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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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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

Quality Level

100

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 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 Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
0000205055
0000205056
0000205056
0000205055
0000193594

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Fabio Mangiacapra et al.
Journal of the American College of Cardiology, 61(6), 615-621 (2013-01-08)
This study investigated the influence of intracoronary enalaprilat on coronary microvascular function and peri-procedural outcome measures in patients with stable angina undergoing percutaneous coronary intervention (PCI). Intracoronary angiotensin-converting enzyme inhibitors have been shown to relieve myocardial ischemia in stable patients
J G Kingma et al.
Experimental physiology, 96(12), 1293-1301 (2011-09-06)
Myocardial perfusion and contraction are closely coupled; however, the effect of recurrent no-flow ischaemia on perfusion-contraction matching remains to be established. In the present studies, we examined the influence of modulating nitric oxide availability on perfusion-contraction matching after recurrent no-flow
Fredrik Palm et al.
Hypertension (Dallas, Tex. : 1979), 55(2), 298-304 (2010-01-06)
Angiotensin II maintains renal cortical blood flow and renal oxygenation in the clipped kidney of early 2-kidney, 1-clip Goldblatt hypertensive (2K,1C) rats. The involvement of Ang II is believed to decline, whereas oxidative stress increases during the progression of 2K,1C
Chinmoy Ghosh et al.
Drug testing and analysis, 4(2), 94-103 (2011-02-23)
A rapid and most sensitive method for simultaneous determination of enalapril (ENP) and its metabolite, enalaprilat (ENPT), in human plasma using ESI-LC-MS/MS (electrospray ionization liquid chromatography tandem mass spectrometry) positive ion multiple reactions monitoring (MRM) mode, was developed and validated.
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
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