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Levocetirizine
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Name

Levocetirizine

 EINECS 1312995-182-4
CAS No. 130018-77-8 Density 1.237 g/cm3
PSA 53.01000 LogP 3.02400
Solubility N/A Melting Point 205-208°C (dec.)
Formula C21H25ClN2O3 Boiling Point 542.1 °C at 760 mmHg
Molecular Weight 388.894 Flash Point 281.6 °C
Transport Information N/A Appearance white powder
Safety Risk Codes N/A
Molecular Structure Molecular Structure of 130018-77-8 (Levocetirizine) Hazard Symbols N/A
Synonyms

Aceticacid, [2-[4-[(4-chlorophenyl)phenylmethyl]-1-piperazinyl]ethoxy]-, (R)-;Aceticacid, [2-[4-[(R)-(4-chlorophenyl)phenylmethyl]-1-piperazinyl]ethoxy]- (9CI);(-)-Cetirizine;(R)-Cetirizine;Acetic acid,2-[2-[4-[(R)-(4-chlorophenyl)phenylmethyl]-1-piperazinyl]ethoxy]-;

Article Data 14

Levocetirizine Synthetic route

C23H29ClN2O3

130018-77-8

levocetirizine

Conditions
ConditionsYield
With lithium hydroxide In tetrahydrofuran; methanol; water at 65℃; for 2h;90%
14869-41-1

(2-chloroethoxy)-acetic acid

300543-56-0

(R)-1-((4-chlorophenyl)(phenyl)methyl)piperazine

130018-77-8

levocetirizine

Conditions
ConditionsYield
With tetrabutylammomium bromide; sodium hydride In N,N-dimethyl-formamide at 95℃; for 5h; Inert atmosphere;86.5%

(R)-(2-{4-[(4-chlorophenyl)phenylmethyl]piperazin-1-yl}ethoxy)acetic acid methyl ester

130018-77-8

levocetirizine

Conditions
ConditionsYield
With hydrogenchloride In water Large scale; enantioselective reaction;74%
Stage #1: (R)-(2-{4-[(4-chlorophenyl)phenylmethyl]piperazin-1-yl}ethoxy)acetic acid methyl ester With water; potassium hydroxide In methanol at 80℃; for 1h;
Stage #2: With hydrogenchloride In dichloromethane; water pH=4 - 4.5; Product distribution / selectivity;
1150310-68-1

levocetirizine N-benzyl amide

130018-77-8

levocetirizine

Conditions
ConditionsYield
Stage #1: levocetirizine N-benzyl amide With sulfuric acid In methanol for 16h; Reflux;
Stage #2: With sodium hydroxide In methanol for 2h; pH=10 - 12;
Stage #3: With hydrogenchloride In methanol; water pH=4.5;		70%
Stage #1: levocetirizine N-benzyl amide With sulfuric acid; water at 80 - 85℃; for 8h;
Stage #2: With sodium hydroxide In water pH=4.0 - 4.5;		n/a
909779-33-5

(R)-2-(2-{4-[(4-chlorophenyl)phenylmethyl]piperazin-1-yl}ethoxy)acetamide

130018-77-8

levocetirizine

Conditions
ConditionsYield
With hydrogenchloride In water at 65℃; for 4h;
Multi-step reaction with 2 steps
1.1: hydrogenchloride / methanol / 4 h / Reflux
1.2: 7 h
2.1: hydrogenchloride / water / Large scale
View Scheme
705289-61-8

(+)-[2-[4-[(4-chlorophenyl)-phenyl methyl]-1-piperazinyl]]ethanol

3926-62-3

sodium monochloroacetic acid

130018-77-8

levocetirizine

Conditions
ConditionsYield
Stage #1: (+)-[2-[4-[(4-chlorophenyl)-phenyl methyl]-1-piperazinyl]]ethanol With potassium hydroxide In N,N-dimethyl-formamide at 0 - 5℃; for 1.5h;
Stage #2: sodium monochloroacetic acid at 0 - 5℃; for 1.5h;
Stage #3: at 30 - 35℃;
Stage #1: (+)-[2-[4-[(4-chlorophenyl)-phenyl methyl]-1-piperazinyl]]ethanol With potassium hydroxide In DMF (N,N-dimethyl-formamide) at 0 - 5℃; for 1.5h;
Stage #2: sodium monochloroacetic acid In DMF (N,N-dimethyl-formamide) at 0 - 35℃;
Stage #3: With hydrogenchloride In DMF (N,N-dimethyl-formamide); water pH=4 - 4.5;
1150310-67-0

(R)-2-[2-[4-[(4-chlorophenyl)phenylmethyl]-1-piperazinyl]ethoxy]-1-(S)-[N-(1-phenyIethyl)]acetamide

130018-77-8

levocetirizine

Conditions
ConditionsYield
With water; hydrogen bromide at 90 - 95℃; for 24h; Product distribution / selectivity;
Stage #1: (R)-2-[2-[4-[(4-chlorophenyl)phenylmethyl]-1-piperazinyl]ethoxy]-1-(S)-[N-(1-phenyIethyl)]acetamide With sulfuric acid; water at 80 - 85℃; for 48h;
Stage #2: With sodium hydroxide In water pH=4.5 - 5.0; Product distribution / selectivity;
83881-51-0

cetirizine

A

(S)-cetirizine

B

130018-77-8

levocetirizine

Conditions
ConditionsYield
Resolution of racemate;
With N,N-diethylaniline In hexane; isopropyl alcohol at 25℃; Reagent/catalyst; Resolution of racemate;
With maltodextrin In aq. buffer at 25℃; pH=3; Reagent/catalyst; pH-value; Temperature; Resolution of racemate;

C19H23ClN2O*ClH

3926-62-3

sodium monochloroacetic acid

130018-77-8

levocetirizine

Conditions
ConditionsYield
Stage #1: C19H23ClN2O*ClH With ammonia In water; toluene for 0.25h; pH=8.5 - 9;
Stage #2: sodium monochloroacetic acid With potassium hydroxide In N,N-dimethyl-formamide at 0 - 10℃;
Stage #3: With hydrogenchloride In dichloromethane; water pH=4.3 - 4.8;
300543-56-0

(R)-1-((4-chlorophenyl)(phenyl)methyl)piperazine

130018-77-8

levocetirizine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: triethylamine / toluene / 7 h / 110 - 115 °C
1.2: 12 h / 25 - 30 °C
2.1: ammonia / toluene; water / 0.25 h / pH 8.5 - 9
2.2: 0 - 10 °C
2.3: pH 4.3 - 4.8
View Scheme
Multi-step reaction with 5 steps
1.1: tetrabutylammomium bromide / dimethyl sulfoxide / 10 h
2.1: oxalyl dichloride / tetrahydrofuran / 0 - 5 °C
3.1: tetrahydrofuran
4.1: dimethylsulfide borane complex / tetrahydrofuran / Reflux
5.1: water; potassium hydroxide / methanol / 1 h / 80 °C
5.2: pH 4 - 4.5
View Scheme

Levocetirizine Chemical Properties


IUPAC Name: 2-[2-[4-[(R)-(4-Chlorophenyl)-phenylmethyl]piperazin-1-yl]ethoxy]acetic acid 
Empirical Formula: C21H25ClN2O3
Molecular Weight: 388.8878
Canonical SMILES: C1CN(CCN1CCOCC(=O)O)C(C2=CC=CC=C2)C3=CC=C(C=C3)Cl
Isomeric SMILES: C1CN(CCN1CCOCC(=O)O)[C@H](C2=CC=CC=C2)C3=CC=C(C=C3)Cl
InChI: InChI=1S/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)/t21-/m1/s1
InChIKey: ZKLPARSLTMPFCP-OAQYLSRUSA-N
Index of Refraction: 1.589
Molar Refractivity: 105.94 cm3
Molar Volume: 314.2 cm3
Surface Tension: 50.7 dyne/cm
Density: 1.237 g/cm3
Flash Point: 281.6 °C
Enthalpy of Vaporization: 86.31 kJ/mol
Boiling Point: 542.1 °C at 760 mmHg
Vapour Pressure: 1.39E-12 mmHg at 25 °C 
Classification Code of Levocetirizine (CAS NO.130018-77-8): Antihistamine; Histamine Agents; Histamine Antagonists; Histamine H1 Antagonists; Histamine H1 Antagonists, Non-Sedating; Neurotransmitter Agents

Levocetirizine History

 Levocetirizine (CAS NO.130018-77-8) was first launched in 2001 by Belgian pharmaceutical company UCB with the brand name Xyzal (pronounced /?za?zæl/) in Austria, Finland, France, Ireland, Netherlands, Portugal, Romania, United States, UK; Xuzal in Mexico; Xusal in Germany; and Xozal in Greece. In India, levocetirizine is marketed by GlaxoSmithKline under the brand name Vozet and Xyzal. On May 25, 2007, the United States Food and Drug Administration approved Xyzal, where it is co-marketed by Sanofi-Aventis.Torrent Pharma launched UVNIL in rural market of INDIA. It is also available as LEZYNCET 5 mg tablets through Unichem in India. In India, generic name of Lev-Cit 5mg is manufactured by VIP Pharmaceuticals. Also marketed in India by Croslands (Ranbaxy Laboratories Ltd.) under the brand name Teczine. It is marked in Egypt by BORG Pharma under the brand name 'Xaltec', Allear by western pharmaceuticals and levcet by marcryl.

Levocetirizine Uses

 Levocetirizine is called a non-sedating antihistamine as it does not enter the brain in significant amounts, and is therefore unlikely to cause drowsiness. However, some people may experience some slight sleepiness, headache, mouth dryness, lightheadedness, vision problems (mainly blurred vision), palpitations and fatigue.

Levocetirizine Specification

  Levocetirizine (CAS NO.130018-77-8), its Synonyms are (-)-Cetirizine ; (2-(4-((R-p-Chloro-alpha-phenylbenzyl)-1-piperazinyl)ethoxy)acetic acid ; Acetic acid, (2-(4-((R)-(4-chlorophenyl)phenylmethyl)-1-piperazinyl)ethoxy)- ; Xusal .

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