Fenleuton

5-lipoxygenase inhibitor

none

Identifiers

IUPAC name

1-{4-[3-(4-Fluorophenoxy)phenyl]-3-butyn-2-yl}-1-hydroxyurea

CAS Number

141579-54-6

ChemSpider

65045

UNII

LG64454O6I

KEGG

D04151

CompTox Dashboard (EPA)

DTXSID40869916

Chemical and physical dataFormulaC₁₇H₁₅FN₂O₃Molar mass314.316 g·mol⁻¹3D model (JSmol)

Interactive image

SMILES

CC(C#Cc1cccc(c1)Oc2ccc(cc2)F)N(C(=O)N)O

InChI

InChI=InChI=1S/C17H15FN2O3/c1-12(20(22)17(19)21)5-6-13-3-2-4-16(11-13)23-15-9-7-14(18)8-10-15/h2-4,7-12,22H,1H3,(H2,19,21)
Key:MWXPQCKCKPYBDR-UHFFFAOYSA-N^[1]

Fenleuton (trade name Lofrin) is a drug that acts as a 5-lipoxygenase inhibitor and inhibits leukotriene (LTB4, LTC4, LTD4, and LTE4) formation. It has been studied for potential use in veterinary medicine to treat respiratory diseases such as chronic obstructive pulmonary disease (COPD) in horses.^[2]

References

^ "1-{4-[3-(4-Fluorophenoxy)phenyl]-3-butyn-2-yl}-1-hydroxyurea". chemspider.com. Retrieved 24 December 2015.
^ Marr KA, Lees P, Page CP, Cunningham FM (1998). "Effect of the 5-lipoxygenase inhibitor, fenleuton, on antigen-induced neutrophil accumulation and lung function changes in horses with chronic obstructive pulmonary disease". J Vet Pharmacol Ther. 21 (3): 241–246. doi:10.1046/j.1365-2885.1998.00127.x. PMID 9673966.

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)