AR-9281 | CAS#913548-29-5 | epoxide hydrolase (s-EH) inhibitor | hypertension | type 2 diabetes

MedKoo Cat#: 524253 | Name: AR-9281

Description:

WARNING: This product is for research use only, not for human or veterinary use.

AR-9281 is a soluble epoxide hydrolase (s-EH) inhibitor potentially for the treatment of hypertension and type 2 diabetes.

Chemical Structure

AR-9281

CAS#913548-29-5

Theoretical Analysis

MedKoo Cat#: 524253

Name: AR-9281

CAS#: 913548-29-5

Chemical Formula: C18H29N3O2

Exact Mass: 319.2260

Molecular Weight: 319.44

Elemental Analysis: C, 67.68; H, 9.15; N, 13.15; O, 10.02

Price and Availability

Size	Price	Availability
10mg	USD 150.00	Ready to ship
25mg	USD 250.00	Ready to ship
50mg	USD 450.00	Ready to ship
100mg	USD 750.00	Ready to ship
200mg	USD 1,250.00	Ready to ship
500mg	USD 2,450.00	Ready to ship
1g	USD 3,850.00	Ready to ship
2g	USD 6,450.00	Ready to ship

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Related CAS #

913548-29-5

Synonym

AR-9281; AR 9281; AR9281; Apau (enzyme inhibitor);

IUPAC/Chemical Name

1-(1-Acetyl-piperidin-4-yl)-3-adamantan-1-yl-urea

InChi Key

HUDQLWBKJOMXSZ-UHFFFAOYSA-N

InChi Code

1S/C18H29N3O2/c1-12(22)21-4-2-16(3-5-21)19-17(23)20-18-9-13-6-14(10-18)8-15(7-13)11-18/h13-16H,2-11H2,1H3,(H2,19,20,23)

SMILES Code

CC(=O)N1CCC(CC1)NC(=O)NC23CC4CC(CC(C4)C2)C3

Appearance

Solid powder

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO, not in water

Shelf Life

>2 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.9001

More Info

Product Data

Product Data

Certificate of Analysis

View CoA: current batch, Lot#S9S01C15

QC Data

View QC data: current batch, Lot#S9S01C15

Safety Data Sheet (SDS)

View Safety Data Sheet (SDS)

Instruction

View handling instruction

Biological target:

AR9281 is an inhibitor of soluble epoxide hydrolase (s-EH), with potential for the treatment of hypertension and type 2 diabetes.

In vitro activity:

N/A

In vivo activity:

The findings of the present study demonstrate the anti-hypertensive effect of AR9281 in an angiotensin dependent model of hypertension. In addition to decreasing blood pressure, AR9281 decreased glomerular injury and renal inflammation. Endothelial dilator responses of the afferent arterioles and mesenteric resistance arteries were also improved in angiotensin hypertensive rats receiving AR9281. More importantly, these results provide strong evidence that besides lowering blood pressure the first-in-class sEHI, AR9821 has added renal and cardiovascular beneficial effects in angiotensin dependent hypertension. The additional anti-inflammatory actions, vascular endothelial and end organ protection provided by AR9281 makes this a promising pharmaceutical agent for the treatment of cardiovascular disease, diabetes, inflammation, and kidney disease. Reference: Pharmaceuticals (Basel). 2009 Dec; 2(3): 217–227. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3978544/

	Solvent	mg/mL	mM
Solubility
	DMSO	25.0	78.26

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 319.44 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:

1. Anandan SK, Webb HK, Chen D, Wang YX, Aavula BR, Cases S, Cheng Y, Do ZN, Mehra U, Tran V, Vincelette J, Waszczuk J, White K, Wong KR, Zhang LN, Jones PD, Hammock BD, Patel DV, Whitcomb R, MacIntyre DE, Sabry J, Gless R. 1-(1-acetyl-piperidin-4-yl)-3-adamantan-1-yl-urea (AR9281) as a potent, selective, and orally available soluble epoxide hydrolase inhibitor with efficacy in rodent models of hypertension and dysglycemia. Bioorg Med Chem Lett. 2011 Feb 1;21(3):983-8. doi: 10.1016/j.bmcl.2010.12.042. Epub 2010 Dec 13. PMID: 21211973; PMCID: PMC3529200. 2. Imig JD, Carpenter MA, Shaw S. The Soluble Epoxide Hydrolase Inhibitor AR9281 Decreases Blood Pressure, Ameliorates Renal Injury and Improves Vascular Function in Hypertension. Pharmaceuticals (Basel). 2009 Dec 18;2(3):217-227. doi: 10.3390/ph2030217. PMID: 27713235; PMCID: PMC3978544.

In vitro protocol:

N/A

In vivo protocol:

1: Despa S, Sharma S, Harris TR, Dong H, Li N, Chiamvimonvat N, Taegtmeyer H, Margulies KB, Hammock BD, Despa F. Cardioprotection by controlling hyperamylinemia in a "humanized" diabetic rat model. J Am Heart Assoc. 2014 Aug 21;3(4). pii: e001015. doi: 10.1161/JAHA.114.001015. PubMed PMID: 25146704; PubMed Central PMCID: PMC4310392. 2: Guglielmino K, Jackson K, Harris TR, Vu V, Dong H, Dutrow G, Evans JE, Graham J, Cummings BP, Havel PJ, Chiamvimonvat N, Despa S, Hammock BD, Despa F. Pharmacological inhibition of soluble epoxide hydrolase provides cardioprotection in hyperglycemic rats. Am J Physiol Heart Circ Physiol. 2012 Oct 1;303(7):H853-62. doi: 10.1152/ajpheart.00154.2012. Epub 2012 Aug 3. PubMed PMID: 22865388; PubMed Central PMCID: PMC3469704. 3: Chen D, Whitcomb R, MacIntyre E, Tran V, Do ZN, Sabry J, Patel DV, Anandan SK, Gless R, Webb HK. Pharmacokinetics and pharmacodynamics of AR9281, an inhibitor of soluble epoxide hydrolase, in single- and multiple-dose studies in healthy human subjects. J Clin Pharmacol. 2012 Mar;52(3):319-28. doi: 10.1177/0091270010397049. Epub 2011 Mar 21. PubMed PMID: 21422238. 4: Anandan SK, Webb HK, Chen D, Wang YX, Aavula BR, Cases S, Cheng Y, Do ZN, Mehra U, Tran V, Vincelette J, Waszczuk J, White K, Wong KR, Zhang LN, Jones PD, Hammock BD, Patel DV, Whitcomb R, MacIntyre DE, Sabry J, Gless R. 1-(1-acetyl-piperidin-4-yl)-3-adamantan-1-yl-urea (AR9281) as a potent, selective, and orally available soluble epoxide hydrolase inhibitor with efficacy in rodent models of hypertension and dysglycemia. Bioorg Med Chem Lett. 2011 Feb 1;21(3):983-8. doi: 10.1016/j.bmcl.2010.12.042. Epub 2010 Dec 13. PubMed PMID: 21211973; PubMed Central PMCID: PMC3529200. 5: Zhang LN, Vincelette J, Chen D, Gless RD, Anandan SK, Rubanyi GM, Webb HK, MacIntyre DE, Wang YX. Inhibition of soluble epoxide hydrolase attenuates endothelial dysfunction in animal models of diabetes, obesity and hypertension. Eur J Pharmacol. 2011 Mar 1;654(1):68-74. doi: 10.1016/j.ejphar.2010.12.016. Epub 2010 Dec 25. PubMed PMID: 21187082.