AUDA
low solubility, rapid metabolization, and high melting point limited the use as human drug
General
Type : Adamantyl,Dodecanoate,Urea derivative
Chemical_Nomenclature : 12-(1-adamantylcarbamoylamino)dodecanoic acid
Canonical SMILES : C1C2CC3CC1CC(C2)(C3)NC(=O)NCCCCCCCCCCCC(=O)O
InChI : InChI=1S\/C23H40N2O3\/c26-21(27)10-8-6-4-2-1-3-5-7-9-11-24-22(28)25-23-15-18-12-19(16-23)14-20(13-18)17-23\/h18-20H,1-17H2,(H,26,27)(H2,24,25,28)
InChIKey : XLGSEOAVLVTJDH-UHFFFAOYSA-N
Other name(s) : 12-(3-adamantan-1-yl-ureido) dodecanoic acid,CHEMBL215387,Urea-based compound, 18,D0S0SH,MLS002415562
MW : 392.58
Formula : C23H40N2O3
CAS_number : 479413-70-2
PubChem : 10069117
UniChem : XLGSEOAVLVTJDH-UHFFFAOYSA-N
IUPHAR :
Wikipedia :
Target
References (13)
| Title : Effect of the sEH inhibitor AUDA on arachidonic acid metabolism and NF-B signaling of rats with postpartum depression-like behavior - Duan_2023_J.Neuroimmunol_385_578250 |
| Author(s) : Duan L , Song L , Qiu C , Li J |
| Ref : Journal of Neuroimmunology , 385 :578250 , 2023 |
| Abstract : Duan_2023_J.Neuroimmunol_385_578250 |
| ESTHER : Duan_2023_J.Neuroimmunol_385_578250 |
| PubMedSearch : Duan_2023_J.Neuroimmunol_385_578250 |
| PubMedID: 38029646 |
| Title : Soluble epoxide hydrolase inhibitor AUDA decreases bleomycin-induced pulmonary toxicity in mice by inhibiting the p38\/Smad3 pathways - Dong_2017_Toxicology_389_31 |
| Author(s) : Dong XW , Jia YL , Ge LT , Jiang B , Jiang JX , Shen J , Jin YC , Guan Y , Sun Y , Xie QM |
| Ref : Toxicology , 389 :31 , 2017 |
| Abstract : Dong_2017_Toxicology_389_31 |
| ESTHER : Dong_2017_Toxicology_389_31 |
| PubMedSearch : Dong_2017_Toxicology_389_31 |
| PubMedID: 28694203 |
| Title : Ingestion of the epoxide hydrolase inhibitor AUDA modulates immune responses of the mosquito, Culex quinquefasciatus during blood feeding - Xu_2016_Insect.Biochem.Mol.Biol_76_62 |
| Author(s) : Xu J , Morisseau C , Yang J , Lee KS , Kamita SG , Hammock BD |
| Ref : Insect Biochemistry & Molecular Biology , 76 :62 , 2016 |
| Abstract : Xu_2016_Insect.Biochem.Mol.Biol_76_62 |
| ESTHER : Xu_2016_Insect.Biochem.Mol.Biol_76_62 |
| PubMedSearch : Xu_2016_Insect.Biochem.Mol.Biol_76_62 |
| PubMedID: 27369469 |
| Title : Soluble epoxide hydrolase inhibitory activity of anthraquinone components from Aloe - Sun_2015_Bioorg.Med.Chem_23_6659 |
| Author(s) : Sun YN , Kim JH , Li W , Jo AR , Yan XT , Yang SY , Kim YH |
| Ref : Bioorganic & Medicinal Chemistry , 23 :6659 , 2015 |
| Abstract : Sun_2015_Bioorg.Med.Chem_23_6659 |
| ESTHER : Sun_2015_Bioorg.Med.Chem_23_6659 |
| PubMedSearch : Sun_2015_Bioorg.Med.Chem_23_6659 |
| PubMedID: 26372074 |
| Title : Identification of potent inhibitors of the chicken soluble epoxide hydrolase - Shihadih_2015_Bioorg.Med.Chem.Lett_25_276 |
| Author(s) : Shihadih DS , Harris TR , Yang J , Merzlikin O , Lee KS , Hammock BD , Morisseau C |
| Ref : Bioorganic & Medicinal Chemistry Lett , 25 :276 , 2015 |
| Abstract : Shihadih_2015_Bioorg.Med.Chem.Lett_25_276 |
| ESTHER : Shihadih_2015_Bioorg.Med.Chem.Lett_25_276 |
| PubMedSearch : Shihadih_2015_Bioorg.Med.Chem.Lett_25_276 |
| PubMedID: 25479771 |
| Title : Mammalian soluble epoxide hydrolase is identical to liver hepoxilin hydrolase - Cronin_2011_J.Lipid.Res_52_712 |
| Author(s) : Cronin A , Decker M , Arand M |
| Ref : J Lipid Res , 52 :712 , 2011 |
| Abstract : Cronin_2011_J.Lipid.Res_52_712 |
| ESTHER : Cronin_2011_J.Lipid.Res_52_712 |
| PubMedSearch : Cronin_2011_J.Lipid.Res_52_712 |
| PubMedID: 21217101 |
| Title : Attenuation of cisplatin nephrotoxicity by inhibition of soluble epoxide hydrolase - Parrish_2009_Cell.Biol.Toxicol_25_217 |
| Author(s) : Parrish AR , Chen G , Burghardt RC , Watanabe T , Morisseau C , Hammock BD |
| Ref : Cell Biol Toxicol , 25 :217 , 2009 |
| Abstract : Parrish_2009_Cell.Biol.Toxicol_25_217 |
| ESTHER : Parrish_2009_Cell.Biol.Toxicol_25_217 |
| PubMedSearch : Parrish_2009_Cell.Biol.Toxicol_25_217 |
| PubMedID: 18386137 |
| Title : Soluble epoxide hydrolase as a therapeutic target for cardiovascular diseases - Imig_2009_Nat.Rev.Drug.Discov_8_794 |
| Author(s) : Imig JD , Hammock BD |
| Ref : Nat Rev Drug Discov , 8 :794 , 2009 |
| Abstract : Imig_2009_Nat.Rev.Drug.Discov_8_794 |
| ESTHER : Imig_2009_Nat.Rev.Drug.Discov_8_794 |
| PubMedSearch : Imig_2009_Nat.Rev.Drug.Discov_8_794 |
| PubMedID: 19794443 |
| Title : Design of bioavailable derivatives of 12-(3-adamantan-1-yl-ureido)dodecanoic acid, a potent inhibitor of the soluble epoxide hydrolase - Kim_2007_Bioorg.Med.Chem_15_312 |
| Author(s) : Kim IH , Nishi K , Tsai HJ , Bradford T , Koda Y , Watanabe T , Morisseau C , Blanchfield J , Toth I , Hammock BD |
| Ref : Bioorganic & Medicinal Chemistry , 15 :312 , 2007 |
| Abstract : Kim_2007_Bioorg.Med.Chem_15_312 |
| ESTHER : Kim_2007_Bioorg.Med.Chem_15_312 |
| PubMedSearch : Kim_2007_Bioorg.Med.Chem_15_312 |
| PubMedID: 17046265 |
| Gene_locus related to this paper: human-EPHX2 |
| Title : Substituted adamantyl-urea inhibitors of the soluble epoxide hydrolase dilate mesenteric resistance vessels - Olearczyk_2006_J.Pharmacol.Exp.Ther_318_1307 |
| Author(s) : Olearczyk JJ , Field MB , Kim IH , Morisseau C , Hammock BD , Imig JD |
| Ref : Journal of Pharmacology & Experimental Therapeutics , 318 :1307 , 2006 |
| Abstract : Olearczyk_2006_J.Pharmacol.Exp.Ther_318_1307 |
| ESTHER : Olearczyk_2006_J.Pharmacol.Exp.Ther_318_1307 |
| PubMedSearch : Olearczyk_2006_J.Pharmacol.Exp.Ther_318_1307 |
| PubMedID: 16772540 |
| Gene_locus related to this paper: human-EPHX2 |
| Title : Soluble epoxide hydrolase is a main effector of angiotensin II-induced hypertension - Jung_2005_Hypertension_45_759 |
| Author(s) : Jung O , Brandes RP , Kim IH , Schweda F , Schmidt R , Hammock BD , Busse R , Fleming I |
| Ref : Hypertension , 45 :759 , 2005 |
| Abstract : Jung_2005_Hypertension_45_759 |
| ESTHER : Jung_2005_Hypertension_45_759 |
| PubMedSearch : Jung_2005_Hypertension_45_759 |
| PubMedID: 15699457 |
| Title : Structural refinement of inhibitors of urea-based soluble epoxide hydrolases - Morisseau_2002_Biochem.Pharmacol_63_1599 |
| Author(s) : Morisseau C , Goodrow MH , Newman JW , Wheelock CE , Dowdy DL , Hammock BD |
| Ref : Biochemical Pharmacology , 63 :1599 , 2002 |
| Abstract : Morisseau_2002_Biochem.Pharmacol_63_1599 |
| ESTHER : Morisseau_2002_Biochem.Pharmacol_63_1599 |
| PubMedSearch : Morisseau_2002_Biochem.Pharmacol_63_1599 |
| PubMedID: 12007563 |
| Title : Potent urea and carbamate inhibitors of soluble epoxide hydrolases - Morisseau_1999_Proc.Natl.Acad.Sci.U.S.A_96_8849 |
| Author(s) : Morisseau C , Goodrow MH , Dowdy D , Zheng J , Greene JF , Sanborn JR , Hammock BD |
| Ref : Proc Natl Acad Sci U S A , 96 :8849 , 1999 |
| Abstract : Morisseau_1999_Proc.Natl.Acad.Sci.U.S.A_96_8849 |
| ESTHER : Morisseau_1999_Proc.Natl.Acad.Sci.U.S.A_96_8849 |
| PubMedSearch : Morisseau_1999_Proc.Natl.Acad.Sci.U.S.A_96_8849 |
| PubMedID: 10430859 |
| Gene_locus related to this paper: mouse-hyes |