Benazepril (CHEM022133)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 18:21:09 UTC
Update Date2016-11-09 01:17:26 UTC
Accession NumberCHEM022133
Identification
Common NameBenazepril
ClassSmall Molecule
DescriptionBenazepril, brand name Lotensin, is a medication used to treat high blood pressure (hypertension), congestive heart failure, and chronic renal failure. Upon cleavage of its ester group by the liver, benazepril is converted into its active form benazeprilat, a non-sulfhydryl angiotensin-converting enzyme (ACE) inhibitor.
Contaminant Sources
  • HMDB Contaminants - Urine
  • STOFF IDENT Compounds
Contaminant TypeNot Available
Chemical Structure
Thumb
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
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot 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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0udi-2009000000-19c2bb5c2c0344b51b24Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00di-3002900000-85952764d74c57097928Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-0ufu-0917700000-5f1f2ae9b1d7afc6eee5Spectrum
LC-MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-00di-0510900000-aef2e71e3edc278d2181Spectrum
LC-MS/MSLC-MS/MS Spectrum - 35V, Positivesplash10-0ufu-0906300000-967f2d700778895024c2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0117900000-5f064fedfa50b268135bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-3329200000-a339e2329a1813e9c056Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05uu-2910000000-1a808fc7adec9b057f0bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00fr-1009600000-5a58d6a23289daee9801Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00ba-3139300000-7836712c89121ae2cdd4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00kb-7941000000-d9aa7d72e1bd3d7292adSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0001900000-9d13e519742f1a70650dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-2449400000-8c87c62f9d64b50b65b5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0603-3982000000-8f24ae77915ed4d4bb86Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0004900000-245f5166b211af2a37eaSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-0309300000-5d9f8f58556e7d05a3d9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0api-2920000000-cf196d3de0f43915f5f6Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
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