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SML2719

Sigma-Aldrich

AVE 0991

≥98% (HPLC)

Synonym(s):

1-Ethyl-3-[3-[4-[(5-formyl-4-methoxy-2-phenylimidazol-1-yl)methyl]phenyl]-5-(2-methylpropyl)thiophen-2-yl]sulfonylurea, 5-Formyl-4-methoxy-2-phenyl-1[[4-[2-(ethylaminocarbonylsulfonamido)-5-isobutyl-3-thienyl]-phenyl]-methyl]-imidazole, AVE-0991, AVE0991, N-[(Ethylamino)carbonyl]-3-[4-[(5-formyl-4-methoxy-2-phenyl-1H-imidazol-1-yl)methyl]phenyl]-5-(2-methylpropyl)-2-thiophenesulfonamide

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About This Item

Empirical Formula (Hill Notation):
C29H32N4O5S2
CAS Number:
Molecular Weight:
580.72
MDL number:
UNSPSC Code:
12352200
NACRES:
NA.77

Quality Level

assay

≥98% (HPLC)

form

powder

color

white to beige

solubility

DMSO: 2 mg/mL, clear

storage temp.

−20°C

SMILES string

O=CC(N1CC2=CC=C(C=C2)C3=C(SC(CC(C)C)=C3)S(NC(NCC)=O)(=O)=O)=C(N=C1C4=CC=CC=C4)OC

InChI

1S/C29H32N4O5S2/c1-5-30-29(35)32-40(36,37)28-24(16-23(39-28)15-19(2)3)21-13-11-20(12-14-21)17-33-25(18-34)27(38-4)31-26(33)22-9-7-6-8-10-22/h6-14,16,18-19H,5,15,17H2,1-4H3,(H2,30,32,35)

InChI key

QTOZBSNPDCWHPV-UHFFFAOYSA-N

Biochem/physiol Actions

AVE 0991 is an orally active, non-peptide-based selective Ang (1-7) receptor (Mas, MasR) agonist with 5-times NO-inducing efficacy than Ang (1-7) in bovine aortic endothelial cell (BAEC) cultures (10 μM; BAEC) and 10-fold higher affinity (IC50 = 21 nM vs 220 nM, respectively, against 10 nM [125I]-Ang-(1-7) for BAEC membrane binding), exhibiting little affinity toward AT1 & AT2 receptors. AVE 0991 is a widely probing Mas-mediated responses in cultures (0.01-10 μM) and in animal disease models in vivo (0.3-10 mg/kg via ip., po. or intranasal; rats and mice).

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable


Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Teng Jiang et al.
Aging, 10(4), 645-657 (2018-04-19)
During the aging process, chronic neuroinflammation induced by microglia is detrimental for the brain and contributes to the etiology of several aging-related neurodegenerative diseases such as Alzheimer's disease and Parkinson's disease. As a newly identified axis of renin-angiotensin system, ACE2/Ang-(1-7)/MAS1
Gabriele Wiemer et al.
Hypertension (Dallas, Tex. : 1979), 40(6), 847-852 (2002-12-07)
Recently, we demonstrated that the heptapeptide angiotensin-(1-7) (Ang-[1-7]) exhibits a favorable kinetic of nitric oxide (NO) release accompanied by extremely low superoxide (O2-) production. In this report we describe AVE 0991, a novel nonpeptide compound that evoked effects similar to
Lirong Guo et al.
American journal of physiology. Heart and circulatory physiology, 312(5), H980-H991 (2017-04-16)
The objectives of the present study were to investigate the effect of ANG-(1-7) on the development of cardiac hypertrophy and to identify the intracellular mechanism underlying this action of ANG-(1-7). Blood pressure and heart rate were recorded using radiotelemetry before
Gurkirat S Brar et al.
Diabetes, 66(8), 2201-2212 (2017-06-01)
Recent work has renewed interest in therapies targeting the renin-angiotensin system (RAS) to improve β-cell function in type 2 diabetes. Studies show that generation of angiotensin-(1-7) by ACE2 and its binding to the Mas receptor (MasR) improves glucose homeostasis, partly
Kate T Murphy et al.
Cancer research, 79(4), 706-719 (2018-11-14)
Cancer cachexia is a multifactorial syndrome characterized by a progressive loss of skeletal muscle mass associated with significant functional impairment. Cachexia robs patients of their strength and capacity to perform daily tasks and live independently. Effective treatments are needed urgently.

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