t-TUCB
human-EPHX2 IC50=0.8nM mouse-hyes IC50=5.7 nM human FAAH IC50=140nM mouse FAAH IC50=6,300 nM. Partial dual sEH/FAAH inhibitor
General
Type : Urea derivative,Multitarget,FAAH inhibitor
Chemical_Nomenclature : 4-[4-[[4-(trifluoromethoxy)phenyl]carbamoylamino]cyclohexyl]oxybenzoic acid
Canonical SMILES : C1CC(CCC1NC(=O)NC2=CC=C(C=C2)OC(F)(F)F)OC3=CC=C(C=C3)C(=O)O
InChI : InChI=1S\/C21H21F3N2O5\/c22-21(23,24)31-18-11-5-15(6-12-18)26-20(29)25-14-3-9-17(10-4-14)30-16-7-1-13(2-8-16)19(27)28\/h1-2,5-8,11-12,14,17H,3-4,9-10H2,(H,27,28)(H2,25,26,29)
InChIKey : XDVFKCZZXOGEMN-UHFFFAOYSA-N
Other name(s) : 4-(4-(3-(4-trifluoromethoxy-phenyl)ureido)cyclohexyloxy)benzoic acid,trans-4-[4-(3-trifluoromethoxyphenyl-l-ureido)-cyclohexyloxy]-benzoic acid,Urea-based compound, 22,MLS002415559,SCHEMBL4256244,SCHEMBL4256246,CHEMBL1552108,CHEMBL2397148,BDBM158481,BXV,EC1728,UC-1728
MW : 438.40
Formula : C21H21F3N2O5
CAS_number : 948304-40-3
PubChem : 16756850
UniChem : XDVFKCZZXOGEMN-UHFFFAOYSA-N
IUPHAR :
Wikipedia :
Target
Families : t-TUCB ligand of proteins in family: Epoxide_hydrolase
Stucture : 6AUM Crystal structure of human soluble epoxide hydrolase complexed with trans-4-[4-(3-trifluoromethoxyphenyl-l-ureido)-cyclohexyloxy]-benzoic acid
Protein : human-EPHX2 || mouse-hyes
References (11)
| Title : Species Differences in Metabolism of Soluble Epoxide Hydrolase Inhibitor, EC1728, Highlight the Importance of Clinically Relevant Screening Mechanisms in Drug Development - McReynolds_2021_Molecules_26_ |
| Author(s) : McReynolds CB , Yang J , Guedes A , Morisseau C , Garcia R , Knych H , Tearney C , Hamamoto B , Hwang SH , Wagner K , Hammock BD |
| Ref : Molecules , 26 : , 2021 |
| Abstract : McReynolds_2021_Molecules_26_ |
| ESTHER : McReynolds_2021_Molecules_26_ |
| PubMedSearch : McReynolds_2021_Molecules_26_ |
| PubMedID: 34443621 |
| Title : Differential Effects of 17,18-EEQ and 19,20-EDP Combined with Soluble Epoxide Hydrolase Inhibitor t-TUCB on Diet-Induced Obesity in Mice - Yang_2021_Int.J.Mol.Sci_22_ |
| Author(s) : Yang Y , Xu X , Wu H , Yang J , Chen J , Morisseau C , Hammock BD , Bettaieb A , Zhao L |
| Ref : Int J Mol Sci , 22 : , 2021 |
| Abstract : Yang_2021_Int.J.Mol.Sci_22_ |
| ESTHER : Yang_2021_Int.J.Mol.Sci_22_ |
| PubMedSearch : Yang_2021_Int.J.Mol.Sci_22_ |
| PubMedID: 34361032 |
| Title : Soluble Epoxide Hydrolase Inhibition by t-TUCB Promotes Brown Adipogenesis and Reduces Serum Triglycerides in Diet-Induced Obesity - Overby_2020_Int.J.Mol.Sci_21_ |
| Author(s) : Overby H , Yang Y , Xu X , Graham K , Hildreth K , Choi S , Wan D , Morisseau C , Zeldin DC , Hammock BD , Wang S , Bettaieb A , Zhao L |
| Ref : Int J Mol Sci , 21 : , 2020 |
| Abstract : Overby_2020_Int.J.Mol.Sci_21_ |
| ESTHER : Overby_2020_Int.J.Mol.Sci_21_ |
| PubMedSearch : Overby_2020_Int.J.Mol.Sci_21_ |
| PubMedID: 32987880 |
| Title : Soluble epoxide hydrolase inhibition with t-TUCB alleviates liver fibrosis and portal pressure in carbon tetrachloride-induced cirrhosis in rats - Zhang_2018_Clin.Res.Hepatol.Gastroenterol_42_118 |
| Author(s) : Zhang CH , Zheng L , Gui L , Lin JY , Zhu YM , Deng WS , Luo M |
| Ref : Clin Res Hepatol Gastroenterol , 42 :118 , 2018 |
| Abstract : Zhang_2018_Clin.Res.Hepatol.Gastroenterol_42_118 |
| ESTHER : Zhang_2018_Clin.Res.Hepatol.Gastroenterol_42_118 |
| PubMedSearch : Zhang_2018_Clin.Res.Hepatol.Gastroenterol_42_118 |
| PubMedID: 29031875 |
| Title : Pharmacokinetics and antinociceptive effects of the soluble epoxide hydrolase inhibitor t-TUCB in horses with experimentally induced radiocarpal synovitis - Guedes_2018_J.Vet.Pharmacol.Ther_41_230 |
| Author(s) : Guedes AGP , Aristizabal F , Sole A , Adedeji A , Brosnan R , Knych H , Yang J , Hwang SH , Morisseau C , Hammock BD |
| Ref : J Vet Pharmacol Ther , 41 :230 , 2018 |
| Abstract : Guedes_2018_J.Vet.Pharmacol.Ther_41_230 |
| ESTHER : Guedes_2018_J.Vet.Pharmacol.Ther_41_230 |
| PubMedSearch : Guedes_2018_J.Vet.Pharmacol.Ther_41_230 |
| PubMedID: 29067696 |
| Title : Identification and optimization of soluble epoxide hydrolase inhibitors with dual potency towards fatty acid amide hydrolase - Kodani_2018_Bioorg.Med.Chem.Lett_28_762 |
| Author(s) : Kodani SD , Bhakta S , Hwang SH , Pakhomova S , Newcomer ME , Morisseau C , Hammock BD |
| Ref : Bioorganic & Medicinal Chemistry Lett , 28 :762 , 2018 |
| Abstract : Kodani_2018_Bioorg.Med.Chem.Lett_28_762 |
| ESTHER : Kodani_2018_Bioorg.Med.Chem.Lett_28_762 |
| PubMedSearch : Kodani_2018_Bioorg.Med.Chem.Lett_28_762 |
| PubMedID: 29366648 |
| Gene_locus related to this paper: human-EPHX2 |
| Title : Inhibition of soluble epoxide hydrolase lowers portal hypertension in cirrhotic rats by ameliorating endothelial dysfunction and liver fibrosis - Deng_2017_Prostaglandins.Other.Lipid.Mediat_131_67 |
| Author(s) : Deng W , Zhu Y , Lin J , Zheng L , Zhang C , Luo M |
| Ref : Prostaglandins Other Lipid Mediat , 131 :67 , 2017 |
| Abstract : Deng_2017_Prostaglandins.Other.Lipid.Mediat_131_67 |
| ESTHER : Deng_2017_Prostaglandins.Other.Lipid.Mediat_131_67 |
| PubMedSearch : Deng_2017_Prostaglandins.Other.Lipid.Mediat_131_67 |
| PubMedID: 28822809 |
| Title : Soluble epoxide hydrolase activity and pharmacologic inhibition in horses with chronic severe laminitis - Guedes_2017_Equine.Vet.J_49_345 |
| Author(s) : Guedes A , Galuppo L , Hood D , Hwang SH , Morisseau C , Hammock BD |
| Ref : Equine Vet J , 49 :345 , 2017 |
| Abstract : Guedes_2017_Equine.Vet.J_49_345 |
| ESTHER : Guedes_2017_Equine.Vet.J_49_345 |
| PubMedSearch : Guedes_2017_Equine.Vet.J_49_345 |
| PubMedID: 27338788 |
| Title : Inhibitors of soluble epoxide hydrolase minimize ischemia-reperfusion-induced cardiac damage in normal, hypertensive, and diabetic rats - Islam_2017_Cardiovasc.Ther_35_ |
| Author(s) : Islam O , Patil P , Goswami SK , Razdan R , Inamdar MN , Rizwan M , Mathew J , Inceoglu B , Stephen Lee KS , Hwang SH , Hammock BD |
| Ref : Cardiovasc Ther , 35 : , 2017 |
| Abstract : Islam_2017_Cardiovasc.Ther_35_ |
| ESTHER : Islam_2017_Cardiovasc.Ther_35_ |
| PubMedSearch : Islam_2017_Cardiovasc.Ther_35_ |
| PubMedID: 28296232 |
| Title : Inhibition of soluble epoxide hydrolase attenuates hepatic fibrosis and endoplasmic reticulum stress induced by carbon tetrachloride in mice - Harris_2015_Toxicol.Appl.Pharmacol_286_102 |
| Author(s) : Harris TR , Bettaieb A , Kodani S , Dong H , Myers R , Chiamvimonvat N , Haj FG , Hammock BD |
| Ref : Toxicol Appl Pharmacol , 286 :102 , 2015 |
| Abstract : Harris_2015_Toxicol.Appl.Pharmacol_286_102 |
| ESTHER : Harris_2015_Toxicol.Appl.Pharmacol_286_102 |
| PubMedSearch : Harris_2015_Toxicol.Appl.Pharmacol_286_102 |
| PubMedID: 25827057 |
| Title : Inhibition of soluble epoxide hydrolase modulates inflammation and autophagy in obese adipose tissue and liver: role for omega-3 epoxides - Lopez-Vicario_2015_Proc.Natl.Acad.Sci.U.S.A_112_536 |
| Author(s) : Lopez-Vicario C , Alcaraz-Quiles J , Garcia-Alonso V , Rius B , Hwang SH , Titos E , Lopategi A , Hammock BD , Arroyo V , Claria J |
| Ref : Proc Natl Acad Sci U S A , 112 :536 , 2015 |
| Abstract : Lopez-Vicario_2015_Proc.Natl.Acad.Sci.U.S.A_112_536 |
| ESTHER : Lopez-Vicario_2015_Proc.Natl.Acad.Sci.U.S.A_112_536 |
| PubMedSearch : Lopez-Vicario_2015_Proc.Natl.Acad.Sci.U.S.A_112_536 |
| PubMedID: 25550510 |