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

• ChemBase ID: 155021
• Molecular Formular: C21H27Cl3N2O3
• Molecular Mass: 461.80968
• Monoisotopic Mass: 460.10872577
• SMILES: c1ccc(cc1)[C@H](c1ccc(cc1)Cl)N1CCN(CC1)CCOCC(=O)O.Cl.Cl
• Canonical SMILES: OC(=O)COCCN1CCN(CC1)[C@@H](c1ccc(cc1)Cl)c1ccccc1.Cl.Cl
• InChI: InChI=1S/C21H25ClN2O3.2ClH/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);2*1H/t21-;;/m1../s1
• InChIKey: PGLIUCLTXOYQMV-GHVWMZMZSA-N

NAMES AND DATABASE IDS

Names

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

Database IDs

• CAS Number: 130018-87-0
• MDL Number: MFCD07366507
• PubChem SID: 162249159
• PubChem CID: 9955977

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: H2O: ≥23 mg/mL
• Apperance: powder

Safety Information

• European Hazard Symbols: Nature polluting (N); Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22-50/53
• Safety Statements: 60-61
• GHS Pictograms: GHS07; GHS09
• GHS Signal Word: Warning
• GHS Hazard statements: H302-H400
• GHS Precautionary statements: P273
• Storage Temperature: room temp

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C21H25ClN2O3·2HCl

DETAILS

Sigma Aldrich - L7795

Biochem/physiol Actions
Levocetirizine hydrochloride is a nonsedating antihistamine. It is a histamine H1-receptor antagonist, the active isomer of cetirizine. Levocetirizine has high bioavailability, high affinity for and occupancy of the H1 receptor.