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Chemistry

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Also known as: 53583-79-2, Barnetil, Topral, Lin 1418, Sultopridum [inn-latin], Lin-1418

Molecular Formula

C₁₇H₂₆N₂O₄S

Molecular Weight

354.5 g/mol

InChI Key

UNRHXEPDKXPRTM-UHFFFAOYSA-N

FDA UNII

AA0G3TW31W

A benzamide derivative that is used as an antipsychotic agent for the treatment of schizophrenia. It is also used as an antidepressive agent.

1 2D Structure

Sultopride

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

N-[(1-ethylpyrrolidin-2-yl)methyl]-5-ethylsulfonyl-2-methoxybenzamide

2.1.2 InChI

InChI=1S/C17H26N2O4S/c1-4-19-10-6-7-13(19)12-18-17(20)15-11-14(24(21,22)5-2)8-9-16(15)23-3/h8-9,11,13H,4-7,10,12H2,1-3H3,(H,18,20)

2.1.3 InChI Key

UNRHXEPDKXPRTM-UHFFFAOYSA-N

2.1.4 Canonical SMILES

CCN1CCCC1CNC(=O)C2=C(C=CC(=C2)S(=O)(=O)CC)OC

2.2 Other Identifiers

2.2.1 UNII

AA0G3TW31W

2.3 Synonyms

2.3.1 MeSH Synonyms

1. 4-amino-n-((1-ethyl-2-pyrrolidinyl)methyl)-5-(ethylsulfonyl)-2-methoxybenzamide

2. Amisulpride

3. Barnetil

4. Dan 2163

5. Dan-2163

6. Lin 1418

7. Lin-1418

8. N-(ethyl-1-pyrrolidinyl- 2-methyl)methoxy-2-ethylsulfonyl-5-benzamide

9. Solian

10. Sultopride Hydrochloride

2.3.2 Depositor-Supplied Synonyms

1. 53583-79-2

2. Barnetil

3. Topral

4. Lin 1418

5. Sultopridum [inn-latin]

6. Lin-1418

7. Aa0g3tw31w

8. Chebi:9356

9. N-((1-ethyl-2-pyrrolidinyl)methyl)-5-(ethylsulfonyl)-o-anisamide

10. Sultopride (inn)

11. Barnotil

12. Benzamide, N-((1-ethyl-2-pyrrolidinyl)methyl)-5-(ethylsulfonyl)-2-methoxy-

13. Sultopride [inn]

14. Sultopridum

15. Sultroprida

16. Sultopride [inn:dcf]

17. N-((1-ethylpyrrolidin-2-yl)methyl)-5-(ethylsulfonyl)-2-methoxybenzamide

18. N-[(1-ethylpyrrolidin-2-yl)methyl]-5-ethylsulfonyl-2-methoxy-benzamide

19. Sultroprida [inn-spanish]

20. (+/-)-sultopride

21. Ncgc00185771-01

22. Einecs 258-641-9

23. Unii-aa0g3tw31w

24. Brn 0494772

25. Sultopride [mi]

26. Sultopride [who-dd]

27. 5-22-08-00103 (beilstein Handbook Reference)

28. Schembl149197

29. Chembl277945

30. Dtxsid9023627

31. Bdbm86720

32. Nsc_5357

33. N-[(1-ethylpyrrolidin-2-yl)methyl]-5-ethylsulfonyl-2-methoxybenzamide

34. Pdsp1_001575

35. Pdsp2_001559

36. Akos024255726

37. O-anisamide, N-((1-ethyl-2-pyrrolidinyl)methyl)-5-(ethylsulfonyl)-

38. Db13273

39. Ks-5337

40. Hy-42849

41. Cas_53583-79-2

42. Db-071706

43. Cs-0040602

44. Ft-0725190

45. D08549

46. L001065

47. Q4445779

48. (+/-)-n-((1-ethyl-2-pyrrolidinyl)methyl)-5-(ethylsulfonyl)-2-methoxybenzamide

49. N-((1-ethyl-2-pyrrolidinyl)methyl)-5-(ethylsulfonyl)-2-methoxybenzamide

50. N-[(1-ethylpyrrolidin-2-yl)methyl]-5-(ethylsulfonyl)-2-(methyloxy)benzamide

2.4 Create Date

2005-03-25

3 Chemical and Physical Properties

Molecular Formula	C₁₇H₂₆N₂O₄S
Molecular Weight	354.5 g/mol
XLogP3	1.6
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	5
Rotatable Bond Count	7
Exact Mass	354.16132849 g/mol
Monoisotopic Mass	354.16132849 g/mol
Topological Polar Surface Area	84.1 Å²
Heavy Atom Count	24
Formal Charge	0
Complexity	517
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	1

4 Pharmacology and Biochemistry

4.1 MeSH Pharmacological Classification

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.)

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.)

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.)

4.2 ATC Code

N - Nervous system

N05 - Psycholeptics

N05A - Antipsychotics

N05AL - Benzamides

N05AL02 - Sultopride

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