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MedKoo Cat#: 461101 | Name: Liarozole fumarate

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Liarozole fumarate is a retinoic acid metabolism blocking agent (RAMBA) and aromatase inhibitor.

Chemical Structure

Liarozole fumarate
Liarozole fumarate
CAS#145858-52-2

Theoretical Analysis

MedKoo Cat#: 461101

Name: Liarozole fumarate

CAS#: 145858-52-2

Chemical Formula: C46H38Cl2N8O12

Exact Mass: 964.1986

Molecular Weight: 965.75

Elemental Analysis: C, 57.21; H, 3.97; Cl, 7.34; N, 11.60; O, 19.88

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
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Synonym
Liarozole fumarate; Liazal; R 85246; R-85246; R85246;
IUPAC/Chemical Name
6-((3-chlorophenyl)(1H-imidazol-1-yl)methyl)-1H-benzo[d]imidazole sesquifumarate
InChi Key
IDTXURCCJVODEQ-VQYXCCSOSA-N
InChi Code
InChI=1S/2C17H13ClN4.3C4H4O4/c2*18-14-3-1-2-12(8-14)17(22-7-6-19-11-22)13-4-5-15-16(9-13)21-10-20-15;3*5-3(6)1-2-4(7)8/h2*1-11,17H,(H,20,21);3*1-2H,(H,5,6)(H,7,8)/b;;3*2-1+
SMILES Code
OC(/C=C/C(O)=O)=O.OC(/C=C/C(O)=O)=O.OC(/C=C/C(O)=O)=O.Clc1cc(C(n2cncc2)c(cc3)cc4c3nc[nH]4)ccc1.Clc5cc(C(n6cncc6)c(cc7)cc8c7nc[nH]8)ccc5
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
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
Shelf Life
>3 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).
HS Tariff Code
2934.99.03.00
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 965.75 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
1: Goss PE, Oza A, Goel R, Nabholtz JM, De Coster R, Bruynseels J, Reid C, Wadden N, Crump M, Tye LM. Liarozole fumarate (R85246): a novel imidazole in the treatment of receptor positive postmenopausal metastatic breast cancer. Breast Cancer Res Treat. 2000 Jan;59(1):55-68. PubMed PMID: 10752680. 2: Van Wauwe J, Coene MC, Cools W, Goossens J, Lauwers W, Le Jeune L, Van Hove C, Van Nyen G. Liarozole fumarate inhibits the metabolism of 4-keto-all-trans-retinoic acid. Biochem Pharmacol. 1994 Feb 11;47(4):737-41. PubMed PMID: 8129749. 3: Vahlquist A, Blockhuys S, Steijlen P, van Rossem K, Didona B, Blanco D, Traupe H. 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. Br J Dermatol. 2014 Jan;170(1):173-81. doi: 10.1111/bjd.12626. PubMed PMID: 24102348; PubMed Central PMCID: PMC4232915. 4: 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. 5: Levy G, Malik M, Britten J, Gilden M, Segars J, Catherino WH. Liarozole inhibits transforming growth factor-β3--mediated extracellular matrix formation in human three-dimensional leiomyoma cultures. Fertil Steril. 2014 Jul;102(1):272-281.e2. doi: 10.1016/j.fertnstert.2014.03.042. Epub 2014 May 10. PubMed PMID: 24825427; PubMed Central PMCID: PMC4152900. 6: 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. 7: 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. 8: Liarozole. Liarozole fumarate, Liazal, R 75251, R 85246. Drugs R D. 1999 Dec;2(6):427-30. PubMed PMID: 10763459. 9: Bryson HM, Wagstaff AJ. Liarozole. Drugs Aging. 1996 Dec;9(6):478-84; discussion 485. PubMed PMID: 8972247. 10: De Coster R, Wouters W, Van Ginckel R, End D, Krekels M, Coene MC, Bowden C. Experimental studies with liarozole (R 75,251): an antitumoral agent which inhibits retinoic acid breakdown. J Steroid Biochem Mol Biol. 1992 Sep;43(1-3):197-201. Review. PubMed PMID: 1525060. 11: Denis L, Debruyne F, De Porre P, Bruynseels J. Early clinical experience with liarozole (Liazal) in patients with progressive prostate cancer. Eur J Cancer. 1998 Mar;34(4):469-75. PubMed PMID: 9713295. 12: 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. 13: Lucker GP, Heremans AM, Boegheim PJ, van de Kerkhof PC, Steijlen PM. Oral treatment of ichthyosis by the cytochrome P-450 inhibitor liarozole. Br J Dermatol. 1997 Jan;136(1):71-5. PubMed PMID: 9039298. 14: Stearns ME, Wang M, Fudge K. Liarozole and 13-cis-retinoic acid anti-prostatic tumor activity. Cancer Res. 1993 Jul 1;53(13):3073-7. Erratum in: Cancer Res 1993 Dec 1;53(23):5831. PubMed PMID: 8319215. 15: Van Wauwe J, Van Nyen G, Coene MC, Stoppie P, Cools W, Goossens J, Borghgraef P, Janssen PA. Liarozole, an inhibitor of retinoic acid metabolism, exerts retinoid-mimetic effects in vivo. J Pharmacol Exp Ther. 1992 May;261(2):773-9. PubMed PMID: 1374473. 16: O'Byrne KJ, Han C, Mitchell K, Lane D, Carmichael J, Harris AL, Talbot DC. Phase II study of liarozole in advanced non-small cell lung cancer. Eur J Cancer. 1998 Aug;34(9):1463-6. PubMed PMID: 9849433. 17: 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. 18: 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. 19: Mahler C, Verhelst J, Denis L. Ketoconazole and liarozole in the treatment of advanced prostatic cancer. Cancer. 1993 Feb 1;71(3 Suppl):1068-73. Review. PubMed PMID: 8428329. 20: Van heusden J, Borgers M, Ramaekers F, Xhonneux B, Wouters W, De Coster R, Smets G. Liarozole potentiates the all-trans-retinoic acid-induced structural remodelling in human breast carcinoma MCF-7 cells in vitro. Eur J Cell Biol. 1996 Sep;71(1):89-98. PubMed PMID: 8884182.

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