A CYP26A1 inhibitor
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Liarozole

Item No. 29491

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
6-[(3-chlorophenyl)-1H-imidazol-1-ylmethyl]-1H-benzimidazole
CAS Number
115575-11-6
Synonyms
  • R 75251
Molecular Formula
C17H13ClN4
Formula Weight
308.8
Purity
≥98%
Formulation
A solid
Solubility(Learn about Variance in Solubility)
DMSO: soluble
SMILES
ClC1=CC=CC(C(N2C=NC=C2)C3=CC=C(N=CN4)C4=C3)=C1
InChi Code
InChI=1S/C17H13ClN4/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)
InChi Key
UGFHIPBXIWJXNA-UHFFFAOYSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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Certificates of Analysis & Batch Specific Data

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    5 mg

    $98

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    10 mg

    $176

    Add

    50 mg

    $784

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    100 mg

    $1,077

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    Product Description

    Liarozole is an inhibitor of the cytochrome P450 (CYP) isoform CYP26A1 (IC50 = 2.1 µM), an enzyme involved in the metabolism of all-trans retinoic acid (Item No. 11017).1 It also inhibits the production of estradiol (Item No. 10006315) induced by follicle-stimulating hormone (FSH) in rat granulosa cells and testosterone and androstenedione production induced by human chorionic gonadotropin (hCG) in rat testicular cells (IC50s = 0.4, 2.3, and 0.7 µM, respectively).2 Liarozole enhances the antiproliferative activity of all-trans retinoic acid in MCF-7 breast cancer cells.3 It decreases plasma levels of retinoic acid in rats in a dose-dependent manner.4 Liarozole (5 and 20 mg/kg) decreases estradiol undecylate-induced vaginal keratinization in ovariectomized rats.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Thatcher, J.E., Buttrick, B., Shaffer, S.A., et al. Substrate specificity and ligand interactions of CYP26A1, the human liver retinoic acid hydroxylase. Mol. Pharmacol. 80(2), 228-239 (2011).

    2. Bruynseels, J., De Coster, R., Rooy, P.V., et al. R 75251, a new inhibitor of steroid biosynthesis. Prostate 16(4), 345-357 (1990).

    3. Wouters, W., van Dun, J., Dillen, A., 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. 52(10), 2841-2846 (1992).

    4. Van Wauwe, J., Van Nyen, G., Coene, M.C., et al. Liarozole, an inhibitor of retinoic acid metabolism, exerts retinoid-mimetic effects in vivo. J. Pharmacol. Exp. Ther. 261(2), 773-779 (1992).