not Available
- Protein binding
Not Available
- Metabolism
- Not Available
- Route of elimination
Not Available
- Half-life
Not Available
- Clearance
Not Available
- Adverse Effects
- Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.
- Toxicity
Not Available
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- 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.Not Available
- Food Interactions
- Not Available
Categories
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as anilides. These are organic heterocyclic compounds derived from oxoacids RkE(=O)l(OH)m (l not 0) by replacing an OH group by the NHPh group or derivative formed by ring substitution.
- Kingdom
- Organic compounds
- Super Class
- Benzenoids
- Class
- Benzene and substituted derivatives
- Sub Class
- Anilides
- Direct Parent
- Anilides
- Alternative Parents
- Styrenes / N-arylamides / 2,4-disubstituted thiazoles / Fatty amides / Heteroaromatic compounds / Secondary carboxylic acid amides / Monocarboxylic acids and derivatives / Carboxylic acids / Azacyclic compounds / Organopnictogen compounds show 3 more
- Substituents
- 2,4-disubstituted 1,3-thiazole / Anilide / Aromatic heteromonocyclic compound / Azacycle / Azole / Carbonyl group / Carboxamide group / Carboxylic acid / Carboxylic acid derivative / Fatty acyl show 15 more
- Molecular Framework
- Aromatic heteromonocyclic compounds
- External Descriptors
- 1,3-thiazole, carboxylic acid (CHEBI:126598)
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- 5E1O433QAI
- CAS number
- 128312-51-6
- InChI Key
- BZMKNPGKXJAIDV-VAWYXSNFSA-N
- InChI
- InChI=1S/C23H28N2O3S/c1-3-23(4-2,22(27)28)14-20(26)24-18-10-5-7-16(13-18)11-12-21-25-19(15-29-21)17-8-6-9-17/h5,7,10-13,15,17H,3-4,6,8-9,14H2,1-2H3,(H,24,26)(H,27,28)/b12-11+
- IUPAC Name
- 3-({3-[(E)-2-(4-cyclobutyl-1,3-thiazol-2-yl)ethenyl]phenyl}carbamoyl)-2,2-diethylpropanoic acid
- SMILES
- CCC(CC)(CC(=O)NC1=CC(\C=C\C2=NC(=CS2)C2CCC2)=CC=C1)C(O)=O
References
- General References
- Not Available
- External Links
- Human Metabolome Database
- HMDB0014725
- KEGG Drug
- D02846
- PubChem Compound
- 6436135
- PubChem Substance
- 46505799
- ChemSpider
- 4940804
- BindingDB
- 50064086
- ChEBI
- 126598
- ChEMBL
- CHEMBL283754
- ZINC
- ZINC000003803377
- Therapeutic Targets Database
- DAP000976
- PharmGKB
- PA164743057
Clinical Trials
- Clinical Trials
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Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
- Not Available
- Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source logP 4 Not Available - Predicted Properties
Property Value Source Water Solubility 0.000872 mg/mL ALOGPS logP 4.98 ALOGPS logP 5.48 Chemaxon logS -5.7 ALOGPS pKa (Strongest Acidic) 4.36 Chemaxon pKa (Strongest Basic) 2.44 Chemaxon Physiological Charge -1 Chemaxon Hydrogen Acceptor Count 4 Chemaxon Hydrogen Donor Count 2 Chemaxon Polar Surface Area 79.29 Å2 Chemaxon Rotatable Bond Count 9 Chemaxon Refractivity 116.75 m3·mol-1 Chemaxon Polarizability 45.8 Å3 Chemaxon Number of Rings 3 Chemaxon Bioavailability 1 Chemaxon Rule of Five No Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule Yes Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9315 Blood Brain Barrier + 0.8337 Caco-2 permeable - 0.6145 P-glycoprotein substrate Substrate 0.5433 P-glycoprotein inhibitor I Non-inhibitor 0.939 P-glycoprotein inhibitor II Non-inhibitor 0.9373 Renal organic cation transporter Non-inhibitor 0.9402 CYP450 2C9 substrate Non-substrate 0.7695 CYP450 2D6 substrate Non-substrate 0.8402 CYP450 3A4 substrate Non-substrate 0.5901 CYP450 1A2 substrate Non-inhibitor 0.7134 CYP450 2C9 inhibitor Non-inhibitor 0.6524 CYP450 2D6 inhibitor Non-inhibitor 0.9247 CYP450 2C19 inhibitor Non-inhibitor 0.6193 CYP450 3A4 inhibitor Inhibitor 0.7242 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.5806 Ames test Non AMES toxic 0.7982 Carcinogenicity Non-carcinogens 0.857 Biodegradation Not ready biodegradable 0.9763 Rat acute toxicity 2.5159 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9993 hERG inhibition (predictor II) Non-inhibitor 0.9064
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS splash10-0a59-4379000000-738e6d7592628c151ba0 Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-08g0-1923100000-5cbbb6f75e8eb4d5d059 Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-03di-0074900000-5f5a24335c5652405029 Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-0ug0-2298000000-752e684f0b7a4277ebd9 Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-0a4i-3294000000-21f278c60fbaf6225714 Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-0ilc-7479100000-851507b3a16b1a6c266b Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-001i-7392000000-919ce86e7817d0727602 Predicted 1H NMR Spectrum 1D NMR Not Applicable Predicted 13C NMR Spectrum 1D NMR Not Applicable - Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 227.7089417 predictedDarkChem Lite v0.1.0 [M-H]- 229.4831417 predictedDarkChem Lite v0.1.0 [M-H]- 196.78464 predictedDeepCCS 1.0 (2019) [M+H]+ 228.6781417 predictedDarkChem Lite v0.1.0 [M+H]+ 230.6534417 predictedDarkChem Lite v0.1.0 [M+H]+ 199.14264 predictedDeepCCS 1.0 (2019) [M+Na]+ 227.7147417 predictedDarkChem Lite v0.1.0 [M+Na]+ 228.6090417 predictedDarkChem Lite v0.1.0 [M+Na]+ 205.45859 predictedDeepCCS 1.0 (2019)
Targets
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Antagonist
- General 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, eosinophil migration and damage to the mucus layer in the lung. This response is mediated via a G-protein that activates a phosphatidylinositol-calcium second messenger system. The rank order of affinities for the leukotrienes is LTD4 >> LTE4 = LTC4 >> LTB4
- Specific Function
- cysteinyl leukotriene receptor activity
- 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]
- Adelroth E, Inman MD, Summers E, Pace D, Modi M, O'Byrne PM: Prolonged protection against exercise-induced bronchoconstriction by the leukotriene D4-receptor antagonist cinalukast. J Allergy Clin Immunol. 1997 Feb;99(2):210-5. [Article]
- Foller M, Mahmud H, Gu S, Wang K, Floride E, Kucherenko Y, Luik S, Laufer S, Lang F: Participation of leukotriene C(4) in the regulation of suicidal erythrocyte death. J Physiol Pharmacol. 2009 Sep;60(3):135-43. [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]
- 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]
- Zhou Y, Zhang Y, Zhao D, Yu X, Shen X, Zhou Y, Wang S, Qiu Y, Chen Y, Zhu F: TTD: Therapeutic Target Database describing target druggability information. Nucleic Acids Res. 2024 Jan 5;52(D1):D1465-D1477. doi: 10.1093/nar/gkad751. [Article]
Drug created at June 13, 2005 13:24 / Updated at October 29, 2024 18:03