Liarozole

• CAT Number: M024780
• CAS Number: 115575-11-6
• Molecular Formula: C17H13ClN4
• Molecular Weight: 308.769
• Purity: ≥95%
• Target: Vitamin D Related/Nuclear Receptor
• Storage: -20°C
• IUPAC Name: 6-[(3-chlorophenyl)-imidazol-1-ylmethyl]-1H-benzimidazole
• InChI: 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)
• InChIKey: UGFHIPBXIWJXNA-UHFFFAOYSA-N
• SMILES: C1=CC(=CC(=C1)Cl)C(C2=CC3=C(C=C2)N=CN3)N4C=CN=C4

Liarozole is a benzimidazole derivative with potential antineoplastic activity. As a retinoic acid metabolism blocking agent (RAMBA), liarozole inhibits cytochrome P450-dependent all-trans-retinoic acid (ATRA)-4-hydroxylase, resulting in an increase in endogenous ATRA production, inhibition of cell proliferation, and induction of cell differentiation. This agent also inhibits aromatase, the enzyme that catalyzes the final, rate-limiting step in estrogen biosynthesis. Check for active clinical trials or closed clinical trials using this agent. (NCI Thesaurus)

Reference

1:Liarozole inhibits transforming growth factor-β3–mediated extracellular matrix formation in human three-dimensional leiomyoma cultures. Levy G, Malik M, Britten J, Gilden M, Segars J, Catherino WH.Fertil Steril. 2014 Jul;102(1):272-281.e2. doi: 10.1016/j.fertnstert.2014.03.042. Epub 2014 May 10. PMID: 24825427 Free PMC Article2:Oral liarozole in the treatment of patients with moderate/severe lamellar ichthyosis: results of a randomized, double-blind, multinational, placebo-controlled phase II/III trial. Vahlquist A, Blockhuys S, Steijlen P, van Rossem K, Didona B, Blanco D, Traupe H.Br J Dermatol. 2014 Jan;170(1):173-81. doi: 10.1111/bjd.12626. PMID: 24102348 Free PMC Article3:Leiomyoma fibrosis inhibited by liarozole, a retinoic acid metabolic blocking agent. Gilden M, Malik M, Britten J, Delgado T, Levy G, Catherino WH.Fertil Steril. 2012 Dec;98(6):1557-62. doi: 10.1016/j.fertnstert.2012.07.1132. Epub 2012 Aug 25. PMID: 22925684 4:Expression of retinoid-regulated genes in lamellar ichthyosis vs. healthy control epidermis: changes after oral treatment with liarozole. Pavez Loriè E, Gånemo A, Borgers M, Wouters L, Blockhuys S, van de Plassche L, Törmä H, Vahlquist A.Acta Derm Venereol. 2009;89(1):12-20. doi: 10.2340/00015555-0573. PMID: 19197536 Free Article5:[Enantiomeric separation of liarozole on amylose chiral stationary phase]. Chen Y, Ma Z, An F, Guo X.Se Pu. 2008 Sep;26(5):643-5. Chinese. PMID: 19160771 6:Effects of liarozole fumarate (R85246) in combination with tamoxifen on N-methyl-N-nitrosourea (MNU)-induced mammary carcinoma and uterus in the rat model. Goss PE, Strasser-Weippl K, Qi S, Hu H.BMC Cancer. 2007 Jan 31;7:26. PMID: 17266767 Free PMC Article7:Oral liarozole vs. acitretin in the treatment of ichthyosis: a phase II/III multicentre, double-blind, randomized, active-controlled study. Verfaille CJ, Vanhoutte FP, Blanchet-Bardon C, van Steensel MA, Steijlen PM.Br J Dermatol. 2007 May;156(5):965-73. Epub 2007 Jan 30. PMID: 17263800 8:Topical liarozole in ichthyosis: a double-blind, left-right comparative study followed by a long-term open maintenance study. Lucker GP, Verfaille CJ, Heremans AM, Vanhoutte FP, Boegheim JP, Steijlen PP.Br J Dermatol. 2005 Mar;152(3):566-9. No abstract available. PMID: 15787831 9: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. Pignatello MA, Kauffman FC, Levin AA.Toxicol Appl Pharmacol. 2002 Feb 1;178(3):186-94. PMID: 11858735 10:Oral liarozole in the treatment of palmoplantar pustular psoriasis: a randomized, double-blind, placebo-controlled study. Bhushan M, Burden AD, McElhone K, James R, Vanhoutte FP, Griffiths CE.Br J Dermatol. 2001 Oct;145(4):546-53. PMID: 11703279