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Mequitazine

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Synopsis

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Chemistry

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Also known as: 29216-28-2, Metaplexan, Primalan, Virginan, Mircol, Instotal

Molecular Formula

C₂₀H₂₂N₂S

Molecular Weight

322.5 g/mol

InChI Key

HOKDBMAJZXIPGC-UHFFFAOYSA-N

FDA UNII

Y463242LY2

Mequitazine is a histamine H1 antagonist (antihistamine). It competes with histamine for the normal H1-receptor sites on effector cells of the gastrointestinal tract, blood vessels and respiratory tract. It provides effective, temporary relief of sneezing, watery and itchy eyes, and runny nose due to hay fever and other upper respiratory allergies.

1 2D Structure

Mequitazine

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

10-(1-azabicyclo[2.2.2]octan-3-ylmethyl)phenothiazine

2.1.2 InChI

InChI=1S/C20H22N2S/c1-3-7-19-17(5-1)22(18-6-2-4-8-20(18)23-19)14-16-13-21-11-9-15(16)10-12-21/h1-8,15-16H,9-14H2

2.1.3 InChI Key

HOKDBMAJZXIPGC-UHFFFAOYSA-N

2.1.4 Canonical SMILES

C1CN2CCC1C(C2)CN3C4=CC=CC=C4SC5=CC=CC=C53

2.2 Other Identifiers

2.2.1 UNII

Y463242LY2

2.3 Synonyms

2.3.1 MeSH Synonyms

1. 3-methylquinuclidinyl-10-phenothiazine

2. Lm 209

3. Mequitazine Hydrochloride

4. Mequitazine Tartrate, (r-(r*,r*))-isomer

5. Mircol

6. Primalan

7. Quitadrill

2.3.2 Depositor-Supplied Synonyms

1. 29216-28-2

2. Metaplexan

3. Primalan

4. Virginan

5. Mircol

6. Instotal

7. Vigigan

8. (r)-(+)-mequitazine

9. Mequitazina [spanish]

10. Kitazemin

11. Mequitazina

12. 10-(1-azabicyclo[2.2.2]oct-3-ylmethyl)-10h-phenothiazine

13. Mequitazinum [inn-latin]

14. Mequitazina [inn-spanish]

15. Lm 209

16. Lm-209

17. 10-(3-quinuclidinylmethyl)phenothiazine

18. 10-(1-azabicyclo[2.2.2]octan-3-ylmethyl)phenothiazine

19. Phenothiazine, 10-(3-quinuclidinylmethyl)-

20. Nsc 303612

21. 10-(quinuclidin-3-ylmethyl)-10h-phenothiazine

22. 10h-phenothiazine, 10-(1-azabicyclo[2.2.2]oct-3-ylmethyl)-

23. Nsc303612

24. Butix

25. Nsc-303612

26. Mls000757058

27. Chebi:31821

28. Y463242ly2

29. Ncgc00183046-01

30. Mequitazinum

31. Zesulan

32. 10h-phenothiazine, 10-(1-azabicyclo(2.2.2)oct-3-ylmethyl)-

33. Dsstox_cid_3262

34. Dsstox_rid_76947

35. Dsstox_gsid_23262

36. Mequitazine [inn:ban:dcf:jan]

37. Kitazemin (tn)

38. Smr000528898

39. 3-methylquinuclidinyl-10-phenothiazine

40. Cas-29216-28-2

41. Einecs 249-521-7

42. Brn 1150945

43. Releas

44. Unii-y463242ly2

45. Mequitazine [mi]

46. Mequitazine [inn]

47. Mequitazine [jan]

48. Mequitazine (jp17/inn)

49. Mequitazine [mart.]

50. Schembl18207

51. Mequitazine [who-dd]

52. Mls001201790

53. Chembl73451

54. Dtxsid8023262

55. Hms2231i03

56. Hms3369o08

57. Hms3604k05

58. Hy-b2168

59. Tox21_113648

60. Mfcd00869383

61. S6435

62. Stk324459

63. Akos000424971

64. Akos022061643

65. Tox21_113648_1

66. Ac-2365

67. Cs-6222

68. Db01071

69. Ncgc00183046-03

70. Ls-14776

71. Nci60_002566

72. Db-047545

73. Ds-016113

74. Ft-0630547

75. Ft-0671023

76. M2807

77. V0162

78. D01324

79. Ab00691111-09

80. 216m282

81. A819820

82. L000704

83. 10-(quinuclidin-3-ylmethyl)phenothiazine;mequitazine

84. J-008412

85. J-017436

86. Q3333256

87. 10-{1-azabicyclo[2.2.2]octan-3-ylmethyl}-10h-phenothiazine

88. (r)-10-(1-azabicyclo[2.2.2]oct-3-ylmethyl)-10h-phenothiazine

89. 10h-phenothiazine,10-[(3s)-1-azabicyclo[2.2.2]oct-3-ylmethyl]-

2.4 Create Date

2005-03-25

3 Chemical and Physical Properties

Molecular Formula	C₂₀H₂₂N₂S
Molecular Weight	322.5 g/mol
XLogP3	4.6
Hydrogen Bond Donor Count	0
Hydrogen Bond Acceptor Count	3
Rotatable Bond Count	2
Exact Mass	322.15036988 g/mol
Monoisotopic Mass	322.15036988 g/mol
Topological Polar Surface Area	31.8 Å²
Heavy Atom Count	23
Formal Charge	0
Complexity	398
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	1
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Drug and Medication Information

4.1 Drug Indication

For the treatment of Hay fever, urticaria (hives) and allergic rhinitis

5 Pharmacology and Biochemistry

5.1 Pharmacology

In allergic reactions an allergen interacts with and cross-links surface IgE antibodies on mast cells and basophils. Once the mast cell-antibody-antigen complex is formed, a complex series of events occurs that eventually leads to cell-degranulation and the release of histamine (and other chemical mediators) from the mast cell or basophil. Once released, histamine can react with local or widespread tissues through histamine receptors. Histamine, acting on H₁-receptors, produces pruritis, vasodilatation, hypotension, flushing, headache, tachycardia, and bronchoconstriction. Histamine also increases vascular permeability and potentiates pain. Mequitazine is a histamine H1 antagonist. It competes with histamine for the normal H₁-receptor sites on effector cells of the gastrointestinal tract, blood vessels and respiratory tract. It provides effective, temporary relief of sneezing, watery and itchy eyes, and runny nose due to hay fever and other upper respiratory allergies.

5.2 MeSH Pharmacological Classification

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.)

5.3 ATC Code

R - Respiratory system

R06 - Antihistamines for systemic use

R06A - Antihistamines for systemic use

R06AD - Phenothiazine derivatives

R06AD07 - Mequitazine

5.4 Mechanism of Action

Mequitazine binds to the histamine H1 receptor sites on effector cells in the gastrointestinal tract, blood vessels, and respiratory tract. This blocks the action of endogenous histamine, which subsequently leads to temporary relief of the negative symptoms brought on by histamine.

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API Reference Price

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