Liarozole dihydrochloride

• CAT Number: I046131
• CAS Number: 1883548-96-6
• Molecular Formula: C17H15Cl3N4
• Molecular Weight: 381.69
• Purity: ≥95%
• Synonyms: 6-[(3-chlorophenyl)-imidazol-1-ylmethyl]-1H-benzimidazole;dihydrochloride
• InChI: InChI=1S/C17H13ClN4.2ClH/c18-14-3-1-2-12(8-14)17(22-7-6-19-11-22)13-4-5-15-16(9-13)21-10-20-15;;/h1-11,17H,(H,20,21);2*1H
• InChIKey: NKDMRTVUEJWCCQ-UHFFFAOYSA-N
• SMILES: C1=CC(=CC(=C1)Cl)C(C2=CC3=C(C=C2)N=CN3)N4C=CN=C4.Cl.Cl

Liarozole (R75251) dihydrochloride is an imidazole derivative and orally active retinoic acid (RA) metabolism-blocking agent (RAMBA). Liarozole dihydrochloride inhibits the cytochrome P450 (CYP26)-dependent 4-hydroxylation of RA (IC50=7 μM), resulting in increased tissue levels of RA. Liarozole dihydrochloride shows antitumoral properties[1][2][3].
Liarozole dihydrochloride (0.01~10 μM; 9 days; MCF-7 cells) inhibits cells proliferation[3].
Liarozole dihydrochloride (1 μM; 4 days; mesenchymal cells) completely inhibits chondrogenesis[4].
Liarozole dihydrochloride (5-20 mg/kg; p.o.) reverses the vaginal keratosis caused by estrogen stimulation[5].
Liarozole dihydrochloride (40 mg/kg; p.o.) reduces tumor burden substantially[6].

Reference

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