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149709-62-6

149709-62-6 structure
149709-62-6 structure
  • Name: AHU 377
  • Chemical Name: Sacubitril
  • CAS Number: 149709-62-6
  • Molecular Formula: C24H29NO5
  • Molecular Weight: 411.491
  • Catalog: Biochemical Inhibitor Endocrinology & Hormones RAAS inhibitor
  • Create Date: 2018-03-29 08:00:00
  • Modify Date: 2024-01-03 17:22:50
  • Sacubitril (AHU-377) is a potent NEP inhibitor with an IC50 of 5 nM. Sacubitril (AHU-377) is a component of the heart failure medicine LCZ696.

Name Sacubitril
Synonyms 4-[[(2S,4R)-5-ethoxy-4-methyl-5-oxo-1-(4-phenylphenyl)pentan-2-yl]amino]-4-oxobutanoic acid
AHU-377
ENTRESTO
4-(((2S,4R)-1-([1,1'-biphenyl]-4-yl)-5-ethoxy-4-methyl-5-oxopentan-2-yl)amino)-4-oxobutanoic acid
4-{[(2S,4R)-1-(4-Biphenylyl)-5-ethoxy-4-methyl-5-oxo-2-pentanyl]amino}-4-oxobutanoic acid
UNII-17ERJ0MKGI
AHU377
Sacubitril
[1,1'-Biphenyl]-4-pentanoic acid, γ-[(3-carboxy-1-oxopropyl)amino]-α-methyl-, α-ethyl ester, (αR,γS)-
Description Sacubitril (AHU-377) is a potent NEP inhibitor with an IC50 of 5 nM. Sacubitril (AHU-377) is a component of the heart failure medicine LCZ696.
Related Catalog
Target

IC50: 5 nM (NEP)[1]

In Vitro Sacubitril (AHU-377) is a single molecule that is comprised of molecular moieties of valsartan, an ARB, and Sacubitril (AHU-377), a neprilysin inhibitor (1:1 ratio). Sacubitril (AHU-377) is converted by enzymatic cleavage of the ethyl ester into the active neprilysin inhibiting metabolite LBQ657[2]. The inactive NEPi precursor, Sacubitril (AHU-377), does not inhibit collagen accumulation in fibroblasts nor cardiac myocyte hypertrophy. In cardiac fibroblasts, the active NEPi LBQ657 had no discernible effects. In contrast, LBQ657 modestly inhibits cardiac myocyte hypertrophy[3].
In Vivo In humans, Sacubitril (AHU-377) (tmax 0.5-1.1 h) are absorbed quickly. Sacubitril (AHU-377) is converted rapidly into LBQ657 with its tmax being reached in 1.9-3.5 h. Mean t1/2 values for the biologically active LBQ657 is 9.9-11.1 h[2]. In vehicle-treated dogs, ANF increases urinary sodium excretion from 17.3±3.6 to 199.5±18.4 pequivkglmin. This effect is potentiated significantly in animals which receive Sacubitril (AHU-377). Urinary volume is also potentiated in animals which receive an iv administration of Sacubitril (AHU-377)[1].
References

[1]. Ksander GM, et al. Dicarboxylic acid dipeptide neutral endopeptidase inhibitors. J Med Chem. 1995 May 12;38(10):1689-700.

[2]. Voors AA, et al. The potential role of valsartan + AHU377 ( LCZ696 ) in the treatment of heart failure. Expert Opin Investig Drugs. 2013 Aug;22(8):1041-7.

[3]. von Lueder TG, et al. Angiotensin receptor neprilysin inhibitor LCZ696 attenuates cardiac remodeling and dysfunction after myocardial infarction by reducing cardiac fibrosis and hypertrophy. Circ Heart Fail. 2015 Jan;8(1):71-8.

Density 1.2±0.1 g/cm3
Boiling Point 656.9±55.0 °C at 760 mmHg
Molecular Formula C24H29NO5
Molecular Weight 411.491
Flash Point 351.1±31.5 °C
Exact Mass 411.204559
PSA 96.19000
LogP 3.96
Vapour Pressure 0.0±2.1 mmHg at 25°C
Index of Refraction 1.549