4-(4-{2-[(1S)-3,4-dihydro-1H-2-benzopyran-1-yl]ethyl}piperazin-1-yl)benzene-1-sulfonamide

• ChemBase ID: 129581
• Molecular Formular: C21H27N3O3S
• Molecular Mass: 401.52238
• Monoisotopic Mass: 401.17731274
• SMILES: O=S(=O)(N)c1ccc(cc1)N1CCN(CC1)CC[C@@H]1OCCc2ccccc12
• Canonical SMILES: NS(=O)(=O)c1ccc(cc1)N1CCN(CC1)CC[C@@H]1OCCc2c1cccc2
• InChI: InChI=1S/C21H27N3O3S/c22-28(25,26)19-7-5-18(6-8-19)24-14-12-23(13-15-24)11-9-21-20-4-2-1-3-17(20)10-16-27-21/h1-8,21H,9-16H2,(H2,22,25,26)/t21-/m0/s1
• InChIKey: WNUQCGWXPNGORO-NRFANRHFSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-(4-{2-[(1S)-3,4-dihydro-1H-2-benzopyran-1-yl]ethyl}piperazin-1-yl)benzene-1-sulfonamide
• IUPAC Traditional name: sonepiprazole
• Synonyms: Sonepiprazole; 4-[4-[2-[(1S)-Isochroman-1-yl]ethyl]piperazin-1-yl]benzenesulfonamide hydrate; PNU-101387; PNU-101387G; U-101387; Sonepiprazole hydrate; 4-[4-[2-[(1S)-3,4-Dihydro-1H-2-benzopyran-1-yl]ethyl]-1-piperazinyl]benzenesulfonamide; PNU 101387; U 101387; (S)-4-[4-[2-(3,4-Dihydro-1H-2-benzopyran-1-yl)ethyl]-1-piperazinyl]benzenesulfonamide; PF-05191680

Database IDs

• CAS Number: 170858-33-0(anhydrous); 170858-33-0; 170858-34-1
• MDL Number: MFCD05662325
• PubChem SID: 162223871
• PubChem CID: 133079
• Chemspider ID: 117441
• Unique Ingredient Identifier: O609V24217
• Wikipedia Title: Sonepiprazole

CALCULATED PROPERTIES

• Acid pKa: 10.941245
• H Acceptors: 5
• H Donor: 1
• LogD (pH = 5.5): -0.30580232
• LogD (pH = 7.4): 1.467651
• Log P: 2.371553
• Molar Refractivity: 112.1959 cm^3
• Polarizability: 43.584248 Å^3
• Polar Surface Area: 75.87 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; DMSO: >10 mg/mL
• Apperance: Off-White Solid; white to off-white powder
• Melting Point: 183-185°C

Safety Information

• Storage Condition: desiccated; Refrigerator
• German water hazard class: 3
• Storage Temperature: room temp

Pharmacology Properties

• Admin Routes: Oral
• Legal Status: Uncontrolled

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C21H27N3O3S · xH2O

DETAILS

Sigma Aldrich - PZ0174

Legal Information
Sold for research purposes under agreement from Pfizer Inc.
Biochem/physiol Actions
Sonepiprazole (U-101387) is a selective D4 dopamine antagonist. Ki = 10 nM for the dopamine D4.2 receptor.

Toronto Research Chemicals - S676800

A selective D4 dopamine antagonist that exhibits low affinity at other monoamine receptors (Ki > 2000 nM). Induces c-fos gene expression in medial prefrontal cortex in a similar manner to Clozapine (C587500).

REFERENCES

• Merchant, K.M. et al.: J. Pharm. Exp. Ther., 279, 1392 (1996)
• Rubinstein, M. et al.: J. Neurosci., 21, 3756 (1996)
• Marona-Lewicka, D. et al.: Behav. Pharmacol., 20, 114 (1996)