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Lisinopril

Basic information Safety Supplier Related

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
Mol File:
76547-98-3.mol
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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)
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Safety Information

Safety Statements 
22-24/25
WGK Germany 
3
RTECS 
TW3589990
Hazardous Substances Data
76547-98-3(Hazardous Substances Data)

MSDS

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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 Preparation Products And Raw materials

Raw materials

LisinoprilSupplier

3B Pharmachem (Wuhan) International Co.,Ltd.
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821-50328103-801 18930552037
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3bsc@sina.com
Adamas Reagent, Ltd.
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400-6009262 16621234537
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zhangsn@titansci.com
Syntechem Co.,Ltd
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BOC Sciences
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1-631-485-4226; 16314854226
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Shanghai T&W Pharmaceutical Co., Ltd.
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+86 21 61551611