Zofenopril
Catalog Number: BT-254888
CAS Number: 81872-10-8
Molecular Formula: C₂₂H₂₃NO₄S₂
Molecular Weight: 429.6 g/mol
The product is for non-human research only. Not for therapeutic or veterinary use.
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Product Introduction
Description
Zofenopril is a thiol-containing angiotensin-converting enzyme (ACE) inhibitor that is used to treat hypertension and heart failure. It was first approved for use in Europe in 1998 and has since been used in several countries worldwide. Zofenopril is known for its high efficacy and safety profile, making it a popular choice for patients with cardiovascular diseases.
Properties
CAS Number
81872-10-8
Product Name
Zofenopril
IUPAC Name
(2S,4S)-1-[(2S)-3-benzoylsulfanyl-2-methylpropanoyl]-4-phenylsulfanylpyrrolidine-2-carboxylic acid
Molecular Formula
C₂₂H₂₃NO₄S₂
Molecular Weight
429.6 g/mol
InChI
InChI=1S/C22H23NO4S2/c1-15(14-28-22(27)16-8-4-2-5-9-16)20(24)23-13-18(12-19(23)21(25)26)29-17-10-6-3-7-11-17/h2-11,15,18-19H,12-14H2,1H3,(H,25,26)/t15-,18+,19+/m1/s1
InChI Key
IAIDUHCBNLFXEF-MNEFBYGVSA-N
SMILES
CC(CSC(=O)C1=CC=CC=C1)C(=O)N2CC(CC2C(=O)O)SC3=CC=CC=C3
Synonyms
SQ 26900
SQ 26991
SQ-26900
SQ-26991
Zofenil
zofenopril
zofenopril, calcium salt, (1(R*),2alpha,4alpha)-isomer
Zofil
SQ 26991
SQ-26900
SQ-26991
Zofenil
zofenopril
zofenopril, calcium salt, (1(R*),2alpha,4alpha)-isomer
Zofil
Canonical SMILES
CC(CSC(=O)C1=CC=CC=C1)C(=O)N2CC(CC2C(=O)O)SC3=CC=CC=C3
Isomeric SMILES
C[C@H](CSC(=O)C1=CC=CC=C1)C(=O)N2C[C@H](C[C@H]2C(=O)O)SC3=CC=CC=C3
Method of Synthesis or Extraction
Zofenopril is synthesized using a multi-step process that involves the reaction of 2-mercaptoacetic acid with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) to form the intermediate compound, 2-(2-mercaptoacetyl)benzoquinone. This intermediate is then reacted with 2-aminothiophenol to form the final product, zofenopril. The yield of this process is typically around 50%, and the process is considered to be environmentally friendly and safe.
Chemical Structure and Biological Activity
Zofenopril has a chemical structure that consists of a thiol group, a carboxylic acid group, and a benzene ring. It works by inhibiting the activity of Zofenopril, which is an enzyme that converts angiotensin I to angiotensin II. By inhibiting this enzyme, zofenopril reduces the production of angiotensin II, which leads to vasodilation and a decrease in blood pressure. Zofenopril also has antioxidant properties, which may contribute to its cardioprotective effects.
Biological Effects
Zofenopril has been shown to have several biological effects on cell function and signal transduction. It has been shown to reduce oxidative stress and inflammation, which are both important factors in the development of cardiovascular diseases. Zofenopril has also been shown to improve endothelial function, which is important for maintaining healthy blood vessels. In terms of potential therapeutic and toxic effects, zofenopril has been shown to be effective in reducing blood pressure and improving heart function in patients with heart failure. However, it may also have side effects such as cough, dizziness, and gastrointestinal disturbances.
Applications
In medical research, zofenopril has been studied for its role in drug development and its potential therapeutic effects in cardiovascular diseases. Clinical trials have shown that zofenopril is effective in reducing blood pressure and improving heart function in patients with heart failure. However, more research is needed to fully understand its potential benefits and side effects. In environmental research, zofenopril has been studied for its effects on ecosystems and its role in pollution management. It has been shown to have low toxicity and is considered to be environmentally friendly. In industrial research, zofenopril has been used in manufacturing processes to improve product quality and efficiency. Health and safety considerations are important when using zofenopril in industrial settings.
Future Perspectives and Challenges
Current limitations in the use and study of zofenopril include the need for more research to fully understand its potential benefits and side effects. Possible solutions and improvements include the development of new formulations and delivery methods to improve its efficacy and safety. Future trends and prospects in the application of zofenopril in scientific research include the development of new drugs that target the renin-angiotensin-aldosterone system, which may lead to more effective treatments for cardiovascular diseases.
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