N-{[(2S)-1-ethylpyrrolidin-2-yl]methyl}-2-(2H3)methoxy-5-sulfamoylbenzamide

• ChemBase ID: 177921
• Molecular Formular: C15H23N3O4S
• Molecular Mass: 341.42582
• Monoisotopic Mass: 341.14092723
• SMILES: C1CC[C@H](N1CC)CNC(=O)c1c(ccc(c1)S(=O)(=O)N)OC
• Canonical SMILES: CCN1CCC[C@H]1CNC(=O)c1cc(ccc1OC)S(=O)(=O)N
• 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)/t11-/m0/s1
• InChIKey: BGRJTUBHPOOWDU-NSHDSACASA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-{[(2S)-1-ethylpyrrolidin-2-yl]methyl}-2-(^2H₃)methoxy-5-sulfamoylbenzamide
• IUPAC Traditional name: N-{[(2S)-1-ethylpyrrolidin-2-yl]methyl}-2-(^2H₃)methoxy-5-sulfamoylbenzamide
• Synonyms: 5-(Aminosulfonyl)-N-[[(2S)-1-ethyl-2-pyrrolidinyl]methyl]-2-(methoxy-d3)benzamide; (-)-N-[(1-Ethyl-2-pyrrolidinyl)methyl]-5-sulfamoyl-o-anisamide-d3; (-)-Sulpiride-d3; L-Sulpiride-d3; Levobren-d3; Levopraid-d3; Levosulpiride-d3; S-(-)-Sulpiride-d3; S-Sulpiride-d3; Levopride-d3; Sulpid-d3; S-(-)-Sulpiride-d3

Database IDs

• CAS Number: 124020-27-5
• PubChem SID: 164233831
• PubChem CID: 12905175

CALCULATED PROPERTIES

• Acid pKa: 10.239752
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): -2.4638896
• LogD (pH = 7.4): -0.7005867
• Log P: 0.21877044
• Molar Refractivity: 88.6331 cm^3
• Polarizability: 34.69616 Å^3
• Polar Surface Area: 101.73 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - S689142

Labelled S-(-)-Sulpiride (S689140). Dopamine D2 and D3-receptor antagonist. Antipsychotic; antidepressant; antiemetic.

REFERENCES

• Pitre, D., et al.: Anal. Profiles Drug Subs., 17, 607 (1988)
• Wagstaff, A.J., et al.: CNS Drugs, 2, 313 (1988)