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Prestwick3_000461

Prestwick3_000461

Synopsis, Chemistry

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Also known as: 57808-66-9, Motilium, Nauzelin, Domperidonum, Domperidona, C22h24cln5o2

Molecular Formula

C₂₂H₂₄ClN₅O₂

Molecular Weight

425.9 g/mol

InChI Key

FGXWKSZFVQUSTL-UHFFFAOYSA-N

FDA UNII

5587267Z69

A specific blocker of dopamine receptors. It speeds gastrointestinal peristalsis, causes prolactin release, and is used as antiemetic and tool in the study of dopaminergic mechanisms.

1 2D Structure

Prestwick3_000461

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

6-chloro-3-[1-[3-(2-oxo-3H-benzimidazol-1-yl)propyl]piperidin-4-yl]-1H-benzimidazol-2-one

2.1.2 InChI

InChI=1S/C22H24ClN5O2/c23-15-6-7-20-18(14-15)25-22(30)28(20)16-8-12-26(13-9-16)10-3-11-27-19-5-2-1-4-17(19)24-21(27)29/h1-2,4-7,14,16H,3,8-13H2,(H,24,29)(H,25,30)

2.1.3 InChI Key

FGXWKSZFVQUSTL-UHFFFAOYSA-N

2.1.4 Canonical SMILES

C1CN(CCC1N2C3=C(C=C(C=C3)Cl)NC2=O)CCCN4C5=CC=CC=C5NC4=O

2.2 Other Identifiers

2.2.1 UNII

5587267Z69

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Apo Domperidone

2. Apo-domperidone

3. Domidon

4. Domperidon

5. Domperidon Al

6. Domperidon Hexal

7. Domperidon Stada

8. Domperidon Teva

9. Domperidon-teva

10. Domperidona Gamir

11. Domperidone Maleate

12. Domperidone Maleate (1:1)

13. Domperidone Monohydrochloride

14. Gamir, Domperidona

15. Gastrocure

16. Hexal, Domperidon

17. Maleate, Domperidone

18. Monohydrochloride, Domperidone

19. Motilium

20. Nauzelin

21. Novo Domperidone

22. Novo-domperidone

23. Nu Domperidone

24. Nu-domperidone

25. Pridys

26. Pms Domperidone

27. Pms-domperidone

28. R-33,812

29. R-33812

30. R33,812

31. R33812

32. Ratio Domperidone

33. Ratio-domperidone

34. Stada, Domperidon

2.3.2 Depositor-Supplied Synonyms

1. 57808-66-9

2. Motilium

3. Nauzelin

4. Domperidonum

5. Domperidona

6. C22h24cln5o2

7. R-33812

8. R 33,812

9. 4-(5-chloro-2-oxo-1-benzimidazolinyl)-1-[3-(2-oxobenzimidazolinyl)propyl]piperidine

10. Nsc299589

11. Nsc-299589

12. 5-chloro-1-(1-(3-(2-oxo-1-benzimidazolinyl)propyl)-4-piperidyl)-2-benzimidazolinone

13. Domperidone (motilium)

14. R33812

15. Nsc-759575

16. Kw 5338

17. 6-chloro-3-[1-[3-(2-oxo-3h-benzimidazol-1-yl)propyl]piperidin-4-yl]-1h-benzimidazol-2-one

18. Mls000069343

19. Chembl219916

20. Chebi:31515

21. Nsc 299589

22. 2h-benzimidazol-2-one, 5-chloro-1-(1-(3-(2,3-dihydro-2-oxo-1h-benzimidazol-1-yl)propyl)-4-piperidinyl)-1,3-dihydro-

23. 5-chloro-1-[1-[3-(2,3-dihydro-2-oxo-1h-benzimidazol-1-yl)propyl]-4-piperidinyl]-1,3-dihydro-2h-benzimidazol-2-one

24. 5-chloro-1-{1-[3-(2-oxo-2,3-dihydro-1h-benzimidazol-1-yl)propyl]piperidin-4-yl}-1,3-dihydro-2h-benzimidazol-2-one

25. Motinorm

26. Costi

27. 5-chloro-1-[1-[3-(2-oxo-1-benzimidazolinyl)propyl]-4-piperidyl]-2-benzimidazolinone

28. Dsstox_cid_25116

29. Dsstox_rid_80682

30. Dsstox_gsid_45116

31. 1-(3-(4-(5-chloro-2-oxo-2,3-dihydrobenzo[d]imidazol-1-yl)piperidin-1-yl)propyl)-1h-benzo[d]imidazol-2(3h)-one

32. 5-chloro-1-(1-(3-(2-oxo-2,3-dihydro-1h-benzo[d]imidazol-1-yl)propyl)piperidin-4-yl)-1h-benzo[d]imidazol-2(3h)-one

33. 5-chloro-1-(1-(3-(2-oxo-2,3-dihydrobenzo[d]imidazol-1-yl)propyl)piperidin-4-yl)-1h-benzo[d]imidazol-2(3h)-one

34. 5-chloro-1-{1-[3-(2-oxo-2,3-dihydro-1h-1,3-benzodiazol-1-yl)propyl]piperidin-4-yl}-2,3-dihydro-1h-1,3-benzodiazol-2-one

35. 5-chloro-1-{1-[3-(2-oxo-2,3-dihydro-benzoimidazol-1-yl)-propyl]-piperidin-4-yl}-1,3-dihydro-benzoimidazol-2-one

36. Domperidonum [inn-latin]

37. Domperidona [inn-spanish]

38. 5587267z69

39. Motillium

40. Motilium (tn)

41. Smr000326802

42. Cas-57808-66-9

43. Kw-5338

44. Lopac-d-122

45. Sr-01000003002

46. Einecs 260-968-7

47. Brn 0903774

48. Nauzelin Od

49. Domperidone,(s)

50. 5-chloro-1-{1-[3-(2,3-dihydro-2-oxo-1h-benzimidazol-1-yl)propyl]-4-piperidinyl}-1,3-dihydro-2h-benzimidazol-2-one

51. Domperidone [usan:inn:ban:jan]

52. Prestwick_794

53. Mfcd00069256

54. Nci299589

55. Unii-5587267z69

56. Hs-0067

57. Spectrum_000391

58. Opera_id_616

59. Specplus_000825

60. Domperidone [mi]

61. Prestwick0_000461

62. Prestwick1_000461

63. Prestwick2_000461

64. Prestwick3_000461

65. Spectrum4_000087

66. Domperidone [inn]

67. Domperidone [jan]

68. Domperidone [usan]

69. Biomol-nt_000022

70. Domperidone - Pharma Grade

71. Domperidone [vandf]

72. Ncistruc1_001686

73. Ncistruc2_001819

74. Domperidone [mart.]

75. Lopac0_000427

76. Schembl43729

77. Bspbio_002350

78. Domperidone [who-dd]

79. Gtpl965

80. Kbiogr_000354

81. Kbioss_000871

82. 5-24-02-00402 (beilstein Handbook Reference)

83. Mls000859942

84. Mls001306482

85. Mls002222324

86. Divk1c_006921

87. Spectrum2300212

88. Spbio_002501

89. Bpbio1_000620

90. Bpbio1_001185

91. Domperidone [green Book]

92. Dtxsid1045116

93. Domperidone (jp17/usan/inn)

94. Kbio1_001865

95. Kbio2_000871

96. Kbio2_003439

97. Kbio2_006007

98. Domperidone [ep Monograph]

99. Hms1922n04

100. Hms2089c14

101. Hms2093n22

102. Hms2096c21

103. Hms2230n18

104. Hms3261e16

105. Hms3269o13

106. Hms3370l03

107. Hms3413f15

108. Hms3656m21

109. Hms3677f15

110. Hms3713c21

111. Hms3884n19

112. Pharmakon1600-02300212

113. Bcp28265

114. Domperidone 1.0 Mg/ml In Methanol

115. Hy-b0411

116. Zinc4175569

117. Tox21_110056

118. Tox21_500427

119. Bbl028136

120. Bdbm50241107

121. Ccg-37870

122. Ncgc00014670

123. Nsc759575

124. S2461

125. Stk622843

126. Akos005555858

127. Tox21_110056_1

128. Ac-2037

129. Db01184

130. Domperidone, Powder, >=98% (hplc)

131. Lp00427

132. Nsc 759575

133. Sdccgsbi-0050412.p004

134. Ncgc00014670-01

135. Ncgc00014670-02

136. Ncgc00014670-03

137. Ncgc00014670-04

138. Ncgc00014670-05

139. Ncgc00014670-06

140. Ncgc00014670-07

141. Ncgc00014670-08

142. Ncgc00014670-09

143. Ncgc00014670-10

144. Ncgc00014670-11

145. Ncgc00014670-12

146. Ncgc00014670-13

147. Ncgc00014670-14

148. Ncgc00014670-16

149. Ncgc00014670-17

150. Ncgc00014670-28

151. Ncgc00015306-01

152. Ncgc00021472-02

153. Ncgc00021472-03

154. Ncgc00021472-04

155. Ncgc00021472-05

156. Ncgc00021472-06

157. Ncgc00021472-07

158. Ncgc00021472-08

159. Ncgc00097773-01

160. Ncgc00261112-01

161. 2h-benzimidazol-2-one, 1,3-dihydro-5-chloro-1-(1-(3-(2,3-dihydro-2-oxo-1h-benzimidazol-1-yl)propyl)-4-piperidinyl)-

162. 5-chloro-1-(1-(3-(2-oxo-2,3-dihydro-1h-benzimidazol-1-yl)propyl)-4-piperidinyl)-1,3-dihydro-2h-benzimidazol-2-one

163. 5-chloro-1-(1-(3-(2-oxo-2,3-dihydro-1h-benzo[d]imidazol-1-yl)propyl)piperidin-4-yl)-1,3-dihydro-2h-benzo[d]imidazol-2-one

164. Bd164379

165. Nci60_002512

166. Smr000058969

167. Ab00052423

168. D4125

169. Eu-0100427

170. Ft-0625588

171. Sw196931-3

172. C75710

173. D01745

174. Ab00052423-06

175. Ab00052423-07

176. Ab00052423_08

177. Ab00052423_09

178. 808d669

179. A831618

180. L000230

181. Q424238

182. R 33812

183. Sr-01000003002-2

184. Sr-01000003002-4

185. Sr-01000003002-7

186. W-105440

187. Brd-k38305202-001-02-6

188. Brd-k38305202-001-08-3

189. Domperidone, European Pharmacopoeia (ep) Reference Standard

190. 5-chloro-1-[1-[3-(2-oxo-1-benzimidazolyl)propyl]-4-piperidyl]benzimidazol-2-one

191. 1h-benzimidazol-2-ol, 5-chloro-1-[1-[3-(2-hydroxy-1h-benzimidazol-1-yl)propyl]-4-piperidinyl]-

192. 2h-benzimidazol-2-one,3-dihydro-2-oxo-1h-benzimidazol-1-yl)propyl]-4-piperidinyl]-1,3-dihydro-

193. 5-chloro-1-[1-[3-(2,3-dihydro-2-oxo -1h-benzimidazol-1-yl)propyl]-4-piperidinyl]-1,3-d Ihydro-2h-benzimidazol-2-one

194. 5-chloro-1-{1-[3-(1,3-dihydro-2-oxo-2h-benzimidazol-1-yl)propyl]-4-piperidinyl}-1,3-dihydro-2h-benzimidazol-2-one

195. 5-chloro-1-{1-[3-(2-hydroxy-2,3-dihydro-benzoimidazol-1-yl)-propyl]-piperidin-4-yl}-2,3-dihydro-1h-benzoimidazol-2-ol

196. 5-chloro-1-{1-[3-(2-oxo-2,3-dihydro-benzoimidazol-1-yl)-propyl]-piperidin-4-yl}-1,3-dihydro-benzoimidazol-2-one(domperidone)

197. 6-chloro-3-[1-[3-(2-oxo-3a,7a-dihydro-3h-benzimidazol-1-yl)propyl]-4-piperidyl]-3a,7a-dihydro-1h-benzimidazol-2-one

198. Domperidone5-chloro-1-{1-[3-(2-oxo-2,3-dihydro-benzoimidazol-1-yl)-propyl]-piperidin-4-yl}-1,3-dihydro-benzoimidazol-2-one

2.4 Create Date

2005-03-25

3 Chemical and Physical Properties

Molecular Formula	C₂₂H₂₄ClN₅O₂
Molecular Weight	425.9 g/mol
XLogP3	3.9
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	3
Rotatable Bond Count	5
Exact Mass	425.1618527 g/mol
Monoisotopic Mass	425.1618527 g/mol
Topological Polar Surface Area	67.9 Å²
Heavy Atom Count	30
Formal Charge	0
Complexity	655
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Drug and Medication Information

4.1 Drug Indication

For management of dyspepsia, heartburn, epigastric pain, nausea, and vomiting.

5 Pharmacology and Biochemistry

5.1 Pharmacology

Domperidone is a specific blocker of dopamine receptors. It speeds gastrointestinal peristalsis, causes prolactin release, and is used as antiemetic and tool in the study of dopaminergic mechanisms.

5.2 MeSH Pharmacological Classification

Antiemetics

Drugs used to prevent NAUSEA or VOMITING. (See all compounds classified as Antiemetics.)

Dopamine Antagonists

Drugs that bind to but do not activate DOPAMINE RECEPTORS, thereby blocking the actions of dopamine or exogenous agonists. Many drugs used in the treatment of psychotic disorders (ANTIPSYCHOTIC AGENTS) are dopamine antagonists, although their therapeutic effects may be due to long-term adjustments of the brain rather than to the acute effects of blocking dopamine receptors. Dopamine antagonists have been used for several other clinical purposes including as ANTIEMETICS, in the treatment of Tourette syndrome, and for hiccup. Dopamine receptor blockade is associated with NEUROLEPTIC MALIGNANT SYNDROME. (See all compounds classified as Dopamine Antagonists.)

5.3 ATC Code

A03FA03

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

A - Alimentary tract and metabolism

A03 - Drugs for functional gastrointestinal disorders

A03F - Propulsives

A03FA - Propulsives

A03FA03 - Domperidone

5.4 Metabolism/Metabolites

Domperidone has known human metabolites that include 1-Propyl-1,3-dihydro-2H-benzimidazol-2-one, 3-[3-[4-(5-Chloro-2-oxo-3H-benzimidazol-1-yl)piperidin-1-yl]propyl]-6-hydroxy-1H-benzimidazol-2-one, and 5-Chloro-1-(piperidin-4-yl)-1H-benzo[d]imidazol-2(3H)-one.

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

5.5 Biological Half-Life

7 hours

5.6 Mechanism of Action

Domperidone acts as a gastrointestinal emptying (delayed) adjunct and peristaltic stimulant. The gastroprokinetic properties of domperidone are related to its peripheral dopamine receptor blocking properties. Domperidone facilitates gastric emptying and decreases small bowel transit time by increasing esophageal and gastric peristalsis and by lowering esophageal sphincter pressure. Antiemetic: The antiemetic properties of domperidone are related to its dopamine receptor blocking activity at both the chemoreceptor trigger zone and at the gastric level. It has strong affinities for the D2 and D3 dopamine receptors, which are found in the chemoreceptor trigger zone, located just outside the blood brain barrier, which - among others - regulates nausea and vomiting