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Key Documents

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:
Molecular Weight:
441.52
MDL number:
UNSPSC Code:
12352200
PubChem Substance ID:
NACRES:
NA.32

Pricing and availability is not currently available.

Quality Level

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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This Item
BP695L0702000Y0001709
Lisinopril ≥98% (HPLC)

L6292

Lisinopril

assay

≥98% (HPLC)

assay

-

assay

-

assay

-

storage temp.

2-8°C

storage temp.

2-8°C

storage temp.

2-8°C

storage temp.

2-8°C

solubility

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

solubility

-

solubility

-

solubility

-

color

white

color

-

color

-

color

-

Gene Information

human ... ACE(1636)

Gene Information

human ... ACE(1636)

Gene Information

human ... ACE(1636)

Gene Information

human ... ACE(1636)

Application

Lisinopril has been used to study the antifibrotic effect in duchenne muscular dystrophy mice.[1] 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.[2]

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

Signal Word

Danger

Hazard Statements

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

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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
    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
    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
    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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