Liarozole

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

MedKoo CAT#: 205976

CAS#: 115575-11-6

Description: 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)


Chemical Structure

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Liarozole
CAS# 115575-11-6

Theoretical Analysis

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

Size Price Shipping out time Quantity
Inquire bulk and customized quantity

Pricing updated 2021-02-26. Prices are subject to change without notice.

Liarozole is not in stock, but may be available through custom synthesis. For cost-effective reason, minimum 1 gram order is requested. The product will be characterized by NMR, HPLC and MS analysis. Purity (HPLC) is usually >98%. CoA, QC data, MSDS will be provided when product is successfully made. The estimated lead time is 2-3 months. Please send email to sales@medkoo.com to inquire quote.

Related CAS #: 145858-50-0 (HCl)   115575-11-6 (free base)  

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

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).

HS Tariff Code:
2934.99.9001

Handling Instructions:

Preparing Stock Solutions

The following data is based on the product molecular weight 308.76492 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.

Select a batch to recalculate based on the batch molecular weight:
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

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 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.

Liarozole

10mg / Not available


Additional Information