An internal standard for the quantification of azilsartan
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Unlabeled Version(s)
26091Azilsartan
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Azilsartan-d5

Item No. 33276

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
2-(ethoxy-d5)-1-((2'-(5-oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl)-[1,1'-biphenyl]-4-yl)methyl)-1H-benzo[d]imidazole-7-carboxylic acid
CAS Number
1346599-45-8
Molecular Formula
C25H15D5N4O5
Formula Weight
461.5
Purity
≥99% deuterated forms (d1-d5)
Formulation
A solid
Solubility(Learn about Variance in Solubility)
DMSO: slightly solubleMethanol: slightly soluble
SMILES
O=C(N1)ON=C1C(C=CC=C2)=C2C(C=C3)=CC=C3CN4C5=C(C(O)=O)C=CC=C5N=C4OC([2H])([2H])C([2H])([2H])[2H]
InChi Code
InChI=1S/C25H20N4O5/c1-2-33-24-26-20-9-5-8-19(23(30)31)21(20)29(24)14-15-10-12-16(13-11-15)17-6-3-4-7-18(17)22-27-25(32)34-28-22/h3-13H,2,14H2,1H3,(H,30,31)(H,27,28,32)/i1D3,2D2
InChi Key
KGSXMPPBFPAXLY-ZBJDZAJPSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

    $374

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    Product Description

    Azilsartan-d5 is intended for use as an internal standard for the quantification of azilsartan (Item No. 26091) by GC- or LC-MS. Azilsartan is an antagonist of the angiotensin II type 1 receptor (AT1; IC50 = 0.42 µM) and the active metabolite of azilsartan medoxomil (Item No. 23805).1,2 Azilsartan is formed from azilsartan medoxomil by hydrolysis in the gastrointestinal tract and liver.3 Azilsartan also acts as an inverse agonist, inhibiting angiotensin II-induced accumulation of inositol-1-phosphate in COS-7 cells expressing recombinant human AT1 (IC50 = 2.6 nM).2 It reduces the maximal contractile response induced by angiotensin II in isolated rabbit aortic strips (pD2 = 9.9).2 Azilsartan (100 ng/kg, i.v.) inhibits the angiotensin II-induced pressor response in conscious normotensive rats.1

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Kohara, Y., Kubo, K., Imamiya, E., et al. Synthesis and angiotensin II receptor antagonistic activities of benzimidazole derivatives bearing acidic heterocycles as novel tetrazole bioisosteres. J. Med. Chem. 39(26), 5228-5235 (1996).

    2. Ojima, M., Igata, H., Tanaka, M., et al. In vitro antagonistic properties of a new angiotensin type 1 receptor blocker, azilsartan, in receptor binding and function studies. J. Pharmacol. Exp. Ther. 336(3), 801-808 (2011).

    3. Clas, S.-D., Sanchez, R.I., and Nofsinger, R. Chemistry-enabled drug delivery (prodrugs): Recent progress and challenges. Drug Discov. Today 19(1), 79-87 (2014).