Etalocib

Etalocib
Names

Preferred IUPAC name 2⁵-Ethyl-1⁴-fluoro-2²-hydroxy-8²-propyl-3,7,9-trioxa-1,10(1),2(1,4),8(1,3)-tetrabenzenadecaphane-10²-carboxylic acid
Other names LY293111 VML 295
Identifiers
CAS Number	161172-51-6^N
3D model (JSmol)	Interactive image
ChEMBL	ChEMBL329123^Y
ChemSpider	154905^Y
IUPHAR/BPS	2948
KEGG	D04074^Y
PubChem CID	177941
UNII	THY6RIW44R^Y
CompTox Dashboard (EPA)	DTXSID70167073
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)^Y Key: YFIZRWPXUYFCSN-UHFFFAOYSA-N^Y
SMILES Fc1ccc(cc1)c4c(O)cc(OCCCOc3cccc(Oc2ccccc2C(=O)O)c3CCC)c(c4)CC
Properties
Chemical formula	C₃₃H₃₃FO₆
Molar mass	544.619 g·mol⁻¹
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). N verify (what is ^YN ?) Infobox references

Chemical compound

Etalocib is a drug candidate that was under development for the treatment of various types of cancer.^[1] It acts as a leukotriene B4 receptor antagonist and a PPARγ agonist.^[2]

Clinical trials were conducted measuring efficacy for treatment of non-small cell lung cancer and pancreatic cancer and the inflammatory conditions asthma, psoriasis, and ulcerative colitis, but were suspended due to lack of efficacy.^[3]

References

^ Jänne, P. A.; Paz-Ares, L; Oh, Y; Eschbach, C; Hirsh, V; Enas, N; Brail, L; von Pawel, J (2014). "Randomized, double-blind, phase II trial comparing gemcitabine-cisplatin plus the LTB4 antagonist LY293111 versus gemcitabine-cisplatin plus placebo in first-line non-small-cell lung cancer". Journal of Thoracic Oncology. 9 (1): 126–31. doi:10.1097/JTO.0000000000000037. PMID 24346102.
^ Adrian, T. E.; Hennig, R; Friess, H; Ding, X (2008). "The Role of PPARgamma Receptors and Leukotriene B(4) Receptors in Mediating the Effects of LY293111 in Pancreatic Cancer". PPAR Research. 2008: 827096. doi:10.1155/2008/827096. PMC 2631651. PMID 19190780.
^ "Etalocib". Adisinsight. Retrieved 31 January 2017.

Drugs for obstructive airway diseases: asthma/COPD (R03)

Adrenergics, inhalants

Short-acting β₂ agonists	Bitolterol Carbuterol Fenoterol Isoetarine Pirbuterol Procaterol Reproterol Rimiterol Salbutamol (albuterol)^#/Levosalbutamol (levalbuterol) Terbutaline Tulobuterol
Long-acting β₂ agonists	Bambuterol Clenbuterol Formoterol/Arformoterol Salmeterol Salmefamol
Ultra-long-acting β₂ agonists	Abediterol Carmoterol Indacaterol Olodaterol Vilanterol
Other	Epinephrine^# Hexoprenaline Isoprenaline (isoproterenol) Orciprenaline (metaproterenol)

Glucocorticoids

Anticholinergics/
muscarinic antagonist

Mast cell stabilizers

Xanthines

Eicosanoid inhibition

Leukotriene antagonists	Montelukast Pranlukast Zafirlukast
Arachidonate 5-lipoxygenase inhibitors	Zileuton
Thromboxane receptor antagonists	Ramatroban Seratrodast
Non-xanthine PDE4 inhibitors	Ibudilast Roflumilast

Others/unknown

Combination products

^#WHO-EM
^‡Withdrawn from market
Clinical trials:
- ^†Phase III
- ^§Never to phase III

Leukotriene signaling modulators

Receptor
(ligands)

BLTTooltip Leukotriene B4 receptor

BLT₁Tooltip Leukotriene B4 receptor 1	Agonists: 12-HETE 20-Hydroxy-LTB₄ Leukotriene B₄ LY-255283 Antagonists: 20-Carboxy-LTB₄ Amelubant CGS-23131 (LY-223982) CGS-25019C CP-105696 CP-195543 Etalocib LY-293111 Moxilubant ONO-4057 RG-14893 RP-69698 SB-209247 SC-53228 Ticolubant U-75302 ZK-158252
BLT₂Tooltip Leukotriene B4 receptor 2	Agonists: 12-HETE 12-HHT 12-HpETE 15-HETE 15-HpETE 20-Hydroxy-LTB₄ Leukotriene B₄ Antagonists: CP-195543 LY-255283 ZK-158252

CysLTTooltip Cysteinyl leukotriene receptor

CysLT₁Tooltip Cysteinyl leukotriene receptor 1	Agonists: Leukotriene C₄ Leukotriene D₄ Leukotriene E₄ Antagonists: Ablukast BAYu9773 BAYu9916 BAYx7195 Cinalukast FPL-55712 ICI-198615 Iralukast LY-170680 Masilukast MK-571 Montelukast ONO-1078 Pobilukast Pranlukast Ritolukast SKF-104353 SR-2640 Sulukast Tipelukast Tomelukast Verlukast Zafirlukast ZD-3523
CysLT₂Tooltip Cysteinyl leukotriene receptor 2	Agonists: Leukotriene C₄ Leukotriene D₄ Leukotriene E₄ Antagonists: BAYu9773 BAYu9916
CysLT_ETooltip Cysteinyl leukotriene receptor E	Agonists: Leukotriene E₄

Enzyme
(inhibitors)

5-LOXTooltip Arachidonate 5-lipoxygenase	2-TEDC Baicalein BW-A4C BW-B70C Caffeic acid CDC CJ-13610 Curcumin Fenleuton Hyperforin Hypericum perforatum (St. John's Wort) Meclofenamic acid (meclofenamate) Minocycline N-Stearoyldopamine Timegadine Zileuton FLAPTooltip Arachidonate 5-lipoxygenase-activating protein inhibitors: AM-103 AM-679 BAYx1005 MK-591 MK-886
12-LOXTooltip Arachidonate 12-lipoxygenase	2-TEDC 3-Methoxytropolone Baicalein CDC
15-LOXTooltip Arachidonate 15-lipoxygenase	2-TEDC CDC Luteolin PD-146176
LTA₄HTooltip Leukotriene A4 hydrolase	Acebilustat Captopril DG-051 Fosinoprilat JNJ-26993135 SA-6541 SC-57461A Ubenimex (bestatin)
LTB₄HTooltip Leukotriene B4 ω-hydroxylase	17-Octadecynoic acid
LTC₄STooltip Leukotriene C4 synthase	Azelastine MK-886
LTC₄HTooltip Leukotriene C4 hydrolase	Acivicin Serine-borate complex
LTD₄Tooltip Leukotriene D4 hydrolase	Cilastatin Ubenimex (bestatin)

Others

Precursors: Linoleic acid
γ-Linolenic acid (gamolenic acid)
Dihomo-γ-linolenic acid
Diacylglycerol
Arachidonic acid
5-HPETE (arachidonic acid 5-hydroperoxide)
Leukotriene A₄

See also: Receptor/signaling modulators; Prostanoid signaling modulators

v t e PPARTooltip Peroxisome proliferator-activated receptor modulators
PPARαTooltip Peroxisome proliferator-activated receptor alpha	Agonists: 15-HETE 15-HpETE Aleglitazar Aluminium clofibrate Arachidonic acid Bezafibrate Chiglitazar Clofibrate CP-775146 Daidzein DHEA (prasterone) (in rodents) Elafibranor Etomoxir Fenofibrate Genistein Gemfibrozil GW-7647 Lanifibranor Leukotriene B₄ LG-101506 LG-100754 Lobeglitazone Muraglitazar Oleylethanolamide Palmitoylethanolamide Pemafibrate Perfluorononanoic acid Perfluorooctanoic acid Pioglitazone Saroglitazar Sodelglitazar Tesaglitazar Tetradecylthioacetic acid Troglitazone WY-14643 Antagonists: GW-6471 MK-886
PPARδTooltip Peroxisome proliferator-activated receptor delta	Agonists: 15-HETE 15-HpETE Arachidonic acid Bezafibrate Daidzein Elafibranor Fonadelpar Genistein GW-0742 GW-501516 L-165,041 Lanifibranor LG-101506 Seladelpar Sodelglitazar Tetradecylthioacetic acid Antagonists: FH-535 GSK-0660 GSK-3787
PPARγTooltip Peroxisome proliferator-activated receptor gamma	Agonists: 5-Oxo-ETE 5-Oxo-15-hydroxy-ETE 15-Deoxy-Δ^12,14-prostaglandin J₂ 15-HETE 15-HpETE Aleglitazar Arachidonic acid Balaglitazone Berberine Bezafibrate Cannabidiol Cevoglitazar Chiglitazar Ciglitazone Daidzein Darglitazone Edaglitazone Efatutazone Englitazone Etalocib Farglitazar Genistein GW-1929 Ibuprofen Imiglitazar Indeglitazar Lanifibranor LG-100268 LG-100754 LG-101506 Lobeglitazone Muraglitazar (muroglitazar) nTZDpa Naveglitazar Netoglitazone Oxeglitazar Peliglitazar Pemaglitazar Perfluorononanoic acid Pioglitazone Prostaglandin J₂ Ragaglitazar Reglitazar Rivoglitazone Rosiglitazone RS5444 Saroglitazar Sipoglitazar Sodelglitazar Telmisartan Tesaglitazar Troglitazone SPPARMsTooltip Selective PPARγ modulator: BADGE EPI-001 INT-131 MK-0533 S26948 Antagonists: FH-535 GW-9662 SR-202 T-0070907 Unknown: SR-1664
Non-selective	Agonists: Ciprofibrate Clinofibrate Clofibride Englitazone Etofibrate Farglitazar Netoglitazone Ronifibrate Rivoglitazone Simfibrate
See also Receptor/signaling modulators