1-[2-(carboxymethoxy)ethyl]-4-[(4-chlorophenyl)(phenyl)methyl]piperazin-1-ium-1-olate

• ChemBase ID: 164017
• Molecular Formular: C21H25ClN2O4
• Molecular Mass: 404.8872
• Monoisotopic Mass: 404.15028497
• SMILES: c1c(ccc(c1)C(N1CC[N+](CC1)(CCOCC(=O)O)[O-])c1ccccc1)Cl
• Canonical SMILES: OC(=O)COCC[N+]1([O-])CCN(CC1)C(c1ccc(cc1)Cl)c1ccccc1
• InChI: InChI=1S/C21H25ClN2O4/c22-19-8-6-18(7-9-19)21(17-4-2-1-3-5-17)23-10-12-24(27,13-11-23)14-15-28-16-20(25)26/h1-9,21H,10-16H2,(H,25,26)
• InChIKey: IVDOUUOLLFEMJQ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-[2-(carboxymethoxy)ethyl]-4-[(4-chlorophenyl)(phenyl)methyl]piperazin-1-ium-1-olate
• IUPAC Traditional name: 1-[2-(carboxymethoxy)ethyl]-4-[(4-chlorophenyl)(phenyl)methyl]piperazin-1-ium-1-olate
• Synonyms: [2-[4-(4-Chlorophenyl)phenylmethyl]-1-oxido-1-piperazinyl]ethoxy]acetic Acid; rac Cetirizine N-Oxide > 70% by HPLC(Mixture of Diastereomers)

Database IDs

• CAS Number: 1076199-80-8
• PubChem SID: 162258152
• PubChem CID: 45038602

CALCULATED PROPERTIES

• Acid pKa: 3.1018505
• H Acceptors: 5
• H Donor: 1
• LogD (pH = 5.5): -0.17175479
• LogD (pH = 7.4): -0.9245809
• Log P: -0.11673441
• Molar Refractivity: 108.9114 cm^3
• Polarizability: 42.034264 Å^3
• Polar Surface Area: 76.65 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: Pale Beige Solid
• Melting Point: 145-147°C

Safety Information

• Storage Condition: Hygroscopic, -20°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - C281110

A metabolite of Cetirizine.

REFERENCES

• Egger, H., et al.: Drug Metab. Dispos., 10, 529 (1982)
• Sale, M., et al.: Clin. Pharmacol. Ther., 56, 295(1982)
• Sasa, M., et al.: Jpn. J. Clin. Pharmacol. Ther., 26, 509 (1982)
• Slater, J., et al.: Drugs, 57, 31 (1982)