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SML2064

Sigma-Aldrich

LBQ657

≥97% (HPLC)

Synonyma:

(2R,4S)-5-(Biphenyl-4-yl)-4-((3-carboxypropionyl)amino)-2-methylpentanoic acid, Desethyl sacubitril, Sacubitrilat

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About This Item

Empirický vzorec (Hillův zápis):
C22H25NO5
Číslo CAS:
149709-44-4
Molekulová hmotnost:
383.44
MDL number:
MFCD00921225
UNSPSC Code:
12352200
NACRES:
NA.77

assay

≥97% (HPLC)

form

powder

optical activity

[α]/D -35 to -27°, c = 1 in methanol

color

white to beige

solubility

DMSO: 2 mg/mL, clear

shipped in

wet ice

storage temp.

−20°C

SMILES string

OC(CCC(N[C@H](CC1=CC=C(C2=CC=CC=C2)C=C1)C[C@H](C(O)=O)C)=O)=O

InChI

1S/C22H25NO5/c1-15(22(27)28)13-19(23-20(24)11-12-21(25)26)14-16-7-9-18(10-8-16)17-5-3-2-4-6-17/h2-10,15,19H,11-14H2,1H3,(H,23,24)(H,25,26)(H,27,28)/t15-,19+/m1/s1

InChI key

DOBNVUFHFMVMDB-BEFAXECRSA-N

Biochem/physiol Actions

LBQ657 is the active metabolite of sacubitril. It is an inhibitor of the enkephalinase neprilysin (neutral endopeptidase, NEP) formed by the action of esterases on its prodrug sacubitril (AHU377), which is half of the heart failure combination drug Entresto, along with the angiotensin-receptor blocker Valsartan. LBQ657 prevents neprilysin′s degradation of atrial and brain natriuretic peptide, two blood pressure lowering peptides.

Pictograms

Health hazardExclamation mark
GHS08,GHS07

signalword

Danger

hcodes

H336,H372

Hazard Classifications

STOT RE 1 - STOT SE 3

target_organs

Bone,Kidney, Central nervous system

Storage Class

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Osvědčení o analýze (COA)

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Duncan J Campbell
Nature reviews. Cardiology, 14(3), 171-186 (2016-12-16)
Neprilysin has a major role in both the generation and degradation of bioactive peptides. LCZ696 (valsartan/sacubitril, Entresto), the first of the new ARNI (dual-acting angiotensin-receptor-neprilysin inhibitor) drug class, contains equimolar amounts of valsartan, an angiotensin-receptor blocker, and sacubitril, a prodrug
Jessie Gu et al.
Journal of clinical pharmacology, 50(4), 401-414 (2009-11-26)
Angiotensin receptor blockade and neprilysin (NEP) inhibition together offer potential benefits for the treatment of hypertension and heart failure. LCZ696 is a novel single molecule comprising molecular moieties of valsartan and NEP inhibitor prodrug AHU377 (1:1 ratio). Oral administration of
Imad Hanna et al.
Xenobiotica; the fate of foreign compounds in biological systems, 48(3), 300-313 (2017-03-11)
1. The potential for drug-drug interactions of LCZ696 (a novel, crystalline complex comprising sacubitril and valsartan) was investigated in vitro. 2. Sacubitril was shown to be a highly permeable P-glycoprotein (P-gp) substrate and was hydrolyzed to the active anionic metabolite LBQ657 by
Sasha A S Kjeldsen et al.
Journal of the Endocrine Society, 5(9), bvab084-bvab084 (2021-08-03)
Inhibitors of the protease neprilysin (NEP) are used for treating heart failure, but are also linked to improvements in metabolism. NEP may cleave proglucagon-derived peptides, including the glucose and amino acid (AA)-regulating hormone glucagon. Studies investigating NEP inhibition on glucagon

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