MedKoo Cat#: 205976 Name: Liarozole CAS#: 115575-11-6 Chemical Formula: C17H13ClN4 Exact Mass: 308.08287 Molecular Weight: 308.76492 Elemental Analysis: C, 66.13; H, 4.24; Cl, 11.48; N, 18.15

Synonym: Liarozole; R 75251; R-75251; R75251

IUPAC/Chemical Name: 5-((3-chlorophenyl)(1H-imidazol-1-yl)methyl)-1H-benzo[d]imidazole

InChi Key: UGFHIPBXIWJXNA-UHFFFAOYSA-N

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)

SMILES Code: ClC1=CC(C(C2=CC=C3NC=NC3=C2)N4C=CN=C4)=CC=C1

Technical Data

Appearance: Solid powder

Purity: >98%

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO, not in water

Shelf Life: >5 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

Harmonized System Code: 293490

Additional Information

References

 1: Gilden M, Malik M, Britten J, Delgado T, Levy G, Catherino WH. Leiomyoma fibrosis inhibited by liarozole, a retinoic acid metabolic blocking agent. Fertil Steril. 2012 Dec;98(6):1557-62. doi: 10.1016/j.fertnstert.2012.07.1132. Epub 2012 Aug 25. PubMed PMID: 22925684.

2: Pavez Loriè E, Gånemo A, Borgers M, Wouters L, Blockhuys S, van de Plassche L, Törmä H, Vahlquist A. Expression of retinoid-regulated genes in lamellar ichthyosis vs. healthy control epidermis: changes after oral treatment with liarozole. Acta Derm Venereol. 2009;89(1):12-20. doi: 10.2340/00015555-0573. PubMed PMID: 19197536.

3: Chen Y, Ma Z, An F, Guo X. [Enantiomeric separation of liarozole on amylose chiral stationary phase]. Se Pu. 2008 Sep;26(5):643-5. Chinese. PubMed PMID: 19160771.

4: Goss PE, Strasser-Weippl K, Qi S, Hu H. Effects of liarozole fumarate (R85246) in combination with tamoxifen on N-methyl-N-nitrosourea (MNU)-induced mammary carcinoma and uterus in the rat model. BMC Cancer. 2007 Jan 31;7:26. PubMed PMID: 17266767; PubMed Central PMCID: PMC1796889.

5: Verfaille CJ, Vanhoutte FP, Blanchet-Bardon C, van Steensel MA, Steijlen PM. Oral liarozole vs. acitretin in the treatment of ichthyosis: a phase II/III multicentre, double-blind, randomized, active-controlled study. Br J Dermatol. 2007 May;156(5):965-73. Epub 2007 Jan 30. PubMed PMID: 17263800.

6: Lucker GP, Verfaille CJ, Heremans AM, Vanhoutte FP, Boegheim JP, Steijlen PP. Topical liarozole in ichthyosis: a double-blind, left-right comparative study followed by a long-term open maintenance study. Br J Dermatol. 2005 Mar;152(3):566-9. PubMed PMID: 15787831.

7: Pignatello MA, Kauffman FC, Levin AA. 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 Feb 1;178(3):186-94. PubMed PMID: 11858735.

8: Bhushan M, Burden AD, McElhone K, James R, Vanhoutte FP, Griffiths CE. Oral liarozole in the treatment of palmoplantar pustular psoriasis: a randomized, double-blind, placebo-controlled study. Br J Dermatol. 2001 Oct;145(4):546-53. PubMed PMID: 11703279.

9: Goss PE, Strasser K, Marques R, Clemons M, Oza A, Goel R, Blackstein M, Kaizer L, Sterns EE, Nabholtz JM, De Coster R, Crump M, Abdolell M, Qi S. Liarozole fumarate (R85246): in the treatment of ER negative, tamoxifen refractory or chemotherapy resistant postmenopausal metastatic breast cancer. Breast Cancer Res Treat. 2000 Nov;64(2):177-88. PubMed PMID: 11194453.

10: Berth-Jones J, Todd G, Hutchinson PE, Thestrup-Pedersen K, Vanhoutte FP. Treatment of psoriasis with oral liarozole: a dose-ranging study. Br J Dermatol. 2000 Dec;143(6):1170-6. PubMed PMID: 11122017.