Liarozole

Names

[ Name ]:
Liarozole

[Synonym ]:
MFCD00864664

Biological Activity

[Description]:

Liarozole (R75251; R85246) is an imidazole derivative and orally active retinoic acid (RA) metabolism-blocking agent (RAMBA). Liarozole inhibits the cytochrome P450 (CYP26)-dependent 4-hydroxylation of retinoic acid (IC50=7 μM), resulting in increased tissue levels of retinoic acid. Liarozole shows antitumoral properties[1][2][3].

[Related Catalog]:

Research Areas >> Cancer

Signaling Pathways >> Metabolic Enzyme/Protease >> Cytochrome P450

Research Areas >> Inflammation/Immunology

Research Areas >> Metabolic Disease

Signaling Pathways >> Metabolic Enzyme/Protease >> RAR/RXR

[Target]

Cytochrome P450 (CYP26):7 μM (IC50)

[In Vitro]

Liarozole (0.01~10 μM; 9 days; MCF-7 cells) inhibits cells proliferation[3]. Liarozole (1 μM; 4 days; mesenchymal cells) completely inhibits chondrogenesis[4]. Cell Proliferation Assay[3] Cell Line: MCF-7 cells Concentration: 0.01~10 μM Incubation Time: 9 days Result: Had an effect of 35% inhibition at 10 μM on cell proliferation. Cell Differentiation Assay[4] Cell Line: Mesenchymal cells Concentration: 1 μM Incubation Time: 4 days Result: Completely inhibited chondrogenesis.

[In Vivo]

Liarozole (5-20 mg/kg; p.o.; 3 days) reverses the vaginal keratosis caused by estrogen stimulation[5]. Liarozole (40 mg/kg; p.o.; 21 days) reduces tumor burden substantially[6]. Animal Model: Ovariectomized rats Dosage: 5~20 mg/kg Administration: P.o.; 3 days Result: Reversed the vaginal keratosis caused by estrogen stimulation. Animal Model: SCID mice Dosage: 40 mg/kg Administration: P.o.; 21 days Result: Inhibited tumor growth and survival.

[References]

[1]. Kuijpers AL, et al. The effects of oral liarozole on epidermal proliferation and differentiation in severe plaque psoriasis are comparable with those of acitretin. Br J Dermatol. 1998;139(3):380-389.

[2]. Lucker GP, et al. Oral treatment of ichthyosis by the cytochrome P-450 inhibitor liarozole. Br J Dermatol. 1997;136(1):71-75.

[3]. Wouters W, et al. Effects of liarozole, a new antitumoral compound, on retinoic acid-induced inhibition of cell growth and on retinoic acid metabolism in MCF-7 human breast cancer cells. Cancer Res. 1992;52(10):2841-2846.

[4]. Pignatello MA, et al. Liarozole markedly increases all trans-retinoic acid toxicity in mouse limb bud cell cultures: a model to explain the potency of the aromatic retinoid (E)-4-[2-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthylenyl)-1-propenyl] benzoic acid. Toxicol Appl Pharmacol. 2002; 178(3):186-194.

[5]. Van Wauwe J, et al. Liarozole, an inhibitor of retinoic acid metabolism, exerts retinoid-mimetic effects in vivo. J Pharmacol Exp Ther. 1992;261(2):773-779.

[6]. Stearns ME, et al. Liarozole and 13-cis-retinoic acid anti-prostatic tumor activity [published correction appears in Cancer Res 1993 Dec 1;53(23):5831]. Cancer Res. 1993;53(13):3073-3077.

Chemical & Physical Properties

[ Density]:
1.36g/cm3

[ Boiling Point ]:
578.2ºC at 760mmHg

[ Molecular Formula ]:
C₁₇H₁₃ClN₄

[ Molecular Weight ]:
308.76500

[ Flash Point ]:
303.5ºC

[ Exact Mass ]:
308.08300

[ PSA ]:
46.50000

[ LogP ]:
4.05050

[ Vapour Pressure ]:
9.2E-13mmHg at 25°C

Related Compounds

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