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

pka

2.18±0.10(Predicted)

color 

white

BCS Class

3

CAS DataBase Reference

76547-98-3(CAS DataBase Reference)

Safety Information

Safety Statements 

22-24/25

WGK Germany 

3

RTECS 

TW3589990

Hazardous Substances Data

76547-98-3(Hazardous Substances Data)

MSDS

• Language:English Provider:SigmaAldrich

Lisinopril Usage And Synthesis

Description

Lisinopril 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).

Originator

Acebitor 5,Biddle Sawyer,India

Uses

Lisinopril is an antihypertensive medication.

Uses

Labeled Lisinopril, intended for use as an internal standard for the quantification fo Lisinopril by GC- or LC-mass spectrometry.

Definition

ChEBI: 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 Process

2-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 name

Prinivil (Merck); Zestril (AstraZeneca).

Therapeutic Function

Antihypertensive

Lisinopril(76547-98-3)Related Product Information

• D-Proline
• DL-Lysine acetylsalicylate
• Poly(L-lysine hydrobromide)
• L-Lysine hydrochloride
• L-Lysine
• LISINOPRIL ESTER,LISINOPRIL (ETHYL) ESTER
• Lisinopril Dihydrate
• N6-Trrifluoroacetyl-L-lysine(for Lisinopril),N-6-TRIFLUORO ACETYL-L-LYSINE ( LISINOPRIL INTERMEDIATE )
• Lisinopril R,S,S-Diketopiperazine
• N6-TRIFLUOROACETYL-L-LYSINE /INTERMEDIATE OF LISINOPRIL
• N6-TrifluoroAcetyl-L-Lysine,Lisinopril
• N∑-BENZYLOXYCARBONYL-L-LYSINYL-L-PROLINE(LISINOPRIL INTERMEDIATE)
• (R) Lisinopril
• (S)Lisinopril-D5
• LISINOPRIL DIHYDRATE FOR PERFORMANCE TEST
• Lisinopril S,S,S-Diketopiperazine
• Lisinopril
• LISINOPRIL DIKETOPIPERAZINE