AUDA

Modify Date: 2024-01-04 13:14:14

AUDA Structure
AUDA structure
Common Name AUDA
CAS Number 479413-70-2 Molecular Weight 392.575
Density 1.1±0.1 g/cm3 Boiling Point 592.7±19.0 °C at 760 mmHg
Molecular Formula C23H40N2O3 Melting Point N/A
MSDS Chinese USA Flash Point 312.3±21.5 °C

 Use of AUDA


AUDA (compound 43) is a potent soluble epoxide hydrolase (sEH) inhibitor with IC50s of 18 and 69 nM for the mouse and human sEH, respectively[1]. AUDA has anti-inflammatory activity[2].

 Names

Name 12-(1-adamantylcarbamoylamino)dodecanoic acid
Synonym More Synonyms

 AUDA Biological Activity

Description AUDA (compound 43) is a potent soluble epoxide hydrolase (sEH) inhibitor with IC50s of 18 and 69 nM for the mouse and human sEH, respectively[1]. AUDA has anti-inflammatory activity[2].
Related Catalog
Target

IC50: 18 nM (mouse sEH) and 69 nM (human sEH)[1]

In Vitro AUDA (0.3-10 μg/mL; 48 hours) dose-dependently suppresses the proliferation of rat VSMCs exposed to PDGF[2]. AUDA (0.3-10 μg/mL; 30 min) dose-dependently upregulats COX-2 expression[2]. AUDA (10, 50 and 100 μM) augments the migratory ability of HCAECs in a dose-dependent manner[3]. AUDA significantly increases the adhesion ability of HCAECs[3]. Cell Proliferation Assay[2] Cell Line: Vascular smooth muscle cell (VSMC) Concentration: 0.3, 1, 3, 10 μg/mL Incubation Time: 48 hours Result: Dose-dependently suppressed the proliferation of rat VSMCs exposed to PDGF. Western Blot Analysis[2] Cell Line: VSMC Concentration: 1, 3, 10, 30 μg/mL Incubation Time: 30 min Result: Dose-dependently upregulated COX-2 expression.
In Vivo AUDA (i.p.; 10 mg/kg; 14 days) reduces TNF-α, MMP-9 and IL-1β expression levels[3]. Animal Model: Male (wild-type) C57BL/6 mice (age, 4-6 weeks; weight, 18-20 g)[3] Dosage: 10 mg/kg Administration: i.p.; 14 days Result: Reduced TNF-α, MMP-9 and IL-1β expression levels.
References

[1]. Morisseau C, et al. Structural refinement of inhibitors of urea-based soluble epoxide hydrolases.Biochem Pharmacol. 2002 May 1;63(9):1599-608.

[2]. Kim HS, et al. Differential Effects of sEH Inhibitors on the Proliferation and Migration of Vascular Smooth Muscle Cells.Int J Mol Sci. 2017 Dec 11;18(12).

[3]. Dai N, et al. Vascular repair and anti-inflammatory effects of soluble epoxide hydrolase inhibitor.Exp Ther Med. 2019 May;17(5):3580-3588.

 Chemical & Physical Properties

Density 1.1±0.1 g/cm3
Boiling Point 592.7±19.0 °C at 760 mmHg
Molecular Formula C23H40N2O3
Molecular Weight 392.575
Flash Point 312.3±21.5 °C
Exact Mass 392.303894
PSA 78.43000
LogP 5.61
Vapour Pressure 0.0±3.6 mmHg at 25°C
Index of Refraction 1.534
Storage condition -20℃

 Safety Information

RIDADR NONH for all modes of transport

 Synthetic Route

~98%

AUDA Structure

AUDA

CAS#:479413-70-2

Literature: THE REGENTS OF THE UNIVERSITY OF CALIFORNIA Patent: WO2006/45119 A2, 2006 ; Location in patent: Page/Page column 44; 52 ; WO 2006/045119 A2

 Precursor & DownStream

Precursor  2

DownStream  0

 Articles11

More Articles
Intimal smooth muscle cells are a source but not a sensor of anti-inflammatory CYP450 derived oxylipins.

Biochem. Biophys. Res. Commun. 463 , 774-80, (2015)

Vascular pathologies are associated with changes in the presence and expression of morphologically distinct vascular smooth muscle cells. In particular, in complex human vascular lesions and models of...

Alkylphloroglucinol derivatives and triterpenoids with soluble epoxide hydrolase inhibitory activity from Callistemon citrinus.

Fitoterapia 109 , 39-44, (2016)

Phytochemical analysis of the leaves and stems of Callistemon citrinus (Curtis) Skeels led to the isolation of two new alkylphloroglucinols, gallomyrtucommulone E and F (1 and 2), along with four othe...

Therapeutic effects of the soluble epoxide hydrolase (sEH) inhibitor AUDA on atherosclerotic diseases.

Pharmazie 70(1) , 24-8, (2015)

In this study, we aimed to detect the effects of the soluble epoxide hydrolase (sEH) inhibitor 12-(3-adamantan-1-yl-ureido)-dodecanoic acid (AUDA) on atherosclerotic diseases and to explore its mechan...

 Synonyms

12-[[(tricyclo[3.3.1.13,7]dec-1-ylamino)carbonyl]amino]-dodecanoic acid
HMS2204E15
12-[(Adamantan-1-ylcarbamoyl)amino]dodecanoic acid
12-{[(3s,5s,7s)-Adamantan-1-ylcarbamoyl]amino}dodecanoic acid
Dodecanoic acid, 12-[[(tricyclo[3.3.1.1]dec-1-ylamino)carbonyl]amino]-
12-(3-adamantan-1-ylureido)dodecanoic acid
Urea-based compound,18
12-[(tricyclo[3.3.1.1]dec-1-ylcarbamoyl)amino]dodecanoic acid
AUDA