CAS No.130018-77-8,Levocetirizine Suppliers

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Basic Information

Molecular Structure:
CAS No.:	130018-77-8
Name:	Levocetirizine
Article Data:	14

Formula:	C₂₁H₂₅ClN₂O₃
Molecular Weight:	388.894
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]-;
EINECS:	1312995-182-4
Density:	1.237 g/cm³
Melting Point:	205-208°C (dec.)
Boiling Point:	542.1 °C at 760 mmHg
Flash Point:	281.6 °C
Appearance:	white powder
PSA:	53.01000
LogP:	3.02400

Synthetic route

: C23H29ClN2O3

: 130018-77-8
levocetirizine

Conditions

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

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Chemistry

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

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.

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.

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 .