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

• ChemBase ID: 225
• Molecular Formular: C21H25ClN2O3
• Molecular Mass: 388.8878
• Monoisotopic Mass: 388.15537035
• SMILES: Clc1ccc(C(N2CCN(CC2)CCOCC(=O)O)c2ccccc2)cc1
• Canonical SMILES: OC(=O)COCCN1CCN(CC1)C(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)
• InChIKey: ZKLPARSLTMPFCP-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-(2-{4-[(4-chlorophenyl)(phenyl)methyl]piperazin-1-yl}ethoxy)acetic acid
• IUPAC Traditional name: cetirizine
• Brand Name: Alerlisin; Cetryn; Formistin; Hitrizin Film Tablet; Reactine; Setir; Virlix; Ziptek; Zirtek; Zyrlex; Zyrtec; Zyrtec Syrup; Zyrtec-D
• Synonyms: [2-[4-[(4-Chlorophenyl)phenylmethyl]-1-piperazinyl]ethoxy]acetic Acid Dihydrochloride; Alercet; Alerid; Alerlisin; Cesta; Cetiriz; Cetrak; Cetrine; Cetrizet; Cistamine; Epirizine; Formistin; Histazine; Histazine-1; Nosemin; P 071; Reactine; Riztec; Ryzen; Sancotec; Selitex; Tomazine; Triz; UCB-P 071; Virlix; Zeran; Zirtec; Zirtek; Zirtin; Zyrlex; Zyrtec; Zyrzine; Cetirizine Dihydrochloride; Cetirizina [Spanish]; Cetirizinum [Latin]; Cetrizine Hcl; Cetirizine; 2-(2-{4-[(4-chlorophenyl)(phenyl)methyl]piperazin-1-yl}ethoxy)acetic acid

Database IDs

• CAS Number: 83881-51-0; 83881-52-1
• MDL Number: MFCD00800721
• PubChem SID: 160963688; 46508368
• PubChem CID: 2678

CALCULATED PROPERTIES

JChem

• 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

ALOGPS 2.1

• Log P: 2.98
• LOG S: -3.77
• Solubility (Water): 6.58e-02 g/l

PROPERTIES

Physical Property

• Solubility: 101 mg/L; Methanol; Water
• Apperance: White Solid
• Melting Point: 212-214°C; 224 - 226°C
• Hydrophobicity(logP): 2.08; 2.8

Safety Information

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

Product Information

• Purity: 95%

DETAILS

DrugBank - DB00341

• Drug Groups: approved
• Description: A potent second-generation histamine H1 antagonist that is effective in the treatment of allergic rhinitis, chronic urticaria, and pollen-induced asthma. Unlike many traditional antihistamines, it does not cause drowsiness or anticholinergic side effects. [PubChem]
• Indication: For the relief of symptoms associated with seasonal allergic rhinitis, perennial allergic rhinitis and the treatment of the uncomplicated skin manifestations of chronic idiopathic urticaria
• Pharmacology: Cetirizine, the active metabolite of the piperazine H₁-receptor antagonist hydroxyzine, is used to treat chronic idiopathic urticaria, perennial allergic rhinitis, seasonal allergic rhinitis, allergic asthma, physical urticaria, and atopic dermatitis.
• Toxicity: Somnolence (sleepiness or unusual drowsiness), restlessness, irritability
• Affected Organisms: Humans and other mammals
• Absorption: mean peak plasma concentration (Cmax) of 114 ng/mL at a time (Tmax) of 2.2 hours postdose was observed for cetirizine
• Half Life: 8.3 hours
• Protein Binding: Very high (93%) plasma protein binding
• Clearance: * 53 mL/min [healthy]
• External Links: Wikipedia; RxList; Drugs.com

Toronto Research Chemicals - C281100

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)