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Nedocromil
Structural formula of nedocromil
Space-filling model of the nedocromil molecule
Clinical data
Trade namesAlocril
AHFS/Drugs.comMonograph
MedlinePlusa601243
Routes of
administration		Inhalation and eye drops
ATC code
Legal status
Legal status
  • AU: S4 (Prescription only)
  • UK: POM (Prescription only)
  • US: ℞-only
Pharmacokinetic data
Protein binding89%
Metabolismnot metabolized
Elimination half-life~3.3 hours
Excretionexcreted unchanged
Identifiers
  • 9-ethyl-4,6-dioxo-10-propyl-6,9-dihydro-4H-pyrano[3,2-g]quinoline-2,8-dicarboxylic acid
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.233.208 Edit this at Wikidata
Chemical and physical data
FormulaC19H17NO7
Molar mass371.345 g·mol−1
3D model (JSmol)
  • O=C\1c3c(N(/C(C(=O)O)=C/1)CC)c(c2O/C(=C\C(=O)c2c3)C(=O)O)CCC
  • 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) checkY
  • Key:RQTOOFIXOKYGAN-UHFFFAOYSA-N checkY
  (verify)

Nedocromil sodium is a medication considered a mast cell stabilizer which acts to prevent wheezing, shortness of breath, and other breathing problems caused by asthma. It is administered by an inhaler under the brand name Tilade, and as an eye drop under the brand name Alocril.[1][2] The effects of nedocromil versus asthma are gradual rather than fast-acting and it is not indicated for acute respiratory distress compared to fast acting bronchodilators like albuterol or other well-known inhaler medications. Liquid preparations of nedocromil are available in the UK under the name Rapitil for use for allergic eye reactions.[3] Nedocromil sodium has been shown to be effective in alleviating symptoms of allergic conjunctivitis.[4]

Nedocromil is classified as a benzopyrone. Nedocromil acts as a mast cell stabilizer, inhibits the degranulation of mast cells, prevents release of histamine and tryptase, so preventing the synthesis of prostaglandins and leukotrienes. US Production of inhaled nedocromil ceased in April 2008 because it used CFCs as propellant.[5]

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References

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Nedocromil

View on Grokipedia
from Grokipedia
Nedocromil sodium is the disodium salt of a pyranoquinoline dicarboxylic acid, functioning as a non-steroidal anti-inflammatory agent and mast cell stabilizer primarily developed for the management of bronchial asthma and allergic ocular conditions.[1][2] Introduced in the 1980s, it inhibits the activation and mediator release from inflammatory cells such as mast cells, eosinophils, and neutrophils, thereby preventing early and late-phase asthmatic responses without bronchodilatory effects.[3][4] Clinically, it was approved by the FDA in 1992 for inhalation aerosol (Tilade) to treat mild to moderate persistent asthma in adults and children over age 6, and in 1999 for ophthalmic solution (Alocril) to relieve itching associated with allergic conjunctivitis.[5][6] It also demonstrated efficacy in preventing exercise-induced bronchoconstriction when administered prophylactically.[7] However, due to market factors, the inhalation formulation was discontinued in the United States in 2008, and the ophthalmic version was discontinued by 2025, though it may remain available in other regions or for specific uses.[8][9]

Medical uses

Asthma

Nedocromil sodium is primarily indicated as maintenance therapy for the prevention of symptoms in adults and children aged 6 years and older with mild to moderate persistent asthma.[10] It serves as a non-steroidal anti-inflammatory agent administered via inhalation to provide long-term control rather than immediate symptom relief.[11] The typical dosage regimen consists of two inhalations (delivering 1.75 mg of nedocromil sodium per inhalation, for a total of 3.5 mg per dose) four times daily at regular intervals, resulting in a daily dose of 14 mg.[12] This prophylactic approach reduces the frequency and severity of asthma attacks by stabilizing mast cells in the airways, thereby inhibiting the release of inflammatory mediators.[13] Clinical trials have demonstrated its efficacy in preventing exercise-induced bronchoconstriction, with nedocromil sodium reducing both the severity and duration of airflow obstruction when administered prior to exercise.[14] Similarly, it attenuates allergen-induced early and late-phase asthmatic responses, including the associated increase in bronchial hyperresponsiveness.[15] However, nedocromil sodium is not suitable for treating acute asthma exacerbations and requires regular use for 2 to 4 weeks to achieve optimal therapeutic effects.[11]

Allergic conjunctivitis

Nedocromil sodium ophthalmic solution is indicated for the treatment of itching associated with allergic conjunctivitis, including vernal keratoconjunctivitis (VKC) and other forms of allergic eye inflammation.[16][17][18] It is approved for use in patients aged 3 years and older, with safety and effectiveness not established in children under this age.[16][19] The recommended dosage is 1 or 2 drops instilled in each affected eye twice daily, administered at regular intervals throughout the period of allergen exposure, such as during allergy seasons.[16][20] Nedocromil acts by inhibiting the release of inflammatory mediators, such as leukotrienes and histamine, from conjunctival mast cells, thereby stabilizing mast cells and preventing the allergic response.[21][22] Clinical studies have demonstrated that regular use of nedocromil 2% eye drops leads to significant reductions in key symptoms of allergic conjunctivitis, including ocular itching, conjunctival hyperemia, and photophobia, with benefits typically emerging within days of consistent application.[23][24] Unlike antihistamine-based treatments, nedocromil is not intended for immediate acute relief but serves primarily as a prophylactic agent to prevent symptom exacerbation during ongoing allergen exposure.[25][26]

Allergic rhinitis

Nedocromil sodium has been investigated as a 1% nasal spray for prophylactic management of seasonal or perennial allergic rhinitis, particularly in countries where it was approved, such as Italy. It was used to reduce key symptoms such as sneezing, rhinorrhea, and nasal congestion by targeting nasal mast cells and inhibiting the release of inflammatory mediators including histamine and leukotrienes. However, this formulation was never approved by the FDA in the United States and is not available there.[27] The studied dosage involved 1-2 sprays per nostril twice daily, with treatment initiated 1-2 weeks prior to anticipated allergen exposure.[28] Clinical studies demonstrated efficacy, particularly in pollen-induced rhinitis, with significant decreases in overall symptom scores compared to placebo during peak seasons.[29] For perennial allergic rhinitis, symptom relief was observed over two months of use.[30] Studies included pediatric patients aged 6 years and older, showing comparable benefits without increased adverse events. Consistent use was essential for effects to build over 1-2 weeks. Note: The inhalation formulation for asthma was discontinued in the US in 2008, and the ophthalmic formulation for allergic conjunctivitis by 2025; the nasal formulation was not approved in the US.[9][8]

Adverse effects

Inhalation administration

Nedocromil sodium administered via inhalation is generally well-tolerated, with common side effects primarily affecting the respiratory tract and occurring in more than 3% of users. These include unpleasant taste (11.6%), bronchospasm (8.4%), cough (8.9%), headache (8.1%), pharyngitis (7.6%), rhinitis (7.3%), and upper respiratory tract infection (6.7%).[10] Less common adverse effects, reported in less than 1% of patients, encompass nausea and dizziness. Paradoxical bronchospasm, a worsening of breathing difficulties shortly after administration that may occur in approximately 5-8% of patients, is a form of bronchospasm requiring immediate medical attention.[31][10][32] Precautions are essential for safe use of inhaled nedocromil. It is not intended for the relief of acute asthma attacks, as it lacks bronchodilator properties and may delay effective treatment if relied upon during exacerbations.[10] Patients should rinse their mouth with water after each inhalation to minimize throat irritation and reduce the risk of local side effects like unpleasant taste or hoarseness.[33] Additionally, monitoring for hypersensitivity reactions is recommended, including symptoms such as wheezing or dyspnea, which may necessitate immediate discontinuation and medical evaluation.[31] In long-term use, inhaled nedocromil exhibits a favorable safety profile, with no significant systemic effects observed due to its low absorption rate of approximately 8% for single doses and 17% for multiple doses from the respiratory tract.[10] Clinical trials extending up to 52 weeks have confirmed its tolerability, with withdrawal rates due to adverse events comparable to placebo (around 6%).[10]

Ophthalmic administration

Nedocromil sodium ophthalmic solution is generally well-tolerated when used for allergic conjunctivitis, with most adverse effects being mild and transient due to minimal systemic absorption (less than 4% of the dose).[34] The primary route of absorption occurs via the nasolacrimal duct, leading to low risk of broader systemic effects.[34] Common side effects include transient ocular burning, irritation, or stinging upon instillation, occurring in 10% to 30% of patients, as well as blurred vision and mild eye redness or itching.[34][35] These local effects typically resolve quickly and do not require discontinuation of therapy.[36] Less common adverse reactions, affecting 1% to 10% of users, encompass headache (reported in up to 40% in some labeling but lower in clinical studies), photophobia, and nasal congestion from drainage.[34][36] Rare events include severe allergic reactions in patients with hypersensitivity to nedocromil or its components, and potential keratitis or other serious ocular damage if contamination occurs during administration.[34] Precautions for safe use include removing contact lenses prior to instillation and waiting at least 15 minutes before reinserting them, as the solution may contain preservatives that could discolor soft lenses.[35] Users should shake the bottle well if specified, avoid touching the dropper tip to the eye or any surface to prevent contamination, and apply drops inside the lower eyelid rather than directly on the cornea.[34]

Pharmacology

Pharmacodynamics

Nedocromil sodium acts primarily as a mast cell stabilizer, inhibiting the degranulation of mast cells and preventing the release of inflammatory mediators such as histamine, leukotriene C4 (LTC4), and prostaglandin D2 (PGD2) in response to allergens and other stimuli.[13][37] This inhibition occurs without direct antihistaminic, bronchodilatory, or corticosteroid-like activity, positioning nedocromil as a prophylactic agent that attenuates early and late asthmatic reactions rather than providing acute symptomatic relief.[13][38] Beyond mast cells, nedocromil exerts anti-inflammatory effects on multiple cell types, including eosinophils, neutrophils, and macrophages. It suppresses eosinophil chemotaxis and activation induced by platelet-activating factor (PAF) and LTB4, with IC50 values of approximately 1.3 × 10⁻⁷ mol/L for PAF and 9.4 × 10⁻⁸ mol/L for LTB4, while also slightly reducing LTC4 release from eosinophils.[39] Similarly, it inhibits neutrophil chemotaxis triggered by fMLP, ZAS, PAF, and LTB4 (IC50 values ranging from 7.3 × 10⁻⁸ to 2.4 × 10⁻⁷ mol/L) and limits mediator release from macrophages and monocytes.[13][39] These actions contribute to reduced recruitment and activation of inflammatory cells in allergic responses.[40] Nedocromil also modulates neurogenic inflammation by inhibiting sensory nerve activation and axon reflexes, thereby suppressing the release of neuropeptides such as substance P, neurokinin A, and calcitonin gene-related peptide.[13][41] This effect is evident in preclinical models where nedocromil prevents bradykinin- or substance P-induced plasma extravasation, bronchial hyperresponsiveness, and nonadrenergic noncholinergic bronchoconstriction.[41] Additionally, it demonstrates anti-inflammatory properties on epithelial cells by protecting against mediator-induced damage and altering cellular responses to osmotic challenges.[40] At the cellular level, nedocromil's effects are linked to dose-dependent inhibition of chloride ion flux through channels in mast cells (IC50: 8 μmol/L), epithelial cells, and neurons, which prevents membrane hyperpolarization, reduces calcium influx, and thereby limits degranulation and neuronal depolarization.[42] This mechanism underlies its broader suppression of inflammatory mediator release and sensory nerve reflexes across various cell types.[42]

Pharmacokinetics

Nedocromil sodium demonstrates low systemic bioavailability across administration routes, primarily due to its topical action at the site of inflammation. Following inhalation, absolute bioavailability is approximately 8% after a single dose and up to 17% with multiple doses, based on urinary excretion relative to intravenous administration.[10] For ophthalmic and nasal administration, systemic absorption is minimal, with less than 4-5% of the dose entering the circulation via the nasolacrimal duct or mucosa.[43] Absorption occurs rapidly from the lungs or mucosal surfaces, leading to peak plasma concentrations within 10 to 30 minutes post-inhalation in healthy volunteers and patients.[10] The drug undergoes no metabolism in humans and is excreted unchanged, with approximately 70% recovered in urine and 30% in feces following systemic exposure.[13] Plasma protein binding is high, at about 89% in human plasma over a concentration range of 0.5 to 50 µg/mL.[13] The elimination half-life of nedocromil in plasma ranges from 1.5 to 3.3 hours, depending on dosing regimen and patient population.[10] Steady-state conditions are achieved after about one week of regular dosing, with no evidence of accumulation during chronic use.[10]

Chemistry

Chemical structure

Nedocromil is a dicarboxylic acid with the molecular formula C19H17NO7 for the free acid form.[2] The commonly used pharmaceutical form is nedocromil sodium, which exists as the trihydrate salt.[44][45] Its IUPAC name is 9-ethyl-6,9-dihydro-4,6-dioxo-10-propyl-4H-pyrano[3,2-g]quinoline-2,8-dicarboxylic acid.[46] The core structure of nedocromil consists of a tricyclic pyranoquinoline ring system, featuring a fused pyran ring, a quinoline core, and an additional heterocyclic ring.[47] This framework is substituted with two carboxylic acid groups at positions 2 and 8, an ethyl group at position 9, and a propyl group at position 10.[46] Nedocromil sodium can exist in various hydrate forms, including monohydrate, trihydrate (stable at 6.4–79.5% relative humidity at 22 °C), and heptahemihydrate.[45] Nedocromil shares a chromone moiety with cromolyn but incorporates an additional quinoline ring, resulting in a more complex tricyclic structure that contributes to its enhanced potency.[47] The molecule is achiral, lacking any defined stereocenters.[48]

Physical and chemical properties

Nedocromil sodium presents as a white to beige crystalline powder. This form is typical for the disodium salt used in pharmaceutical applications.[44] The compound demonstrates high solubility in water, with practical solubilities in pure water around 20–25 mg/mL, making it suitable for aqueous formulations.[44] It is sparingly soluble in alcohols, with solubility in ethanol approximately 2.4 mg/mL (1 in 410 parts). The pKa values for the carboxylic acid groups are 2.4 and 4.3, underscoring its acidic nature and influencing its ionization in physiological environments. Nedocromil sodium remains stable under normal storage conditions, including inert atmospheres at 2–8 °C, with no known decomposition products or hazardous reactions.[44] In solution, approved formulations are stable at pH 4.0–5.5.[49]

History

Development

Nedocromil was developed in the 1970s by Fisons Pharmaceuticals in the United Kingdom as an advancement over cromolyn sodium, a chromone-based mast cell stabilizer introduced earlier for treating allergic conditions.[4] The initial synthesis efforts focused on creating compounds with enhanced potency and longer duration of action in stabilizing mast cells, thereby improving inhibition of mediator release during allergic responses.[4] This work built on the limitations of cromolyn, aiming for broader anti-inflammatory effects in the airways.[50] Preclinical studies conducted in the 1980s using animal models, such as rats and guinea pigs, demonstrated nedocromil's superior inhibition of antigen-induced airway inflammation compared to cromolyn, including reduced bronchoconstriction and eosinophil accumulation.[51] These investigations highlighted nedocromil's ability to suppress both early and late-phase responses in sensitized models, supporting its potential for topical treatment of reversible obstructive airway diseases.[51] Research was led by multidisciplinary teams at Fisons, with key contributions from chemists and pharmacologists who explored structure-activity relationships (SAR) among novel derivatives.[50] The first major publications on SAR appeared in 1985, detailing the synthesis and evaluation of pyranoquinoline compounds that optimized antiallergic activity.[50] A significant innovation in the development was the transition from traditional cromone derivatives, like cromolyn, to a pyranoquinoline scaffold, which provided improved tissue penetration and pharmacokinetic properties for better delivery to mucosal sites in the respiratory tract.[50] This structural evolution allowed nedocromil to exhibit greater potency against a wider range of inflammatory cells beyond mast cells alone.[4]

Regulatory approval and discontinuation

Nedocromil sodium received approval from the U.S. Food and Drug Administration (FDA) for its inhalation formulation, marketed as Tilade, in December 1992 for the preventive management of mild-to-moderate asthma in adults and children aged 6 years and older.[52] The ophthalmic solution, Alocril, was approved by the FDA on December 8, 1999, for the treatment of itching associated with allergic conjunctivitis. In Europe, nedocromil formulations for inhalation, ophthalmic, and nasal use gained marketing authorizations through national agencies in the 1990s, with the UK approving Tilade for asthma prophylaxis in the 1990s. Similarly, the Therapeutic Goods Administration in Australia approved nedocromil inhalation aerosol on September 21, 1995, for the prevention of asthma symptoms induced by exercise or allergens.[53] The inhalation form of nedocromil faced discontinuation in major markets due to a combination of regulatory requirements and commercial factors. In the United States, King Pharmaceuticals announced the discontinuation of Tilade in May 2008, citing challenges in sourcing a qualified manufacturer for a chlorofluorocarbon (CFC)-free version amid the global phase-out of CFC propellants in metered-dose inhalers.[8] The FDA mandated the cessation of CFC-based Tilade sales by June 14, 2010, as part of environmental protection efforts under the Montreal Protocol.[54] In the United Kingdom, Tilade was withdrawn from the market around 2019-2020 by the marketing authorization holder, following earlier phase-outs in other European countries during the 2010s, primarily driven by low demand and the preference for more effective therapies.[55] Ophthalmic and nasal formulations of nedocromil were also progressively discontinued. Alocril was phased out in the U.S. by 2025 for business reasons, with all branded and generic versions no longer available as of October 2025.[9] Nasal sprays, approved in Europe and Australia in the 1990s for allergic rhinitis, were discontinued earlier in various markets due to limited efficacy compared to newer antihistamines and corticosteroids; they were never approved in the U.S. Post-marketing surveillance for nedocromil products revealed no major safety concerns leading to withdrawals; adverse events were generally mild and comparable to placebo in clinical data.[56] The overall decline in use stemmed from evolving asthma and allergy treatment guidelines, which increasingly favored inhaled corticosteroids and other controller medications as first-line options over mast cell stabilizers like nedocromil, reflecting their superior impact on inflammation and symptom control.[57]

Society and culture

Brand names

Nedocromil sodium was primarily developed and marketed by Fisons Corporation under various brand names for inhalation, ophthalmic, and nasal formulations, with subsequent rights transferred to companies including Rhone-Poulenc Rorer (later Aventis and Sanofi-Aventis) and King Pharmaceuticals in certain regions.[13] For inhalation therapy, it was sold as Tilade in the United States and United Kingdom, and as Rapitil in parts of Europe.[56][58] The ophthalmic formulation was marketed as Alocril in the US, while internationally it appeared under names such as Tilavist (in countries including Australia, Austria, Denmark, Germany, Ireland, Italy, Netherlands, Norway, Sweden, Switzerland, and the UK), Tilade (in Brazil, Canada, Indonesia, and New Zealand), and Tilarin (in Finland).[25][19][59] Nasal formulations were available as Tilarin nasal spray internationally.[60] In various countries, nedocromil sodium was also available in generic forms without specific brand names.[9]

Availability and legal status

Nedocromil has been largely discontinued in major markets including the United States, European Union, and United Kingdom as of 2025, with all branded formulations such as Alocril (ophthalmic solution) and Tilade (inhaler) no longer commercially available.[9][61][62] In the US, the inhalation product was withdrawn in 2008 due to manufacturing challenges, with sales ending in 2010 due to the phase-out of CFC propellants; the ophthalmic product was discontinued by approximately 2019.[57][63][9] In the UK, the Rapitil eye drops were discontinued in 2018.[62] Limited availability persists in some developing countries in Asia, Africa, and Latin America through bulk export of the active pharmaceutical ingredient for niche or custom formulations.[64] Where nedocromil remains accessible, it is strictly prescription-only (Rx) in all jurisdictions, with no over-the-counter status and classification as a non-controlled substance not subject to scheduling under drug control laws.[61][11] The limited access stems primarily from its replacement by more effective therapies, such as leukotriene receptor antagonists (e.g., montelukast) and biologics (e.g., omalizumab), which offer superior efficacy in managing asthma and allergic conditions.[65][66] For patients in regions without commercial supply, options include importing bulk nedocromil sodium or compounding it into formulations, though no FDA-approved generics exist and such preparations lack regulatory approval for widespread use.[9][64] Cromolyn sodium, a related mast cell stabilizer, continues to be available in various forms for similar indications like allergic conjunctivitis and asthma prophylaxis, serving as a primary alternative.[66][67]

References

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  4. The Anti-allergic Cromones: Past, Present, and Future - PMC
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  7. Nedocromil sodium for preventing exercise‐induced ...
  8. King discontinues Tilade Inhaler - MPR - eMPR.com
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  12. Nedocromil Dosage Guide + Max Dose, Adjustments - Drugs.com
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  19. Nedocromil (Ophthalmic) | Drug Lookup | Pediatric Care Online
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  21. Nedocromil - an overview | ScienceDirect Topics
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  31. A multicenter trial of nedocromil sodium, 1% nasal ... - PubMed
  32. Treatment of Allergic Rhinitis and Allergic Conjunctivitis
  33. Tilade Side Effects: Common, Severe, Long Term - Drugs.com
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  40. https://www.sigmaaldrich.com/AO/en/product/sigma/sml1101
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  43. Effects of Nedocromil Sodium on Airway Neurogenic Mechanisms
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  48. Nedocromil - an overview | ScienceDirect Topics
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  50. New antiallergic pyrano[3,2-g]quinoline-2,8-dicarboxylic acids with ...
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