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NCGC00024714-07
Also known as: 486-12-4, Actidil, Triprolidin, Triprolidinum, Tripolidina, Myidyl
Molecular Formula
C19H22N2
Molecular Weight
278.4  g/mol
InChI Key
CBEQULMOCCWAQT-WOJGMQOQSA-N
FDA UNII
2L8T9S52QM

Histamine H1 antagonist used in allergic rhinitis; ASTHMA; and URTICARIA. It is a component of COUGH and COLD medicines. It may cause drowsiness.
1 2D Structure

NCGC00024714-07

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
2-[(E)-1-(4-methylphenyl)-3-pyrrolidin-1-ylprop-1-enyl]pyridine
2.1.2 InChI
InChI=1S/C19H22N2/c1-16-7-9-17(10-8-16)18(19-6-2-3-12-20-19)11-15-21-13-4-5-14-21/h2-3,6-12H,4-5,13-15H2,1H3/b18-11+
2.1.3 InChI Key
CBEQULMOCCWAQT-WOJGMQOQSA-N
2.1.4 Canonical SMILES
CC1=CC=C(C=C1)C(=CCN2CCCC2)C3=CC=CC=N3
2.1.5 Isomeric SMILES
CC1=CC=C(C=C1)/C(=C\CN2CCCC2)/C3=CC=CC=N3
2.2 Other Identifiers
2.2.1 UNII
2L8T9S52QM
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Actidil

2. Anhydrous, Triprolidine Hydrochloride

3. Hydrochloride Anhydrous, Triprolidine

4. Hydrochloride, Triprolidine

5. Pro Actidil

6. Triprolidine Hydrochloride

7. Triprolidine Hydrochloride Anhydrous

8. Triprolidine Monohydrochloride

9. Triprolidine Monohydrochloride, (z)-isomer

10. Triprolidine Monohydrochloride, Monohydrate

11. Triprolidine Oxalate

12. Triprolidine Oxalate, (trans)-isomer

13. Triprolidine, (z)-isomer

2.3.2 Depositor-Supplied Synonyms

1. 486-12-4

2. Actidil

3. Triprolidin

4. Triprolidinum

5. Tripolidina

6. Myidyl

7. Histafed

8. Actifed

9. Trans-1-(2-pyridyl)-3-pyrrolidino-1-p-tolylprop-1-ene

10. Actahist

11. Allerfed

12. Corphed

13. Myfed

14. Trilitron

15. Triphed

16. Triprolidine (inn)

17. Trans-1-(4-methylphenyl)-1-(2-pyridyl)-3-pyrrolidinoprop-1-ene

18. 2-[(e)-1-(4-methylphenyl)-3-pyrrolidin-1-ylprop-1-enyl]pyridine

19. Trans-2-(3-(1-pyrrolidinyl)-1-p-tolylpropenyl)pyridine

20. Chembl855

21. (e)-2-(3-(pyrrolidin-1-yl)-1-(p-tolyl)prop-1-en-1-yl)pyridine

22. 2l8t9s52qm

23. Chebi:84116

24. Ncgc00024714-03

25. Nci-c61450

26. Dsstox_cid_3718

27. Triprolidine [inn]

28. Dsstox_rid_77161

29. Dsstox_gsid_23718

30. Triprolidine [inn:ban]

31. Tripolidina [inn-spanish]

32. Triprolidinum [inn-latin]

33. (e)-2-[3-(1-pyrrolidinyl)-1-p-toluenepropenyl]pyridine

34. Hsdb 6316

35. 2-[(1e)-1-(4-methylphenyl)-3-(pyrrolidin-1-yl)prop-1-en-1-yl]pyridine

36. Cas-486-12-4

37. Pyridine, 2-(3-(1-pyrrolidinyl)-1-p-tolylpropenyl)-, (e)-

38. Ccris 7212

39. Einecs 207-627-0

40. Unii-2l8t9s52qm

41. (e)-2-(1-(4-methylphenyl)-3-(1-pyrrolidinyl)-1-propenyl)pyridine

42. 550-70-9

43. Prestwick2_000262

44. Prestwick3_000262

45. Spectrum5_001467

46. Triprolidine [mi]

47. Triprolidine [hsdb]

48. Schembl4905

49. Triprolidine [vandf]

50. Lopac0_001130

51. Bspbio_000104

52. Bspbio_002255

53. (e)-2-(3-(pyrrolidin-1-yl)-1-p-tolylprop-1-enyl)pyridine

54. Bidd:gt0569

55. Triprolidine [who-dd]

56. Bpbio1_000116

57. Gtpl1228

58. Dtxsid3023718

59. Hms2089m21

60. 10191-42-1

61. Hy-b1808

62. Tox21_110919

63. Bdbm50292411

64. Ccg-12422

65. Zinc12503099

66. Tox21_110919_1

67. Db00427

68. Sdccgsbi-0025383.p005

69. Idi1_000297

70. Ncgc00024714-02

71. Ncgc00024714-04

72. Ncgc00024714-05

73. Ncgc00024714-06

74. Ncgc00024714-07

75. Ncgc00024714-08

76. Ncgc00024714-11

77. Ncgc00024714-15

78. Bim-0025383.p001

79. Sbi-0025383.p004

80. Cs-0013854

81. D08648

82. Ab00053563-02

83. Ab00053563-13

84. Ab00053563_14

85. 486t124

86. L000901

87. Q417654

88. 2-(3-pyrrolidin-1-yl-1-p-tolyl-propenyl)-pyridine

89. Brd-k11742128-003-05-1

90. Brd-k11742128-003-15-0

91. 1-((e)-3-pyridin-2-yl-3-p-tolyl-allyl)-pyrrolidinium

92. 2-((e)-3-pyrrolidin-1-yl-1-p-tolyl-propenyl)-pyridine

93. 2-(3-(pyrrolidin-1-yl)-1-p-tolylprop-1-enyl)pyridine

94. 2-[(e)-1-(4-methylphenyl)-3-pyrrolidin-1-yl-prop-1-enyl]pyridine

95. (e)-2-1-(4-methylphenyl)-3-(1-pyrrolidinyl)-1-propenyl-pyridine

2.4 Create Date
2005-07-07
3 Chemical and Physical Properties
Molecular Weight 278.4 g/mol
Molecular Formula C19H22N2
XLogP33.9
Hydrogen Bond Donor Count0
Hydrogen Bond Acceptor Count2
Rotatable Bond Count4
Exact Mass278.178298710 g/mol
Monoisotopic Mass278.178298710 g/mol
Topological Polar Surface Area16.1 Ų
Heavy Atom Count21
Formal Charge0
Complexity336
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count1
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Drug and Medication Information
4.1 Therapeutic Uses

Anti-Allergic Agents; Histamine H1 Antagonists

National Library of Medicine's Medical Subject Headings online file (MeSH, 1999)


Antihistamines are indicated in the prophylactic and symptomatic treatment of perennial and seasonal allergic rhinitis, vasomotor rhinitis, and allergic conjunctivitis due to inhalant allergens and foods. /Antihistamines; Included in US product labeling/

USP Convention. USPDI - Drug Information for the Health Care Professional. 15 th ed. Volume 1. Rockville, MD: United States Pharmacopeial Convention, Inc., 1995. (Plus updates.), p. 303


Antihistamines are indicated for the symptomatic treatment of pruritus associated with allergic reactions and of mild, uncomplicated allergic skin manifestations of urticaria and angioedema, in dermatographism, and in urticaria associated with transfusions. /Antihistamines; Included in US product labeling/

USP Convention. USPDI - Drug Information for the Health Care Professional. 15 th ed. Volume 1. Rockville, MD: United States Pharmacopeial Convention, Inc., 1995. (Plus updates.), p. 303


Antihistamines are also used in the treatment of pruritus associated with pityriasis rosea. /Antihistamines; NOT included in US product labeling/

USP Convention. USPDI - Drug Information for the Health Care Professional. 15 th ed. Volume 1. Rockville, MD: United States Pharmacopeial Convention, Inc., 1995. (Plus updates.), p. 303


For more Therapeutic Uses (Complete) data for TRIPROLIDINE (8 total), please visit the HSDB record page.


4.2 Drug Warning

Use is not recommended in newborn or premature infants because this age group has an increased susceptibility to anticholinergic side effects, such as central nervous system excitation, and an increased tendency toward convulsions. A paradoxical reaction characterized by hyperexcitability may occur in children taking antihistamines. /Antihistamines/

USP Convention. USPDI - Drug Information for the Health Care Professional. 15 th ed. Volume 1. Rockville, MD: United States Pharmacopeial Convention, Inc., 1995. (Plus updates.), p. 306


Dizziness, sedation, confusion, and hypotension may be more likely to occur in geriatric patients taking antihistamines. Geriatric patients are especially susceptible to the anticholinergic side effects, such as dryness of mouth and urinary retention (especially in males), of the antihistamines. If these side effects occur and continue or are severe, medication should probably be discontinued. /Antihistamines/

USP Convention. USPDI - Drug Information for the Health Care Professional. 15 th ed. Volume 1. Rockville, MD: United States Pharmacopeial Convention, Inc., 1995. (Plus updates.), p. 306


Prolonged use of antihistamines ... may decrease or inhibit salivary flow, thus contributing to the development of caries, periodontal disease, oral candidiasis, and discomfort. /Antihistamines/

USP Convention. USPDI - Drug Information for the Health Care Professional. 15 th ed. Volume 1. Rockville, MD: United States Pharmacopeial Convention, Inc., 1995. (Plus updates.), p. 306


Maternal Medication usually Compatible with Breast-Feeding: Triprolidine: Reported Sign or Symptom in Infant or Effect on Lactation: None. /From Table 6/

Report of the American Academy of Pediatrics Committee on Drugs in Pediatrics 93 (1): 142 (1994)


For more Drug Warnings (Complete) data for TRIPROLIDINE (10 total), please visit the HSDB record page.


4.3 Drug Indication

For the symptomatic relief of seasonal or perennial allergic rhinitis or nonallergic rhinitis; allergic conjunctivitis; and mild, uncomplicated allergic skin manifestations of urticaria and angioedema. Also used in combination with other agents for the symptomatic relief of symptoms associated with the common cold.


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. Triprolidine, is a histamine H1 antagonist that 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. Triprolidine has anticholinergic and sedative effects.


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.)


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

R06AX - Other antihistamines for systemic use

R06AX07 - Triprolidine


5.4 Absorption, Distribution and Excretion

Absorption

Rapidly absorbed in the intestinal tract.


The H1 antagonists are well absorbed from the GI tract. Following oral administration, peak plasma concn are achieved in 2 to 3 hr and effects usually last 4 to 6 hr; however, some of the drugs are much longer acting ... . /Histamine Antagonists: H1 Antagonists/

Gilman, A.G., T.W. Rall, A.S. Nies and P. Taylor (eds.). Goodman and Gilman's The Pharmacological Basis of Therapeutics. 8th ed. New York, NY. Pergamon Press, 1990., p. 584


... H1 antagonists are eliminated more rapidly by children than by adults and more slowly in those with severe liver disease. /Histamine Antagonists: H1 Antagonists/

Gilman, A.G., T.W. Rall, A.S. Nies and P. Taylor (eds.). Goodman and Gilman's The Pharmacological Basis of Therapeutics. 8th ed. New York, NY. Pergamon Press, 1990., p. 584


5.5 Metabolism/Metabolites

MAIN SITE OF METABOLIC TRANSFORMATION IS LIVER. /ANTIHISTAMINES/

Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 607


5.6 Biological Half-Life

4 to 6 hours.


Elimination: 3 to 3.3 hours

USP Convention. USPDI - Drug Information for the Health Care Professional. 15 th ed. Volume 1. Rockville, MD: United States Pharmacopeial Convention, Inc., 1995. (Plus updates.), p. 305


5.7 Mechanism of Action

Triprolidine 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.


Antihistamines used in the treatment of allergy act by competing with histamine for H1-receptor sites on effector cells. They thereby prevent, but do not reverse, responses mediated by histamine alone. Antihistamines antagonize, in varying degrees, most of the pharmacological effects of histamine, including urticaria and pruritus. Also, the anticholinergic actions of most antihistamines provide a drying effect on the nasal mucosa. /Antihistamines/

USP Convention. USPDI - Drug Information for the Health Care Professional. 15 th ed. Volume 1. Rockville, MD: United States Pharmacopeial Convention, Inc., 1995. (Plus updates.), p. 304


Antihistamines used in the treatment of allergy act by competing with histamine for H1-receptor sites on effector cells. They thereby prevent, but do not reverse, responses mediated by histamine alone. Antihistamines antagonize, in varying degrees, most of the pharmacological effects of histamine, including urticaria and pruritus. Also, the anticholinergic actions of most antihistamines provide a drying effect on the nasal mucosa. /Antihistamines/

USP Convention. USPDI - Drug Information for the Health Care Professional. 15 th ed. Volume 1. Rockville, MD: United States Pharmacopeial Convention, Inc., 1995. (Plus updates.), p. 304


H1 antagonists inhibit most responses of smooth muscle to histamine. Antagonism of the constrictor action of histamine on respiratory smooth muscle is easily shown in vivo and in vitro. /Histamine Antagonists: H1 Antagonists/

Gilman, A.G., T.W. Rall, A.S. Nies and P. Taylor (eds.). Goodman and Gilman's The Pharmacological Basis of Therapeutics. 8th ed. New York, NY. Pergamon Press, 1990., p. 582


/SRP:/ The action of histamine results in increased permeability and formation of edema and wheal. H1 antagonists block that action.

Gilman, A.G., T.W. Rall, A.S. Nies and P. Taylor (eds.). Goodman and Gilman's The Pharmacological Basis of Therapeutics. 8th ed. New York, NY. Pergamon Press, 1990., p. 583


For more Mechanism of Action (Complete) data for TRIPROLIDINE (7 total), please visit the HSDB record page.


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