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E9658

Sigma-Aldrich

Enalaprilat dihydrate

≥98% (HPLC)

Sinónimos:

(2S)-1-[(2S)-2-[[(1S)-1-Carboxy-3-phenyl-propyl]amino]propanoyl]pyrrolidine-2-carboxylic acid, Vasotec

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About This Item

Fórmula empírica (notación de Hill):
C18H24N2O5 ·2H2O
Número de CAS:
84680-54-6
Peso molecular:
384.42
EC Number:
278-459-3
MDL number:
MFCD00941393
UNSPSC Code:
12352200
PubChem Substance ID:
329799089
NACRES:
NA.77

assay

≥98% (HPLC)

solubility

H2O: 14 mg/mL at 60 °C (warming for 5 minutes)
DMSO: 64 mg/mL

originator

Merck & Co., Inc., Kenilworth, NJ, U.S.

storage temp.

room temp

SMILES string

O.O.C[C@H](N[C@@H](CCc1ccccc1)C(O)=O)C(=O)N2CCC[C@H]2C(O)=O

InChI

1S/C18H24N2O5.2H2O/c1-12(16(21)20-11-5-8-15(20)18(24)25)19-14(17(22)23)10-9-13-6-3-2-4-7-13;;/h2-4,6-7,12,14-15,19H,5,8-11H2,1H3,(H,22,23)(H,24,25);2*1H2/t12-,14-,15-;;/m0../s1

InChI key

MZYVOFLIPYDBGD-MLZQUWKJSA-N

Gene Information

human ... ACE(1636)

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Biochem/physiol Actions

Enalapril, the ethyl ester of enalaprilat exhibits slight pharmacological activity until it is hydrolyzed in the liver to enalaprilat. Enalaprilat, a IV form of an angiotensin-converting-enzyme inhibitor (ACE) prevents the transformation of angiotensin I to angiotensin II, a potent vasoconstrictor.
Enalaprilat is an inhibitor of angiotensin converting enzyme (ACE), antihypertensive, and a Bradykinin B1 receptor activator. Enalaprilat has nM potency versus ACE and also activates B1 receptors to release NO.

Features and Benefits

This compound is featured on the Angiotensin Receptors and Bradykinin Receptors pages of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.
This compound was developed by Merck & Co., Inc., Kenilworth, NJ, U.S.. To browse the list of other pharma-developed compounds and Approved Drugs/Drug Candidates, click here.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Certificados de análisis (COA)

Busque Certificados de análisis (COA) introduciendo el número de lote del producto. Los números de lote se encuentran en la etiqueta del producto después de las palabras «Lot» o «Batch»

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Gérémy Abdull Koumbadinga et al.
Peptides, 31(8), 1546-1554 (2010-05-11)
Angiotensin converting enzyme (ACE) is a drug target and an effective bradykinin (BK)-inactivating ectopeptidase. We exploited a recently described [(3)H]enalaprilat binding assay to quantify the full dynamic range of ACE expression in intact human umbilical vein endothelial cells (HUVECs) stimulated
Diamantino Ribeiro Salgado et al.
Shock (Augusta, Ga.), 35(6), 542-549 (2011-02-02)
Severe sepsis is frequently associated with microcirculatory abnormalities despite seemingly adequate hemodynamic resuscitation. As increased serum angiotensin II levels may play a role in this dysfunction, we evaluated the microcirculatory effects of enalaprilat in an experimental model of septic shock.
P F O'Tierney et al.
American journal of physiology. Regulatory, integrative and comparative physiology, 299(2), R573-R578 (2010-05-21)
The fetal heart is highly sensitive to changes in mechanical load. We have previously demonstrated that increased cardiac load can stimulate cell cycle activity and maturation of immature cardiomyocytes, but the effects of reduced load are not known. Sixteen fetal
Jiandong Zhang et al.
American journal of physiology. Renal physiology, 301(4), F723-F732 (2011-07-29)
The limited antifibrotic effect of therapeutic angiotensin blockade, the fact that angiotensin blockade dramatically elevates renin levels, and recent evidence that renin has an angiotensin-independent, receptor-mediated profibrotic action led us to hypothesize that combining renin receptor inhibition and ANG II
Min Yu et al.
Molecules (Basel, Switzerland), 17(3), 2738-2751 (2012-03-08)
Enalaprilat (Ena.), an angiotensin II (Ang II) converting enzyme inhibitor (ACEI), can produce some therapeutic effects on hypertension, ventricular hypertrophy and myocardial remodeling in clinic, but its precise mechanism, especially its signaling pathways remain elusive. In this study, cardiac fibroblasts
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