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Methdilazine

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ACTIVE PHARMA INGREDIENTS

4 API Suppliers, 4 USDMF

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4 FDF Dossiers, 4 FDA Orange Book

4 FDF Dossiers
4 FDA Orange Book

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1 USP , 1 Others

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1 USP
1 Others

Synopsis

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Chemistry

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Also known as: Tacaryl, 1982-37-2, Methdilazinum, Tacazyl, Methdilazinum [inn-latin], Metodilazina [inn-spanish]

Molecular Formula

C₁₈H₂₀N₂S

Molecular Weight

296.4 g/mol

InChI Key

HTMIBDQKFHUPSX-UHFFFAOYSA-N

FDA UNII

4Q13LY9Z8X

Methdilazine is a phenothiazine compound with antihistaminic activity. It is used in the treatment of various dermatoses to relieve pruritus.

1 2D Structure

Methdilazine

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

10-[(1-methylpyrrolidin-3-yl)methyl]phenothiazine

2.1.2 InChI

InChI=1S/C18H20N2S/c1-19-11-10-14(12-19)13-20-15-6-2-4-8-17(15)21-18-9-5-3-7-16(18)20/h2-9,14H,10-13H2,1H3

2.1.3 InChI Key

HTMIBDQKFHUPSX-UHFFFAOYSA-N

2.1.4 Canonical SMILES

CN1CCC(C1)CN2C3=CC=CC=C3SC4=CC=CC=C42

2.2 Other Identifiers

2.2.1 UNII

4Q13LY9Z8X

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Methdilazine Hydrochloride

2.3.2 Depositor-Supplied Synonyms

1. Tacaryl

2. 1982-37-2

3. Methdilazinum

4. Tacazyl

5. Methdilazinum [inn-latin]

6. Metodilazina [inn-spanish]

7. Nci-c60720

8. 10-[(1-methylpyrrolidin-3-yl)methyl]phenothiazine

9. Methdilazine (inn)

10. 10-[(1-methylpyrrolidin-3-yl)methyl]-10h-phenothiazine

11. 10-((1-methyl-3-pyrrolidinyl)methyl)phenothiazine

12. 4q13ly9z8x

13. Chebi:6823

14. Methodilazine

15. Metodilazina

16. 10h-phenothiazine, 10-((1-methyl-3-pyrrolidinyl)methyl)-

17. 10h-phenothiazine, 10-[(1-methyl-3-pyrrolidinyl)methyl]-

18. Tacryl

19. Methdilazine [inn]

20. Nsc169091

21. Mj 5022

22. 10-[(1-methyl-3-pyrrolidinyl)methyl]phenothiazine

23. Phenothiazine, 10-((1-methyl-3-pyrrolidinyl)methyl)-

24. Phenothiazine, 10-[(1-methyl-3-pyrrolidinyl)methyl]-

25. 10-[(1-methyl-3-pyrrolidinyl)methyl]phenothiazine; Mj 5022

26. Tacaryl (tn)

27. Product 5022

28. Einecs 217-841-6

29. Metdilazina

30. Unii-4q13ly9z8x

31. Methdilazine [usp:inn:ban]

32. 10-((1-methyl-3-pyrrolidinyl)methyl)phenothiazine Monohydrochloride

33. Dilosyn (salt/mix)

34. Disyncram (salt/mix)

35. Disyncran (salt/mix)

36. 10h-phenothiazine, 10-((1-methyl-3-pyrrolidinyl)methyl)-, Monohydrochloride

37. Methdilazine [mi]

38. Methdilazine [vandf]

39. Methdilazine [mart.]

40. Methdilazine(200mg)

41. Methdilazine [who-dd]

42. Schembl121507

43. Gtpl7231

44. 10-((1-methyl-3-pyrrolidinyl)methyl)-10h-phenothiazine

45. Chembl1200959

46. Dtxsid6023282

47. Bdbm81470

48. Methdilazine (200 Mg)

49. Methdilazine [orange Book]

50. Hy-b1690

51. 10h-phenothiazine, Tannate (5:1)

52. Cas_14677

53. Nsc_14677

54. Nsc244191

55. Pdsp1_000149

56. Pdsp2_000148

57. Db00902

58. Nsc-244191

59. Nci60_001351

60. Cs-0013673

61. C07175

62. D04979

63. L001130

64. Sr-01000944494

65. Q6665709

66. Sr-01000944494-1

67. 10-[(1-methyl-3-pyrrolidinyl)methyl]-10h-phenothiazine #

2.4 Create Date

2005-03-26

3 Chemical and Physical Properties

Molecular Formula	C₁₈H₂₀N₂S
Molecular Weight	296.4 g/mol
XLogP3	5.2
Hydrogen Bond Donor Count	0
Hydrogen Bond Acceptor Count	3
Rotatable Bond Count	2
Exact Mass	296.13471982 g/mol
Monoisotopic Mass	296.13471982 g/mol
Topological Polar Surface Area	31.8 Å²
Heavy Atom Count	21
Formal Charge	0
Complexity	339
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

Used for the symptomatic relief of hypersensitivity reactions and particularly for the control of pruritic skin disorders

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. Methdilazine 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 ATC Code

R - Respiratory system

R06 - Antihistamines for systemic use

R06A - Antihistamines for systemic use

R06AD - Phenothiazine derivatives

R06AD04 - Methdilazine

5.3 Absorption, Distribution and Excretion

Absorption

Well absorbed in the digestive tract.

5.4 Mechanism of Action

Methdilazine binds to the histamine H₁ receptor. 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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