Benazepril |
![]() Last updated: 13/09/2025 |
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(Not known by any other names) |
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A phenylpropylamine medicinal prodrug which is a second generation ACE inhibitor | |
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Used to treat congestive heart failure, high blood pressure and chronic renal failure | |
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Dogs; Cats |
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Approved - usually available as a prescription only medicine to be authorised by a veterinarian (POM-V) | |
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Approved |
Chemical structure |
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Benazepril exhibits optical isomerism due to the presence of two stereogenic centres in its molecular structure. These chiral centres give rise to four possible stereoisomers: two pairs of enantiomers: (S,S) and (R,R), and two diastereomers: (R,S) and (S,R). Among these, the (S,S)-enantiomer is the pharmacologically active form. | |
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C₂₄H₂₈N₂O₅₄₂₄.₅ | |
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CCOC(=O)C(CCC1=CC=CC=C1)NC2CCC3=CC=CC=C3N(C2=O)CC(=O)O | |
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CCOC(=O)[C@H](CCC1=CC=CC=C1)N[C@H]2CCC3=CC=CC=C3N(C2=O)CC(=O)O | |
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XPCFTKFZXHTYIP-PMACEKPBSA-N | |
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InChI=1S/C24H28N2O5/c1-2-31-24(30)20(14-12-17-8-4-3-5-9-17)25-19-15-13-18-10-6-7-11-21(18)26(23(19)29)16-22(27)28/h3-11,19-20,25H,2,12-16H2,1H3,(H,27,28)/t19-,20-/m0/s1 | |
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Yes |
General status |
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Medicinal drug, Hypertensive agent, Prodrug | |
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Phenylpropylamine | |
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>99% | |
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The pharmacologically inactive isomers may occur as impurities | |
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Synthetic | |
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A second generation ACE (angiotensin-converting enzyme) inhibitor which prevents the catalytic conversion of angiotensin I to angiotensin II and in turn causes vasodilation and an increase in capillary blood volume | |
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[Angiotensin-converting enzyme, Antagonist] | |
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86541-75-5 | |
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Alimentary tract & metabolism: Agents acting on the renin-angiotensin system; ACE inhibitor | |
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QC09AA07 | |
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No | |
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460.96 | |
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2-[(3S)-3-[[(2S)-1-ethoxy-1-oxo-4-phenylbutan-2-yl]amino]-2-oxo-4,5-dihydro-3H-1-benzazepin-1-yl]acetic acid | |
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2-[(3S)-3-[[(2S)-1-ethoxy-1-oxo-4-phenylbutan-2-yl]amino]-2-oxo-4,5-dihydro-3H-1-benzazepin-1-yl]acetic acid | |
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Commercial |
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Current | |||
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1981, patented; 1990, first medical use | |||
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Usually supplied in tablet form for oral administration | |||
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Benazepril is synthesised through a multi-step chemical process that begins with the formation of a key intermediate: 3-bromo-2,3,4,5-tetrahydro-2H-benzo[b]azepin-2-one, which provides the core benzazepine ring. This intermediate is then coupled with (S)-homophenylalanine using a dynamic kinetic resolution technique to ensure the correct stereochemistry. The resulting compound undergoes esterification to introduce the ethyl ester moiety, followed by treatment with hydrogen chloride gas to form benazepril hydrochloride, the active pharmaceutical ingredient. | |||
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Published GHG data is not available for most pharmaceuticals. However, according to industry, global averages suggest producing 1 kg of a typical active pharmaceutical ingredient can range from 10 to 100 kg CO₂e for small molecule drugs and potentially up to 1000 kg CO₂e for complex biologicals such as vaccines, depending on the drug type, its formulation, complexity of synthesis, solvent recovery, and energy sources used. |
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As this parameter is not normally measured directly, a surrogate measure is used: ‘Photochemical oxidative DT₅₀’. Where data is available, this can be found in the Fate Indices section below. | ||||||||||
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Fate indices |
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Known metabolites |
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Terrestrial ecotoxicology |
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> 5000 | V3 V = ChemID Online Databases; Chemspider; PubChem. (ChemID ) Rat3 = Unverified data of known source |
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General |
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High (class III) | - | - | ||||||||
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> 5000 | V3 V = ChemID Online Databases; Chemspider; PubChem. (ChemID ) Rat3 = Unverified data of known source |
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Metabolised in the liver to the active substance Benazeprilat. Equally excreted by both liver and kidney. Also excreted in breast milk and unmetabolized in faeces. | Q3 Q = Miscellaneous data from online sources 3 = Unverified data of known source |
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Health issues |
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May cause diarrhoea, hypotension; disturbances in heart rhythm |
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Incompatible with oxidising agents Emits toxic fumes in a fire |
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Not listed (Not listed) | |||
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benazepril | ||
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Record last updated: | 13/09/2025 |
Contact: | aeru@herts.ac.uk |
Please cite as: | Lewis, K.A., Tzilivakis, J., Warner, D. and Green, A. (2016) An international database for pesticide risk assessments and management. Human and Ecological Risk Assessment: An International Journal, 22(4), 1050-1064. DOI: 10.1080/10807039.2015.1133242 |