A potent, orally bioavailable sEH inhibitor
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trans-AUCB

Item No. 16568

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
4-[[trans-4-[[(tricyclo[3.3.1.13,7]dec-1-ylamino)carbonyl]amino]cyclohexyl]oxy]-benzoic acid
CAS Number
885012-33-9
Molecular Formula
C24H32N2O4
Formula Weight
412.5
Purity
≥90%
Formulation
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 20 mg/mlDMSO: 30 mg/mlDMSO:PBS (pH 7.2) (1:1): 0.5 mg/ml
λmax
256 nm
SMILES
O=C(O)C(C=C1)=CC=C1O[C@H]2CC[C@H](NC(NC34C[C@H]5C[C@H](C[C@H](C5)C4)C3)=O)CC2
InChi Code
InChI=1S/C24H32N2O4/c27-22(28)18-1-5-20(6-2-18)30-21-7-3-19(4-8-21)25-23(29)26-24-12-15-9-16(13-24)11-17(10-15)14-24/h1-2,5-6,15-17,19,21H,3-4,7-14H2,(H,27,28)(H2,25,26,29)/t15-,16+,17-,19-,21-,24?
InChi Key
KNBWKJBQDAQARU-GVVVSFATSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

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    50 mg

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    Cayman Chemical
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    Product Description

    Soluble epoxide hydrolase (sEH) converts epoxides to their corresponding diols. Inhibitors of sEH have anti-inflammatory, anti-hypertensive, neuroprotective, and cardioprotective effects.1,2 trans-AUCB is a very potent inhibitor of sEH (IC50 = 0.5 nM).3 It displays high oral bioavailability for doses ranging from 0.01 to 1 mg/kg.4,5 Dual inhibition of COX-2 and sEH, by celecoxib (Item No. 10008672) and trans-AUCB, suppresses tumor angiogenesis, inhibiting tumor growth and metastasis in a Lewis lung carcinoma model in mice.6

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Schmelzer, K.R., Kubala, L., Newman, J.W., et al. Soluble epoxide hydrolase is a therapeutic target for acute inflammation. Proc. Natl. Acad. Sci. USA 102(28), 9772-9777 (2005).

    2. Yu, Z., Xu, F., Huse, L.M., et al. Soluble epoxide hydrolase regulates hydrolysis of vasoactive epoxyeicosatrienoic acids. Circ. Res. 87(11), 992-998 (2000).

    3. Hwang, S.H., Wagner, K.M., Morisseau, C., et al. Synthesis and structure-activity relationship studies of urea-containing pyrazoles as dual inhibitors of cyclooxygenase-2 and soluble epoxide hydrolase. J. Med. Chem. 54(8), 3037-3050 (2011).

    4. Tsai, H.J., Hwang, S.H., Morisseau, C., et al. Pharmacokinetic screening of soluble epoxide hydrolase inhibitors in dogs. Eur. J. Pharm. Sci. 40(3), 222-238 (2010).

    5. Imig, J.D., and Hammock, B.D. Soluble epoxide hydrolase as a therapeutic target for cardiovascular diseases. Nat. Rev. Drug Discov. 8(10), 794-805 (2009).

    6. Zhang, G., Panigrahy, D., Hwang, S.H., et al. Dual inhibition of cyclooxygenase-2 and soluble epoxide hydrolase synergistically suppresses primary tumor growth and metastasis. Proc. Natl. Acad. Sci. USA 111(30), 11127-11132 (2014).