479413-70-2

Basic information

• Product Name: AUDA
• Synonyms: AUDA;12-[[(tricyclo[3.3.1.13,7]dec-1-ylamino)carbonyl]amino]-dodecanoic acid
• CAS NO: 479413-70-2
• Molecular Formula: C₂₃H₄₀N₂O₃
• Molecular Weight: 392.5753
• Mol File: 479413-70-2.mol

Chemical Properties

• Melting Point: 114 °C(Solv: hexane (110-54-3))
• Boiling Point: 592.7±19.0 °C(Predicted)
• Appearance: white to beige/
• Density: 1.09±0.1 g/cm3(Predicted)
• Storage Temp.: ?20°C
• Solubility: DMSO: ≥10mg/mL at warmed to 60°C
• PKA: 4.78±0.10(Predicted)
• CAS DataBase Reference: AUDA(CAS DataBase Reference)
• NIST Chemistry Reference: AUDA(479413-70-2)
• EPA Substance Registry System: AUDA(479413-70-2)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 479413-70-2(Hazardous Substances Data)

Usage

Uses

AUDA is an inhibitor of sEH and selective activator of PPARα.

Upstream product

• 4411-25-0 1-adamantyl isocyanate 
• 693-57-2 12-Aminododecanoic acid 

Relevant articles and documents

Structure-activity relationships of cycloalkylamide derivatives as inhibitors of the soluble epoxide hydrolase

Structure-activity relationships of cycloalkylamide compounds as inhibitors of human sEH were investigated. When the left side of amide function was modified by a variety of cycloalkanes, at least a C6 like cyclohexane was necessary to yield reasonable inhibition potency on the target enzyme. In compounds with a smaller cycloalkane or with a polar group on the left side of amide function, no inhibition was observed. On the other hand, increased hydrophobicity dramatically improved inhibition potency. Especially, a tetrahydronaphthalene (20) effectively increased the potency. When a series of alkyl or aryl derivatives of cycloalkylamide were investigated to continuously optimize the right side of the amide pharmacophore, a benzyl moiety functionalized with a polar group produced highly potent inhibition. A nonsubstituted benzyl, alkyl, aryl, or biaryl structure present on the right side of the cycloalkylamide function induced a big decrease in inhibition potency. Also, the resulting potent cycloalkylamide (32) showed reasonable physical properties.

Design of bioavailable derivatives of 12-(3-adamantan-1-yl-ureido)dodecanoic acid, a potent inhibitor of the soluble epoxide hydrolase

The soluble epoxide hydrolase (sEH) plays an important role in the metabolism of endogenous chemical mediators involved in blood pressure regulation and vascular inflammation. 12-(3-Adamantan-1-yl-ureido)-dodecanoic acid (AUDA, 1) is a very active inhibit

IMPROVED INHIBITORS FOR THE SOLUBLE EPOXIDE HYDROLASE

Inhibitors of the soluble epoxide hydrolase (sEH) are provided that incorporate multiple pharmacophores and are useful in the treatment of diseases

Inhibitors for the soluble epoxide hydrolase

Inhibitors of the soluble epoxide hydrolase (sEH) are provided that incorporate multiple pharmacophores and are useful in the treatment of diseases.

Structural refinement of inhibitors of urea-based soluble epoxide hydrolases

The soluble epoxide hydrolase (sEH) is involved in the metabolism of arachidonic, linoleic, and other fatty acid epoxides, endogenous chemical mediators that play an important role in blood pressure regulation and inflammation. 1,3-Disubstituted ureas, carbamates, and amides are new potent and stable inhibitors of sEH. However, the poor solubility of the lead compounds limits their use. Inhibitor structure-activity relationships were investigated to better define the structural requirements for inhibition and to identify points in the molecular topography that could accept polar groups without diminishing inhibition potency. Results indicate that lipophilicity is an important factor controlling inhibitor potency. Polar groups could be incorporated into one of the alkyl groups without loss of activity if they were placed at a sufficient distance from the urea function. The resulting compounds had a 2-fold higher water solubility. These findings will facilitate the rational design and optimization of sEH inhibitors with better physical properties.