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83881-51-0

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83881-51-0 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.

Check Digit Verification of cas no

The CAS Registry Mumber 83881-51-0 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 8,3,8,8 and 1 respectively; the second part has 2 digits, 5 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 83881-51:
(7*8)+(6*3)+(5*8)+(4*8)+(3*1)+(2*5)+(1*1)=160
160 % 10 = 0
So 83881-51-0 is a valid CAS Registry Number.
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)

83881-51-0SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 18, 2017

Revision Date: Aug 18, 2017

1.Identification

1.1 GHS Product identifier

Product name cetirizine

1.2 Other means of identification

Product number -
Other names Zirtek

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:83881-51-0 SDS

83881-51-0Relevant articles and documents

Process for obtaining cetirizine dihydrochloride

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Page/Page column 4; 5, (2009/02/11)

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

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Page 15-16, (2008/06/13)

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

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Page/Page column 5, (2008/06/13)

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.

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