Cetirizine

Base Information

• Chemical Name: Cetirizine
• CAS No.: 83881-51-0
• Molecular Formula: C21H25ClN2O3
• Molecular Weight: 425.355
• Hs Code.: 2933599090
• European Community (EC) Number: 695-115-1
• UNII: YO7261ME24
• DSSTox Substance ID: DTXSID4022787
• Nikkaji Number: J23.322F
• Wikipedia: Cetirizine
• Wikidata: Q423075
• NCI Thesaurus Code: C1042
• RXCUI: 20610
• Pharos Ligand ID: 5XYT51ZQWLNN
• Metabolomics Workbench ID: 38714
• ChEMBL ID: CHEMBL1000
• Mol file: 83881-51-0.mol

Synonyms:(2-(4-((4-Chlorophenyl)phenylmethyl)-1-piperazinyl)ethoxy)acetic Acid;Alerlisin;Aller-Tec;Cetalerg;Ceterifug;Ceti TAD;Ceti-Puren;Cetiderm;Cetidura;Cetil von ct;CetiLich;Cetirigamma;Cetirizin AL;Cetirizin AZU;Cetirizin Basics;Cetirizine;Cetirizine Dihydrochloride;Cetirlan;Dihydrochloride, Cetirizine;P 071;P-071;P071;Reactine;Virlix;Voltric;Zetir;Zirtek;Zyrtec

Chemical Property of Cetirizine

Chemical Property:

• Appearance/Colour: powder
• Melting Point: 110-115 °C
• Boiling Point: 542.1 °C at 760 mmHg
• PKA: 3.46±0.10(Predicted)
• Flash Point: 281.6 °C
• PSA: 53.01000
• Density: 1.237 g/cm³
• LogP: 3.02400
• Storage Temp.: 2-8°C
• Solubility.: insoluble in EtOH; ≥122 mg/mL in H2O; ≥19.44 mg/mL in DMSO
• Water Solubility.: 101 mg/L
• XLogP3: 1.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 8
• Exact Mass: 388.1553704
• Heavy Atom Count: 27
• Complexity: 443

Purity/Quality:

99.9% ^*data from raw suppliers

Cetirizine >98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CN(CCN1CCOCC(=O)O)C(C2=CC=CC=C2)C3=CC=C(C=C3)Cl
• Recent ClinicalTrials: Topical Cetirizine in Androgenetic Alopecia in Females
• Recent EU Clinical Trials: Flu-like syndrome Inhibition Giving anti-histaminic Therapy. Randomized cross-over, single-center, randomized, placebo-controlled, double-blind study to evaluate the efficacy of cetirizine on Flu-like syndrome (FLS) in patients with multiple sclerosis treated with interferoneβ.
• Recent NIPH Clinical Trials: Randomized, double blind, crossover clinical study to evaluate the sedative effect after the treatment of 1 mg dose of ketotifen, or 10 or 20 mg dose of cetirizine using saccadic eye movement analysis in healthy male volunteers
• Uses: Cetirizine is a metabolite of the first-generation H1 antihistamine hydroxyzine. A reduced dosage (5 mg daily) is recommended in patients with chronic renal or hepatic impairment. Sedative side effects increase with dosages of cetirizine >10 mg per day.
• Clinical Use: Cetirizine, the acid metabolite from oxidation of the primary alcohol of the antihistamine hydroxyzine, is a widely used antihistamine. It has a long duration of action and is highly selective for H1 receptors. No cardiotoxicity has been reported, but some drowsiness occurs.

Technology Process of Cetirizine

There total 11 articles about Cetirizine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 85.3%

2-{2-[4-[(4-chlorophenyl)phenylmethyl]-1-piperazinyl]ethoxy}acetaldehyde diethylacetal (290362-10-6) → cetirizine (83881-51-0)

Guidance literature:

2-{2-[4-[(4-chlorophenyl)phenylmethyl]-1-piperazinyl]ethoxy}acetaldehyde diethylacetal; With hydrogenchloride; In water; at 60 ℃; for 0.5h;

With sodium hydroxide; dihydrogen peroxide; In ethanol; water; at 20 ℃; pH=6.5 - 7;

Reference yield: 60.0%

jones reagent + hydroxyzine dihydrochloride (2192-20-3,163837-37-4) + pyrographite (7440-44-0) → cetirizine (83881-51-0)

Guidance literature:

With hydrogenchloride; sodium hydroxide; sulfuric acid; In water; isopropyl alcohol; acetone;

Reference yield: 58.7%

hydroxyzine hydrochloride (1244-76-4,163837-37-4) → cetirizine (83881-51-0)

Guidance literature:

Pt/C; In 1,4-dioxane;

upstream raw materials:

2-{4-[(4-chlorophenyl)(phenyl)methyl]piperazin-1-yl}ethan-1-ol

sodium monochloroacetic acid

cetirizine dihydrochloride

2-(2-(4-((4-chlorophenyl)(phenyl)methyl)piperazin-1-yl)ethoxy)acetamide

Downstream raw materials:

cetirizine hydrochloride

levocetirizine

cetirizine N-oxide

Refernces

• 1、 -. "Crystalline cetirizine monohydrochloride". Page 5. . Retrieved 2008/06/13.
• 2、 -. "Novel amorphous form of [2-[4-[(4-chlorophenyl)-phenyl methyl]-1-piperazinyl]ethoxy]acetic acid and process for the preparation thereof". Page/Page column 5-6. . Retrieved 2008/06/13.