130018-77-8 Usage
Description
The (R)-enantiomer of the second-generation antihistamine cetirizine, levocetirizine,
was first introduced in Germany for seasonal allergic rhinitis (including ocular symptoms),
perennial allergic rhinitis and chronic idiopathic urticaria. The dihydrochloride salt can be
prepared in four steps from optically active 4-chlorobenzhydrylamine obtained by
resolution of its racemate with (+)-tartaric acid. Levocetirizine (eutomer) is a 2-fold more
potent H1 antagonist than cetirizine whereas the other enantiomer (distomer) is 10-fold
less potent compared to levocetirizine. Pharmacodynamic studies on healthy volunteers
showed that compared to cetirizine, half the dose of levocetirizine (5 mg) was necessary to
obtain similar inhibitory effects in the skin test of histamine-induced wheal and flare as well
as on histamine-induced nasal congestion and nasal resistance. There was no evidence of
chiral inversion of levocetirizine in vivo in several species including human. The daily dose
of drug is rapidly and extensively absorbed in human. Interestingly, its volume of
distribution (0.41 kg/L) is smaller than that of the distomer (0.60 kg/L). The low volume of
distribution is considered as favorable for an antihistamine both in terms of efficacy and
safety. Due to its high metabolic stability and lack of effect on the activities of the major
CYP isoenzymes, levocetirizine is unlikely to cause interactions with other administered
drugs. No clinically relevant effect on electrocardiograms of healthy volunteers was
detected.
Chemical Properties
Off-White Solid
Originator
Sepracor (US)
Uses
Different sources of media describe the Uses of 130018-77-8 differently. You can refer to the following data:
1. A nonsedating type histamine H1-receptor antagonist. A major metabolite of Hydroxyzine. Pharmacological activity resides primarily in the (R)-isomer. Antihystaminic.
2. H1 antihistamine, antiallergic
3. Labeled cetirizine, intended for use as an internal standard for the quantification of cetirizine by GC- or LC-mass spectrometry.
Brand name
Xusal
Metabolism
The extent of metabolism of levocetirizine in humans is
less than 14% of the dose. Metabolic pathways include
aromatic oxidation, N- and O- dealkylation and taurine
conjugation. Dealkylation pathways are primarily
mediated by CYP 3A4 while aromatic oxidation involved
multiple and/or unidentified CYP isoforms.
The major route of excretion of levocetirizine and
metabolites is via urine. Excretion via faeces accounts for
only 12.9% of the dose. Levocetirizine is excreted both by
glomerular filtration and active tubular secretion.
Check Digit Verification of cas no
The CAS Registry Mumber 130018-77-8 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, 7 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 130018-77:
(8*1)+(7*3)+(6*0)+(5*0)+(4*1)+(3*8)+(2*7)+(1*7)=78
78 % 10 = 8
So 130018-77-8 is a valid CAS Registry Number.
InChI:InChI=1/C21H25ClN2O3.2ClH/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);2*1H/t21-;;/m1../s1
130018-77-8Relevant articles and documents
Investigation of maltodextrin-based synergistic system with amino acid chiral ionic liquid as additive for enantioseparation in capillary electrophoresis
Chen, Jiaquan,Du, Yingxiang,Sun, Xiaodong
, p. 824 - 835 (2017)
The combined use of chiral ionic liquids (ILs) and chiral selectors in capillary electrophoresis (CE) to establish a synergistic system has proven to be an effective approach for enantioseparation. In this article, tetramethylammonium-L-arginine, a kind of amino acid chiral IL, was applied to investigate its potential synergistic effect with maltodextrin in CE enantioseparation. The established maltodextrin-based synergistic system showed markedly improved enantioseparations compared with the single maltodextrin system. Parameters such as the chiral IL concentration, maltodextrin concentration, buffer pH, applied voltage, and capillary temperature were optimized. Satisfactory enantioseparation of the five studied drugs, including nefopam, duloxetine, ketoconazole, cetirizine, and citalopram was achieved in 50 mM Tris-H3PO4 buffer solution (pH 3.0) containing 7.0% (m/v) maltodextrin and 60 mM tetramethylammonium-L-arginine. In addition, the chiral configuration of tetramethylammonium-L-arginine was also investigated to demonstrate the existence of a synergistic effect between chiral ILs and maltodextrin.
Preparation method of levocetirizine
-
, (2020/04/17)
The invention provides a preparation method of levocetirizine. The method comprises the following steps of: the step 1, carrying out a cyclization reaction on (R)-4-chlorodiphenyl methylamine and tris(2-chloroethyl)amine to obtain a compound represented by a formula (I); 2, performing condensation reaction of the compound shown in the formula (I) and 2-ethyl glycolate to obtain a compound shown ina formula (II); and the step 3, converting the compound shown in the formula (II) into levocetirizine. According to the preparation method, (R)-4-chlorodiphenyl methylamine and tris(2-chloroethyl)amine are taken as the initial raw materials, and cyclization reaction, condensation reaction and hydrolysis reaction are carried out so as to obtain levocetirizine. The synthetic route provided by the invention is short, the yield is high, and experimental results show that the yield of the levocetirizine prepared by the method provided by the invention can reach 47%, and the purity can reach 99.7%.
Enantiomeric separation and simulation studies of pheniramine, oxybutynin, cetirizine, and brinzolamide chiral drugs on amylose-based columns
Ali, Imran,Al-Othman, Zeid A.,Al-Warthan, Abdulrahman,Alam, Syed Dilshad,Farooqi, Javed A.
, p. 136 - 143 (2014/03/21)
Solid phase extraction (SPE)-chiral separation of the important drugs pheniramine, oxybutynin, cetirizine, and brinzolamide was achieved on the C 18 cartridge and AmyCoat (150 x 46 mm) and Chiralpak AD (25 cm x 0.46 cm id) chiral columns in hum
