5475. Liarozole

Nomenclature

CAS number: 115575-11-6
5-[(3-Chlorophenyl)-1H-imidazol-1-ylmethyl]-1H-benzimidazole; (±)-5-(m-chloro-α-imidazol-1-ylbenzyl)benzimidazole.
C17H13ClN4; mol wt 308.76.
C 66.13%, H 4.24%, Cl 11.48%, N 18.15%.

Description and references

Inhibits cytochrome P450-dependent enzymes involved in steroid biosynthesis and retinoic acid catabolism. Prepn: A. H. M. Raeymaekers et al., EP 260744; eidem, US 4859684 (1988, 1989 both to Janssen). In vivo antitumor activity: R. Van Ginckel et al., Prostate 16, 313 (1990). Pharmacology and effect on steroid synthesis: J. Bruynseels et al., ibid. 345; and effect on retinoic acid: R. De Coster et al., J. Steroid Biochem. Mol. Biol. 43, 197 (1992). Clinical evaluation in prostate cancer: C. Mahler et al., Cancer 71, 1068 (1993); in psoriasis: P. Dockx et al., Br. J. Dermatol. 133, 426 (1995); in combination therapy for malignant brain tumors: M. E. Westarp et al., Onkologie 16, 22 (1993).

Chemical structure

Properties

mp 108.2°.

Derivative

Fumarate.

Nomenclature

CAS number: 145858-52-2
R-85246; Liazal (Janssen).
2C17H13ClN4.3C4H4O4; mol wt 965.75.
C 57.21%, H 3.97%, Cl 7.34%, N 11.60%, O 19.88%.

Derivative

Hydrochloride.

Nomenclature

CAS number: 145858-50-0
R-75251.
C17H13ClN4.HCl; mol wt 345.23.
C 59.14%, H 4.09%, Cl 20.54%, N 16.23%.

Therapeutic Category

Antineoplastic.

Keywords

Antineoplastic