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Emedastine Difumarate

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Synopsis

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Chemistry

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Also known as: 87233-62-3, Rapimine, Emedastine fumarate, Kb-2413, Al-3432a, Daren

Molecular Formula

C₂₅H₃₄N₄O₉

Molecular Weight

534.6 g/mol

InChI Key

FWLKKPKZQYVAFR-LVEZLNDCSA-N

FDA UNII

42MB94QOSM

Emedastine Difumarate is the difumarate salt form of emedastine, a second generation, selective histamine H1 receptor antagonist with anti-allergic activity. Emedastine reversibly and competitively blocks histamine by binding to H1 receptors, thus blocking its downstream activity. As a result, this agent interferes with mediator release from mast cells either by inhibiting calcium ion influx across mast cell/basophil plasma membrane or by inhibiting intracellular calcium ion release within the cells. In addition, emedastine may also inhibit the late-phase allergic reaction mediated through leukotrienes or prostaglandins, or by producing an anti-platelet activating factor effect. Upon ocular administration, emedastine causes a dose-dependent inhibition of histamine-stimulated vascular permeability in the conjunctiva. Emedastine does not affect adrenergic, dopamine, or serotonin receptors.

1 2D Structure

Emedastine Fumarate

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(E)-but-2-enedioic acid;1-(2-ethoxyethyl)-2-(4-methyl-1,4-diazepan-1-yl)benzimidazole

2.1.2 InChI

InChI=1S/C17H26N4O.2C4H4O4/c1-3-22-14-13-21-16-8-5-4-7-15(16)18-17(21)20-10-6-9-19(2)11-12-20;2*5-3(6)1-2-4(7)8/h4-5,7-8H,3,6,9-14H2,1-2H3;2*1-2H,(H,5,6)(H,7,8)/b;2*2-1+

2.1.3 InChI Key

FWLKKPKZQYVAFR-LVEZLNDCSA-N

2.1.4 Canonical SMILES

CCOCCN1C2=CC=CC=C2N=C1N3CCCN(CC3)C.C(=CC(=O)O)C(=O)O.C(=CC(=O)O)C(=O)O

2.1.5 Isomeric SMILES

CCOCCN1C(=NC2=CC=CC=C12)N3CCN(CCC3)C.C(=C/C(=O)O)\C(=O)O.C(=C/C(=O)O)\C(=O)O

2.2 Other Identifiers

2.2.1 UNII

42MB94QOSM

2.3 Synonyms

2.3.1 MeSH Synonyms

1. 1-(2-ethoxyethyl)-2-(4-methyl-1-homopiperazinyl)benzimidazole Difumarate

2. Emadine

3. Emedastine

4. Kb 2413

5. Kb-2413

6. Kg 2413

7. Kg-2413

2.3.2 Depositor-Supplied Synonyms

1. 87233-62-3

2. Rapimine

3. Emedastine Fumarate

4. Kb-2413

5. Al-3432a

6. Daren

7. 1-(2-ethoxyethyl)-2-(4-methyl-1-homopiperazinyl)benzimidazole Difumarate

8. Kg-2413

9. Dsstox_cid_26911

10. 42mb94qosm

11. Emedastine (difumarate)

12. Ly-188695

13. 1-(2-ethoxyethyl)-2-(4-methyl-1,4-diazepan-1-yl)-1h-benzo[d]imidazole Difumarate

14. Ly188695

15. Emadine (tn)

16. Dsstox_rid_82009

17. Dsstox_gsid_46911

18. (e)-but-2-enedioic Acid;1-(2-ethoxyethyl)-2-(4-methyl-1,4-diazepan-1-yl)benzimidazole

19. 1-(2-ethoxyethyl)-2-(hexahydro-4-methyl-1h-1,4-diazepin-1-yl)benzimidazole Fumarate (1:2)

20. 1h-benzimidazole, 1-(2-ethoxyethyl)-2-(hexahydro-4-methyl-1h-1,4-diazepin-1-yl)-, (e)-2-butenedioate (1:2)

21. Cas-87233-62-3

22. 1-(2-ethoxyethyl)-2-(4-methylhexahydro-1h-1,4-diazepin-1-yl)benzimidazole Fumarate (1:2)

23. Ncgc00181341-01

24. Unii-42mb94qosm

25. Remicut

26. Emedastine Difumarate [usan]

27. Al 3432a

28. Mfcd00923844

29. Daren (tn)

30. Emedastine Difumarate [usan:usp:jan]

31. Kb 2413

32. Emedastinefumarate

33. Ly 188695

34. Schembl41384

35. Schembl41386

36. Chembl2103739

37. Dtxsid2046911

38. C25h34n4o9

39. Hms3713h04

40. Hms3886e14

41. Emedastine Difumarate (jp17/usp)

42. Emedastine Difumarate [jan]

43. Emedastine Fumarate [mart.]

44. Ex-a3661

45. Hy-b2178

46. Tox21_112800

47. Ac-391

48. Emedastine Difumarate [vandf]

49. Emedastine Fumarate [who-dd]

50. S5647

51. Emedastine Difumarate [usp-rs]

52. Tox21_112800_1

53. Ccg-220591

54. Ncgc00181341-02

55. As-57174

56. Benzimidazole, 1-(2-ethoxyethyl)-2-(4-methylhexahydro-1h-1,4-diazepin-1-yl)-, Fumarate (1:2)

57. Emedastine Difumarate [orange Book]

58. Emedastine Difumarate [ep Monograph]

59. Emedastine Difumarate [usp Impurity]

60. Cs-0021561

61. E0936

62. Emedastine Difumarate [usp Monograph]

63. D02249

64. T73020

65. Sr-01000872706

66. Sr-01000872706-1

67. Bis((2e)-but-2-enedioic Acid); 1-(2-ethoxyethyl)-2-(4-methyl-1,4-diazepan-1-yl)-1h-1,3-benzodiazole

2.4 Create Date

2005-10-11

3 Chemical and Physical Properties

Molecular Formula	C₂₅H₃₄N₄O₉
Molecular Weight	534.6 g/mol
Hydrogen Bond Donor Count	4
Hydrogen Bond Acceptor Count	12
Rotatable Bond Count	9
Exact Mass	534.23257867 g/mol
Monoisotopic Mass	534.23257867 g/mol
Topological Polar Surface Area	183 Å²
Heavy Atom Count	38
Formal Charge	0
Complexity	460
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	2
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	3

4 Drug and Medication Information

4.1 Drug Indication

Symptomatic treatment of seasonal allergic conjunctivitis.

5 Pharmacology and Biochemistry

5.1 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.)

Histamine H1 Antagonists

Drugs that selectively bind to but do not activate histamine H1 receptors, thereby blocking the actions of endogenous histamine. Included here are the classical antihistaminics that antagonize or prevent the action of histamine mainly in immediate hypersensitivity. They act in the bronchi, capillaries, and some other smooth muscles, and are used to prevent or allay motion sickness, seasonal rhinitis, and allergic dermatitis and to induce somnolence. The effects of blocking central nervous system H1 receptors are not as well understood. (See all compounds classified as Histamine H1 Antagonists.)

5.2 ATC Code

S01GX06

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