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Lodoxamide

Synopsis, Chemistry

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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

Lodoxamide

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 Formula	C₁₁H₆ClN₃O₆
Molecular Weight	311.63 g/mol
XLogP3	0.5
Hydrogen Bond Donor Count	4
Hydrogen Bond Acceptor Count	7
Rotatable Bond Count	4
Exact Mass	310.9945126 g/mol
Monoisotopic Mass	310.9945126 g/mol
Topological Polar Surface Area	157 Å²
Heavy Atom Count	21
Formal Charge	0
Complexity	489
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

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.