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L6292

Sigma-Aldrich

Lisinopril

≥98% (HPLC)

Synonym(s):

(S)-1-[N2-(1-carboxy-3-phenylpropyl)-lysyl-proline dihydrate, MK-521

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About This Item

Empirical Formula (Hill Notation):
C21H31O5N3 · 2H2O
CAS Number:
83915-83-7
Molecular Weight:
441.52
MDL number:
MFCD01698825
UNSPSC Code:
12352200
PubChem Substance ID:
329817636
NACRES:
NA.32

Assay

≥98% (HPLC)

form

solid

color

white

solubility

H2O: ≥10 mg/mL
DMSO: ~6.5 mg/mL (with heating and sonicating)

storage temp.

2-8°C

SMILES string

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

InChI

1S/C21H31N3O5.2H2O/c22-13-5-4-9-16(19(25)24-14-6-10-18(24)21(28)29)23-17(20(26)27)12-11-15-7-2-1-3-8-15;;/h1-3,7-8,16-18,23H,4-6,9-14,22H2,(H,26,27)(H,28,29);2*1H2/t16-,17-,18-;;/m0../s1

InChI key

CZRQXSDBMCMPNJ-ZUIPZQNBSA-N

Gene Information

human ... ACE(1636)

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Application

Lisinopril has been used to study the antifibrotic effect in duchenne muscular dystrophy mice. It has been used to study the changes in renal-structure and -function in TGR(mRen2)27 (transgenic rat harboring the murine Ren-2 gene) rats upon long term darbepoetin α treatment.

Biochem/physiol Actions

Angiotensin converting enzyme (ACE) inhibitor.

Features and Benefits

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

Danger

Hazard Statements

H360D,H373

Hazard Classifications

Repr. 1A - STOT RE 2

Target Organs

Kidney

Storage Class Code

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

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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Anne-Roos S Frenay et al.
Journal of the renin-angiotensin-aldosterone system : JRAAS, 13(2), 232-238 (2012-01-28)
Erytropoietin (EPO) has cytoprotective and angiogenic properties and has a beneficial effect in ischaemic conditions. Since the development of renal interstitial abnormalities are often associated with ischaemia, we studied the effects of the long-acting EPO analogue darbepoetin alpha (DA) on
Saleh Yazdani et al.
PloS one, 7(11), e50209-e50209 (2012-11-29)
Proteinuria is an important cause of progressive tubulo-interstitial damage. Whether proteinuria could trigger a renal lymphangiogenic response has not been established. Moreover, the temporal relationship between development of fibrosis, inflammation and lymphangiogenesis in chronic progressive kidney disease is not clear
Nadir Ulu et al.
The Journal of pharmacology and experimental therapeutics, 345(3), 393-403 (2013-03-27)
Transactivation of epidermal growth factor receptor (EGFR) signaling by G protein-coupled receptors has been implicated in several cardiovascular (CV) conditions, including hypertension, heart failure, and cardiac and vascular hypertrophy. However, the therapeutic potential of EGFR inhibition in these conditions is
Tatjana Ignjatovic et al.
The Journal of biological chemistry, 277(19), 16847-16852 (2002-03-07)
Angiotensin I converting enzyme (kininase II; ACE) inhibitors are important therapeutic agents widely used for treatment in cardiovascular and renal diseases. They inhibit angiotensin II release and bradykinin inactivation; these actions do not explain completely the clinical benefits. We found
Jill A Rafael-Fortney et al.
Circulation, 124(5), 582-588 (2011-07-20)
Nearly universal cardiomyopathy in Duchenne muscular dystrophy (DMD) contributes to heart failure and death. Because DMD patients show myocardial fibrosis well before functional impairment, we postulated that earlier treatment using drugs with antifibrotic effect may be beneficial. Three groups of
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