Identification
- Summary
Nedocromil is a pyrano quinoline used to treat allergic conjunctivitis.
- Brand Names
- Alocril
- Generic Name
- Nedocromil
- DrugBank Accession Number
- DB00716
- Background
A pyranoquinolone derivative that inhibits activation of inflammatory cells which are associated with asthma, including eosinophils, neutrophils, macrophages, mast cells, monocytes, and platelets.
- Type
- Small Molecule
- Groups
- Approved, Investigational
- Structure
Structure for Nedocromil (DB00716)
- Weight
- Average: 371.3408
Monoisotopic: 371.100501903 - Chemical Formula
- C19H17NO7
- Synonyms
- 9-Ethyl-6,9-dihydro-4,6-dioxo-10-propyl-4H-pyrano(3,2-g)chinolin-2,8-dicarbonsäure
- 9-ethyl-6,9-dihydro-4,6-dioxo-10-propyl-4H-pyrano(3,2-g)quinoline-2,8-dicarboxylic acid
- Nedocromil
- Nédocromil
- Nedocromilo
- Nedocromilum
- External IDs
- FPL 59002
Pharmacology
- Indication
For the treatment of mild to moderate asthma
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Associated Conditions
Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Treatment of Allergic rhinitis (ar) ••• ••• ••••• ••••• Adjunct therapy in treatment of Asthma ••• ••••• •••••••• Treatment of Itching of the eye •••••••••••• •••••••••• - Contraindications & Blackbox Warnings
Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API- Pharmacodynamics
Nedocromil is a anti-inflammatory agent and can be administered directly to the bronchial mucosa. It has significant inhibitory effect on allergen-induced early and late asthmatic reactions and on bronchial hyperresponsiveness.
- Mechanism of action
Nedocromil has been shown to inhibit the in vitro activation of, and mediator release from, a variety of inflammatory cell types associated with asthma, including eosinophils, neutrophils, macrophages, mast cells, monocytes, and platelets. Nedocromil inhibits activation and release of inflammatory mediators such as histamine, prostaglandin D2 and leukotrienes c4 from different types of cells in the lumen and mucosa of the bronchial tree. These mediators are derived from arachidonic acid metabolism through the lipoxygenase and cyclo-oxygenase pathways. The mechanism of action of nedocromil may be due partly to inhibition of axon reflexes and release of sensory neuropeptides, such as substance P, neurokinin A, and calcitonin-geneñrelated peptides. The result is inhibition of bradykinin-induced bronchoconstriction. Nedocromil does not posess any bronchodilator, antihistamine, or corticosteroid activity.
Target Actions Organism ACysteinyl leukotriene receptor 1 antagonistHumans ACysteinyl leukotriene receptor 2 antagonistHumans UfMet-Leu-Phe receptor antagonistHumans UProstaglandin D2 receptor unknownHumans UHeat shock protein HSP 90-alpha Not Available Humans - Absorption
Low
- Volume of distribution
Not Available
- Protein binding
approximately 89% protein bound in human plasma over a concentration range of 0.5 to 50 µg/mL
- Metabolism
Nedocromil is not metabolized after IV administration and is excreted unchanged.
- Route of elimination
It is not metabolized and is eliminated primarily unchanged in urine (70%) and feces (30%).
- Half-life
~3.3 hours
- 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
Side effects include headache, nasal congestion, ocular burning, irritation and stinging, unpleasant taste, cough, difficulty breathing, noisy breathing, shortness of breath, tightness in chest, wheezing, conjunctivitis, blurred vision, change in color vision, difficulty seeing at night, increased sensitivity of eyes to sunlight.
- 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 softwareAbacavir Nedocromil may decrease the excretion rate of Abacavir which could result in a higher serum level. Aceclofenac Aceclofenac may decrease the excretion rate of Nedocromil which could result in a higher serum level. Acemetacin Acemetacin may decrease the excretion rate of Nedocromil which could result in a higher serum level. Acetaminophen Acetaminophen may decrease the excretion rate of Nedocromil which could result in a higher serum level. Acetazolamide Acetazolamide may increase the excretion rate of Nedocromil which could result in a lower serum level and potentially a reduction in efficacy. - Food Interactions
- No interactions found.
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- Product Ingredients
Ingredient UNII CAS InChI Key Nedocromil sodium ET8IF4KS1T 69049-74-7 JQEKDNLKIVGXAU-UHFFFAOYSA-L - Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Alocril Solution / drops 20 mg/1mL Ophthalmic Allergan, Inc. 2000-02-03 Not applicable US 
Alocril Liquid 2 % Ophthalmic Allergan 2000-02-29 2019-04-01 Canada 
Mireze Liquid 2 % Ophthalmic Allergan 1997-08-06 2000-03-14 Canada Tilade Aerosol, metered 2 mg/1 Respiratory (inhalation) Pfizer Laboratories Div Pfizer Inc. 1992-12-30 2008-11-05 US Tilade Aerosol, metered 2 mg / dose Oral Aventis Pharma Ltd. 1998-12-06 2006-07-28 Canada - Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Nedocromil Sodium Solution / drops 20 mg/1mL Ophthalmic Akorn 2012-09-10 Not applicable US
Categories
- ATC Codes
- R03BC03 — Nedocromil
- R03BC — Antiallergic agents, excl. corticosteroids
- R03B — OTHER DRUGS FOR OBSTRUCTIVE AIRWAY DISEASES, INHALANTS
- R03 — DRUGS FOR OBSTRUCTIVE AIRWAY DISEASES
- R — RESPIRATORY SYSTEM
- R01AC — Antiallergic agents, excl. corticosteroids
- R01A — DECONGESTANTS AND OTHER NASAL PREPARATIONS FOR TOPICAL USE
- R01 — NASAL PREPARATIONS
- R — RESPIRATORY SYSTEM
- Drug Categories
- 4-Quinolones
- Anti-Allergic Agents
- Anti-Asthmatic Agents
- Anti-Inflammatory Agents
- Antiallergic Agents, Excl. Corticosteroids
- Decongestants and Antiallergics
- Decreased Histamine Release
- Drugs for Obstructive Airway Diseases
- Drugs that are Mainly Renally Excreted
- Heterocyclic Compounds, Fused-Ring
- Immunologic Factors
- Mast Cell Stabilizers
- Nasal Preparations
- Ophthalmologicals
- Quinolines
- Quinolones
- Respiratory Agents, Miscellaneous
- Respiratory System Agents
- Sensory Organs
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as chromenopyridines. These are aromatic heterocyclic compounds structurally characterized by a pyridine ring fused to a chromene moiety.
- Kingdom
- Organic compounds
- Super Class
- Organoheterocyclic compounds
- Class
- Benzopyrans
- Sub Class
- 1-benzopyrans
- Direct Parent
- Chromenopyridines
- Alternative Parents
- Quinoline carboxylic acids / Chromones / Hydroquinolones / Hydroquinolines / Pyridinecarboxylic acids / Pyranones and derivatives / Benzenoids / Dicarboxylic acids and derivatives / Vinylogous amides / Heteroaromatic compounds show 8 more
- Substituents
- Aromatic heteropolycyclic compound / Azacycle / Benzenoid / Carboxylic acid / Carboxylic acid derivative / Chromenopyridine / Chromone / Dicarboxylic acid or derivatives / Dihydroquinoline / Dihydroquinolone show 17 more
- Molecular Framework
- Aromatic heteropolycyclic compounds
- External Descriptors
- organic heterotricyclic compound, dicarboxylic acid (CHEBI:7492)
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- 0B535E0BN0
- CAS number
- 69049-73-6
- InChI Key
- RQTOOFIXOKYGAN-UHFFFAOYSA-N
- InChI
- InChI=1S/C19H17NO7/c1-3-5-9-16-10(13(21)7-12(18(23)24)20(16)4-2)6-11-14(22)8-15(19(25)26)27-17(9)11/h6-8H,3-5H2,1-2H3,(H,23,24)(H,25,26)
- IUPAC Name
- 9-ethyl-4,6-dioxo-10-propyl-4H,6H,9H-chromeno[7,6-b]pyridine-2,8-dicarboxylic acid
- SMILES
- CCCC1=C2N(CC)C(=CC(=O)C2=CC2=C1OC(=CC2=O)C(O)=O)C(O)=O
References
- Synthesis Reference
Andrew R. Clark, "Nedocromil sodium compositions and methods for their preparation." U.S. Patent US4935244, issued July, 1988.
US4935244- General References
- Not Available
- External Links
- Human Metabolome Database
- HMDB0014854
- KEGG Drug
- D05129
- KEGG Compound
- C07255
- PubChem Compound
- 50294
- PubChem Substance
- 46507587
- ChemSpider
- 45608
- BindingDB
- 50239990
- 31563
- ChEBI
- 7492
- ChEMBL
- CHEMBL746
- ZINC
- ZINC000003782807
- PharmGKB
- PA450601
- RxList
- RxList Drug Page
- Drugs.com
- Drugs.com Drug Page
- PDRhealth
- PDRhealth Drug Page
- Wikipedia
- Nedocromil
- FDA label
- Download (362 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 4 Terminated Basic Science Exercise-induced Arterial Hypoxemia 1 3 Completed Treatment Asthma / Lung Disorder 1 1 Completed Treatment Asthma 1 Not Available Completed Treatment Asthma / Lung Disorder 1
Pharmacoeconomics
- Manufacturers
- King pharmaceuticals inc
- Allergan inc
- Sanofi aventis us llc
- Packagers
- Allergan Inc.
- Fisons PLC
- King Pharmaceuticals Inc.
- Rhone Poulenc Rorer Respiratory
- Sanofi-Aventis Inc.
- Dosage Forms
Form Route Strength Liquid Ophthalmic 2 % Solution / drops Ophthalmic 20 mg/1mL Spray Nasal 1 % Aerosol Respiratory (inhalation) 2 MG Aerosol, metered Oral 2 mg / dose Aerosol, metered Respiratory (inhalation) 2 mg/1 Aerosol, metered Respiratory (inhalation) 2 MG Aerosol; suspension Respiratory (inhalation) 2 MG Spray Nasal 10 MG/2ML Aerosol, metered Respiratory (inhalation) Aerosol, metered Respiratory (inhalation) 2 mg / act Spray Nasal 10 MG/ML Solution / drops Ophthalmic Solution / drops Ophthalmic 2 % - Prices
Unit description Cost Unit Alocril 2% Solution 5ml Bottle 100.57USD bottle Alocril 2% eye drops 19.34USD ml DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.- Patents
Patent Number Pediatric Extension Approved Expires (estimated) Region USRE38628 No 2004-10-19 2012-08-22 US
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 299 dec °C PhysProp water solubility 145 mg/L Not Available logP 2.22 SANGSTER (1994) - Predicted Properties
Property Value Source Water Solubility 0.0459 mg/mL ALOGPS logP 2.18 ALOGPS logP 2.5 Chemaxon logS -3.9 ALOGPS pKa (Strongest Acidic) 2.2 Chemaxon pKa (Strongest Basic) -4.2 Chemaxon Physiological Charge -2 Chemaxon Hydrogen Acceptor Count 8 Chemaxon Hydrogen Donor Count 2 Chemaxon Polar Surface Area 121.21 Å2 Chemaxon Rotatable Bond Count 5 Chemaxon Refractivity 98.09 m3·mol-1 Chemaxon Polarizability 37.15 Å3 Chemaxon Number of Rings 3 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.917 Blood Brain Barrier - 0.7048 Caco-2 permeable - 0.5125 P-glycoprotein substrate Substrate 0.5954 P-glycoprotein inhibitor I Non-inhibitor 0.8426 P-glycoprotein inhibitor II Non-inhibitor 0.5435 Renal organic cation transporter Non-inhibitor 0.8157 CYP450 2C9 substrate Non-substrate 0.8194 CYP450 2D6 substrate Non-substrate 0.8091 CYP450 3A4 substrate Non-substrate 0.5338 CYP450 1A2 substrate Inhibitor 0.7062 CYP450 2C9 inhibitor Non-inhibitor 0.8555 CYP450 2D6 inhibitor Non-inhibitor 0.9076 CYP450 2C19 inhibitor Non-inhibitor 0.6715 CYP450 3A4 inhibitor Non-inhibitor 0.8646 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.8278 Ames test Non AMES toxic 0.6198 Carcinogenicity Non-carcinogens 0.9488 Biodegradation Not ready biodegradable 0.9798 Rat acute toxicity 2.6400 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9113 hERG inhibition (predictor II) Non-inhibitor 0.8385
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS splash10-0fi3-1079000000-d564312728bd150fe31c Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-0fk9-0009000000-6bcfb42daed31d8de264 Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-0fi0-0029000000-2e11ac9debecb4a39a82 Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-001i-0093000000-466b5fdb29b8ab51c4e8 Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-00ai-0093000000-db1ded6664220a645cfc Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-000t-0093000000-de07b7601a3a68157a46 Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-001j-0093000000-2c89faa2c6ebd43bf06a 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]- 197.7100097 predictedDarkChem Lite v0.1.0 [M-H]- 181.32335 predictedDeepCCS 1.0 (2019) [M+H]+ 199.9889097 predictedDarkChem Lite v0.1.0 [M+H]+ 183.68135 predictedDeepCCS 1.0 (2019) [M+Na]+ 199.0360097 predictedDarkChem Lite v0.1.0 [M+Na]+ 191.38339 predictedDeepCCS 1.0 (2019)
Targets
Build, predict & validate machine-learning models
Use our structured and evidence-based datasets to unlock newinsights and accelerate drug research.
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- 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
- Monteseirin J, Chacon P, Vega A, Sanchez-Monteseirin H, Asturias JA, Martinez A, Guardia P, Perez-Cano R, Conde J: L-selectin expression on neutrophils from allergic patients. Clin Exp Allergy. 2005 Sep;35(9):1204-13. [Article]
- Yazid S, Leoni G, Getting SJ, Cooper D, Solito E, Perretti M, Flower RJ: Antiallergic cromones inhibit neutrophil recruitment onto vascular endothelium via annexin-A1 mobilization. Arterioscler Thromb Vasc Biol. 2010 Sep;30(9):1718-24. doi: 10.1161/ATVBAHA.110.209536. Epub 2010 Jun 17. [Article]
- Radeau T, Godard P, Chavis C, Michel FB, Descomps B, Damon M: Effect of nedocromil sodium on sulfidopeptide leukotrienes-stimulated human alveolar macrophages in asthma. Pulm Pharmacol. 1993 Mar;6(1):27-31. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Antagonist
- General Function
- Leukotriene receptor activity
- Specific Function
- Receptor for cysteinyl leukotrienes. The response is mediated via a G-protein that activates a phosphatidylinositol-calcium second messenger system. Stimulation by BAY u9773, a partial agonist, ind...
- Gene Name
- CYSLTR2
- Uniprot ID
- Q9NS75
- Uniprot Name
- Cysteinyl leukotriene receptor 2
- Molecular Weight
- 39634.815 Da
References
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
- Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]
- Monteseirin J, Chacon P, Vega A, Sanchez-Monteseirin H, Asturias JA, Martinez A, Guardia P, Perez-Cano R, Conde J: L-selectin expression on neutrophils from allergic patients. Clin Exp Allergy. 2005 Sep;35(9):1204-13. [Article]
- Yazid S, Leoni G, Getting SJ, Cooper D, Solito E, Perretti M, Flower RJ: Antiallergic cromones inhibit neutrophil recruitment onto vascular endothelium via annexin-A1 mobilization. Arterioscler Thromb Vasc Biol. 2010 Sep;30(9):1718-24. doi: 10.1161/ATVBAHA.110.209536. Epub 2010 Jun 17. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Antagonist
- General Function
- Receptor activity
- Specific Function
- High affinity receptor for N-formyl-methionyl peptides (fMLP), which are powerful neutrophil chemotactic factors (PubMed:2161213, PubMed:2176894, PubMed:10514456, PubMed:15153520). Binding of fMLP ...
- Gene Name
- FPR1
- Uniprot ID
- P21462
- Uniprot Name
- fMet-Leu-Phe receptor
- Molecular Weight
- 38445.115 Da
References
- Peroni DG, Melotti P, Piacentini GL, Bonizzato C, Boner AL: Effects of nedocromil sodium on the binding of N-formyl-methionyl-leucyl-phenylalanine in human neutrophils. Agents Actions. 1992 Jul;36(3-4):212-4. [Article]
- Carolan EJ, Casale TB: Effects of nedocromil sodium and WEB 2086 on chemoattractant-stimulated neutrophil migration through cellular and noncellular barriers. Ann Allergy. 1992 Oct;69(4):323-8. [Article]
- Warringa RA, Mengelers HJ, Maikoe T, Bruijnzeel PL, Koenderman L: Inhibition of cytokine-primed eosinophil chemotaxis by nedocromil sodium. J Allergy Clin Immunol. 1993 Mar;91(3):802-9. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Unknown
- General Function
- Prostaglandin j receptor activity
- Specific Function
- Receptor for prostaglandin D2 (PGD2). The activity of this receptor is mainly mediated by G(s) proteins that stimulate adenylate cyclase, resulting in an elevation of intracellular cAMP. A mobiliza...
- Gene Name
- PTGDR
- Uniprot ID
- Q13258
- Uniprot Name
- Prostaglandin D2 receptor
- Molecular Weight
- 40270.11 Da
References
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
- Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]
- Lane SJ, Lee TH: Mast cell effector mechanisms. J Allergy Clin Immunol. 1996 Nov;98(5 Pt 2):S67-71; discussion S71-2. [Article]
- Ahluwalia P, Anderson DF, Wilson SJ, McGill JI, Church MK: Nedocromil sodium and levocabastine reduce the symptoms of conjunctival allergen challenge by different mechanisms. J Allergy Clin Immunol. 2001 Sep;108(3):449-54. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Tpr domain binding
- Specific Function
- Molecular chaperone that promotes the maturation, structural maintenance and proper regulation of specific target proteins involved for instance in cell cycle control and signal transduction. Under...
- Gene Name
- HSP90AA1
- Uniprot ID
- P07900
- Uniprot Name
- Heat shock protein HSP 90-alpha
- Molecular Weight
- 84659.015 Da
References
- Okada M, Itoh H, Hatakeyama T, Tokumitsu H, Kobayashi R: Hsp90 is a direct target of the anti-allergic drugs disodium cromoglycate and amlexanox. Biochem J. 2003 Sep 1;374(Pt 2):433-41. [Article]
- Nishikawa M, Takemoto S, Takakura Y: Heat shock protein derivatives for delivery of antigens to antigen presenting cells. Int J Pharm. 2008 Apr 16;354(1-2):23-7. Epub 2007 Sep 29. [Article]
Drug created at June 13, 2005 13:24 / Updated at February 20, 2024 23:55