Lisinopril

Base Information

• Chemical Name: Lisinopril
• CAS No.: 76547-98-3
• Molecular Formula: C21H31N3O5
• Molecular Weight: 405.494
• European Community (EC) Number: 278-488-1,934-016-2
• NSC Number: 758151,751176
• UNII: 7Q3P4BS2FD
• DSSTox Substance ID: DTXSID6040537
• Nikkaji Number: J32.520A
• Wikipedia: Lisinopril
• Wikidata: Q412208
• NCI Thesaurus Code: C29159,C83924
• RXCUI: 29046,1546022
• Pharos Ligand ID: 6Y1P65W348W7
• Metabolomics Workbench ID: 37944
• ChEMBL ID: CHEMBL1237
• Mol file: 76547-98-3.mol

Synonyms:Lisinopril;Lisinopril Maleate (1:1);Lisinopril Sulfate (1:2);Lysinopril;MK-521;Prinivil;Zestril

Chemical Property of Lisinopril

Chemical Property:

• Appearance/Colour: white solid
• Vapor Pressure: 1.14E-18mmHg at 25°C
• Melting Point: 162-165 °C
• Boiling Point: 666.4 °C at 760 mmHg
• PKA: 2.18±0.10(Predicted)
• Flash Point: 356.9 °C
• Density: 1.251 g/cm³
• Storage Temp.: 2-8°C
• Solubility.: H2O: ≥10 mg/mL
• XLogP3: -2.9
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 12
• Exact Mass: 405.22637110
• Heavy Atom Count: 29
• Complexity: 550

Purity/Quality:

99%, ^*data from raw suppliers

Lisinopril >98% ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Drug Classes: Angiotensin-Converting Enzyme Inhibitors
• Canonical SMILES: C1CC(N(C1)C(=O)C(CCCCN)NC(CCC2=CC=CC=C2)C(=O)O)C(=O)O
• Isomeric SMILES: C1C[C@H](N(C1)C(=O)[C@H](CCCCN)N[C@@H](CCC2=CC=CC=C2)C(=O)O)C(=O)O
• Recent ClinicalTrials: A Study to Evaluate the Effect of Sodium Zirconium Cyclosilicate on Chronic Kidney Disease (CKD) Progression in Participants With CKD and Hyperkalaemia or at Risk of Hyperkalaemia
• Recent EU Clinical Trials: The effects of medication induced blood pressure reduction on cerebral hemodynamics in hypertensive frail elderly
• Recent NIPH Clinical Trials: A Study to Evaluate the Effect of Sodium Zirconium Cyclosilicate on Chronic Kidney Disease (CKD) Progression in Participants With CKD and Hyperkalaemia or at Risk of Hyperkalaemia
• 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).
• Uses: Labeled Lisinopril, intended for use as an internal standard for the quantification fo Lisinopril by GC- or LC-mass spectrometry. Lisinopril is an antihypertensive medication.
• Therapeutic Function: Antihypertensive

Technology Process of Lisinopril

There total 20 articles about Lisinopril which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 92.0%

Nε-(trifluoroacetyl)-Nα-<(S)-1-(ethoxycarbonyl)-3-phenylpropyl>-L-lysyl-L-proline (103300-91-0) → Lisinopril (76547-98-3)

Guidance literature:

With water; sodium hydroxide; at 40 - 45 ℃; pH=12 - 13;

Reference yield: 75.8%

N2-<(S)-1-(ethoxycarbonyl)-3-phenylpropyl>-L-lysyl-L-proline (85955-58-4) → Lisinopril (76547-98-3)

Guidance literature:

With sodium hydroxide; for 24h; Ambient temperature;

DOI:10.1248/cpb.37.280

Reference yield: 75.0%

(S)-1-[N2-(1-carboxy-3-phenylpropyl]-L-lysyl]-L-proline (77726-95-5) → Lisinopril (76547-98-3) + lisinopril (85955-59-5)

Guidance literature:

With hydrogenchloride; In water; Resolution of racemate;

upstream raw materials:

2-oxo-4-phenylbutyric acid

H-Lys(Boc)-Pro-OH

N^ε-(trifluoroacetyl)-N^α-<(S)-1-(ethoxycarbonyl)-3-phenylpropyl>-L-lysyl-L-proline

N⁶-(tert-butoxycarbonyl)-N²-<(S)-1-(ethoxycarbonyl)-3-phenylpropyl>-L-lysyl-L-proline tert-butylester

Downstream raw materials:

(S)-1-[N₂-(1-carboxy-3-phenylpropyl)-L-lysyl(boc)]-L-proline

lisinopril diethyl ester

N-{N-[(S)-1-cyclohexylcarboxy-3-propyl]-L-lysyl}-L-proline

Refernces

• 1、 -. "A process for preparing high-purity lisinopril". Paragraph 0045-0074. . Retrieved 2019/05/15.
• 2、 -. "Process for separating the diastereomers of RSS-snd SSS-N- a [1-carboxy -3-Phenylpropyl] lysylproline". Page/Page column 2. . Retrieved 2011/04/19.