enalapril
Overview
Description
Scientific Research Applications
enalapril has a wide range of scientific research applications, including:
Chemistry: Used as a model compound to study angiotensin-converting enzyme inhibition.
Biology: Investigated for its effects on cellular pathways related to blood pressure regulation.
Medicine: Extensively studied for its therapeutic effects in treating hypertension and heart failure.
Industry: Used in the development of new antihypertensive drugs and formulations
Preparation Methods
Synthetic Routes and Reaction Conditions
enalapril is synthesized through a multi-step process involving the reaction of L-proline with ethyl 4-phenylbutanoate to form an intermediate, which is then coupled with L-alanine . The reaction conditions typically involve the use of organic solvents and catalysts to facilitate the formation of the desired product.
Industrial Production Methods
In industrial settings, the production of this compound involves large-scale synthesis using optimized reaction conditions to ensure high yield and purity. The process includes rigorous quality control measures to meet pharmaceutical standards .
Chemical Reactions Analysis
Types of Reactions
enalapril undergoes various chemical reactions, including:
Oxidation: This compound can be oxidized to form enalaprilat, its active metabolite.
Hydrolysis: This compound is hydrolyzed in the liver to produce enalaprilat.
Substitution: This compound can undergo substitution reactions with other chemical groups under specific conditions.
Common Reagents and Conditions
Oxidation: Common oxidizing agents such as hydrogen peroxide or potassium permanganate can be used.
Hydrolysis: Acidic or basic conditions can facilitate the hydrolysis of this compound.
Substitution: Various nucleophiles can be used for substitution reactions.
Major Products Formed
Enalaprilat: The primary active metabolite formed through hydrolysis.
Oxidized derivatives: Formed through oxidation reactions.
Mechanism of Action
enalapril exerts its effects by inhibiting the angiotensin-converting enzyme, which is responsible for converting angiotensin I to angiotensin II, a potent vasoconstrictor . By inhibiting this enzyme, this compound reduces the levels of angiotensin II, leading to vasodilation and decreased blood pressure. The molecular targets include the angiotensin-converting enzyme and the renin-angiotensin-aldosterone system .
Comparison with Similar Compounds
Similar Compounds
Lisinopril: Another angiotensin-converting enzyme inhibitor with similar antihypertensive effects.
Ramipril: Used for treating hypertension and heart failure, similar to enalapril.
Captopril: An older angiotensin-converting enzyme inhibitor with a shorter duration of action.
Uniqueness
This compound is unique due to its specific molecular structure, which allows for effective inhibition of the angiotensin-converting enzyme. It has a longer duration of action compared to some other angiotensin-converting enzyme inhibitors, making it a preferred choice for long-term management of hypertension .
Properties
IUPAC Name |
(2S)-1-[(2S)-2-[[(2R)-1-ethoxy-1-oxo-4-phenylbutan-2-yl]amino]propanoyl]pyrrolidine-2-carboxylic acid |
Source
|
|---|---|---|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
InChI |
InChI=1S/C20H28N2O5/c1-3-27-20(26)16(12-11-15-8-5-4-6-9-15)21-14(2)18(23)22-13-7-10-17(22)19(24)25/h4-6,8-9,14,16-17,21H,3,7,10-13H2,1-2H3,(H,24,25)/t14-,16+,17-/m0/s1 |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
InChI Key |
GBXSMTUPTTWBMN-UAGQMJEPSA-N |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
Canonical SMILES |
CCOC(=O)C(CCC1=CC=CC=C1)NC(C)C(=O)N2CCCC2C(=O)O |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
Isomeric SMILES |
CCOC(=O)[C@@H](CCC1=CC=CC=C1)N[C@@H](C)C(=O)N2CCC[C@H]2C(=O)O |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
Molecular Formula |
C20H28N2O5 |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
DSSTOX Substance ID |
DTXSID601181936 |
Source
|
| Record name | N-[(1R)-1-(Ethoxycarbonyl)-3-phenylpropyl]-L-alanyl-L-proline | |
| Source | EPA DSSTox | |
| URL | https://comptox.epa.gov/dashboard/DTXSID601181936 | |
| Description | DSSTox provides a high quality public chemistry resource for supporting improved predictive toxicology. | |
Molecular Weight |
376.4 g/mol |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
CAS No. |
76420-74-1 |
Source
|
| Record name | N-[(1R)-1-(Ethoxycarbonyl)-3-phenylpropyl]-L-alanyl-L-proline | |
| Source | CAS Common Chemistry | |
| URL | https://commonchemistry.cas.org/detail?cas_rn=76420-74-1 | |
| Description | CAS Common Chemistry is an open community resource for accessing chemical information. Nearly 500,000 chemical substances from CAS REGISTRY cover areas of community interest, including common and frequently regulated chemicals, and those relevant to high school and undergraduate chemistry classes. This chemical information, curated by our expert scientists, is provided in alignment with our mission as a division of the American Chemical Society. | |
| Explanation | The data from CAS Common Chemistry is provided under a CC-BY-NC 4.0 license, unless otherwise stated. | |
| Record name | Enalapril maleate impurity A | |
| Source | ChemIDplus | |
| URL | https://pubchem.ncbi.nlm.nih.gov/substance/?source=chemidplus&sourceid=0076420741 | |
| Description | ChemIDplus is a free, web search system that provides access to the structure and nomenclature authority files used for the identification of chemical substances cited in National Library of Medicine (NLM) databases, including the TOXNET system. | |
| Record name | N-[(1R)-1-(Ethoxycarbonyl)-3-phenylpropyl]-L-alanyl-L-proline | |
| Source | EPA DSSTox | |
| URL | https://comptox.epa.gov/dashboard/DTXSID601181936 | |
| Description | DSSTox provides a high quality public chemistry resource for supporting improved predictive toxicology. | |
| Record name | (2S)-1-((2S)-2-(((1R)-1-(ETHOXYCARBONYL)-3-PHENYLPROPYL)AMINO)PROPANOYL)PYRROLIDINE-2-CARBOXYLIC ACID | |
| Source | FDA Global Substance Registration System (GSRS) | |
| URL | https://gsrs.ncats.nih.gov/ginas/app/beta/substances/S7IJ7OBG9V | |
| Description | The FDA Global Substance Registration System (GSRS) enables the efficient and accurate exchange of information on what substances are in regulated products. Instead of relying on names, which vary across regulatory domains, countries, and regions, the GSRS knowledge base makes it possible for substances to be defined by standardized, scientific descriptions. | |
| Explanation | Unless otherwise noted, the contents of the FDA website (www.fda.gov), both text and graphics, are not copyrighted. They are in the public domain and may be republished, reprinted and otherwise used freely by anyone without the need to obtain permission from FDA. Credit to the U.S. Food and Drug Administration as the source is appreciated but not required. | |
Synthesis routes and methods
Procedure details
Retrosynthesis Analysis
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Strategy Settings
| Precursor scoring | Relevance Heuristic |
|---|---|
| Min. plausibility | 0.01 |
| Model | Template_relevance |
| Template Set | Pistachio/Bkms_metabolic/Pistachio_ringbreaker/Reaxys/Reaxys_biocatalysis |
| Top-N result to add to graph | 6 |
Feasible Synthetic Routes
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