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Technical details about Prestwick3_000117, learn more about the structure, uses, toxicity, action, side effects and more

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2D Structure
Also known as: Chlorphenamine, 132-22-9, Teldrin, Chlorophenylpyridamine, Chlor-trimeton, Clorfeniramina
Molecular Formula
C16H19ClN2
Molecular Weight
274.79  g/mol
InChI Key
SOYKEARSMXGVTM-UHFFFAOYSA-N
FDA UNII
3U6IO1965U

A histamine H1 antagonist used in allergic reactions, hay fever, rhinitis, urticaria, and asthma. It has also been used in veterinary applications. One of the most widely used of the classical antihistaminics, it generally causes less drowsiness and sedation than PROMETHAZINE.
Chlorpheniramine is a Histamine-1 Receptor Antagonist. The mechanism of action of chlorpheniramine is as a Histamine H1 Receptor Antagonist.
1 2D Structure

2D Structure

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
3-(4-chlorophenyl)-N,N-dimethyl-3-pyridin-2-ylpropan-1-amine
2.1.2 InChI
InChI=1S/C16H19ClN2/c1-19(2)12-10-15(16-5-3-4-11-18-16)13-6-8-14(17)9-7-13/h3-9,11,15H,10,12H2,1-2H3
2.1.3 InChI Key
SOYKEARSMXGVTM-UHFFFAOYSA-N
2.1.4 Canonical SMILES
CN(C)CCC(C1=CC=C(C=C1)Cl)C2=CC=CC=N2
2.2 Other Identifiers
2.2.1 UNII
3U6IO1965U
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Aller-chlor

2. Antihistaminico Llorens

3. Chlo-amine

4. Chlor-100

5. Chlor-trimeton

6. Chlor-tripolon

7. Chlorphenamine

8. Chlorpheniramine Maleate

9. Chlorpheniramine Tannate

10. Chlorpro

11. Chlorprophenpyridamine

12. Chlorspan 12

13. Chlortab-4

14. Cloro-trimeton

15. Efidac 24

16. Kloromin

17. Maleate, Chlorpheniramine

18. Piriton

19. Tannate, Chlorpheniramine

20. Teldrin

2.3.2 Depositor-Supplied Synonyms

1. Chlorphenamine

2. 132-22-9

3. Teldrin

4. Chlorophenylpyridamine

5. Chlor-trimeton

6. Clorfeniramina

7. Phenetron

8. Haynon

9. Clorfenamina

10. Chloropheniramine-d4

11. Chlorpheniraminum

12. Polaronil

13. Chlorphenaminum

14. Chlorpheniramine Polistirex

15. Clofeniramina

16. 3-(4-chlorophenyl)-n,n-dimethyl-3-(pyridin-2-yl)propan-1-amine

17. 1-(p-chlorophenyl)-1-(2-pyridyl)-3-dimethylaminopropane

18. 3-(p-chlorophenyl)-3-(2-pyridyl)-n,n-dimethylpropylamine

19. Gamma-(4-chlorophenyl)-gamma-(2-pyridyl)propyldimethylamine

20. Gamma-(4-chlorophenyl)-n,n-dimethyl-2-pyridinepropanamine

21. 1-(p-chlorophenyl)-1-(2-pyridyl)-3-n,n-dimethylpropylamine

22. Chlo-amine

23. 3-(4-chlorophenyl)-n,n-dimethyl-3-pyridin-2-ylpropan-1-amine

24. Chlorphenamine [inn]

25. D-chlorpheniramine

26. 2-pyridinepropanamine, Gamma-(4-chlorophenyl)-n,n-dimethyl-

27. Chembl505

28. Chloropheniramine

29. Chlorprophenpyridamine

30. Dexchlorpheniramine Free Base

31. Chloropheniramine Maleate

32. Allergican

33. Allergisan

34. Chloropiril

35. Cloropiril

36. Histadur

37. Chebi:52010

38. Chloroprophenpyridamine

39. 3u6io1965u

40. 25523-97-1 (free Base)

41. Chlorphenamine (inn)

42. 2-(p-chloro-alpha-(2-(dimethylamino)ethyl)benzyl)pyridine

43. 3-(4-chlorophenyl)-n,n-dimethyl-3-(2-pyridyl)propan-1-amine

44. Aller-chlor

45. 4-chloropheniramine

46. 2-[p-chloro-alpha-[2-(dimethylamino)ethyl]benzyl]pyridine

47. Chlorphenamin

48. Telachlor

49. Clorfeniramina [italian]

50. Clorfenamina [inn-spanish]

51. Chlorphenaminum [inn-latin]

52. Pyridine, 2-(p-chloro-alpha-(2-(dimethylamino)ethyl)benzyl)-

53. Hsdb 3032

54. 113-92-8

55. Einecs 205-054-0

56. Chlorphenamine [inn:ban]

57. Piriiton

58. Unii-3u6io1965u

59. Chlor-pro

60. [3h]chlorphenamine

61. Clofeniramina (tn)

62. [3h]chlorpheniramine

63. Chlorpheniramine-[d6]

64. Chlorpheniaramine Maleate

65. S-(+)-chlorpheniramine

66. Prestwick0_000117

67. Prestwick1_000117

68. Prestwick2_000117

69. Prestwick3_000117

70. Ncgc00015227-04

71. 5-ht,n-acetyl

72. Schembl4219

73. Lopac0_000261

74. Oprea1_779072

75. Bspbio_000134

76. Chlorpheniramine [mi]

77. Divk1c_000596

78. Chlorpheniramine Maleate B.p.

79. Spbio_002073

80. Chlorpheniramine [hsdb]

81. Bpbio1_000148

82. Gtpl6976

83. Chlorphenamine [who-dd]

84. Chlorpheniramine [vandf]

85. Dtxsid0022804

86. Bdbm35938

87. Kbio1_000596

88. Chlorpheniramine-d6see C424303

89. Ninds_000596

90. 783ahi015x

91. Hms2090m21

92. Hms3428j07

93. Chlorpheniramine Polistirex [usan]

94. 2-pyridinepropanamine, .gamma.-(4-chlorophenyl)-n,n-dimethyl-

95. Hy-b0286

96. Bbl012285

97. Stk736174

98. Akos001650136

99. Ccg-108982

100. Db01114

101. Sb19135

102. Sdccgsbi-0050249.p002

103. Idi1_000596

104. Ncgc00015227-03

105. Ncgc00015227-05

106. Ncgc00015227-06

107. Ncgc00015227-09

108. Ncgc00015227-19

109. Ncgc00162108-01

110. Ncgc00162108-02

111. Chlorpheniramine Component Of Tuzistra

112. Cs-0009285

113. Ft-0665002

114. Ft-0772034

115. Tuzistra Componenet Of Chlorpheniramine

116. C06905

117. D07398

118. L000003

119. Q420133

120. W-108317

121. Brd-a04553218-050-03-0

122. Brd-a04553218-050-08-9

123. .gamma.-(4-chlorophenyl)-n,n-dimethyl-2-pyridinepropanamine

124. 2-(p-chloro-.alpha.-(2-(dimethylamino)ethyl)benzyl)pyridine

125. N-[3-(4-chlorophenyl)-3-(2-pyridinyl)propyl]-n,n-dimethylamine #

126. N.-propanamine, 3-(4-chlorophenyl)-3-(2-pyridyl)-n,n-dimethyl-

127. (?)-3-(4-chlorophenyl)-n,n-dimethyl-3-(2-pyridinyl)propan-1-amine

128. 2-pyridinepropanamine, .gamma.-(4-chlorophenyl)-n,n-dimethyl-, (s)-

129. Pyridine, 2-[p-chloro-.alpha.-[2-(dimethylamino)ethyl]benzyl]-, (s)-(+)-

2.4 Create Date
2005-03-25
3 Chemical and Physical Properties
Molecular Weight 274.79 g/mol
Molecular Formula C16H19ClN2
XLogP33.4
Hydrogen Bond Donor Count0
Hydrogen Bond Acceptor Count2
Rotatable Bond Count5
Exact Mass274.1236763 g/mol
Monoisotopic Mass274.1236763 g/mol
Topological Polar Surface Area16.1 Ų
Heavy Atom Count19
Formal Charge0
Complexity249
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count1
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Drug and Medication Information
4.1 Drug Information
1 of 4  
Drug NameChlorpheniramine maleate
Drug LabelEd Chlortan Tablets are yellow, round, plain bottom, debossed "PH above 012" on top....
Active IngredientChlorpheniramine maleate
Dosage FormTablet, extended release
RouteOral
Strength12mg
Market StatusOver the Counter
CompanyAvanthi

2 of 4  
Drug NameChlor-trimeton
Active IngredientChlorpheniramine maleate; pseudoephedrine sulfate
Dosage FormTablet, extended release
RouteOral
Strength12mg; 8mg; 120mg
Market StatusOver the Counter
CompanySchering Plough

3 of 4  
Drug NameChlorpheniramine maleate
Drug LabelEd Chlortan Tablets are yellow, round, plain bottom, debossed "PH above 012" on top....
Active IngredientChlorpheniramine maleate
Dosage FormTablet, extended release
RouteOral
Strength12mg
Market StatusOver the Counter
CompanyAvanthi

4 of 4  
Drug NameChlor-trimeton
Active IngredientChlorpheniramine maleate; pseudoephedrine sulfate
Dosage FormTablet, extended release
RouteOral
Strength12mg; 8mg; 120mg
Market StatusOver the Counter
CompanySchering Plough

4.2 Therapeutic Uses

Anti-Allergic Agents; Antipruritics; 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 CHLORPHENIRAMINE (10 total), please visit the HSDB record page.


4.3 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


ANTIHISTAMINE DRUGS MAY BE OF SOME USE IN MINIMIZING SERUM REACTIONS BUT ARE OF NO THERAPEUTIC VALUE...& MAY EVEN POTENTIATE TOXIC ACTION OF VENOM... /ANTIHISTAMINES/

Garner's Veterinary Toxicology. 3rd ed., rev. by E.G.C. Clarke and M.L. Clarke. Baltimore: Williams and Wilkins, 1967., p. 445


For more Drug Warnings (Complete) data for CHLORPHENIRAMINE (14 total), please visit the HSDB record page.


4.4 Minimum/Potential Fatal Human Dose

5. 5= EXTREMELY TOXIC: PROBABLE ORAL LETHAL DOSE (HUMAN) 5-50 MG/KG, BETWEEN 7 DROPS & 1 TEASPOONFUL FOR 70 KG PERSON (150 LB). /ANTIHISTAMINICS/

Gosselin, R.E., R.P. Smith, H.C. Hodge. Clinical Toxicology of Commercial Products. 5th ed. Baltimore: Williams and Wilkins, 1984., p. II-15


4.5 Drug Indication

For the treatment of rhinitis, urticaria, allergy, common cold, asthma and hay fever.


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. Chlorpheniramine, is a histamine H1 antagonist (or more correctly, an inverse histamine agonist) of the alkylamine class. 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.)


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.)


Antipruritics

Agents, usually topical, that relieve itching (pruritus). (See all compounds classified as Antipruritics.)


5.3 FDA Pharmacological Classification
5.3.1 Active Moiety
CHLORPHENIRAMINE
5.3.2 FDA UNII
3U6IO1965U
5.3.3 Pharmacological Classes
Established Pharmacologic Class [EPC] - Histamine-1 Receptor Antagonist
5.4 ATC Code

R06AB54

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


R - Respiratory system

R06 - Antihistamines for systemic use

R06A - Antihistamines for systemic use

R06AB - Substituted alkylamines

R06AB04 - Chlorphenamine


5.5 Absorption, Distribution and Excretion

Absorption

Well absorbed in the gastrointestinal tract.


STUDIES IN MAN & EXPTL ANIMALS INDICATE THAT (3)H-CHLORPHENIRAMINE MALEATE IS RAPIDLY & QUANT ABSORBED FROM GUT. ALTHOUGH PLASMA LEVELS OF TOTAL RADIOACTIVITY ARE PROLONGED, PLASMA T/2 OF CHLORPHENIRAMINE IS ONLY 12-15 HR IN MAN & 3 HR IN DOG. T/2 IN MAN IS ABOUT 3 TIMES LONGER THAN THERAPEUTIC EFFECT...

The Chemical Society. Foreign Compound Metabolism in Mammals Volume 3. London: The Chemical Society, 1975., p. 194


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 blockers are among the many drugs that induce hepatic microsomal enzymes, and they may facilitate their own metabolism. /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


5.6 Metabolism/Metabolites

Primarily hepatic via Cytochrome P450 (CYP450) enzymes.


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


5.7 Biological Half-Life

21-27 hours


IN MAN...PLASMA T/2 OF CHLORPHENIRAMINE IS...12-15 HR...ALTHOUGH PLASMA LEVELS OF TOTAL RADIOACTIVITY ARE PROLONGED...

The Chemical Society. Foreign Compound Metabolism in Mammals Volume 3. London: The Chemical Society, 1975., p. 194


Elimination: 14 to 25 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


5.8 Mechanism of Action

Chlorpheniramine 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


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


H1 antagonists strongly block the action of histamine that results in increased permeability and formation of edema and wheal. /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. 583


Within the vascular tree, the H1 antagonists inhibit both the vasoconstrictor effects of histamine and, to a degree, the more rapid vasodilator effects that are mediated by H1 receptors on endothelial cells. Residual vasodilatation reflects the involvement of H2 receptors on smooth muscle and can be suppressed only by the concurrent administration of an H2 antagonist. Effects of the histamine antagonists on histamine induced changes in systemic blood pressure parallel these vascular effects. /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. 583


Many of the H1 antagonists tend to inhibit responses to acetylcholine that are mediated by muscarinic receptors. These atropine like actions are sufficiently prominent in some of the drugs to be manifest during clinical usage ... . /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


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