130018-87-0 Usage
Description
Levocetirizine dihydrochloride, also known as (R)-[2-[4-[(4-chlorophenyl) phenylmethyl]-1-piperazinyl] ethoxy] acetic acid dihydrochloride or Xyzal, is a white, crystalline powder that is water-soluble. This R-enantiomer has a 30-fold higher affinity than the S-enantiomer and dissociates more slowly from H1-receptors. Pharmacologically, it exhibits the same receptor and CNS selectivity profile as the racemate, cetirizine, and thus shares the same therapeutic advantages.
Uses
Used in Pharmaceutical Industry:
Levocetirizine dihydrochloride is used as an antihistamine for the relief of symptoms associated with allergic rhinitis (both seasonal and perennial) in adults and children aged 6 years and older. It is also used for the treatment of uncomplicated skin manifestations of chronic idiopathic urticaria in the same age group.
Used in Analytical Chemistry:
Levocetirizine dihydrochloride has been utilized as a standard in the optimization of thin layer chromatography and in the preparation of racemic cetirizine standard for subcritical fluid chromatography-tandem mass spectrometry analysis. This application aids in the development and refinement of analytical techniques for drug testing and quality control.
Biochem/physiol Actions
Levocetirizine hydrochloride is a nonsedating antihistamine. It is a histamine H1-receptor antagonist, the active isomer of cetirizine. Levocetirizine has high bioavailability, high affinity for and occupancy of the H1 receptor.
Check Digit Verification of cas no
The CAS Registry Mumber 130018-87-0 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,3,0,0,1 and 8 respectively; the second part has 2 digits, 8 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 130018-87:
(8*1)+(7*3)+(6*0)+(5*0)+(4*1)+(3*8)+(2*8)+(1*7)=80
80 % 10 = 0
So 130018-87-0 is a valid CAS Registry Number.
InChI:InChI=1/C21H25ClN2O2.ClH/c22-19-10-8-18(9-11-19)21(17-5-2-1-3-6-17)24-15-13-23(14-16-24)12-4-7-20(25)26;/h1-3,5-6,8-11,21H,4,7,12-16H2,(H,25,26);1H/t21-;/m0./s1
130018-87-0Relevant articles and documents
A novel synthesis of the enantiomers of an antihistamine drug by piperazine formation from a primary amine
Opalka,D'Ambra,Faccone,Bodson,Cossement
, p. 766 - 768 (1995)
An enantioselective synthesis of each enantiomer of the antihistamine drug 2-(2-{4-[(4-chlorophenyl)phenylmethyl]-1-piperazinyl}ethoxy)acetic acid dihydrochloride (1) is described, involving the preparation of the benzhydrylpiperazine portion of the molecule from reaction of each enantiomer of 4-chlorobenzhydrylamine with N,N-bis(2-chloroethyl)-4-methylbenzenesulfonamide. A modification of standard toluenesulfonamide deprotection with hydrogen bromide in acetic acid was introduced, substituting 4-hydroxybenzoic acid for phenol.
New manufacturing procedure of cetirizine
Reiter, Jozsef,Trinka, Peter,Bartha, Ferenc L.,Pongo, Laszlo,Volk, Balazs,Simig, Gyula
, p. 1279 - 1282 (2012/09/08)
A new procedure for the manufacture of cetirizine dihydrochloride via the new intermediate 2-(2-{4-[(4-chlorophenyl)(phenyl)methyl]piperazin-1-yl}ethoxy)- N,N-dimethylacetamide dihydrochloride, synthesized by O-alkylation of 2-{4-[(4-chlorophenyl)(phenyl)methyl]piperazin-1-yl}ethanol with 2-chloro-N,N-dimethylacetamide, is elaborated. Hydrolysis of the resulting amide and subsequent salification provided cetirizine dihydrochloride.
Processes for the Synthesis of Levocetirizine and Intermediates for Use Therein
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Page/Page column 8, (2011/08/06)
The present invention provides a compound of formula (IV) wherein R is Cl, Br, NO2, OH or OR′, and R′ is alkyl, and its use in the synthesis of levocetirizine, including its use in the synthesis of (?)-1-[(4-chlorophenyl)-phenylmethyl]piperazin