83881-51-0

Basic information

• Product Name: Cetirizine
• Synonyms: (2-(4-((4-chlorophenyl)phenylmethyl)-1-piperazinyl)ethoxy)-aceticaci;(2-(4-((4-chlorophenyl)phenylmethyl)-1-piperazinyl)ethoxy)aceticacid;CETIRIZINE;(2-(4-[(4-CHLORO-PHENYL)-PHENYL-METHYL]-PIPERAZIN-1-YL)-ETHOXY)-ACETIC ACID;Cetirizine Hydrochloride BP;Cetirizine (Cetrizine) Di HCl;CERTIRIZINE 2HCL;CETIRIZINE IMPURITY A(RS)-1-[(4-CHLOROPHENYL)PHENYLMETHYL]PIPERAZINE EPC(CRM STANDARD)
• CAS NO: 83881-51-0
• Molecular Formula: C₂₁H₂₅ClN₂O₃
• Molecular Weight: 388.89
• Mol File: 83881-51-0.mol
• Article Data: 8

Chemical Properties

• Melting Point: 110-115°C
• Boiling Point: 542.1 °C at 760 mmHg
• Flash Point: 281.6 °C
• Appearance: powder
• Density: 1.237 g/cm³
• Storage Temp.: 2-8°C
• Solubility: insoluble in EtOH; ≥122 mg/mL in H2O; ≥19.44 mg/mL in DMSO
• PKA: 3.46±0.10(Predicted)
• Water Solubility: 101 mg/L
• CAS DataBase Reference: Cetirizine(CAS DataBase Reference)
• NIST Chemistry Reference: Cetirizine(83881-51-0)
• EPA Substance Registry System: Cetirizine(83881-51-0)

Safety Data

• WGK Germany: 3
• RTECS: AG0977500
• Hazardous Substances Data: 83881-51-0(Hazardous Substances Data)

Usage

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.

Definition

ChEBI: A member of the class of piperazines that is piperazine in which the hydrogens attached to nitrogen are replaced by a (4-chlorophenyl)(phenyl)methyl and a 2-(carboxymethoxy)ethyl group respectively.

Brand name

Zyrtec (Pfizer).

General Description

Cetirizine, (±)-[2-[4-[(4-chlorophenyl)phenylmethyl]- 1-piperazinyl]ethoxy]acetic acid (Zyrtec), is a racemic compound available as a white crystalline powder that is water soluble. Cetirizine is the primary acid metabolite of hydroxyzine, resulting from complete oxidation of the primary alcohol moiety. This compound is zwitterionic and relatively polar and thus does not penetrate or accumulate in the CNS. Before its introduction in the United States, cetirizine was one of the most widely prescribed H1-antihistamines in Europe. Cetirizine is indicated for the temporary relief of runny nose, sneezing, itching of the nose or throat, and/or itchy, watery eyes caused by hay fever or other upper respiratory allergies. It also relieves itching caused by hives (urticaria), but it will not prevent hives or an allergic skin reaction from occurring.

Biological Activity

cetirizine, a second-generation antihistamine, is a major metabolite of hydroxyzine, and a racemic selective h1 receptor inverse agonist used in the treatment of allergies, hay fever, angioedema, and urticaria. cetirizine crosses the blood-brain barrier only slightly, reducing the sedative side-effect common with older antihistamines. it has also been shown to inhibit eosinophil chemotaxis and ltb4 release. at a dosage of 20 mg, boone et al. found that it inhibited the expression of vcam-1 in patients with atopic dermatitis. the levorotary enantiomer of cetirizine, known as levocetirizine, is the more active form. from wikipedia.

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.

InChI:InChI=1/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)

Upstream product

• 109806-71-5 2-{4-[(4-chlorophenyl)(phenyl)methyl]piperazin-1-yl}ethan-1-ol 
• 79-11-8 chloroacetic acid 
• 83881-52-1 cetirizine dihydrochloride 
• 290362-10-6 2-{2-[4-[(4-chlorophenyl)phenylmethyl]-1-piperazinyl]ethoxy}acetaldehyde diethylacetal 
• 83881-37-2 2-(2-(4-((4-chlorophenyl)(phenyl)methyl)piperazin-1-yl)ethoxy)acetamide 
• 3926-62-3 sodium monochloroacetic acid 
• 1244-76-4 hydroxyzine hydrochloride 
• 2192-20-3 hydroxyzine dihydrochloride 
• 7440-44-0 pyrographite 

Downstream Products

• 83881-51-0 cetirizine hydrochloride 
• 1076199-80-8 cetirizine N-oxide 
• 130018-77-8 levocetirizine 
• 83881-52-1 cetirizine dihydrochloride 

Relevant articles and documents

Process for obtaining cetirizine dihydrochloride

Process for the synthesis of cetirizine dihydrochloride, wherein (a) a solution of {2-[4-(α-phenyl-p-chlorobenzyl)piperazin-1-yl]}ethanol in 1-7 volumes, referred to the weight of {2-[4-(α-phenyl-p-chlorobenzyl)piperazin-1-yl]}ethanol, of an organic solvent having a boiling point higher than 90° C. and being chosen from the group consisting of aliphatic, cycloalifatic or aromatic solvents is provided, whereafter(b) per equivalent of {2-[4-(α-phenyl-p-chlorobenzyl)piperazin-1-yl]}ethanol employed, 1-2 equivalents of a metal haloacetate or of haloacetic acid, as well as 3-7 equivalents of an alkaly metal hydroxyde are added to the solution as per (a), providing a reaction mixture, where 0.05-0.3 volumes, referred to the weight of {2-[4-(α-phenyl-p-chlorobenzyl)piperazin-1-yl]}ethanol employed, of water and 0.1-1.2 volumes, referred to the weight of {2-[4-(α-phenyl-p-chlorobenzyl)piperazin-1-yl]}ethanol employed, of a polar aprotic, water miscible solvent are added, keeping the internal temperature of the reaction mixture below 60° C., whereafter(c) the cetirizine base formed within the reaction mixture is converted into its dihydrochloride salt and isolated as such.

2-[2-[4-[(4-CHLOROPHENYL) PHENYLMETHYL]-1-PIPERAZINYL]ETHOXY]ACETIC ACID MONOHYDROCHLORIDE AS ANTI-ALLERGENIC COMPOUND AND PROCESS FOR ITS PRODUCTION

An anti-allergenic compound having therapeutic value and a process for its manufacture. The disclosure is directed to 2-[2-[4-[(4-chlorophenyl)phenylmethyl]-1piperazinyl]ethoxy]acetic acid monohydrochloride, to compositions containing 2-[2-[4-[(4chlorophenyl)phenylmethyl]-1-piperazinyl]ethoxy]acetic acid monohydrochloride, and to a process for the preparation of 2-[2-[4-[(4-chlorophenyl)phenylmethyl]-1-piperazinyl]ethoxy]acetic acid monohydrochloride.

A PROCESS FOR THE PREPARATION OF 2- 2- 4-(DIPHENYLMETHYL)-1-PIPERAZINYL]ETHOXY ACETIC ACID COMPOUNDS OR SALTS THEREOF

2-{2-[4-(diphenylmethyl)-1-piperazinyl]ethoxy}acetic acid compounds of general formula (I) wherein R and R independently represent hydrogen, halogen, lower alkoxy or trifluoromethyl, or salts thereof are prepared by reacting a corresponding 2-[4-(diphenylmethyl)-1-piperazinyl]ethanol with a 2-substituted acetaldehyde dialkylacetal in the presence of a proton acceptor in an inert solvent to form a corresponding diphenylmethylpiperazinoethoxyacetaldehyde dialkylacetal, and thereafter hydrolysing the acetal to the corresponding aldehyde, catalysed by a proton donor, and then oxidising the aldehyde to the acid (I) by means of a suitable oxidation agent. If desired, the acid (I) is converted into a salt thereof. The process is cheap, easy to perform and gives a high yield. The most interesting compound is 2-{2-[4-[(4-chlorophenyl)phenylmethyl]-1-piperazinyl]-ethoxy}acetic acid in the form of its dihydrochloride known by the generic name of cetirizine. The 2-{2-[4-(diphenylmethyl)-1-piperazinyl]ethoxy}acetaldehyde compounds and their dialkylacetals are novel compounds.