nbAUDA
The free acid AUDA and several of its esters inhibit the soluble epoxide hydrolase with IC50s of 2-10 nM. n-butyl ester can be considered a prodrug for AUDA
General
Type : Adamantyl,Urea derivative,Dodecanoate,Laurate
Chemical_Nomenclature : butyl 12-(1-adamantylcarbamoylamino)dodecanoate
Canonical SMILES : CCCCOC(=O)CCCCCCCCCCCNC(=O)NC12CC3CC(C1)CC(C3)C2
InChI : InChI=1S\/C27H48N2O3\/c1-2-3-15-32-25(30)13-11-9-7-5-4-6-8-10-12-14-28-26(31)29-27-19-22-16-23(20-27)18-24(17-22)21-27\/h22-24H,2-21H2,1H3,(H2,28,29,31)
InChIKey : LVDWKYLLAAFQOW-UHFFFAOYSA-N
Other name(s) : CHEMBL223281,12-(3-adamantan-1-yl-ureido)-dodecanoic acid butyl ester,AUDA-BE,SCHEMBL654142,SCHEMBL14622065
MW : 448.7
Formula : C27H48N2O3
CAS_number :
PubChem : 11236241
UniChem : LVDWKYLLAAFQOW-UHFFFAOYSA-N
IUPHAR :
Wikipedia :
Target
References (9)
| Title : Soluble epoxide hydrolase: a new target for cardioprotection - Gross_2009_Curr.Opin.Investig.Drugs_10_253 |
| Author(s) : Gross GJ , Nithipatikom K |
| Ref : Curr Opin Investig Drugs , 10 :253 , 2009 |
| Abstract : Gross_2009_Curr.Opin.Investig.Drugs_10_253 |
| ESTHER : Gross_2009_Curr.Opin.Investig.Drugs_10_253 |
| PubMedSearch : Gross_2009_Curr.Opin.Investig.Drugs_10_253 |
| PubMedID: 19333883 |
| Gene_locus related to this paper: human-EPHX2 |
| 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 inhibition and gene deletion are protective against myocardial ischemia-reperfusion injury in vivo - Motoki_2008_Am.J.Physiol.Heart.Circ.Physiol_295_H2128 |
| Author(s) : Motoki A , Merkel MJ , Packwood WH , Cao Z , Liu L , Iliff J , Alkayed NJ , Van Winkle DM |
| Ref : American Journal of Physiology Heart Circ Physiol , 295 :H2128 , 2008 |
| Abstract : Motoki_2008_Am.J.Physiol.Heart.Circ.Physiol_295_H2128 |
| ESTHER : Motoki_2008_Am.J.Physiol.Heart.Circ.Physiol_295_H2128 |
| PubMedSearch : Motoki_2008_Am.J.Physiol.Heart.Circ.Physiol_295_H2128 |
| PubMedID: 18835921 |
| Gene_locus related to this paper: human-EPHX2 |
| 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 : Soluble epoxide hydrolase: a novel therapeutic target in stroke - Zhang_2007_J.Cereb.Blood.Flow.Metab_27_1931 |
| Author(s) : Zhang W , Koerner IP , Noppens R , Grafe M , Tsai HJ , Morisseau C , Luria A , Hammock BD , Falck JR , Alkayed NJ |
| Ref : Journal of Cerebral Blood Flow & Metabolism , 27 :1931 , 2007 |
| Abstract : Zhang_2007_J.Cereb.Blood.Flow.Metab_27_1931 |
| ESTHER : Zhang_2007_J.Cereb.Blood.Flow.Metab_27_1931 |
| PubMedSearch : Zhang_2007_J.Cereb.Blood.Flow.Metab_27_1931 |
| PubMedID: 17440491 |
| Gene_locus related to this paper: human-EPHX2 |
| Title : Enhancement of antinociception by coadministration of nonsteroidal anti-inflammatory drugs and soluble epoxide hydrolase inhibitors - Schmelzer_2006_Proc.Natl.Acad.Sci.U.S.A_103_13646 |
| Author(s) : Schmelzer KR , Inceoglu B , Kubala L , Kim IH , Jinks SL , Eiserich JP , Hammock BD |
| Ref : Proc Natl Acad Sci U S A , 103 :13646 , 2006 |
| Abstract : Schmelzer_2006_Proc.Natl.Acad.Sci.U.S.A_103_13646 |
| ESTHER : Schmelzer_2006_Proc.Natl.Acad.Sci.U.S.A_103_13646 |
| PubMedSearch : Schmelzer_2006_Proc.Natl.Acad.Sci.U.S.A_103_13646 |
| PubMedID: 16950874 |
| Gene_locus related to this paper: human-EPHX2 |
| Title : Soluble epoxide hydrolase is a therapeutic target for acute inflammation - Schmelzer_2005_Proc.Natl.Acad.Sci.U.S.A_102_9772 |
| Author(s) : Schmelzer KR , Kubala L , Newman JW , Kim IH , Eiserich JP , Hammock BD |
| Ref : Proc Natl Acad Sci U S A , 102 :9772 , 2005 |
| Abstract : Schmelzer_2005_Proc.Natl.Acad.Sci.U.S.A_102_9772 |
| ESTHER : Schmelzer_2005_Proc.Natl.Acad.Sci.U.S.A_102_9772 |
| PubMedSearch : Schmelzer_2005_Proc.Natl.Acad.Sci.U.S.A_102_9772 |
| PubMedID: 15994227 |
| Gene_locus related to this paper: human-EPHX2 |
| 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 |