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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

signalword

Danger

Hazard Classifications

Repr. 1A - STOT RE 2

target_organs

Kidney

Storage Class

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

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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
Jason V Baker et al.
PloS one, 7(10), e46894-e46894 (2012-10-20)
Treatments that reduce inflammation and cardiovascular disease (CVD) risk among individuals with HIV infection receiving effective antiretroviral therapy (ART) are needed. We conducted a 2 × 2 factorial feasibility study of lisinopril (L) (10 mg daily) vs L-placebo in combination
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
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
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
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