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CAS No.: | 130018-77-8 |
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Name: | Levocetirizine |
Article Data: | 14 |
Molecular Structure: | |
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 |
levocetirizine
Conditions | Yield |
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With lithium hydroxide In tetrahydrofuran; methanol; water at 65℃; for 2h; | 90% |
(2-chloroethoxy)-acetic acid
(R)-1-((4-chlorophenyl)(phenyl)methyl)piperazine
levocetirizine
Conditions | Yield |
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With tetrabutylammomium bromide; sodium hydride In N,N-dimethyl-formamide at 95℃; for 5h; Inert atmosphere; | 86.5% |
levocetirizine
Conditions | Yield |
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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
levocetirizine
Conditions | Yield |
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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
levocetirizine
Conditions | Yield |
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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
sodium monochloroacetic acid
levocetirizine
Conditions | Yield |
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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
levocetirizine
Conditions | Yield |
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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; |
Conditions | Yield |
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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; |
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; |
(R)-1-((4-chlorophenyl)(phenyl)methyl)piperazine
levocetirizine
Conditions | Yield |
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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 |
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 (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 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 (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 .