Product Name

  • Name

    Levocetirizine

  • EINECS 1312995-182-4
  • CAS No. 130018-77-8
  • Article Data14
  • CAS DataBase
  • Density 1.237 g/cm3
  • Solubility
  • 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
  • Appearance white powder
  • Safety
  • Risk Codes
  • Molecular Structure Molecular Structure of 130018-77-8 (Levocetirizine)
  • Hazard Symbols
  • 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]-;
  • PSA 53.01000
  • LogP 3.02400

Synthetic route

C23H29ClN2O3

C23H29ClN2O3

levocetirizine
130018-77-8

levocetirizine

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

(2-chloroethoxy)-acetic acid

(R)-1-((4-chlorophenyl)(phenyl)methyl)piperazine
300543-56-0

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

levocetirizine
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

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

levocetirizine
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;
levocetirizine N-benzyl amide
1150310-68-1

levocetirizine N-benzyl amide

levocetirizine
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
(R)-2-(2-{4-[(4-chlorophenyl)phenylmethyl]piperazin-1-yl}ethoxy)acetamide
909779-33-5

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

levocetirizine
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
(+)-[2-[4-[(4-chlorophenyl)-phenyl methyl]-1-piperazinyl]]ethanol
705289-61-8

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

sodium monochloroacetic acid
3926-62-3

sodium monochloroacetic acid

levocetirizine
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;
(R)-2-[2-[4-[(4-chlorophenyl)phenylmethyl]-1-piperazinyl]ethoxy]-1-(S)-[N-(1-phenyIethyl)]acetamide
1150310-67-0

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

levocetirizine
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;
cetirizine
83881-51-0

cetirizine

A

(S)-cetirizine

(S)-cetirizine

B

levocetirizine
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

C19H23ClN2O*ClH

sodium monochloroacetic acid
3926-62-3

sodium monochloroacetic acid

levocetirizine
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;
(R)-1-((4-chlorophenyl)(phenyl)methyl)piperazine
300543-56-0

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

levocetirizine
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
(R)-(4-chlorophenyl)(phenyl)methylamine
163837-57-8

(R)-(4-chlorophenyl)(phenyl)methylamine

levocetirizine
130018-77-8

levocetirizine

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: N-ethyl-N,N-diisopropylamine / 128 - 130 °C
2.1: potassium hydroxide / isopropyl alcohol / 9 h / 80 - 85 °C
3.1: triethylamine / toluene / 7 h / 110 - 115 °C
3.2: 12 h / 25 - 30 °C
4.1: ammonia / toluene; water / 0.25 h / pH 8.5 - 9
4.2: 0 - 10 °C
4.3: pH 4.3 - 4.8
View Scheme
Multi-step reaction with 6 steps
1.1: N-ethyl-N,N-diisopropylamine / 3 h / Reflux
1.2: 60 °C / Reflux
2.1: tetrabutylammomium bromide / dimethyl sulfoxide / 10 h
3.1: oxalyl dichloride / tetrahydrofuran / 0 - 5 °C
4.1: tetrahydrofuran
5.1: dimethylsulfide borane complex / tetrahydrofuran / Reflux
6.1: water; potassium hydroxide / methanol / 1 h / 80 °C
6.2: pH 4 - 4.5
View Scheme
Multi-step reaction with 3 steps
1: N-ethyl-N,N-diisopropylamine / 3 h / 120 °C
2: sodium hydride; sodium iodide / N,N-dimethyl-formamide; acetone / 3 h / 25 °C
3: lithium hydroxide / water; tetrahydrofuran; methanol / 2 h / 65 °C
View Scheme
C2H2O4*C17H19ClN2

C2H2O4*C17H19ClN2

levocetirizine
130018-77-8

levocetirizine

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: sodium hydroxide / water / 0.5 h / 65 - 70 °C
2.1: triethylamine / toluene / 7 h / 110 - 115 °C
2.2: 12 h / 25 - 30 °C
3.1: ammonia / toluene; water / 0.25 h / pH 8.5 - 9
3.2: 0 - 10 °C
3.3: pH 4.3 - 4.8
View Scheme
C22H27ClN2O2
1391851-21-0

C22H27ClN2O2

levocetirizine
130018-77-8

levocetirizine

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: potassium hydroxide / isopropyl alcohol / 9 h / 80 - 85 °C
2.1: triethylamine / toluene / 7 h / 110 - 115 °C
2.2: 12 h / 25 - 30 °C
3.1: ammonia / toluene; water / 0.25 h / pH 8.5 - 9
3.2: 0 - 10 °C
3.3: pH 4.3 - 4.8
View Scheme
N-benzyl-2-(2-(bis(2-chloroethyl)amino)ethoxy)acetamide
1150310-73-8

N-benzyl-2-(2-(bis(2-chloroethyl)amino)ethoxy)acetamide

(R)-(4-chlorophenyl)(phenyl)methylamine
163837-57-8

(R)-(4-chlorophenyl)(phenyl)methylamine

levocetirizine
130018-77-8

levocetirizine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: N-ethyl-N,N-diisopropylamine / 4 h / 130 °C / Inert atmosphere
2.1: sulfuric acid / methanol / 16 h / Reflux
2.2: 2 h / pH 10 - 12
2.3: pH 4.5
View Scheme
p-chlorobenzhydrylamine
28022-43-7

p-chlorobenzhydrylamine

levocetirizine
130018-77-8

levocetirizine

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: hydrogenchloride; borane-ammonia complex / aq. phosphate buffer / 37 °C / pH 7.8
2.1: N-ethyl-N,N-diisopropylamine / 4 h / 130 °C / Inert atmosphere
3.1: sulfuric acid / methanol / 16 h / Reflux
3.2: 2 h / pH 10 - 12
3.3: pH 4.5
View Scheme
Multi-step reaction with 4 steps
1: L-Tartaric acid / 30 - 90 °C / Inert atmosphere
2: N-ethyl-N,N-diisopropylamine / 3 h / 120 °C
3: sodium hydride; sodium iodide / N,N-dimethyl-formamide; acetone / 3 h / 25 °C
4: lithium hydroxide / water; tetrahydrofuran; methanol / 2 h / 65 °C
View Scheme
N-benzyl-2-(2-(bis(2-hydroxyethyl)amino)ethoxy)acetamide
1150310-72-7

N-benzyl-2-(2-(bis(2-hydroxyethyl)amino)ethoxy)acetamide

levocetirizine
130018-77-8

levocetirizine

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: N-ethyl-N,N-diisopropylamine; methanesulfonyl chloride / dichloromethane / 0 - 20 °C / Inert atmosphere
2.1: N-ethyl-N,N-diisopropylamine / 4 h / 130 °C / Inert atmosphere
3.1: sulfuric acid / methanol / 16 h / Reflux
3.2: 2 h / pH 10 - 12
3.3: pH 4.5
View Scheme
cetirizine dihydrochloride
83881-52-1

cetirizine dihydrochloride

A

(S)-cetirizine

(S)-cetirizine

B

levocetirizine
130018-77-8

levocetirizine

Conditions
ConditionsYield
With CHIRALPAK human serum albumin (HSA) column In aq. phosphate buffer; isopropyl alcohol at 25℃; pH=7; Solvent; Concentration; Temperature; Resolution of racemate;
R-2-(2-(4-((4-chlorophenyl)(phenyl)methyl)piperazin-1-yl)-2-oxoethoxy)acetyl chloride

R-2-(2-(4-((4-chlorophenyl)(phenyl)methyl)piperazin-1-yl)-2-oxoethoxy)acetyl chloride

levocetirizine
130018-77-8

levocetirizine

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: tetrahydrofuran
2.1: dimethylsulfide borane complex / tetrahydrofuran / Reflux
3.1: water; potassium hydroxide / methanol / 1 h / 80 °C
3.2: pH 4 - 4.5
View Scheme
R-2-(2-(4-((4-chlorophenyl)(phenyl)methyl)piperazin-1-yl)-2-oxoethoxy)acetic acid
1058165-14-2

R-2-(2-(4-((4-chlorophenyl)(phenyl)methyl)piperazin-1-yl)-2-oxoethoxy)acetic acid

levocetirizine
130018-77-8

levocetirizine

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: oxalyl dichloride / tetrahydrofuran / 0 - 5 °C
2.1: tetrahydrofuran
3.1: dimethylsulfide borane complex / tetrahydrofuran / Reflux
4.1: water; potassium hydroxide / methanol / 1 h / 80 °C
4.2: pH 4 - 4.5
View Scheme
R-methyl 2-(2-(4-((4-chlorophenyl)(phenyl)methyl)piperazin-1-yl)-2-oxoethoxy)acetate
1201648-47-6

R-methyl 2-(2-(4-((4-chlorophenyl)(phenyl)methyl)piperazin-1-yl)-2-oxoethoxy)acetate

levocetirizine
130018-77-8

levocetirizine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: dimethylsulfide borane complex / tetrahydrofuran / Reflux
2.1: water; potassium hydroxide / methanol / 1 h / 80 °C
2.2: pH 4 - 4.5
View Scheme
triethanolamine
102-71-6

triethanolamine

levocetirizine
130018-77-8

levocetirizine

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: thionyl chloride / dichloromethane / 3 h / 38 - 42 °C
2: N-ethyl-N,N-diisopropylamine / 3 h / 120 °C
3: sodium hydride; sodium iodide / N,N-dimethyl-formamide; acetone / 3 h / 25 °C
4: lithium hydroxide / water; tetrahydrofuran; methanol / 2 h / 65 °C
View Scheme
tris-(2-chloro-ethyl)-amine
555-77-1

tris-(2-chloro-ethyl)-amine

levocetirizine
130018-77-8

levocetirizine

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: N-ethyl-N,N-diisopropylamine / 3 h / 120 °C
2: sodium hydride; sodium iodide / N,N-dimethyl-formamide; acetone / 3 h / 25 °C
3: lithium hydroxide / water; tetrahydrofuran; methanol / 2 h / 65 °C
View Scheme
4-chlorobenzophenone
134-85-0

4-chlorobenzophenone

levocetirizine
130018-77-8

levocetirizine

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: formamide / 170 - 175 °C / Inert atmosphere
2: L-Tartaric acid / 30 - 90 °C / Inert atmosphere
3: N-ethyl-N,N-diisopropylamine / 3 h / 120 °C
4: sodium hydride; sodium iodide / N,N-dimethyl-formamide; acetone / 3 h / 25 °C
5: lithium hydroxide / water; tetrahydrofuran; methanol / 2 h / 65 °C
View Scheme
triphenyltin(IV) hydroxide
76-87-9

triphenyltin(IV) hydroxide

levocetirizine
130018-77-8

levocetirizine

(R)-triphenylstannyl 2-(2-(4-((4-chlorophenyl)(phenyl)methyl)piperazin-1-yl)ethoxy) acetate

(R)-triphenylstannyl 2-(2-(4-((4-chlorophenyl)(phenyl)methyl)piperazin-1-yl)ethoxy) acetate

Conditions
ConditionsYield
With sulfuric acid In ethanol; acetone Reflux;71%
hydrogenchloride
7647-01-0

hydrogenchloride

levocetirizine
130018-77-8

levocetirizine

(+)-Cetirizine dihydrochloride

(+)-Cetirizine dihydrochloride

Conditions
ConditionsYield
In acetone at 40 - 50℃;
In water; acetone at 20 - 35℃; for 0.166667 - 0.5h;
levocetirizine
130018-77-8

levocetirizine

levocetirizine dihydrochloride

levocetirizine dihydrochloride

Conditions
ConditionsYield
With hydrogenchloride In acetone at 55℃;
With hydrogenchloride In acetone at 0 - 30℃; for 4h; pH=1.0 - 2.0;
Stage #1: levocetirizine With hydrogenchloride In water; acetone at 20℃; for 0.166667 - 0.5h;
Stage #2: In cyclohexane at 30 - 35℃; for 0.5h;
Stage #1: levocetirizine In ethyl acetate at 25 - 35℃; for 0.166667 - 0.25h;
Stage #2: With hydrogenchloride In isopropyl alcohol pH=2;
Stage #3: for 1 - 2h;
With hydrogenchloride In water; acetone at 25 - 30℃; for 12h;
levocetirizine
130018-77-8

levocetirizine

C21H23ClN2O3

C21H23ClN2O3

Conditions
ConditionsYield
In methanol; water at 130℃; for 30.3333h; Temperature;2.3 g
curcumin
458-37-7

curcumin

levocetirizine
130018-77-8

levocetirizine

C21H25ClN2O3*C21H20O6

C21H25ClN2O3*C21H20O6

Conditions
ConditionsYield
In methanol at 25℃;

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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