Lisinopril

Lisinopril Basic information
Product Name:Lisinopril
Synonyms:(S)-1-[(S)-6-AMINO-2-((S)-1-CARBOXY-3-PHENYL-PROPYLAMINO)-HEXANOYL]-PYRROLIDINE-2-CARBOXYLIC ACID;TENSOPRIL;VIVATEC;ZESTRIL;mk522;PRINIL;PRINIVIL;n-{n-[(s)-1-carboxy-3-phenylpropyl]-l-lysyl}-l-proline
CAS:76547-98-3
MF:C21H31N3O5
MW:405.49
EINECS:278-488-1
Product Categories:
Mol File:76547-98-3.mol
Lisinopril Structure
Lisinopril Chemical Properties
Melting point 162-165 °C
Boiling point 666.4±55.0 °C(Predicted)
density 1.251±0.06 g/cm3(Predicted)
storage temp. Keep in dark place,Inert atmosphere,2-8°C
solubility H2O: ≥10 mg/mL
form solid
pka2.18±0.10(Predicted)
color white
BCS Class3
CAS DataBase Reference76547-98-3(CAS DataBase Reference)
Safety Information
Safety Statements 22-24/25
WGK Germany 3
RTECS TW3589990
Hazardous Substances Data76547-98-3(Hazardous Substances Data)
MSDS Information
ProviderLanguage
SigmaAldrich English
Lisinopril Usage And Synthesis
DescriptionLisinopril is an angiotensin-converting enzyme (ACE) inhibitor (IC50 = 1.2 nM). It reduces the formation of endothelin-1 and increases nitric oxide (NO) in human vascular endothelial cells when used at a concentration of 0.1 nM. Lisinopril inhibits the pressor response to angiotensin I in anesthetized rats and dogs (ID50s = 2.3 and 6.5 μg/kg, respectively).
OriginatorAcebitor 5,Biddle Sawyer,India
UsesLabeled Lisinopril, intended for use as an internal standard for the quantification fo Lisinopril by GC- or LC-mass spectrometry.
UsesLisinopril is an antihypertensive medication.
DefinitionChEBI: Lisinopril is a dipeptide. It has a role as an EC 3.4.15.1 (peptidyl-dipeptidase A) inhibitor. It contains a L-prolino group and a L-lysine residue.
Manufacturing Process2-Oxo-4-phenylbutyric acid and t-BOC-L-lysyl-L-proline are condensed in the presence of sodium cyanoborohydride. Essentially all of the t-BOC protecting group is cleaved when the product is absorbed on strong acid ion exchange resin. The crude N-(1-carboxy-3-phenylpropyl)-L-lysyl-L-proline is eluted from the resin with 10% ammonia, freeze dried, and purified by gel filtration chromatography (LH-20). A minute peak for t-BOC protons in the NMR spectrum disappears when the product is treated with ethyl acetate that is 4 N in hydrogen chloride gas. The NMR spectrum of the resulting HCl salt of the product is consistent with structure. The mass spectrum shows a molecular ion at 693 m/e for the tetrasilylated species. Chromatography on XAD-2 resin using 3.5% acetonitrile in 0.1 molar ammonium hydroxide affords N-α-((1S)- 1-carboxy-3-phenylpropyl)-L-lysyl-L-proline. The last peptide can be produced if 2-oxo-4-phenylbutyric acid and N-t-Boc-L-lysyl-L-proline are condensed in the presence of sodium cyanoborohydride. The product is absorbed on strong acid ion exchange resin, and eluted with 2% pyridine in water. Product-rich cuts are stripped to a glass and treated with 4 N HCl in ethylacetate to remove the t-Boc protecting group. The resulting hydrochloride salt is converted to the free base by absorbing on strong acid ion exchange resin and eluting with 2% pyridine in water. Freeze drying of product-rich cuts affords N-α-(1-carboxy-3-phenylpropyl)-L-lysyl-L-proline as a white fluffy solid. The NMR spectrum is consistent with structure. The mass spectrum shows a molecular ion at 549 for the disilylated species. Chromatography affords the desired isomer.
Brand namePrinivil (Merck); Zestril (AstraZeneca).
Therapeutic FunctionAntihypertensive
Lisinopril Preparation Products And Raw materials
Raw materialsTrifluoroacetic acid-->L-Proline-->L-Lysine-->Sodium cyanoborohydride-->LIPOPHILIC SEPHADEX-->2-Oxo-4-phenylbutyric acid
LISINOPRIL DIHYDRATE FOR PERFORMANCE TEST EPL (S)Lisinopril-D5 Lisinopril R,S,S-Diketopiperazine D-Proline Lisinopril Dihydrate LISINOPRIL ESTER,LISINOPRIL (ETHYL) ESTER LISINOPRIL DIHYDRATE FOR PERFORMANCE TEST Poly(L-lysine hydrobromide) N6-Trrifluoroacetyl-L-lysine(for Lisinopril),N-6-TRIFLUORO ACETYL-L-LYSINE ( LISINOPRIL INTERMEDIATE ) L-Lysine DL-Lysine acetylsalicylate LISINOPRIL USP 24 LISINOPRIL DIHYDRATE IMP. B (EP) AS HYDRATE: 4-METHYLBENZENESULPHONIC ACID HYDRATE MM Lisinopril L-Lysine hydrochloride LISINOPRIL DIHYDRATE IMP. A (EP): (2RS)-2-AMINO-4-PHENYLBUTANOIC ACID (R) Lisinopril N6-TRIFLUOROACETYL-L-LYSINE /INTERMEDIATE OF LISINOPRIL

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