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    Lodoxamide

    ACTIVE PHARMA INGREDIENTS

    FINISHED DOSAGE FORMULATIONS

    PharmaCompass
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    2D Structure
    Also known as: 53882-12-5, Lodoxamidum, 2-[2-chloro-5-cyano-3-(oxaloamino)anilino]-2-oxoacetic acid, U-42585e (free acid), Spu695od73, Lodoxamide (inn)
    Molecular Formula
    C11H6ClN3O6
    Molecular Weight
    311.63  g/mol
    InChI Key
    RVGLGHVJXCETIO-UHFFFAOYSA-N
    FDA UNII
    SPU695OD73
    Lodoxamide is a synthetic mast cell stabilizing compound with anti-inflammatory activity. Lodoxamide appears to inhibit the antigen-stimulated calcium transport across the mast cell membrane, thereby inhibiting mast cell degranulation and the release of histamine, leukotrienes, and other substances that cause hypersensitivity reactions. Lodoxamide also inhibits eosinophil chemotaxis. When applied topically to the eye, this drug prevents the symptoms associated with keratitis or conjunctivitis.
    Lodoxamide is a Mast Cell Stabilizer. The physiologic effect of lodoxamide is by means of Decreased Histamine Release.
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    2-[2-chloro-5-cyano-3-(oxaloamino)anilino]-2-oxoacetic acid
    2.1.2 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)
    2.1.3 InChI Key
    RVGLGHVJXCETIO-UHFFFAOYSA-N
    2.1.4 Canonical SMILES
    C1=C(C=C(C(=C1NC(=O)C(=O)O)Cl)NC(=O)C(=O)O)C#N
    2.2 Other Identifiers
    2.2.1 UNII
    SPU695OD73
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. Diethyl N,n'-(2-chloro-5-cyano-m-phenylene)dioxamate

    2. Lodoxamide Ethyl

    3. U-42,718

    2.3.2 Depositor-Supplied Synonyms

    1. 53882-12-5

    2. Lodoxamidum

    3. 2-[2-chloro-5-cyano-3-(oxaloamino)anilino]-2-oxoacetic Acid

    4. U-42585e (free Acid)

    5. Spu695od73

    6. Lodoxamide (inn)

    7. 2,2'-((2-chloro-5-cyano-1,3-phenylene)bis(azanediyl))bis(2-oxoacetic Acid)

    8. Lodoxamide [inn]

    9. Alomide (tn)

    10. N,n'-(2-chloro-5-cyano-m-phenylene)dioxamate

    11. Lodoxamida

    12. Lodoxamide [inn:ban]

    13. Lodoxamidum [inn-latin]

    14. Acetic Acid, 2,2'-((2-chloro-5-cyano-1,3-phenylene)diimino)bis(2-oxo-

    15. Acetic Acid, 2,2'-[(2-chloro-5-cyano-1,3-phenylene)diimino]bis[2-oxo-

    16. Lodoxamida [inn-spanish]

    17. Unii-spu695od73

    18. N,n'-(2-chlor-5-cyan-3-phenylen)dioxamsaeure

    19. Lodoxamide [mi]

    20. Lodoxamide [vandf]

    21. Lodoxamide [mart.]

    22. Dsstox_cid_31556

    23. Dsstox_rid_97441

    24. Lodoxamide [who-dd]

    25. Dsstox_gsid_57767

    26. Schembl119881

    27. Gtpl9743

    28. Chembl1201266

    29. Dtxsid9057767

    30. Chebi:135333

    31. Hms3715i21

    32. Zinc2000707

    33. Tox21_113669

    34. Bdbm50259889

    35. Ccg-221010

    36. Cs-6498

    37. Db06794

    38. Ncgc00249893-01

    39. As-76953

    40. Hy-14270

    41. Cas-53882-12-5

    42. Ft-0627968

    43. D08139

    44. W18254

    45. 882l125

    46. A901322

    47. Q6666510

    48. 2-[[2-chloro-5-cyano-3-(oxaloamino)phenyl]amino]-2-oxoacetic Acid

    49. 2,2'-[(2-chloro-5-cyano-1,3-phenylene)diimino]bis[2-oxoacetic Acid]

    50. Acetic Acid, 2,2'-((2-chloro-5-cyano-1,3-phenylene)diimino)-, Bis 2-oxo-

    2.4 Create Date
    2005-08-08
    3 Chemical and Physical Properties
    Molecular Weight 311.63 g/mol
    Molecular Formula C11H6ClN3O6
    XLogP30.5
    Hydrogen Bond Donor Count4
    Hydrogen Bond Acceptor Count7
    Rotatable Bond Count4
    Exact Mass310.9945126 g/mol
    Monoisotopic Mass310.9945126 g/mol
    Topological Polar Surface Area157 Ų
    Heavy Atom Count21
    Formal Charge0
    Complexity489
    Isotope Atom Count0
    Defined Atom Stereocenter Count0
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    4 Drug and Medication Information
    4.1 Drug Indication

    Indicated in the treatment of the ocular disorders referred to by the terms vernal keratoconjunctivitis, vernal conjunctivitis, and vernal keratitis.

    FDA Label

    5 Pharmacology and Biochemistry
    5.1 Pharmacology

    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.

    5.2 MeSH Pharmacological Classification

    Anti-Allergic Agents

    Agents that are used to treat allergic reactions. Most of these drugs act by preventing the release of inflammatory mediators or inhibiting the actions of released mediators on their target cells. (From AMA Drug Evaluations Annual, 1994, p475) (See all compounds classified as Anti-Allergic Agents.)

    5.3 FDA Pharmacological Classification
    5.3.1 Active Moiety
    LODOXAMIDE
    5.3.2 FDA UNII
    SPU695OD73
    5.3.3 Pharmacological Classes
    Established Pharmacologic Class [EPC] - Mast Cell Stabilizer
    5.4 ATC Code

    S01GX05

    S76 | LUXPHARMA | Pharmaceuticals Marketed in Luxembourg | Pharmaceuticals marketed in Luxembourg, as published by d'Gesondheetskeess (CNS, la caisse nationale de sante, www.cns.lu), mapped by name to structures using CompTox by R. Singh et al. (in prep.). List downloaded from https://cns.public.lu/en/legislations/textes-coordonnes/liste-med-comm.html. Dataset DOI:10.5281/zenodo.4587355

    S - Sensory organs

    S01 - Ophthalmologicals

    S01G - Decongestants and antiallergics

    S01GX - Other antiallergics

    S01GX05 - Lodoxamide

    5.5 Absorption, Distribution and Excretion

    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.

    Route of Elimination

    Urinary excretion is the major route of elimination.

    5.6 Biological Half-Life

    Elimination half-life was 8.5 hours in urine.

    5.7 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.