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

• ChemBase ID: 129667
• Molecular Formular: C17H26N2O4S
• Molecular Mass: 354.46434
• Monoisotopic Mass: 354.16132832
• SMILES: O=S(=O)(c1cc(c(OC)cc1)C(=O)NCC1N(CC)CCC1)CC
• Canonical SMILES: CCN1CCCC1CNC(=O)c1cc(ccc1OC)S(=O)(=O)CC
• 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)
• InChIKey: UNRHXEPDKXPRTM-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5-(ethanesulfonyl)-N-[(1-ethylpyrrolidin-2-yl)methyl]-2-methoxybenzamide
• IUPAC Traditional name: sultopride
• Synonyms: Sultopride; N-[(1-Ethyl-2-pyrrolidinyl)methyl]-5-(ethylsulfonyl)-2-methoxybenzamide Monohydrochloride; (+/-)-Sultopride Hydrochloride; Barnetil Hydrochloride; Barnotil Hydrochloride; LIN 1418 Hydrochloride; Sultopride Hydrochloride

Database IDs

• CAS Number: 23694-17-9; 53583-79-2
• PubChem SID: 162223956
• PubChem CID: 5357
• ATC CODE: N05AL02
• CHEMBL: 277945
• Chemspider ID: 5164
• KEGG ID: D08549
• Unique Ingredient Identifier: AA0G3TW31W
• Wikipedia Title: Sultopride

CALCULATED PROPERTIES

• Acid pKa: 13.224751
• H Acceptors: 5
• H Donor: 1
• LogD (pH = 5.5): -0.4231061
• LogD (pH = 7.4): 0.9364668
• Log P: 1.0802137
• Molar Refractivity: 95.1444 cm^3
• Polarizability: 37.211655 Å^3
• Polar Surface Area: 75.71 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Acetonitrile; Methanol; Water
• Apperance: White Solid
• Melting Point: 183-185°C

Safety Information

• Storage Condition: Refrigerator

Pharmacology Properties

• Admin Routes: Oral, IM
• Half Life: 3–5 hours
• Legal Status: Rx-only

DETAILS

Toronto Research Chemicals - S790510

Dopamine D2-receptor antagonist. An antipsychotic.

REFERENCES

• Lavelle, C., et al.: J. Pharmacol., 5, 58 (1974)
• Morel, D., et al.: Sem. Hop., 59, 2337 (1974)
• Kamizono, A., et al.: Biol. Pharm. Bull., 16, 1121 (1974)