4068. Fexofenadine

Nomenclature

CAS number: 83799-24-0
α,α-Dimethyl-4-[1-hydroxy-4-[4-(hydroxydiphenylmethyl)-1-piperidinyl]butyl]benzeneacetic acid; carboxyterfenadine; terfenadine carboxylate; MDL-16455.
C32H39NO4; mol wt 501.66.
C 76.61%, H 7.84%, N 2.79%, O 12.76%.

Description and references

Nonsedating-type histamine H1-receptor antagonist. Prepn: A.A. Carr et al., DE 3007498; eidem, US 4254129 (1980, 1981 both to Richardson-Merrell). Identification as active metabolite of terfenadine, q.v.: D. A. Garteiz et al., Arzneim.-Forsch. 32, 1185 (1982). Synthesis: S. H. Kawai et al., J. Org. Chem. 59, 2620 (1994). HPLC separation from terfenadine: K. Y. Chan et al., J. Chromatogr. 571, 291 (1991); determn in biological fluids: A. Terhechte, G. Blaschke, J. Chromatogr. A 694, 219 (1995). Effects on cardiac K+ channels: D. Rampe et al., Mol. Pharmacol. 44, 1240 (1993). Comparative analysis of cardiotoxic potential: J. A. Hey et al., Arzneim.-Forsch. 46, 153 (1996). Clinical pharmacology in children: F. E. R. Simons et al., J. Allergy Clin. Immunol. 98, 1062 (1996).

Chemical structure

Properties

Crystals from methanol-butanone, mp 195-197° (Carr); also reported as white crystals from methanol, mp 142-143° (Kawai).

Derivative

Hydrochloride.

Nomenclature

CAS number: 153439-40-8
Allegra (Aventis); Telfast (Aventis).
C32H39NO4.HCl; mol wt 538.12.
C 71.42%, H 7.49%, N 2.60%, O 11.89%, Cl 6.59%.

Therapeutic Category

Antihistaminic.

Keywords

Antihistaminic