N-{2-[4-(5-chloro-2-oxo-2,3-dihydro-1H-1,3-benzodiazol-1-yl)piperidin-1-yl]ethyl}-4-fluorobenzamide

• ChemBase ID: 155576
• Molecular Formular: C21H22ClFN4O2
• Molecular Mass: 416.8763832
• Monoisotopic Mass: 416.14153186
• SMILES: c1cc(ccc1C(=O)NCCN1CCC(CC1)n1c2ccc(cc2[nH]c1=O)Cl)F
• Canonical SMILES: Fc1ccc(cc1)C(=O)NCCN1CCC(CC1)n1c(=O)[nH]c2c1ccc(c2)Cl
• InChI: InChI=1S/C21H22ClFN4O2/c22-15-3-6-19-18(13-15)25-21(29)27(19)17-7-10-26(11-8-17)12-9-24-20(28)14-1-4-16(23)5-2-14/h1-6,13,17H,7-12H2,(H,24,28)(H,25,29)
• InChIKey: NBHPRWLFLUBAIE-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-{2-[4-(5-chloro-2-oxo-2,3-dihydro-1H-1,3-benzodiazol-1-yl)piperidin-1-yl]ethyl}-4-fluorobenzamide
• IUPAC Traditional name: halopemide
• Synonyms: N-(2-(4-(5-Chloro-2-oxo-1-benzimidazolinyl)piperidino)ethyl)-p-fluorobenzamide; Halopemide

Database IDs

• CAS Number: 59831-65-1
• MDL Number: MFCD00866684
• PubChem SID: 162249714
• PubChem CID: 65490

CALCULATED PROPERTIES

• Acid pKa: 12.747263
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 1.5195162
• LogD (pH = 7.4): 2.7422905
• Log P: 2.8399987
• Molar Refractivity: 111.6471 cm^3
• Polarizability: 41.45886 Å^3
• Polar Surface Area: 64.68 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO: >10 mg/mL
• Apperance: off-white powder

Safety Information

• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C21H22ClFN4O2

DETAILS

Sigma Aldrich - H3041

Biochem/physiol Actions
Halopemide is a dopamine receptor antagonist and a phospholipase D2 inhibitor. Halopemide may be used as a screen to identify inhibitors of human PLD2 using an in vitro biochemical assay. It is also inhibitory at benzodiazepine binding sites.1