Etalocib | LY293111 | CAS#161172-51-6

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Etalocib

Description of LY293111: LY293111, a novel diaryl ether carboxylic acid derivative, is a potent and selective inhibitor of the lipoxygenase pathway either directly through 5'-lipoxygenase or via antagonism of the leukotriene B4 (LTB4) receptor. LY293111 has antineoplastic activity in a variety of preclinical models.

Current developer: El Lilly

MedKoo Code#: 201310

Name: Etalocib

CAS#: 161172-51-6

Synonym: VML 295；PDSP1_001237；PDSP2_001221；LY293111。 LY 293111。

IUPAC/Chemical name:

sodium 2-(3-(3-((5-ethyl-4'-fluoro-2-hydroxy-[1,1'-biphenyl]-4-yl)oxy)propoxy)-2-propylphenoxy)benzoate

Chemical structure:

Theoretical analysis

Etalocib sodium (salt from)

Chemical Formula: C33H32FNaO6

Molecular Weight: 566.59

Elemental Analysis: C, 69.95; H, 5.69; F, 3.35; Na, 4.06; O, 16.94

Etalocib (free acid form0

Chemical Formula: C18H39NO

Exact Mass: 285.30316

Molecular Weight: 285.51

Elemental Analysis: C, 75.72; H, 13.77; N, 4.91; O, 5.60

Availability and price:

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Quality control data:

Product will be shipped with supporting analytical data.

Information about this agent

Etalocib is a leukotriene B4 receptor antagonist, which was found to be safe and tolerable in Phase I clinical trials. LY293111 inhibited proliferation of both ALK(+) and ALK(-) ALCL cell in a dose-dependent fashion and induced complete G(1)-S cell cycle arrest, which was accompanied by upregulation of p27 and downregulation of cyclin E. Pretreatment with LY293111 for 4 h resulted in profound inhibition of serum-induced phosphorylation of extracellular-regulated kinases-1 and 2 and Akt and a concomitant increase in the phosphorylation of the stress-activated kinase c-jun N-terminal kinases (JNK). Simultaneously, LY293111 induced caspase-dependent apoptosis via activation of the intrinsic pathway, including early loss of mitochondrial inner transmembrane potential and the production of reactive oxygen species (ROS), cleavage of caspases-9, -3, poly ADP-ribose polymerase (PARP) and X-linked inhibitor of apoptosis. The phospho-JNK inhibitor SP600125 partially protected Sup-M2 cells from LY293111-induced apoptosis, PARP cleavage and ROS generation, suggesting a role for JNK in LY293111-induced cell death. These results warrant further studies of LY293111 in ALCL. see:http://www.ncbi.nlm.nih.gov/pubmed/16151469.

References

1: Saif MW, Oettle H, Vervenne WL, Thomas JP, Spitzer G, Visseren-Grul C, Enas N, Richards DA. Randomized double-blind phase II trial comparing gemcitabine plus LY293111 versus gemcitabine plus placebo in advanced adenocarcinoma of the pancreas. Cancer J. 2009 Jul-Aug;15(4):339-43. PubMed PMID: 19672152.

2: Adrian TE, Hennig R, Friess H, Ding X. The Role of PPARgamma Receptors and Leukotriene B(4) Receptors in Mediating the Effects of LY293111 in Pancreatic Cancer. PPAR Res. 2008;2008:827096. Epub 2009 Jan 27. PubMed PMID: 19190780; PubMed Central PMCID: PMC2631651.

3: Tong WG, Ding XZ, Talamonti MS, Bell RH, Adrian TE. Leukotriene B4 receptor antagonist LY293111 induces S-phase cell cycle arrest and apoptosis in human pancreatic cancer cells. Anticancer Drugs. 2007 Jun;18(5):535-41. PubMed PMID: 17414622.

4: Baetz T, Eisenhauer E, Siu L, MacLean M, Doppler K, Walsh W, Fisher B, Khan AZ, de Alwis DP, Weitzman A, Brail LH, Moore M. A phase I study of oral LY293111 given daily in combination with irinotecan in patients with solid tumours. Invest New Drugs. 2007 Jun;25(3):217-25. Epub 2006 Dec 5. PubMed PMID: 17146732.

5: Zhang W, McQueen T, Schober W, Rassidakis G, Andreeff M, Konopleva M. Leukotriene B4 receptor inhibitor LY293111 induces cell cycle arrest and apoptosis in human anaplastic large-cell lymphoma cells via JNK phosphorylation. Leukemia. 2005 Nov;19(11):1977-84. PubMed PMID: 16151469.

6: Hennig R, Ventura J, Segersvard R, Ward E, Ding XZ, Rao SM, Jovanovic BD, Iwamura T, Talamonti MS, Bell RH Jr, Adrian TE. LY293111 improves efficacy of gemcitabine therapy on pancreatic cancer in a fluorescent orthotopic model in athymic mice. Neoplasia. 2005 Apr;7(4):417-25. PubMed PMID: 15967119; PubMed Central PMCID: PMC1501143.

7: Schwartz GK, Weitzman A, O'Reilly E, Brail L, de Alwis DP, Cleverly A, Barile-Thiem B, Vinciguerra V, Budman DR. Phase I and pharmacokinetic study of LY293111, an orally bioavailable LTB4 receptor antagonist, in patients with advanced solid tumors. J Clin Oncol. 2005 Aug 10;23(23):5365-73. Epub 2005 Jun 6. PubMed PMID: 15939925.

8: Ding XZ, Talamonti MS, Bell RH Jr, Adrian TE. A novel anti-pancreatic cancer agent, LY293111. Anticancer Drugs. 2005 Jun;16(5):467-73. Review. PubMed PMID: 15846111.

9: Hennig R, Ding XZ, Tong WG, Witt RC, Jovanovic BD, Adrian TE. Effect of LY293111 in combination with gemcitabine in colonic cancer. Cancer Lett. 2004 Jul 8;210(1):41-6. PubMed PMID: 15172119.

10: Tong WG, Ding XZ, Hennig R, Witt RC, Standop J, Pour PM, Adrian TE. Leukotriene B4 receptor antagonist LY293111 inhibits proliferation and induces apoptosis in human pancreatic cancer cells. Clin Cancer Res. 2002 Oct;8(10):3232-42. PubMed PMID: 12374694.

11: Jackson WT, Froelich LL, Boyd RJ, Schrementi JP, Saussy DL Jr, Schultz RM, Sawyer JS, Sofia MJ, Herron DK, Goodson T Jr, Snyder DW, Pechous PA, Spaethe SM, Roman CR, Fleisch JH. Pharmacologic actions of the second-generation leukotriene B4 receptor antagonist LY293111: in vitro studies. J Pharmacol Exp Ther. 1999 Jan;288(1):286-94. PubMed PMID: 9862783.

12: van Pelt JP, de Jong EM, van Erp PE, Mitchell MI, Marder P, Spaethe SM, van Hooijdonk CA, Kuijpers AL, van de Kerkhof PC. The regulation of CD11b integrin levels on human blood leukocytes and leukotriene B4-stimulated skin by a specific leukotriene B4 receptor antagonist (LY293111). Biochem Pharmacol. 1997 Apr 4;53(7):1005-12. PubMed PMID: 9174114.

13: Sofia MJ, Floreancig P, Bach N, Baker SR, Nelson K, Sawyer JS, Baldwin R, Cockerham SL, Fleisch JH, Froelich LL, Jackson WT, Marder P, Roman CR, Saussy DL Jr, Silbaugh SA, Spaethe SM, Stengel PW. The discovery of LY293111, a novel, potent and orally active leukotriene B4 receptor antagonist of the biphenylphenol class. Adv Exp Med Biol. 1997;400A:381-6. PubMed PMID: 9547580.

14: Evans DJ, Barnes PJ, Spaethe SM, van Alstyne EL, Mitchell MI, O'Connor BJ. Effect of a leukotriene B4 receptor antagonist, LY293111, on allergen induced responses in asthma. Thorax. 1996 Dec;51(12):1178-84. PubMed PMID: 8994512; PubMed Central PMCID: PMC472760.

15: Marder P, Spaethe SM, Froelich LL, Cerimele BJ, Petersen BH, Tanner T, Lucas RA. Inhibition of ex vivo neutrophil activation by oral LY293111, a novel leukotriene B4 receptor antagonist. Br J Clin Pharmacol. 1996 Oct;42(4):457-64. PubMed PMID: 8904617; PubMed Central PMCID: PMC2042691.

16: Marder P, Sawyer JS, Froelich LL, Mann LL, Spaethe SM. Blockade of human neutrophil activation by 2-[2-propyl-3-[3-[2-ethyl-4-(4-fluorophenyl)-5- hydroxyphenoxy]propoxy]phenoxy]benzoic acid (LY293111), a novel leukotriene B4 receptor antagonist. Biochem Pharmacol. 1995 May 26;49(11):1683-90. PubMed PMID: 7786309.

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