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

Description

Cetirizine, also known as (±)-[2-[4-[(4-chlorophenyl)phenylmethyl]-1-piperazinyl]ethoxy]acetic acid, is a racemic compound available as a white crystalline powder that is water soluble. It is a member of the class of piperazines and is the primary acid metabolite of hydroxyzine, resulting from complete oxidation of the primary alcohol moiety. Cetirizine is zwitterionic and relatively polar, which means it does not penetrate or accumulate in the CNS. It is marketed under the brand name Zyrtec by Pfizer.

Uses

Used in Pharmaceutical Industry:
Cetirizine is used as an H1-antihistamine for the temporary relief of symptoms caused by hay fever or other upper respiratory allergies. It is effective in treating runny nose, sneezing, itching of the nose or throat, and itchy, watery eyes. Additionally, it is used to relieve itching caused by hives (urticaria), although it will not prevent hives or an allergic skin reaction from occurring. A reduced dosage of 5 mg daily is recommended for patients with chronic renal or hepatic impairment, as sedative side effects increase with dosages of cetirizine greater than 10 mg per day.

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

Downstream Products

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

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.

Novel amorphous form of [2-[4-[(4-chlorophenyl)-phenyl methyl]-1-piperazinyl]ethoxy]acetic acid and process for the preparation thereof

A novel amorphous form of cetirizine and processes for making the amorphous form as well as compositions, pharmaceutical compositions, and methods utilizing the crystalline form are described.

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.