2022. Cetirizine

Nomenclature

CAS number: 83881-51-0
[2-[4-[(4-Chlorophenyl)phenylmethyl]-1-piperazinyl]ethoxy]acetic acid; [2-[4-(p-chloro-α-phenylbenzyl)-1-piperazinyl]ethoxy]acetic acid.
C21H25ClN2O3; mol wt 388.89.
C 64.86%, H 6.48%, Cl 9.12%, N 7.20%, O 12.34%.

Description and 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).

Chemical structure

Properties

Crystals from ethanol, mp 110-115°.

Derivative

Dihydrochloride.

Nomenclature

CAS number: 83881-52-1
P-071; Alerlisin (Prodes); Formistin (Formenti); Reactine (Pfizer); Virlix (Sanofi-Synthelabo); Zirtek (UCB); Zyrtec (Pfizer); Zyrlex (UCB).
C21H25ClN2O3.2HCl; mol wt 461.81.
C 54.62%, H 5.89%, Cl 23.03%, N 6.07%, O 10.39%.

Properties

Crystals from isopropanol, mp 225°. Sol in water.

Derivative

(R)-Form.

Nomenclature

CAS number: 130018-77-8
Levocetirizine; (-)-cetirizine.

Derivative

(R)-Form dihydrochloride.

Nomenclature

CAS number: 130018-87-0
Levocetirizine hydrochloride; UCB-28556; Xusal (UCB); Xyzal (UCB).

Properties

mp 229.3°. [α]D25 -12.79° (c = 1 in water).

Therapeutic Category

Antihistaminic.

Keywords

Antihistaminic; Piperazines