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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

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 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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Kyong-Jin Lee et al.
Heart (British Cardiac Society), 97(16), 1343-1348 (2011-06-08)
The bidirectional cavopulmonary connection (BCPC) is used in the staged palliation of univentricular hearts and places the cerebral and pulmonary vascular beds in series. Angiotensin-converting enzyme inhibitors (ACEI) are often used in this complex circulation, but the effects of their
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
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)
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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