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E9658

Sigma-Aldrich

Enalaprilat dihydrate

≥98% (HPLC)

Synonym(s):

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

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5 MG
$138.00
25 MG
$528.00

$138.00

Available to ship onMay 01, 2025Details

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5 MG
$138.00
25 MG
$528.00

About This Item

Empirical Formula (Hill Notation):
C18H24N2O5 ·2H2O
CAS Number:
84680-54-6
Molecular Weight:
384.42
EC Number:
278-459-3
MDL number:
MFCD00941393
UNSPSC Code:
12352200
PubChem Substance ID:
329799089
NACRES:
NA.77

$138.00

Available to ship onMay 01, 2025Details

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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.[1] Enalaprilat, a IV form of an angiotensin-converting-enzyme inhibitor (ACE) prevents the transformation of angiotensin I to angiotensin II, a potent vasoconstrictor.[2]
Enalaprilat is an inhibitor of angiotensin converting enzyme (ACE), antihypertensive, and a Bradykinin B1 receptor activator.
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)

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Certificates of Analysis (COA)

Lot/Batch Number
0000205056
0000205055
061M4728V
0000193594
090M4710V

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Drugs used in the management of heart disease and cardiac arrhythmias
Small Animal Clinical Pharmacology, 2, 412-418 (2008)
Hypertension in the Pediatric Intensive Care Unit
Pediatric Critical Care Medicine : A Journal of the Society of Critical Care Medicine and the World Federation of Pediatric Intensive and Critical Care Societies, 2, 1043-1057 (2011)
Kristy L Jackson et al.
Hypertension (Dallas, Tex. : 1979), 62(4), 775-781 (2013-07-31)
Genetically hypertensive mice (BPH/2J) are hypertensive because of an exaggerated contribution of the sympathetic nervous system to blood pressure. We hypothesize that an additional contribution to elevated blood pressure is via sympathetically mediated activation of the intrarenal renin-angiotensin system. Our
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
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.
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