Identification
- Summary
Lodoxamide is an ophthalmic agent used for the treatment of the ocular disorders referred to by the terms vernal keratoconjunctivitis, vernal conjunctivitis, and vernal keratitis.
- Brand Names
- Alomide
- Generic Name
- Lodoxamide
- DrugBank Accession Number
- DB06794
- Background
Lodoxamide is a mast-cell stabilizer for topical administration into the eye. Mast-cell stabilizers, first one approved being cromolyn sodium, are used in treatment of ocular hypersensitivity reactions such as vernal conjunctivitis. These conditions often require treatment with anti-inflammatory medications such as ophthalmic NSAIDs or topical steroids which may cause systemic or toxic effects long-term. Although less effective than topical steroids at decreasing inflammation, mast-cell stabilizers offer another treatment option and exhibit minimal adverse effects. Lodoxamide is marketed under the brand name Alomide by Alcon.
- Type
- Small Molecule
- Groups
- Approved
- Structure
Structure for Lodoxamide (DB06794)
- Weight
- Average: 311.63
Monoisotopic: 310.9945126 - Chemical Formula
- C11H6ClN3O6
- Synonyms
- Lodoxamida
- Lodoxamide
- N,N'-(2-chloro-5-cyano-m-phenylene)dioxamate
- External IDs
- U-42585E
Pharmacology
- Indication
Indicated in the treatment of the ocular disorders referred to by the terms vernal keratoconjunctivitis, vernal conjunctivitis, and vernal keratitis.
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Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Management of Atopic conjunctivitis •••••••••••• Management of Giant papillary conjunctivitis •••••••••••• Treatment of Vernal keratoconjunctivitis •••••••••••• Treatment of Vernal conjunctivitis •••••••••••• Treatment of Vernal keratitis •••••••••••• - Contraindications & Blackbox Warnings
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Lodoxamide is a mast cell stabilizer that inhibits the in vivo Type 1 immediate hypersensitivity reaction. Lodoxamide therapy inhibits the increases in cutaneous vascular permeability that are associated with reagin or IgE and antigen-mediated reactions.
- Mechanism of action
Although lodoxamide's precise mechanism of action is unknown, it is postulated that it prevents calcium influx into mast cells upon antigen stimulation and therefore stabilizes the membrane. By stabilizing the mast cell membrane from degranulation, lodoxamide consequently inhibits the release of intracellular histamine and other chemoattractant factors that primarily cause ocular symptoms. Lodoxamide's mechanism of action may be similar to cromolyn sodium, as both exhibit cross-tachyphylaxis.
- Absorption
In a study of twelve healthy adult volunteers, topical administration of lodoxamide tromethamine ophthalmic solution 0.1%, one drop in each eye four times per day for ten days, did not result in any measurable lodoxamide plasma levels at a detection limit of 2.5 ng/mL.
- Volume of distribution
Not Available
- Protein binding
Not Available
- Metabolism
- Not Available
- Route of elimination
Urinary excretion is the major route of elimination.
- Half-life
Elimination half-life was 8.5 hours in urine.
- Clearance
Not Available
- Adverse Effects
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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
- 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 Lodoxamide tromethamine 50LV9A548L 63610-09-3 JJOFNSLZHKIJEV-UHFFFAOYSA-N - Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Alomide Solution 0.1 % w/v Ophthalmic Novartis 1992-12-31 Not applicable Canada 
Alomide Solution / drops 1 mg/1mL Ophthalmic ALCON LABORATORIES, INC. 1993-09-30 2023-09-30 US 
Alomide Solution / drops 1 mg/1mL Ophthalmic Novartis Pharmaceuticals Corporation 1993-09-30 Not applicable US
Categories
- ATC Codes
- S01GX05 — Lodoxamide
- Drug Categories
- Acids, Aldehydic
- Alcohols
- Amino Acids
- Amino Acids, Peptides, and Proteins
- Anti-Allergic Agents
- Antioxidants
- Decongestants and Antiallergics
- Decreased Histamine Release
- Glycols
- Glyoxylates
- Histamine Agents
- Mast Cell Stabilizers
- Neurotransmitter Agents
- Ophthalmologicals
- Propylene Glycols
- Sensory Organs
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as alpha amino acids and derivatives. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon), or a derivative thereof.
- Kingdom
- Organic compounds
- Super Class
- Organic acids and derivatives
- Class
- Carboxylic acids and derivatives
- Sub Class
- Amino acids, peptides, and analogues
- Direct Parent
- Alpha amino acids and derivatives
- Alternative Parents
- Anilides / N-arylamides / Benzonitriles / Chlorobenzenes / Dicarboxylic acids and derivatives / Aryl chlorides / Secondary carboxylic acid amides / Nitriles / Carboxylic acids / Organopnictogen compounds show 4 more
- Substituents
- Alpha-amino acid or derivatives / Anilide / Aromatic homomonocyclic compound / Aryl chloride / Aryl halide / Benzenoid / Benzonitrile / Carbonitrile / Carbonyl group / Carboxamide group show 17 more
- Molecular Framework
- Aromatic homomonocyclic compounds
- External Descriptors
- Not Available
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- SPU695OD73
- CAS number
- 53882-12-5
- InChI Key
- RVGLGHVJXCETIO-UHFFFAOYSA-N
- InChI
- InChI=1S/C11H6ClN3O6/c12-7-5(14-8(16)10(18)19)1-4(3-13)2-6(7)15-9(17)11(20)21/h1-2H,(H,14,16)(H,15,17)(H,18,19)(H,20,21)
- IUPAC Name
- {[3-(carboxyformamido)-2-chloro-5-cyanophenyl]carbamoyl}formic acid
- SMILES
- OC(=O)C(=O)NC1=CC(=CC(NC(=O)C(O)=O)=C1Cl)C#N
References
- General References
- Avunduk AM, Avunduk MC, Kapicioglu Z, Akyol N, Tavli L: Mechanisms and comparison of anti-allergic efficacy of topical lodoxamide and cromolyn sodium treatment in vernal keratoconjunctivitis. Ophthalmology. 2000 Jul;107(7):1333-7. [Article]
- Lee S, Allard TR: Lodoxamide in vernal keratoconjunctivitis. Ann Pharmacother. 1996 May;30(5):535-7. [Article]
- Das D, Khan M, Gul A, Alam R: Safety and efficacy of lodoxamide in vernal keratoconjunctivitis. J Pak Med Assoc. 2011 Mar;61(3):239-41. [Article]
- External Links
- KEGG Drug
- D04762
- PubChem Compound
- 44564
- PubChem Substance
- 310264890
- ChemSpider
- 40543
- BindingDB
- 50259889
- 52151
- ChEBI
- 135333
- ChEMBL
- CHEMBL1201266
- ZINC
- ZINC000002000707
- PDBe Ligand
- WYB
- RxList
- RxList Drug Page
- Drugs.com
- Drugs.com Drug Page
- Wikipedia
- Lodoxamide
- PDB Entries
- 8h8j
- FDA label
- Download (95.1 KB)
Clinical Trials
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Solution Ophthalmic 0.1 % w/v Solution / drops Ophthalmic Solution / drops Ophthalmic 1 mg/1mL Solution / drops Ophthalmic 0.1 % Solution / drops Ophthalmic 5 ml - Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
- Not Available
- Predicted Properties
Property Value Source Water Solubility 0.0361 mg/mL ALOGPS logP 0.72 ALOGPS logP 0.83 Chemaxon logS -3.9 ALOGPS pKa (Strongest Acidic) -6.7 Chemaxon pKa (Strongest Basic) 0.73 Chemaxon Physiological Charge -2 Chemaxon Hydrogen Acceptor Count 7 Chemaxon Hydrogen Donor Count 4 Chemaxon Polar Surface Area 156.59 Å2 Chemaxon Rotatable Bond Count 4 Chemaxon Refractivity 69.9 m3·mol-1 Chemaxon Polarizability 26.52 Å3 Chemaxon Number of Rings 1 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
- Not Available
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-03di-0029000000-2a626be04e7522057566 Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-014i-0090000000-de62d26383559dd1828d Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-014i-0090000000-904332e9eaf7ab4e8a5d Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-014i-0920000000-250046f18a623fb70538 Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-014i-2090000000-726fefa00a595ff37150 Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-014l-0900000000-7994e5721b898466116b 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]- 160.3733 predictedDeepCCS 1.0 (2019) [M+H]+ 162.7313 predictedDeepCCS 1.0 (2019) [M+Na]+ 169.20067 predictedDeepCCS 1.0 (2019)
Drug created at September 14, 2010 16:21 / Updated at April 19, 2024 20:55