A potent inhibitor of soluble epoxide hydrolase
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AUDA

Item No. 10007927

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
12-[[(tricyclo[3.3.1.13,7]dec-1-ylamino)carbonyl]amino]-dodecanoic acid
CAS Number
479413-70-2
Molecular Formula
C23H40N2O3
Formula Weight
392.6
Purity
≥98%
Formulation
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 2 mg/mlDMF:PBS (pH 7.2) (1:1): 0.5 mg/mlDMSO: 1 mg/mlEthanol: 0.15 mg/ml
SMILES
O=C(NCCCCCCCCCCCC(O)=O)NC12C[C@@H](C[C@H](C3)C2)C[C@@H]3C1
InChi Code
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)/t18-,19+,20-,23?
InChi Key
XLGSEOAVLVTJDH-HXRQYLNASA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    5 mg

    $35

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    10 mg

    $54

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    50 mg

    $253

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    100 mg

    $472

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    Product Description

    Epoxyeicosatrienoic acid (EpETrE) metabolites of arachidonic acid such as 11(12)-EpETrE and 14(15)-EpETrE have been identified as endothelium derived hyperpolarizing factors with vasodilator activity.1 Soluble epoxide hydrolase (sEH) catalyzes the conversion of EpETrEs to the corresponding dihydroxy eicosatrienoic acids (DiHETrEs) thereby diminishing their activity. AUDA is an inhibitor of sEH exhibiting IC50 values of 18 and 69 nM for the mouse and human enzymes, respectively.2 In angiotensin-infused rats, a dose of 25 mg/l AUDA administered in drinking water decreased mean arterial blood pressure from 161 ± 4 mmHg to 140 ± 5 mmHg. This hypotensive effect was accompanied by an increase in urinary epoxide-to-diol ratios.3 AUDA activates peroxisome proliferator-activated receptor α (PPARα) 3-fold at a concentration of 10 µM but exhibits no affect on PPARδ or PPARγ.4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Fleming, I. Cytochrome P450 epoxygenases as EDHF synthase(s). Pharmacol. Res. 49(6), 525-533 (2004).

    2. Morisseau, C., Goodrow, M.H., Newman, J.W., et al. Structural refinement of inhibitors of urea-based soluble epoxide hydrolases. Biochem. Pharmacol. 63(9), 1599-1608 (2002).

    3. Imig, J.D., Zhao, X., Zaharis, C.Z., et al. An orally active epoxide hydrolase inhibitor lowers blood pressure and provides renal protection in salt-sensitive hypertension. Hypertension 46(2), 975-981 (2005).

    4. Fang, X., Hu, S., Watanabe, T., et al. Activation of peroxisome proliferator-activated receptor α by substituted urea-derived soluble epoxide hydrolase inhibitors. J. Pharmacol. Exp. Ther. 314(1), 260-270 (2005).

    Product Citations

    Walker, R.E., Savinova, O.V., Pedersen, T.L., et al. Effects of inflammation and soluble epoxide hydrolase inhibition on oxylipin composition of very low-density lipoproteins in isolated perfused rat livers. Physiol. Rep. 9(4), e14480 (2021).

    Van Anh, T.T., Mostafa, A., Rao, Z., et al. From Vietnamese plants to a biflavonoid that relieves inflammation by triggering the lipid mediator class switch to resolution. Acta Pharm. Sin. B. 11(6), 1629-1647 (2021).

    McDougle, D.R., Watson, J.E., Abdeen, A.A., et al. Anti-inflammatory ω-3 endocannabinoid epoxides. Proc. Natl. Acad. Sci. USA 114(30), E6034-E6043 (2017).

    Morisseau, C., and Hammock, B.D. Measurement of soluble epoxide hydrolase (sEH) activity. Curr. Protoc. Toxicol. 4.23.2(Suppl. 33), (2007).