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E6888

Sigma-Aldrich

Enalapril maleate salt

powder, ≥98% (TLC)

Synonym(s):

(S)-N-[1-(Ethoxycarbonyl)-3-phenylpropyl]-Ala-Pro maleate salt

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About This Item

Empirical Formula (Hill Notation):
C20H28N2O5 · C4H4O4
CAS Number:
76095-16-4
Molecular Weight:
492.52
EC Number:
278-375-7
UNSPSC Code:
12352200
PubChem Substance ID:
24894639
NACRES:
NA.77

Quality Level

100

Assay

≥98% (TLC)

form

powder

color

white to off-white

solubility

methanol: ≥50 mg/mL, clear, colorless to yellow

originator

Merck & Co., Inc., Kenilworth, NJ, U.S.

SMILES string

C[C@@H](C(N1[C@H](C(O)=O)CCC1)=O)N[C@H](CC(OCC)=O)CCC2=CC=CC=C2.O=C(OO)/C=C\C(O)=O

InChI

1S/C21H30N2O5.C4H4O5/c1-3-28-19(24)14-17(12-11-16-8-5-4-6-9-16)22-15(2)20(25)23-13-7-10-18(23)21(26)27;5-3(6)1-2-4(7)9-8/h4-6,8-9,15,17-18,22H,3,7,10-14H2,1-2H3,(H,26,27);1-2,8H,(H,5,6)/b;2-1-/t15-,17-,18-;/m0./s1

InChI key

UQKQUZOIQFOJOI-KJHLASMFSA-N

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General description

Enalapril is an angiotensin-converting enzyme inhibitor. It is used to treat heart failure and high blood pressure.

Application

Enalapril maleate salt has been used:
  • to reduce albumin excretion rate (AER) and glomerular lesions
  • to examine the effects of enalapril pre-treatment on myocardial injury
  • to investigate its efficacious doses and schedules for mitigation of radiation lung injury

Biochem/physiol Actions

A long-acting angiotensin-converting enzyme inhibitor.

Features and Benefits

This compound is a featured product for ADME Tox research. Click here to discover more featured ADME Tox products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.
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.

Pictograms

Health hazard
GHS08

Signal Word

Warning

Hazard Statements

H361fd

Hazard Classifications

Repr. 2

Storage Class Code

11 - Combustible Solids

WGK

WGK 2

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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Urinary peptidomics provides a noninvasive humanized readout of diabetic nephropathy in mice
Klein J, et al.
Kidney International, 90(5), 1045-1055 (2016)
Enalapril
Todd PA and Heel RC
Drugs, 31(3), 198-248 (1986)
Lufei Hu et al.
PloS one, 17(1), e0261000-e0261000 (2022-01-28)
Diabetic nephropathy is associated with endothelial dysfunction and oxidative stress, in which the nitric oxide-soluble guanylate cyclase-cyclic guanosine monophosphate (NO-sGC-cGMP) signaling pathway is impaired. We hypothesize that sGC stimulator Compound 1 can enhance NO signaling, reduce proteinuria in a diabetic
Guang Liu et al.
American journal of physiology. Renal physiology, 319(4), F697-F711 (2020-09-01)
Praliciguat, a clinical-stage soluble guanylate cyclase (sGC) stimulator, increases cGMP via the nitric oxide-sGC pathway. Praliciguat has been shown to be renoprotective in rodent models of hypertensive nephropathy and renal fibrosis. In the present study, praliciguat alone and in combination
Enalapril protects against myocardial ischemia/reperfusion injury in a swine model of cardiac arrest and resuscitation
Wang G, et al.
International Journal of Molecular Sciences, 38(5), 1463-1473 (2016)
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