Etalocib

• CAT Number: M038594
• CAS Number: 161172-51-6
• Molecular Formula: C33H33FO6
• Molecular Weight: 544.619
• Purity: ≥95%
• Storage: -20°C
• IUPAC Name: 2-[3-[3-[2-ethyl-4-(4-fluorophenyl)-5-hydroxyphenoxy]propoxy]-2-propylphenoxy]benzoic acid
• InChI: InChI=1S/C33H33FO6/c1-3-9-25-29(12-7-13-30(25)40-31-11-6-5-10-26(31)33(36)37)38-18-8-19-39-32-21-28(35)27(20-22(32)4-2)23-14-16-24(34)17-15-23/h5-7,10-17,20-21,35H,3-4,8-9,18-19H2,1-2H3,(H,36,37)
• InChIKey: YFIZRWPXUYFCSN-UHFFFAOYSA-N
• SMILES: CCCC1=C(C=CC=C1OCCCOC2=C(C=C(C(=C2)O)C3=CC=C(C=C3)F)CC)OC4=CC=CC=C4C(=O)O

Etalocib, also known as LY293111 and VML295, is 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.

Reference

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.