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Chemistry

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Also known as: 15676-16-1, Sulpyrid, Sulpirid, Aiglonyl, Dolmatil, Dogmatil
Molecular Formula
C15H23N3O4S
Molecular Weight
341.4  g/mol
InChI Key
BGRJTUBHPOOWDU-UHFFFAOYSA-N
FDA UNII
7MNE9M8287

Sulpiride
A dopamine D2-receptor antagonist. It has been used therapeutically as an antidepressant, antipsychotic, and as a digestive aid. (From Merck Index, 11th ed)
1 2D Structure

Sulpiride

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
N-[(1-ethylpyrrolidin-2-yl)methyl]-2-methoxy-5-sulfamoylbenzamide
2.1.2 InChI
InChI=1S/C15H23N3O4S/c1-3-18-8-4-5-11(18)10-17-15(19)13-9-12(23(16,20)21)6-7-14(13)22-2/h6-7,9,11H,3-5,8,10H2,1-2H3,(H,17,19)(H2,16,20,21)
2.1.3 InChI Key
BGRJTUBHPOOWDU-UHFFFAOYSA-N
2.1.4 Canonical SMILES
CCN1CCCC1CNC(=O)C2=C(C=CC(=C2)S(=O)(=O)N)OC
2.2 Other Identifiers
2.2.1 UNII
7MNE9M8287
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Aiglonyl

2. Arminol

3. Deponerton

4. Desisulpid

5. Digton

6. Dogmatil

7. Dolmatil

8. Eglonyl

9. Ekilid

10. Guastil

11. Lebopride

12. Meresa

13. Neogama

14. Pontiride

15. Psicocen

16. Sulp

17. Sulperide

18. Sulpitil

19. Sulpivert

20. Sulpor

21. Syndil

22. Tepavil

23. Vertigo Meresa

24. Vertigo Neogama

25. Vertigo-meresa

26. Vertigo-neogama

2.3.2 Depositor-Supplied Synonyms

1. 15676-16-1

2. Sulpyrid

3. Sulpirid

4. Aiglonyl

5. Dolmatil

6. Dogmatil

7. (+/-)-sulpiride

8. Guastil

9. Dobren

10. (rs)-(+/-)-sulpiride

11. Dogmatyl

12. Mirbanil

13. Misulvan

14. Sursumid

15. Abilit

16. Meresa

17. Miradol

18. Neogama

19. Omperan

20. Splotin

21. Coolspan

22. Sernevin

23. Eglonyl

24. Pyrkappl

25. Sulpitil

26. N-[(1-ethylpyrrolidin-2-yl)methyl]-2-methoxy-5-sulfamoylbenzamide

27. Synedil

28. Sulpiridum [inn-latin]

29. Sulpirida [inn-spanish]

30. Pyrikappl

31. Sulpirida

32. Sulpiridum

33. Sulpor

34. Dl-sulpiride

35. Rd 1403

36. N-((1-ethyl-2-pyrrolidinyl)methyl)-5-sulfamoyl-o-anisamide

37. 5-(aminosulfonyl)-n-((1-ethyl-2-pyrrolidinyl)methyl)-2-methoxybenzamide

38. (+-)-sulpiride

39. N-((1-ethyl-2-pyrrolidinyl)methyl)-2-methoxy-5-sulfamoylbenzamide

40. R.d. 1403

41. N05al01

42. Chembl26

43. Psicocen

44. Benzamide, 5-(aminosulfonyl)-n-((1-ethyl-2-pyrrolidinyl)methyl)-2-methoxy-

45. C15h23n3o4s

46. Calmoflorine

47. Championyl

48. Lisopiride

49. Stamonevrol

50. Alimoral

51. Darleton

52. Desmenat

53. Dresent

54. Eglonil

55. Equilid

56. Eusulpid

57. Fardalan

58. Fidelan

59. Isnamide

60. Kylistro

61. Mariastel

62. Norestran

63. Nufarol

64. Ozoderpin

65. Restful

66. Suprium

67. Valirem

68. Zemorcon

69. Chebi:32168

70. Enimon

71. Normum

72. O-anisamide, N-((1-ethyl-2-pyrrolidinyl)methyl)-5-sulfamoyl-

73. Omiryl

74. Levosulpiridum [inn-latin]

75. 7mne9m8287

76. N-[(1-ethylpyrrolidin-2-yl)methyl]-2-methoxy-5-sulfamoyl-benzamide

77. Levosulpirida [inn-spanish]

78. Benzamide, 5-(aminosulfonyl)-n-[(1-ethyl-2-pyrrolidinyl)methyl]-2-methoxy-

79. Nsc-757850

80. Rd-1403

81. N-((1-ethylpyrrolidin-2-yl)methyl)-2-methoxy-5-sulfamoylbenzamide

82. Sulpiride-r

83. (+)-n-[(1-ethylpyrrolidin-2-yl)methyl]-2-methoxy-5-sulfamoyl-benzamide

84. Smr000038923

85. Ccris 4248

86. Sulpiride,(+)

87. Sulpiride [usan:inn:ban:jan]

88. Sr-01000075402

89. Einecs 239-753-7

90. Brn 0494008

91. Unii-7mne9m8287

92. (s)-n-((1-ethylpyrrolidin-2-yl)methyl)-2-methoxy-5-sulfamoylbenzamide

93. (y)-sulpiride

94. Sulpiride, Slp

95. (plusmn)-sulpiride

96. Dogmatyl (tn)

97. Magnetic Resonance Imaging Sulpiride

98. (?)-sulpiride

99. Prestwick_431

100. Cas-15676-16-1

101. Mfcd00055061

102. Sulpiride [inn]

103. Sulpiride [jan]

104. Sulpiride [mi]

105. Sulpiride [usan]

106. (.+/-.)-sulpiride

107. Prestwick0_000056

108. Prestwick1_000056

109. Prestwick2_000056

110. Prestwick3_000056

111. Sulpiride,(-)

112. Biomol-nt_000037

113. Biomol-nt_000162

114. Sulpiride [mart.]

115. Schembl8421

116. Sulpiride [who-dd]

117. Dsstox_cid_22574

118. Dsstox_rid_80050

119. Dsstox_gsid_42574

120. Lopac0_001050

121. Oprea1_602476

122. Bspbio_000211

123. 5-22-08-00105 (beilstein Handbook Reference)

124. Mls000069434

125. Mls001306443

126. Divk1c_000278

127. Spbio_002132

128. Bpbio1_000233

129. Bpbio1_000463

130. Bpbio1_001255

131. Ccris-4248

132. Gtpl5501

133. Sulpiride (jp17/usan/inn)

134. Sulpiride [ep Impurity]

135. Dtxsid1042574

136. Sulpiride [ep Monograph]

137. Bdbm11638

138. Hms500n20

139. Kbio1_000278

140. Ninds_000278

141. Sulpiride 1.0 Mg/ml In Methanol

142. Hms1568k13

143. Hms2095k13

144. Hms2231k07

145. Hms3263a22

146. Hms3266p12

147. Hms3371p16

148. Hms3372o01

149. Hms3393a08

150. Hms3411d18

151. Hms3651g12

152. Hms3675d18

153. Hms3712k13

154. Hms3885j14

155. Bcp04500

156. Bcp13871

157. Hy-b1019

158. Str09321

159. ( Inverted Question Mark)-sulpiride

160. Tox21_302205

161. Tox21_501050

162. S4655

163. Stk368596

164. Sulpiride 100 Microg/ml In Methanol

165. 5-(aminosufonyl)-n-[(1-ethyl-2-pyrrolidinyl)methyl]-2-methoxybenzamide

166. Akos004912732

167. Ccg-205127

168. Cs-4534

169. Db00391

170. Lp01050

171. Nsc 757850

172. Sdccgsbi-0051020.p002

173. Idi1_000278

174. Ncgc00015966-03

175. Ncgc00015966-04

176. Ncgc00015966-05

177. Ncgc00015966-06

178. Ncgc00015966-07

179. Ncgc00015966-08

180. Ncgc00015966-16

181. Ncgc00024852-02

182. Ncgc00024852-03

183. Ncgc00024852-04

184. Ncgc00024852-05

185. Ncgc00255813-01

186. Ncgc00261735-01

187. Ac-12181

188. Db-046215

189. Eu-0001755

190. Eu-0101050

191. Ft-0630504

192. Ft-0652244

193. Ft-0674703

194. R. D. 1403

195. D01226

196. S 8010

197. 676s161

198. A809768

199. L000579

200. Q422418

201. Sr-01000075402-2

202. Sr-01000075402-3

203. Sr-01000075402-6

204. Brd-a55272860-001-03-9

205. Brd-a55272860-001-04-7

206. Brd-a55272860-001-08-8

207. Z84655412

208. Sulpiride, British Pharmacopoeia (bp) Reference Standard

209. 1-ethyl-2-(2-methoxy-5-sulfamoylbenzamidomethyl)pyrrolidine

210. Sulpiride, European Pharmacopoeia (ep) Reference Standard

211. N-(1-ethyl-pyrrolidin-2-ylmethyl)-2-methoxy-5-sulfamoyl-benzamide

212. (+/-)-n-[(1-ethylpyrrolidin-2-yl)methyl]-2-methoxy-5-sulfamoylbenzamide

213. (2r)-1-ethyl-2-((2-methoxy-5-sulfamoylbenzamido)methyl)pyrrolidin-1-ium

214. Benzamide,5-(aminosulfonyl)-n-[(1-ethyl-2-pyrrolidinyl)methyl]-2-methoxy-

215. N-(1-ethyl-2-pyrrolidinylmethyl)-2-methoxy-5-sulfamidobenzamide

216. (rs)-(+/-)-5-aminosulfonyl-n-[(1-ethyl -2-pyrrolidinyl)methyl]-2-methoxybenzamide

217. (rs)-(+/-)-5-aminosulfonyl-n-[(1-ethyl-2-pyrrolidinyl)methyl]-2-methoxybenzamide

218. ( Inverted Question Mark)-5-(aminosulfonyl)-n-[(1-ethyl-2-pyrrolidinyl)methyl]-2-methoxybenzamide

2.4 Create Date
2005-03-25
3 Chemical and Physical Properties
Molecular Weight 341.4 g/mol
Molecular Formula C15H23N3O4S
XLogP30.6
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count6
Rotatable Bond Count6
Exact Mass341.14092740 g/mol
Monoisotopic Mass341.14092740 g/mol
Topological Polar Surface Area110 Ų
Heavy Atom Count23
Formal Charge0
Complexity505
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 Indication

Sulpiride is indicated for the treatment of acute and chronic schizophrenia.


5 Pharmacology and Biochemistry
5.1 Pharmacology

Sulpiride is a substituted benzamide derivative and a selective dopamine D2 antagonist indicated to treat acute and chronic schizophrenia. It has a short duration of action as it is given twice daily, and a wide therapeutic window as patients have survived single doses as high as 16g. Patients should be counselled regarding increased motor agitation, extrapyramidal reactions, and neuroleptic malignant syndrome.


5.2 MeSH Pharmacological Classification

Antipsychotic Agents

Agents that control agitated psychotic behavior, alleviate acute psychotic states, reduce psychotic symptoms, and exert a quieting effect. They are used in SCHIZOPHRENIA; senile dementia; transient psychosis following surgery; or MYOCARDIAL INFARCTION; etc. These drugs are often referred to as neuroleptics alluding to the tendency to produce neurological side effects, but not all antipsychotics are likely to produce such effects. Many of these drugs may also be effective against nausea, emesis, and pruritus. (See all compounds classified as Antipsychotic Agents.)


Antidepressive Agents, Second-Generation

A structurally and mechanistically diverse group of drugs that are not tricyclics or monoamine oxidase inhibitors. The most clinically important appear to act selectively on serotonergic systems, especially by inhibiting serotonin reuptake. (See all compounds classified as Antidepressive Agents, Second-Generation.)


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

N05AL01

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


N - Nervous system

N05 - Psycholeptics

N05A - Antipsychotics

N05AL - Benzamides

N05AL01 - Sulpiride


5.4 Absorption, Distribution and Excretion

Absorption

Sulpiride has an oral bioavailability of 27 9%. A 100-108 mg dose of sulpiride reaches a Cmax of 232-403 ng/mL, with a Tmax of 8.3 h. In another study, the AUC of a 100mg oral dose of sulpiride is 1156 522 h\*ng/mL and for an intravenous dose is 3981 813 h\*ng/mL.


Route of Elimination

An intravenous dose of sulpiride is 70 9% eliminated in the urine within 36 hours, while an oral dose is 27 9% eliminated in urine. In both cases, the dose is recovered as the unchanged parent compound.


Volume of Distribution

The average volume of distribution of sulpiride is 2.72 0.66 L/kg.


Clearance

The total systemic clearance of sulpiride if 415 84 mL/min, while the mean renal clearance was 310 91 mL/min.


5.5 Metabolism/Metabolites

95% of a dose of sulpiride is not metabolized.


5.6 Biological Half-Life

Reports of the half life of sulpiride have only been performed with small numbers of subjects. Therefore, the average half life may be 7.15 hours to 8.3 hours.


5.7 Mechanism of Action

Sulpiride is a selective dopamine D2 and D3 receptor antagonist. _In silico_ studies show that sulpiride may interact with the Asp-119 and Phe-417 amino acid residues of these receptors. It is estimated that D2 receptors should be 65-80% occupied for optimal treatment and minimal adverse effects.


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05-Jan-2021
28-Aug-2024
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