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ACTIVE PHARMA INGREDIENTS

13 API Suppliers, 1 USDMF, 6 CEP/COS, 5 EU WC, 1 NDC API, 9 Listed Suppliers, $ API Reference Price

13 API Suppliers
1 USDMF
6 CEP/COS
5 EU WC
1 NDC API
9 Listed Suppliers
$ API Reference Price

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3 Intermediates Suppliers

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37 FDF Dossiers, 19 Europe, 6 South Africa, 12 Listed Dossiers

37 FDF Dossiers
19 Europe
6 South Africa
12 Listed Dossiers

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12 APIs, 2 FDF Dossiers

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12 APIs
2 FDF Dossiers

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2 EDQM , 2 Others

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2 EDQM
2 Others

Synopsis

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Chemistry

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Also known as: 298-57-7, Stugeron, Stutgin, Cinarizine, Dimitronal, Stutgeron

Molecular Formula

C₂₆H₂₈N₂

Molecular Weight

368.5 g/mol

InChI Key

DERZBLKQOCDDDZ-JLHYYAGUSA-N

FDA UNII

3DI2E1X18L

A piperazine derivative having histamine H1-receptor and calcium-channel blocking activity with vasodilating and antiemetic properties but it induces PARKINSONIAN DISORDERS.

1 2D Structure

Cinnarizine

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

1-benzhydryl-4-[(E)-3-phenylprop-2-enyl]piperazine

2.1.2 InChI

InChI=1S/C26H28N2/c1-4-11-23(12-5-1)13-10-18-27-19-21-28(22-20-27)26(24-14-6-2-7-15-24)25-16-8-3-9-17-25/h1-17,26H,18-22H2/b13-10+

2.1.3 InChI Key

DERZBLKQOCDDDZ-JLHYYAGUSA-N

2.1.4 Canonical SMILES

C1CN(CCN1CC=CC2=CC=CC=C2)C(C3=CC=CC=C3)C4=CC=CC=C4

2.1.5 Isomeric SMILES

C1CN(CCN1C/C=C/C2=CC=CC=C2)C(C3=CC=CC=C3)C4=CC=CC=C4

2.2 Other Identifiers

2.2.1 UNII

3DI2E1X18L

2.3 Synonyms

2.3.1 MeSH Synonyms

1. 1-(diphenylmethyl)-4-(3-phenyl-2-propenyl)piperazine

2. Cinarizina Inkey

3. Cinarizina Ratiopharm

4. Cinarizine

5. Cinazire

6. Cinna

7. Cinnarizin Al

8. Cinnarizin Ratiopharm

9. Cinnarizin Siegfried

10. Cinnarizin Von Ct

11. Cinnarizin-ratiopharm

12. Cinnarizine L Tartrate

13. Cinnarizine L-tartrate

14. Cinnarizine L-tartrate (1:1)

15. Cinnarizine, (e)-isomer

16. Cinnarizine, Dihydrochloride

17. Cinnipirine

18. Cisaken

19. Dihydrochloride Cinnarizine

20. Dimitronal

21. L-tartrate, Cinnarizine

22. R 516

23. R-516

24. R516

25. Stugeron

26. Stugeron Forte

27. Von Ct, Cinnarizin

2.3.2 Depositor-Supplied Synonyms

1. 298-57-7

2. Stugeron

3. Stutgin

4. Cinarizine

5. Dimitronal

6. Stutgeron

7. Dimitron

8. Folcodal

9. Labyrin

10. Midronal

11. Mitronal

12. Glanil

13. Sepan

14. Cinazyn

15. Aplactan

16. Cinnageron

17. Lazeta

18. Marisan

19. Toliman

20. Cinaperazine

21. Cinnipirine

22. Cerepar

23. Cinnarizinum

24. Cerebolan

25. Cinarizina

26. Cinnacet

27. Corathiem

28. Giganten

29. Hilactan

30. Katoseran

31. Processine

32. Sedatromin

33. Siptazin

34. Spaderizine

35. Aplexal

36. Artate

37. Carecin

38. Denapol

39. Ixertol

40. Olamin

41. Eglen

42. 1-benzhydryl-4-cinnamylpiperazine

43. 16699-20-0

44. R 516

45. 1-cinnamyl-4-(diphenylmethyl)piperazine

46. R 1575

47. 516 Md

48. Piperazine, 1-(diphenylmethyl)-4-(3-phenyl-2-propenyl)-

49. 1-benzhydryl-4-cinnamylpiperazin

50. 1-benzhydryl-4-[(e)-3-phenylprop-2-enyl]piperazine

51. Stunarone

52. 1-(diphenylmethyl)-4-[(2e)-3-phenylprop-2-en-1-yl]piperazine

53. (e)-1-benzhydryl-4-cinnamylpiperazine

54. 1-(diphenylmethyl)-4-(3-phenyl-2-propenyl)piperazine

55. R-516

56. 1-trans-cinnamyl-4-diphenylmethylpiperazine

57. 1-benzhydryl-4-[(e)-cinnamyl]piperazine

58. Chembl43064

59. Mls000028498

60. 3di2e1x18l

61. Piperazine, 1-cinnamyl-4-(diphenylmethyl)-

62. Chebi:31403

63. R-1575

64. 516-md

65. Nsc-758400

66. 1-(diphenylmethyl)-4-(3-phenyl-2-propen-1-yl)piperazine

67. Libotasin

68. Senoger

69. Smr000058307

70. Votegol

71. Zepamol

72. Cero-aterin

73. Dsstox_cid_2821

74. Dsstox_rid_76744

75. Dsstox_gsid_22821

76. Cinarizina [inn-spanish]

77. Cinnarizinum [inn-latin]

78. Apotomin

79. Stonoron

80. Cinnarizine [usan:inn:ban:jan]

81. Sr-01000003093

82. Einecs 206-064-8

83. Md 516

84. Brn 0626121

85. Unii-3di2e1x18l

86. Cinnarizine (jan/usan/inn)

87. 1-cinnamyl-4-diphenylmethylpiperazine

88. N-benzhydryl-n'-cinnamylpiperazine

89. Ncgc00015246-02

90. 1185242-27-6

91. Cas-298-57-7

92. Cinnarizine, Powder

93. Prestwick_115

94. Mfcd00056037

95. Piperazine, (e)-

96. Cinnarizine [mi]

97. Opera_id_1776

98. Prestwick2_000278

99. Prestwick3_000278

100. Cinnarizine [inn]

101. Cinnarizine [jan]

102. 1-(diphenylmethyl)-4-(3-phenylprop-2-enyl)piperazine

103. Cinnarizine [usan]

104. C 5270

105. Cinnarizine [mart.]

106. Lopac0_000314

107. Schembl44957

108. Schembl44958

109. Bspbio_000156

110. Cinnarizine [who-dd]

111. Mls001148649

112. Mls002207295

113. Mls002222167

114. Bpbio1_000172

115. Gtpl9072

116. 1-(diphenylmethyl)-4-(3-phenyl-2-propenyl)-piperazine

117. Cid_1547484

118. Cinnarizine [ep Impurity]

119. Dtxsid80859311

120. Chebi:131176

121. 4-((2e)-3-phenylprop-2-enyl)-1-(diphenylmethyl)piperazine

122. Cinnarizine [ep Monograph]

123. Hms1568h18

124. Hms2095h18

125. Hms2234b20

126. Hms3260p10

127. Hms3712h18

128. Hms3885f20

129. Component Of Emesazine (salt/mix)

130. Hy-b1090

131. Tox21_110109

132. Tox21_500314

133. Bdbm50017657

134. Nsc290687

135. Nsc771642

136. Stk216257

137. Zinc19632891

138. Akos002134299

139. Stugeron

140. Dimitronal

141. Stutgin

142. Cinarizine

143. Tox21_110109_1

144. Ccg-204409

145. Cs-4656

146. Ks-5155

147. Lp00314

148. Nsc 758400

149. Nsc-290687

150. Nsc-771642

151. Sdccgsbi-0050302.p002

152. Qtl1_000023

153. Ncgc00018187-03

154. Ncgc00018187-04

155. Ncgc00018187-05

156. Ncgc00018187-06

157. Ncgc00018187-07

158. Ncgc00018187-09

159. Ncgc00018187-14

160. Ncgc00021488-03

161. Ncgc00021488-04

162. Ncgc00021488-05

163. Ncgc00260999-01

164. Bc167081

165. Ls-15144

166. Eu-0100314

167. S4727

168. A16455

169. D01295

170. D89561

171. 298c577

172. A820077

173. L001227

174. Q775073

175. 1-benzhydryl-4-[3-phenyl-2-propenyl]piperazine #

176. Sr-01000003093-2

177. Sr-01000003093-6

178. W-106970

179. W-110442

180. 1-benzhydryl-4-[(2e)-3-phenylprop-2-enyl]piperazine

181. Brd-k07220430-001-03-6

182. Brd-k74927006-001-01-2

183. 1-[di(phenyl)methyl]-4-(3-phenylprop-2-enyl)piperazine

184. 1-(diphenylmethyl)-4-(3-phenylprop-2-en-1-yl)piperazine

185. Cinnarizine, European Pharmacopoeia (ep) Reference Standard

186. Piperazine, 1-(diphenylmethyl)-4-(3-phenyl-2-propen-1-yl)-

187. N90

2.4 Create Date

2005-03-25

3 Chemical and Physical Properties

Molecular Formula	C₂₆H₂₈N₂
Molecular Weight	368.5 g/mol
XLogP3	5.8
Hydrogen Bond Donor Count	0
Hydrogen Bond Acceptor Count	2
Rotatable Bond Count	6
Exact Mass	368.225248902 g/mol
Monoisotopic Mass	368.225248902 g/mol
Topological Polar Surface Area	6.5 Å²
Heavy Atom Count	28
Formal Charge	0
Complexity	429
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	1
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Pharmacology and Biochemistry

4.1 MeSH Pharmacological Classification

Calcium Channel Blockers

A class of drugs that act by selective inhibition of calcium influx through cellular membranes. (See all compounds classified as Calcium Channel Blockers.)

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.)

4.2 ATC Code

N - Nervous system

N07 - Other nervous system drugs

N07C - Antivertigo preparations

N07CA - Antivertigo preparations

N07CA02 - Cinnarizine

4.3 Metabolism/Metabolites

Cinnarizine has known human metabolites that include 1-Benzhydrylpiperazine, 1-Cinnamylpiperazine, 4-{3-[4-(diphenylmethyl)piperazin-1-yl]prop-1-en-1-yl}phenol, 4-{phenyl[4-(3-phenylprop-2-en-1-yl)piperazin-1-yl]methyl}phenol, Benzophenone, and Cinnamaldehyde.

S73 | METXBIODB | Metabolite Reaction Database from BioTransformer | DOI:10.5281/zenodo.4056560

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