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Cetirizine Hydrochloride

Synopsis, Chemistry

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SOLUTION;ORAL - 5MG/5ML
CAPSULE;ORAL - 10MG
CAPSULE;ORAL - 5MG

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Also known as: Cetirizine dihydrochloride, 83881-52-1, Zyrtec, Reactine, Cetirizine dihcl, Cetrine

Molecular Formula

C₂₁H₂₇Cl₃N₂O₃

Molecular Weight

461.8 g/mol

InChI Key

PGLIUCLTXOYQMV-UHFFFAOYSA-N

FDA UNII

64O047KTOA

A potent second-generation histamine H1 antagonist that is effective in the treatment of allergic rhinitis, chronic urticaria, and pollen-induced asthma. Unlike many traditional antihistamines, it does not cause drowsiness or anticholinergic side effects.

1 2D Structure

Cetirizine Hydrochloride

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

2-[2-[4-[(4-chlorophenyl)-phenylmethyl]piperazin-1-yl]ethoxy]acetic acid;dihydrochloride

2.1.2 InChI

InChI=1S/C21H25ClN2O3.2ClH/c22-19-8-6-18(7-9-19)21(17-4-2-1-3-5-17)24-12-10-23(11-13-24)14-15-27-16-20(25)26;;/h1-9,21H,10-16H2,(H,25,26);2*1H

2.1.3 InChI Key

PGLIUCLTXOYQMV-UHFFFAOYSA-N

2.1.4 Canonical SMILES

C1CN(CCN1CCOCC(=O)O)C(C2=CC=CC=C2)C3=CC=C(C=C3)Cl.Cl.Cl

2.2 Other Identifiers

2.2.1 UNII

64O047KTOA

2.3 Synonyms

2.3.1 MeSH Synonyms

1. (2-(4-((4-chlorophenyl)phenylmethyl)-1-piperazinyl)ethoxy)acetic Acid

2. Alerlisin

3. Aller-tec

4. Cetalerg

5. Ceterifug

6. Ceti Tad

7. Ceti-puren

8. Cetiderm

9. Cetidura

10. Cetil Von Ct

11. Cetilich

12. Cetirigamma

13. Cetirizin Al

14. Cetirizin Azu

15. Cetirizin Basics

16. Cetirizine

17. Cetirizine Dihydrochloride

18. Cetirlan

19. Dihydrochloride, Cetirizine

20. P 071

21. P-071

22. P071

23. Reactine

24. Virlix

25. Voltric

26. Zetir

27. Zirtek

28. Zyrtec

2.3.2 Depositor-Supplied Synonyms

1. Cetirizine Dihydrochloride

2. 83881-52-1

3. Zyrtec

4. Reactine

5. Cetirizine Dihcl

6. Cetrine

7. 2-(2-(4-((4-chlorophenyl)(phenyl)methyl)piperazin-1-yl)ethoxy)acetic Acid Dihydrochloride

8. Alerlisin

9. Cetirizine Hcl

10. Virlix

11. P 071

12. Zirtek

13. P-071

14. Zerviate

15. Cetirizine (dihydrochloride)

16. 2-[2-[4-[(4-chlorophenyl)-phenylmethyl]piperazin-1-yl]ethoxy]acetic Acid;dihydrochloride

17. 83881-52-1 (hcl)

18. 64o047ktoa

19. Nsc-759102

20. Cetirigamma

21. Alercet

22. Alergex

23. Alertisin

24. Cetalerg

25. Ceterifug

26. Cetidura

27. Cetirlan

28. Cetriler

29. Cetzine

30. Formistin

31. Ressital

32. Salvalerg

33. Setiral

34. Stopaler

35. Voltric

36. Zyrzine

37. Alerid

38. Riztec

39. Virdos

40. Zirtin

41. Cezin

42. Ryzen

43. Zetir

44. Cetilich

45. Triz

46. Cetirizin Basics

47. Xero-sed

48. Ceti-puren

49. Cetil Von Ct

50. Cetirizin Azu

51. Children's Zyrtec

52. (2-(4-((4-chlorophenyl)phenylmethyl)-1-piperazinyl)ethoxy)acetic Acid Dihydrochloride

53. [2-[4-[(4-chlorophenyl)phenylmethyl]-1-piperazinyl]ethoxy]acetic Acid Dihydrochloride

54. Dsstox_cid_24268

55. Dsstox_rid_80138

56. Dsstox_gsid_44268

57. Ceti Tad

58. Alleroff

59. Allergy Relief

60. Apo-cetirizine

61. Zyrtec Allergy

62. Zyrtec Hives Relief

63. Cetirizine Hydrochloride [usan]

64. Ucb-p 071

65. Topcare All Day Allergy

66. Sun Mark All Day Allergy

67. Children's Zyrtec Allergy

68. Unii-64o047ktoa

69. Cetirizine Hydrochloride Hives

70. Cetirizine Di

71. Children's Zyrtec Hives Relief

72. Sr-01000688282

73. Cetirizine Hydrochloride Allergy

74. Cetirizine 2hcl

75. Up And Up All Day Allergy Relief

76. Prestwick_841

77. Cetirizine Hydrochloride [usan:usp]

78. Xyzal Dihydrochloride

79. Zyrtec (tn)

80. Quzyttir

81. 774596-22-4

82. Ox-nla

83. Children's Cetirizine Hydrochloride Allergy

84. Ncgc00016949-01

85. Cetirizine-d8 Hydrochloride

86. Cas-83881-52-1

87. Children's Cetirizine Hydrochloride Hives Relief

88. (+-)-(2-(4-(p-chloro-alpha-phenylbenzyl)-1-piperazinyl)ethoxy)acetic Acid, Dihydrochloride

89. Schembl41107

90. Spectrum1505371

91. Chebi:3562

92. Ucb P071

93. Cetirizine Hydrochloride (1:2)

94. Chembl1607273

95. Dtxsid2044268

96. Hms1569f07

97. Hms1922h04

98. Bcp09018

99. Tox21_110704

100. Tox21_302261

101. Tox21_500362

102. Hy-17042a

103. Mfcd00941428

104. S1291

105. Cetirizine Hydrochloride (jp17/usp)

106. Cetirizine Hydrochloride [jan]

107. Akos000280979

108. Akos016340521

109. Tox21_110704_1

110. Ac-1600

111. Ccg-213404

112. Cetirizine Dihydrochloride [mi]

113. Cs-1798

114. Ks-1042

115. Lp00362

116. Nsc 759102

117. Cetirizine Hydrochloride [mart.]

118. Cetirizine Hydrochloride [vandf]

119. Cetirizine Hydrochloride [usp-rs]

120. Cetirizine Hydrochloride [who-dd]

121. Ncgc00095180-01

122. Ncgc00095180-02

123. Ncgc00255965-01

124. Ncgc00261047-01

125. Ncgc00263567-01

126. Acetic Acid, (2-(4-((4-chlorophenyl)phenylmethyl)-1-piperazinyl)ethoxy)-, Dihydrochloride, (+-)-

127. Bc164297

128. Cetirizine Dihydrochloride, >=98% (hplc)

129. Db-056756

130. (r)-cetirizine Dihcl (levocetirizine Dihcl)

131. Ft-0603000

132. Ft-0631130

133. Ft-0664487

134. Sw196972-3

135. Cetirizin Dihydrochloride, >=98.0% (hplc)

136. Cetirizine Hydrochloride [orange Book]

137. Cetirizine Hydrochloride [usp Monograph]

138. D00664

139. F20462

140. Cetirizine Dihydrochloride [ep Monograph]

141. 881c510

142. A840675

143. Zyrtec-d Component Cetirizine Hydrochloride

144. Sr-01000688282-3

145. Cetirizine Hydrochloride Component Of Zyrtec-d

146. Q27263769

147. Cetirizine Dihydrochloride 1.0 Mg/ml In Water (as Free Base)

148. Cetirizine Dihydrochloride, European Pharmacopoeia (ep) Reference Standard

149. Cetirizine Hydrochloride, British Pharmacopoeia (bp) Reference Standard

150. (rs)-{2-[4-(alpha-phenyl-p-chlorobenzyl)-piperazin-1-yl]ethoxy}-acetic Acid Dihydrochloride

151. [2-[4-[(4-chlorophenyl)phenylmethyl]-1-piperazinyl]ethoxy]aceticaciddihydrochloride

152. 2-(2-(4-((4-chlorophenyl)(phenyl)methyl)piperazin-1-yl)ethoxy)acetic Acid 2hcl

153. 2-(2-(4-((4-chlorophenyl)(phenyl)methyl)piperazin-1-yl)ethoxy)aceticaciddihydrochloride

154. Cetirizine Dihydrochloride, United States Pharmacopeia (usp) Reference Standard

155. Cetirizine For Peak Identification, European Pharmacopoeia (ep) Reference Standard

156. Cetirizine Hydrochloride, Pharmaceutical Secondary Standard; Certified Reference Material

157. (+) {2-[4-(alpha-phenyl-p-chlorobenzyl)-piperazine-1-yl] -ethoxy}-acetic Acid Dihydrochloride

158. (+/-)-(2-(4-(p-chloro-a-phenylbenzyl)-1-piperazinyl)ethoxy)acetic Acid, Dihydrochloride

159. (+/-){2-[4-(alpha-phenyl-p-chlorobenzyl)-piperazin-1-yl]-ethoxy}-acetic Acid Dihydrochloride

160. (rs)-{2-[4-(alpha-phenyl-p-chlorobenzyl)-piperazin-1-yl]ethoxy }-acetic Acid Dihydrochloride

161. 2-(2-(4-(p-chloro-alpha-phenylbenzyl)1-piperazinyl)ethoxy) Acetic Acid Dihydrochloride

162. 2-(2-{4-[(4-chlorophenyl)(phenyl)-methyl]piperazino}ethoxy)acetic Acid Dihydrochloride;cetirizine Dihydrochloride

163. Acetic Acid, (2-(4-((4-chlorophenyl)phenylmethyl)-1-piperazinyl)ethoxy)-, Dihydrochloride, (+/-)-

164. Acetic Acid, 2-[2-[4-[(4-chlorophenyl)phenylmethyl]-1-piperazinyl]ethoxy]-, Hydrochloride (1:2)

165. Cetirizine Dihydrochloride Solution, 1.0 Mg/ml In Acetonitrile: Water (9:1) (as Free Base), Ampule Of 1 Ml, Certified Reference Material

2.3.3 Other Synonyms

1. Cetirizin Dihydrochloride

2. Cetirizine Hcl

2.4 Create Date

2005-06-24

3 Chemical and Physical Properties

Molecular Formula	C₂₁H₂₇Cl₃N₂O₃
Molecular Weight	461.8 g/mol
Hydrogen Bond Donor Count	3
Hydrogen Bond Acceptor Count	5
Rotatable Bond Count	8
Exact Mass	460.108726 g/mol
Monoisotopic Mass	460.108726 g/mol
Topological Polar Surface Area	53 Å²
Heavy Atom Count	29
Formal Charge	0
Complexity	443
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	3

4 Drug and Medication Information

4.1 Drug Information

1 of 20
Drug Name	Cetirizine hydrochloride
Drug Label	Cetirizine hydrochloride is an orally active and selective H1-receptor antagonist. The chemical name is () - [2- [4- [ (4-chlorophenyl) phenylmethyl]- 1 - piperazinyl] ethoxy] acetic acid, dihydrochloride. Cetirizine hydrochloride is a racemic comp...
Active Ingredient	Cetirizine hydrochloride
Dosage Form	Syrup
Route	Oral
Strength	5mg/5ml
Market Status	Prescription
Company	Perrigo R And D; Amneal Pharms; Wockhardt; Silarx; Teva Pharms; Caraco; Breckenridge Pharm; Bio Pharm; Vintage; Taro

2 of 20
Drug Name	Cetirizine hydrochloride allergy
Active Ingredient	Cetirizine hydrochloride
Dosage Form	Tablet; Capsule; Tablet, chewable
Route	Oral
Strength	5mg; 10mg
Market Status	Over the Counter
Company	Perrigo R And D; Wockhardt; Ranbaxy; Amneal Pharms Ny; Ipca Labs; Unichem; Apotex; Contract Pharmacal; Sun Pharm Inds; Taro; Torrent Pharms; Cadista Pharms; Dr Reddys Labs; Sandoz; Unique Pharm Labs; Banner Pharmacaps; Cipla; Orchid Hlthcare; Mylan

3 of 20
Drug Name	Cetirizine hydrochloride hives
Active Ingredient	Cetirizine hydrochloride
Dosage Form	Tablet
Route	Oral
Strength	5mg; 10mg
Market Status	Over the Counter
Company	Perrigo R And D; Ranbaxy; Ipca Labs; Unichem; Sun Pharm Inds; Cadista Pharms; Dr Reddys Labs; Unique Pharm Labs; Orchid Hlthcare; Mylan

4 of 20
Drug Name	Children's cetirizine hydrochloride allergy
Active Ingredient	Cetirizine hydrochloride
Dosage Form	Syrup; Tablet, chewable
Route	Oral
Strength	5mg; 10mg; 5mg/5ml
Market Status	Over the Counter
Company	Perrigo R And D; Amneal Pharms; Silarx; Cypress Pharm; Caraco; Bio Pharm; Aurobindo Pharma; Taro; Sun Pharma Global; Tris Pharma

5 of 20
Drug Name	Children's cetirizine hydrochloride hives relief
Active Ingredient	Cetirizine hydrochloride
Dosage Form	Syrup; Tablet, chewable
Route	Oral
Strength	5mg; 10mg; 5mg/5ml
Market Status	Over the Counter
Company	Perrigo R And D; Amneal Pharms; Silarx; Cypress Pharm; Caraco; Bio Pharm; Aurobindo Pharma; Taro; Sun Pharma Global; Tris Pharma

6 of 20
Drug Name	Children's zyrtec allergy
Active Ingredient	Cetirizine hydrochloride
Dosage Form	Syrup
Route	Oral
Strength	5mg/5ml
Market Status	Over the Counter
Company	Mcneil Consumer

7 of 20
Drug Name	Children's zyrtec hives relief
Active Ingredient	Cetirizine hydrochloride
Dosage Form	Syrup
Route	Oral
Strength	5mg/5ml
Market Status	Over the Counter
Company	Mcneil Consumer

8 of 20
Drug Name	Zyrtec
Active Ingredient	Cetirizine hydrochloride
Dosage Form	Syrup
Route	Oral
Strength	5mg/5ml
Market Status	Prescription
Company	Mcneil Consumer

9 of 20
Drug Name	Zyrtec allergy
Active Ingredient	Cetirizine hydrochloride
Dosage Form	Tablet; Tablet, orally disintegrating
Route	Oral
Strength	5mg; 10mg
Market Status	Over the Counter
Company	Mcneil Consumer

10 of 20
Drug Name	Zyrtec hives relief
Active Ingredient	Cetirizine hydrochloride
Dosage Form	Tablet
Route	Oral
Strength	5mg; 10mg
Market Status	Over the Counter
Company	Mcneil Consumer

11 of 20
Drug Name	Cetirizine hydrochloride
Drug Label	Cetirizine hydrochloride is an orally active and selective H1-receptor antagonist. The chemical name is () - [2- [4- [ (4-chlorophenyl) phenylmethyl]- 1 - piperazinyl] ethoxy] acetic acid, dihydrochloride. Cetirizine hydrochloride is a racemic comp...
Active Ingredient	Cetirizine hydrochloride
Dosage Form	Syrup
Route	Oral
Strength	5mg/5ml
Market Status	Prescription
Company	Perrigo R And D; Amneal Pharms; Wockhardt; Silarx; Teva Pharms; Caraco; Breckenridge Pharm; Bio Pharm; Vintage; Taro

12 of 20
Drug Name	Cetirizine hydrochloride allergy
Active Ingredient	Cetirizine hydrochloride
Dosage Form	Tablet; Capsule; Tablet, chewable
Route	Oral
Strength	5mg; 10mg
Market Status	Over the Counter
Company	Perrigo R And D; Wockhardt; Ranbaxy; Amneal Pharms Ny; Ipca Labs; Unichem; Apotex; Contract Pharmacal; Sun Pharm Inds; Taro; Torrent Pharms; Cadista Pharms; Dr Reddys Labs; Sandoz; Unique Pharm Labs; Banner Pharmacaps; Cipla; Orchid Hlthcare; Mylan

13 of 20
Drug Name	Cetirizine hydrochloride hives
Active Ingredient	Cetirizine hydrochloride
Dosage Form	Tablet
Route	Oral
Strength	5mg; 10mg
Market Status	Over the Counter
Company	Perrigo R And D; Ranbaxy; Ipca Labs; Unichem; Sun Pharm Inds; Cadista Pharms; Dr Reddys Labs; Unique Pharm Labs; Orchid Hlthcare; Mylan

14 of 20
Drug Name	Children's cetirizine hydrochloride allergy
Active Ingredient	Cetirizine hydrochloride
Dosage Form	Syrup; Tablet, chewable
Route	Oral
Strength	5mg; 10mg; 5mg/5ml
Market Status	Over the Counter
Company	Perrigo R And D; Amneal Pharms; Silarx; Cypress Pharm; Caraco; Bio Pharm; Aurobindo Pharma; Taro; Sun Pharma Global; Tris Pharma

15 of 20
Drug Name	Children's cetirizine hydrochloride hives relief
Active Ingredient	Cetirizine hydrochloride
Dosage Form	Syrup; Tablet, chewable
Route	Oral
Strength	5mg; 10mg; 5mg/5ml
Market Status	Over the Counter
Company	Perrigo R And D; Amneal Pharms; Silarx; Cypress Pharm; Caraco; Bio Pharm; Aurobindo Pharma; Taro; Sun Pharma Global; Tris Pharma

16 of 20
Drug Name	Children's zyrtec allergy
Active Ingredient	Cetirizine hydrochloride
Dosage Form	Syrup
Route	Oral
Strength	5mg/5ml
Market Status	Over the Counter
Company	Mcneil Consumer

17 of 20
Drug Name	Children's zyrtec hives relief
Active Ingredient	Cetirizine hydrochloride
Dosage Form	Syrup
Route	Oral
Strength	5mg/5ml
Market Status	Over the Counter
Company	Mcneil Consumer

18 of 20
Drug Name	Zyrtec
Active Ingredient	Cetirizine hydrochloride
Dosage Form	Syrup
Route	Oral
Strength	5mg/5ml
Market Status	Prescription
Company	Mcneil Consumer

19 of 20
Drug Name	Zyrtec allergy
Active Ingredient	Cetirizine hydrochloride
Dosage Form	Tablet; Tablet, orally disintegrating
Route	Oral
Strength	5mg; 10mg
Market Status	Over the Counter
Company	Mcneil Consumer

20 of 20
Drug Name	Zyrtec hives relief
Active Ingredient	Cetirizine hydrochloride
Dosage Form	Tablet
Route	Oral
Strength	5mg; 10mg
Market Status	Over the Counter
Company	Mcneil Consumer

5 Pharmacology and Biochemistry

5.1 MeSH Pharmacological Classification

Histamine H1 Antagonists, Non-Sedating

A class of non-sedating drugs that bind to but do not activate histamine receptors (DRUG INVERSE AGONISM), thereby blocking the actions of histamine or histamine agonists. These antihistamines represent a heterogenous group of compounds with differing chemical structures, adverse effects, distribution, and metabolism. Compared to the early (first generation) antihistamines, these non-sedating antihistamines have greater receptor specificity, lower penetration of BLOOD-BRAIN BARRIER, and are less likely to cause drowsiness or psychomotor impairment. (See all compounds classified as Histamine H1 Antagonists, Non-Sedating.)

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.)

5.2 FDA Pharmacological Classification

5.2.1 Pharmacological Classes

Histamine-1 Receptor Antagonist [EPC]; Histamine H1 Receptor Antagonists [MoA]