Cetirizine
Title: Cetirizine
CAS Registry Number: 83881-51-0
CAS Name: [2-[4-[(4-Chlorophenyl)phenylmethyl]-1-piperazinyl]ethoxy]acetic acid
Additional Names: [2-[4-(p-chloro-a-phenylbenzyl)-1-piperazinyl]ethoxy]acetic acid
Molecular Formula: C21H25ClN2O3
Molecular Weight: 388.89
Percent Composition: C 64.86%, H 6.48%, Cl 9.12%, N 7.20%, O 12.34%
Literature References: Nonsedating type histamine H1-receptor antagonist; major metabolite of hydroxyzine, q.v. Pharmacological activity resides primarily in the (R)-isomer. Prepn: E. Baltes et al., EP 58146; eidem, US 4525358 (1982, 1985 both to UCB); of enantiomers: E. Cossement et al., GB 2225321 (1989 to UCB). See also: eidem, US 5478941 (1995 to UCB). Enantioselective HPLC determn in urine: S. O. Choi et al., Arch. Pharmacal Res. 23, 178 (2000). Stereoselective binding study: M. Gillard et al., Mol. Pharmacol. 61, 391 (2002). Clinical pharmacokinetics: E. Baltes et al., Fundam. Clin. Pharmacol. 15, 269 (2001). Clinical comparison with enantiomers on cutaneous response: J. L. Devalia et al., Allergy 56, 50 (2001); on nasal response: D. Y. Wang et al., ibid. 339. Review of pharmacology and clinical experience in allergic disorders: J. M. Portnoy, C. Dinakar, Expert Opin. Pharmacother. 5, 125-135 (2004).
Properties: Crystals from ethanol, mp 110-115°.
Melting point: mp 110-115°
 
Derivative Type: Dihydrochloride
CAS Registry Number: 83881-52-1
Manufacturers' Codes: P-071
Trademarks: Alerlisin (Prodes); Formistin (Formenti); Reactine (Pfizer); Virlix (Sanofi-Synthelabo); Zirtek (UCB); Zyrtec (Pfizer); Zyrlex (UCB)
Molecular Formula: C21H25ClN2O3.2HCl
Molecular Weight: 461.81
Percent Composition: C 54.62%, H 5.89%, Cl 23.03%, N 6.07%, O 10.39%
Properties: Crystals from isopropanol, mp 225°. Sol in water.
Melting point: mp 225°
 
Derivative Type: (R)-Form
CAS Registry Number: 130018-77-8
Additional Names: Levocetirizine; (-)-cetirizine
 
Derivative Type: (R)-Form dihydrochloride
CAS Registry Number: 130018-87-0
Additional Names: Levocetirizine hydrochloride
Manufacturers' Codes: UCB-28556
Trademarks: Xusal (UCB); Xyzal (UCB)
Properties: mp 229.3°. [a]D25 -12.79° (c = 1 in water).
Melting point: mp 229.3°
Optical Rotation: [a]D25 -12.79° (c = 1 in water)
 
Therap-Cat: Antihistaminic.
Keywords: Antihistaminic; Piperazines.

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