2-(2-{4-[(R)-(4-chlorophenyl)(phenyl)methyl]piperazin-1-yl}ethoxy)acetic acid

• ChemBase ID: 164015
• Molecular Formular: C21H25ClN2O3
• Molecular Mass: 388.8878
• Monoisotopic Mass: 388.15537035
• SMILES: c1c(ccc(c1)[C@H](N1CCN(CC1)CCOCC(=O)O)c1ccccc1)Cl
• Canonical SMILES: OC(=O)COCCN1CCN(CC1)[C@@H](c1ccc(cc1)Cl)c1ccccc1
• InChI: InChI=1S/C21H25ClN2O3/c22-19-8-6-18(7-9-19)21(17-4-2-1-3-5-17)24-12-10-23(11-13-24)14-15-27-16-20(25)26/h1-9,21H,10-16H2,(H,25,26)/t21-/m1/s1
• InChIKey: ZKLPARSLTMPFCP-OAQYLSRUSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-(2-{4-[(R)-(4-chlorophenyl)(phenyl)methyl]piperazin-1-yl}ethoxy)acetic acid
• IUPAC Traditional name: (-)-cetirizine
• Synonyms: 2-[2-[4-[(R)-(4-Chlorophenyl)phenylmethyl]-1-piperazinyl]ethoxy]acetic Acid Dihydrochloride; (-)-Cetirizine Dihydrochloride; Levocetirizine Dihydrochloride; (R)-Cetirizine Dihydrochloride

Database IDs

• CAS Number: 130018-77-8
• PubChem SID: 162258150
• PubChem CID: 1549000

CALCULATED PROPERTIES

• Acid pKa: 3.596631
• H Acceptors: 5
• H Donor: 1
• LogD (pH = 5.5): 0.86074764
• LogD (pH = 7.4): 0.74475133
• Log P: 0.8598093
• Molar Refractivity: 106.8665 cm^3
• Polarizability: 41.878716 Å^3
• Polar Surface Area: 53.01 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol; Water
• Apperance: Off-White Solid
• Melting Point: 205-208°C (dec.)

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - C281106

A nonsedating type histamine H1-receptor antagonist. A major metabolite of Hydroxyzine. Pharmacological activity resides primarily in the (R)-isomer. Antihystaminic.

REFERENCES

• De Vos, C., et al.: Ann. Allergy, 59, 278 (1987)
• Juhlin, L., et al.: J. Allergy Clin. Immunol., 80, 599 (1987)
• Fadel, R., et al.: Clin. Allergy, 17, 373 (1987)
• Gengo, F.M., et al.: Clin. Pharmacol. Ther., 42, 265 (1987)