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MedKoo Cat#: 598805 | Name: Liarozole HCl

Description:

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

Liarozole HCl 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

Liarozole HCl
Liarozole HCl
CAS#145858-50-0

Theoretical Analysis

MedKoo Cat#: 598805

Name: Liarozole HCl

CAS#: 145858-50-0

Chemical Formula: C17H14Cl2N4

Exact Mass: 344.0596

Molecular Weight: 345.22

Elemental Analysis: C, 59.15; H, 4.09; Cl, 20.54; N, 16.23

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 #
145858-50-0 (HCl) 115575-11-6 (free base)
Synonym
Liarozole hydrochloride; Liarozole HCl; R 75251; R-75251; R75251;
IUPAC/Chemical Name
5-((3-chlorophenyl)(1H-imidazol-1-yl)methyl)-1H-benzo[d]imidazole hydrochloride
InChi Key
OTSZCHORPMQCBZ-UHFFFAOYSA-N
InChi Code
InChI=1S/C17H13ClN4.ClH/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);1H
SMILES Code
ClC1=CC(C(C2=CC=C3C(N=CN3)=C2)N4C=CN=C4)=CC=C1.[H]Cl
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 345.22 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: 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, GÃ¥nemo 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.