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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
MDL number:
MFCD00941393
UNSPSC Code:
41116107
PubChem Substance ID:
329749718
NACRES:
NA.24

grade

pharmaceutical primary standard

API family

enalaprilat

manufacturer/tradename

USP

application(s)

pharmaceutical (small molecule)

format

neat

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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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.

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 has nM potency versus ACE and also activates B1 receptors to release NO.

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.  ​

Other Notes

Sales restrictions may apply.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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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Enalapril maleate salt powder, ≥98% (TLC)

Sigma-Aldrich

E6888

Enalapril maleate salt

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
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
Enalaprilat.
Dimensions of critical care nursing : DCCN, 19(2), 22-22 (2000-07-06)
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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