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Merck
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1235274

USP

Enalaprilat

United States Pharmacopeia (USP) Reference Standard

Synonym(s):

Enalaprilat dihydrate, (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
NACRES:
NA.24
PubChem Substance ID:
329749718
UNSPSC Code:
41116107
MDL number:
MFCD00941393

Key Documents

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Product Name

Enalaprilat, United States Pharmacopeia (USP) Reference Standard

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

SMILES string

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

InChI key

MZYVOFLIPYDBGD-MLZQUWKJSA-N

grade

pharmaceutical primary standard

API family

enalaprilat

manufacturer/tradename

USP

application(s)

pharmaceutical (small molecule)

format

neat

Gene Information

human ... ACE(1636)

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Analysis Note

These products are for test and assay use only. They are not meant for administration to humans or animals and cannot be used to diagnose, treat, or cure diseases of any kind.  ​

Application

Enalaprilat USP reference standard, intended for use in specified quality tests and assays as specified in the USP compendia. Also, for use with USP monographs such as:
  • Enalapril Maleate and Hydrochlorothiazide Tablets
  • Enalapril Maleate Tablets
  • Enalaprilat
  • Enalaprilat Injection

Biochem/physiol Actions

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.

General description

This product is provided as delivered and specified by the issuing Pharmacopoeia. All information provided in support of this product, including SDS and any product information leaflets have been developed and issued under the Authority of the issuing Pharmacopoeia.For further information and support please go to the website of the issuing Pharmacopoeia.

Other Notes

Sales restrictions may apply.

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificates of Analysis (COA)

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Kristy L Jackson et al.
Hypertension (Dallas, Tex. : 1979), 63(4), 811-818 (2014-01-22)
BPH/2J mice are recognized as a neurogenic model of hypertension primarily based on overactivity of the sympathetic nervous system and greater neuronal activity in key autonomic cardiovascular regulatory brain regions. The medial amygdala (MeAm) is a forebrain region that integrates
Enalaprilat.
Dimensions of critical care nursing : DCCN, 19(2), 22-22 (2000-07-06)
K Chatterjee et al.
Drugs, 39 Suppl 4, 29-40 (1990-01-01)
Enalapril is an effective angiotensin-converting enzyme (ACE) inhibitor which produces salutary, beneficial haemodynamic effects in patients with congestive heart failure. Enalapril also produces beneficial neurohumoral changes, as well as improving abnormal coronary haemodynamics and myocardial energetics that are frequently encountered
Brian C Ferslew et al.
Drug metabolism and disposition: the biological fate of chemicals, 42(9), 1567-1574 (2014-06-25)
Hepatic uptake and efflux transporters govern the systemic and hepatic exposure of many drugs and metabolites. Enalapril is a pharmacologically inactive prodrug of enalaprilat. Following oral administration, enalapril is converted to enalaprilat in hepatocytes and undergoes translocation into the systemic
Sylwia Magiera et al.
Journal of chromatography. B, Analytical technologies in the biomedical and life sciences, 980, 79-87 (2015-01-16)
Given the increasing popularity of aliskiren, particularly in combination with angiotensin converting enzyme inhibitor (e.g. enalapril), it is important to determine whether its use in combination with these agents is associated with potentially life threatening safety events. Analytical methods for

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