Benazepril (CED0004872)

Record Information
Version1.0
Creation Date2016-05-25 18:21:09 UTC
Update Date2026-08-22 03:39:34 UTC
Accession NumberCHEM022133
Identification
Common NameBenazepril
ClassSmall Molecule
Description
Benazepril is an organic compound with the formula C24H28N2O5 and an average molecular weight of 424.49 g/mol. Benazepril belongs to the amino acids, peptides, and analogues, a subclass of carboxylic acids and derivatives within the organic compounds. The compound acts as an inhibitor of the protein target Angiotensin-converting enzyme (ACE). Benazepril is found in or released from two recorded sources: antennas within electrical and electronic equipment and ACE inhibitors within healthcare, pharmaceuticals, and veterinary products. The recorded route of exposure for this substance is oral.
Contaminant TypeNot Available
Chemical Structure
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
BenazeprilumChEBI
Benazepril sandozKegg
ForteekorKegg
CGS-14824-aHMDB
LotensinHMDB
BriemHMDB
CibacèneHMDB
LabopalHMDB
CibacenHMDB
BenazaprilHMDB
Benazepril hydrochlorideHMDB
BenzazeprilHMDB
Chemical FormulaC24H28N2O5
Average Molecular Mass424.490 g/mol
Monoisotopic Mass424.200 g/mol
CAS Registry Number86541-75-5
IUPAC Name2-[(3S)-3-{[(2S)-1-ethoxy-1-oxo-4-phenylbutan-2-yl]amino}-2-oxo-2,3,4,5-tetrahydro-1H-1-benzazepin-1-yl]acetic acid
Traditional Namebenazepril
SMILESCCOC(=O)[C@H](CCC1=CC=CC=C1)N[C@H]1CCC2=CC=CC=C2N(CC(O)=O)C1=O
InChI IdentifierInChI=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
InChI KeyXPCFTKFZXHTYIP-PMACEKPBSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as dipeptides. These are organic compounds containing a sequence of exactly two alpha-amino acids joined by a peptide bond.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentDipeptides
Alternative Parents
Substituents
  • Alpha-dipeptide
  • Alpha-amino acid ester
  • Benzazepine
  • Alpha-amino acid or derivatives
  • Azepine
  • Fatty acid ester
  • Aralkylamine
  • Dicarboxylic acid or derivatives
  • Monocyclic benzene moiety
  • Fatty acyl
  • Benzenoid
  • Tertiary carboxylic acid amide
  • Carboxylic acid ester
  • Amino acid or derivatives
  • Amino acid
  • Lactam
  • Carboxamide group
  • Carboxylic acid
  • Secondary aliphatic amine
  • Azacycle
  • Secondary amine
  • Organoheterocyclic compound
  • Organic nitrogen compound
  • Organonitrogen compound
  • Carbonyl group
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Amine
  • Organic oxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Organoleptic EffectsNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.01 g/LALOGPS
logP1.14ALOGPS
logP1.54ChemAxon
logS-4.6ALOGPS
pKa (Strongest Acidic)3.53ChemAxon
pKa (Strongest Basic)5.36ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area95.94 ŲChemAxon
Rotatable Bond Count10ChemAxon
Refractivity115.23 m³·mol⁻¹ChemAxon
Polarizability44.98 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrumsplash10-0udi-2009000000-19c2bb5c2c0344b51b24Not AvailableView Spectrum
Predicted GC-MSPredicted GC-MS Spectrumsplash10-00di-3002900000-85952764d74c57097928Not AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0ufu-0917700000-5f1f2ae9b1d7afc6eee5Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00di-0510900000-aef2e71e3edc278d2181Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0ufu-0906300000-967f2d700778895024c2Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-004i-0117900000-5f064fedfa50b268135bNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-004i-3329200000-a339e2329a1813e9c056Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-05uu-2910000000-1a808fc7adec9b057f0bNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00fr-1009600000-5a58d6a23289daee9801Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00ba-3139300000-7836712c89121ae2cdd4Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00kb-7941000000-d9aa7d72e1bd3d7292adNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00di-0001900000-9d13e519742f1a70650dNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00di-2449400000-8c87c62f9d64b50b65b5Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0603-3982000000-8f24ae77915ed4d4bb86Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-004i-0004900000-245f5166b211af2a37eaNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-004i-0309300000-5d9f8f58556e7d05a3d9Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0api-2920000000-cf196d3de0f43915f5f6Not AvailableView Spectrum
Toxicity Profile
Mechanism of ToxicityNot Available
Carcinogenicity (IARC Classification)Not Available
Minimum Risk LevelNot Available
SymptomsNot Available
TreatmentNot Available
Toxicity Values
Toxicity ValueUnitValue RangeOrganismDose DescriptorRoute of ExposurePredicted or ExperimentalReference
2107.0Log mg/kg[1200:3700]RatLD50oralpredictedNot Available
Health Effects
Health EffectRelationshipDirectionReference
Exposure Sources
Source IDSourceSectorReference
295ACE inhibitorsHealthcare, pharmaceuticals & veterinary productsNot Available
506AntennasElectrical & Electronic EquipmentNot Available
Pathways
4 pathways
Benazepril Action Pathway
Benazepril Action Pathway
Benazepril Metabolism Pathway
Benazepril Metabolism Pathway
Benazepril ACE inhibitor Action Pathway
Benazepril ACE inhibitor Action Pathway
Benazepril Drug Metabolism Action Pathway
Benazepril Drug Metabolism Action Pathway
Targets
StructureProteinUniProt IDOrganismRelationshipDetails
Angiotensin-converting enzyme structureClick to view 3D structureAngiotensin-converting enzymeP12821HumansPredicted (SEA)39.3917
Click to view 3D structureAngiotensin-converting enzymeP47820Rattus norvegicusPredicted (SEA)16.1926
Click to view 3D structureAngiotensin-converting enzymeP12822Oryctolagus cuniculusPredicted (SEA)26.7801
Click to view 3D structureGrowth hormone secretagogue receptor type 1Q95254Sus scrofaPredicted (SEA)7.39568
Muscarinic acetylcholine receptor M4 structureClick to view 3D structureMuscarinic acetylcholine receptor M4P08173HumansPredicted (SEA)146.045
Muscarinic acetylcholine receptor M1 structureClick to view 3D structureMuscarinic acetylcholine receptor M1P11229HumansPredicted (SEA)244.602
Muscarinic acetylcholine receptor M3 structureClick to view 3D structureMuscarinic acetylcholine receptor M3P20309HumansPredicted (SEA)172.592
Click to view 3D structurePeptidyl-glycine alpha-amidating monooxygenaseP19021HumansPredicted (SEA)41.8829
Click to view 3D structureSigma non-opioid intracellular receptor 1Q60492Cavia porcellusPredicted (SEA)297.306
D(4) dopamine receptor structureClick to view 3D structureD(4) dopamine receptorP21917HumansPredicted (SEA)500.96
Muscarinic acetylcholine receptor M5 structureClick to view 3D structureMuscarinic acetylcholine receptor M5P08912HumansPredicted (SEA)179.52
D(3) dopamine receptor structureClick to view 3D structureD(3) dopamine receptorP35462HumansPredicted (SEA)639.064
Muscarinic acetylcholine receptor M2 structureClick to view 3D structureMuscarinic acetylcholine receptor M2P08172HumansPredicted (SEA)267.49
D(2) dopamine receptor structureClick to view 3D structureD(2) dopamine receptorP14416HumansPredicted (SEA)820.453
Click to view 3D structureNeprilysinP07861Rattus norvegicusPredicted (SEA)111.324
Pyruvate carboxylase structureClick to view 3D structurePyruvate carboxylaseA0A0H3JRU9Staphylococcus aureus (strain Mu50 / ATCC 700699)Predicted (SEA)4.35956
Prostaglandin E2 receptor EP3 subtype structureClick to view 3D structureProstaglandin E2 receptor EP3 subtypeP43115HumansPredicted (SEA)47.2545
Click to view 3D structureProstaglandin E2 receptor EP1 subtypeP34995HumansPredicted (SEA)44.7633
Click to view 3D structureReceptor (TNFRSF)-interacting serine-threonine kinase 1 (Predicted)D3ZYL0Rattus norvegicusPredicted (SEA)7.23998
72 kDa type IV collagenase structureClick to view 3D structure72 kDa type IV collagenaseP08253HumansPredicted (SEA)441.249
Voltage-gated inwardly rectifying potassium channel KCNH2 structureClick to view 3D structureVoltage-gated inwardly rectifying potassium channel KCNH2Q12809HumansPredicted (SEA)1750.75
Cathepsin B structureClick to view 3D structureCathepsin BP07858HumansPredicted (SEA)271.305
Click to view 3D structureSodium-dependent serotonin transporterP31652Rattus norvegicusPredicted (SEA)319.026
Click to view 3D structureRalA-binding protein 1Q62172Mus musculusPredicted (SEA)6.85073
Click to view 3D structureSodium-dependent dopamine transporterP23977Rattus norvegicusPredicted (SEA)206.612
Concentrations
Not Available
External Links
DrugBank IDDB00542
HMDB IDHMDB0014682
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDCPD-15329
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkBenazepril
Chemspider ID4514935
ChEBI ID3011
PubChem Compound ID5362124
Kegg Compound IDC06843
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. De Feo P, Torlone E, Perriello G, Fanelli C, Epifano L, Di Vincenzo A, Modarelli F, Motolese M, Brunetti P, Bolli GB: Short-term metabolic effects of the ACE-inhibitor benazepril in type 2 diabetes mellitus associated with arterial hypertension. Diabete Metab. 1992 Jul-Aug;18(4):283-8.
2. MacNab M, Mallows S: Safety profile of benazepril in essential hypertension. Clin Cardiol. 1991 Aug;14(8 Suppl 4):IV33-7; discussion IV51-5.
3. Gengo FM, Brady E: The pharmacokinetics of benazepril relative to other ACE inhibitors. Clin Cardiol. 1991 Aug;14(8 Suppl 4):IV44-50; discussion IV51-5.
4. Chan KK, Buch A, Glazer RD, John VA, Barr WH: Site-differential gastrointestinal absorption of benazepril hydrochloride in healthy volunteers. Pharm Res. 1994 Mar;11(3):432-7.
5. Szekacs B, Vajo Z, Dachman W: Effect of ACE inhibition by benazepril, enalapril and captopril on chronic and post exercise proteinuria. Acta Physiol Hung. 1996;84(4):361-7.
6. Hou FF, Zhang X, Zhang GH, Xie D, Chen PY, Zhang WR, Jiang JP, Liang M, Wang GB, Liu ZR, Geng RW: Efficacy and safety of benazepril for advanced chronic renal insufficiency. N Engl J Med. 2006 Jan 12;354(2):131-40.
7. Ishimitsu T, Akashiba A, Kameda T, Takahashi T, Ohta S, Yoshii M, Minami J, Ono H, Numabe A, Matsuoka H: Benazepril slows progression of renal dysfunction in patients with non-diabetic renal disease. Nephrology (Carlton). 2007 Jun;12(3):294-8.
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=25224804
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=25738503
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=25784709
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=25912588