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Record Information
Version3.6
Creation Date2012-09-06 15:16:50 UTC
Update Date2016-02-11 01:29:30 UTC
HMDB IDHMDB14682
Secondary Accession NumbersNone
Metabolite Identification
Common NameBenazepril
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.
Structure
Thumb
Synonyms
ValueSource
Benazepril sandozKegg
ForteekorKegg
Chemical FormulaC24H28N2O5
Average Molecular Weight424.4895
Monoisotopic Molecular Weight424.199822016
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
CAS Registry Number86541-75-5
SMILES
CCOC(=O)[C@H](CCC1=CC=CC=C1)N[C@H]1CCC2=CC=CC=C2N(CC(O)=O)C1=O
InChI Identifier
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
InChI KeyInChIKey=XPCFTKFZXHTYIP-PMACEKPBSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as alpha amino acid esters. These are ester derivatives of alpha amino acids.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentAlpha amino acid esters
Alternative Parents
Substituents
  • Alpha-amino acid ester
  • Benzazepine
  • Phenylpropylamine
  • Aralkylamine
  • Fatty acid ester
  • Azepine
  • Fatty acyl
  • Benzenoid
  • Dicarboxylic acid or derivatives
  • Monocyclic benzene moiety
  • Tertiary carboxylic acid amide
  • Tertiary amine
  • Lactam
  • Carboxylic acid ester
  • Carboxamide group
  • Azacycle
  • Organoheterocyclic compound
  • Secondary amine
  • Secondary aliphatic amine
  • Carboxylic acid
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Drug
Biofunction
  • Angiotensin-converting Enzyme Inhibitors
  • Antihypertensive Agents
Application
  • Pharmaceutical
Cellular locations
  • Extracellular
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point148 - 149 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility1.05e-02 g/LNot Available
LogP3.3Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.011 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count10ChemAxon
Refractivity115.23 m3·mol-1ChemAxon
Polarizability44.98 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid Locations
  • Blood
  • Urine
Tissue LocationNot Available
Pathways
NameSMPDB LinkKEGG Link
Benazepril Metabolism PathwaySMP00591Not Available
Benazepril PathwaySMP00145Not Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00542
  • Not Applicable
details
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00542
  • Not Applicable
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00542
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID4514935
KEGG Compound IDC06843
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkBenazepril
NuGOwiki LinkHMDB14682
Metagene LinkHMDB14682
METLIN IDNot Available
PubChem Compound5362124
PDB IDNot Available
ChEBI ID3011
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. 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. [16407508 ]
  2. 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. [1459316 ]
  3. MacNab M, Mallows S: Safety profile of benazepril in essential hypertension. Clin Cardiol. 1991 Aug;14(8 Suppl 4):IV33-7; discussion IV51-5. [1893640 ]
  4. 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. [1893642 ]
  5. 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. [8008712 ]
  6. 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. [9328608 ]
  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. [17498126 ]

Enzymes

General function:
Involved in methylenetetrahydrofolate reductase (NADPH) activity
Specific function:
Catalyzes the conversion of 5,10-methylenetetrahydrofolate to 5-methyltetrahydrofolate, a co-substrate for homocysteine remethylation to methionine.
Gene Name:
MTHFR
Uniprot ID:
P42898
Molecular weight:
74595.895
References
  1. Jiang S, Yu Y, Venners SA, Zhang Y, Xing H, Wang X, Xu X: Effects of MTHFR and MS gene polymorphisms on baseline blood pressure and Benazepril effectiveness in Chinese hypertensive patients. J Hum Hypertens. 2011 Mar;25(3):172-7. Epub 2010 May 6. [20445573 ]
  2. Jiang S, Hsu YH, Niu T, Xu X, Xing H, Chen C, Wang X, Zhang Y, Peng S, Xu X: A common haplotype on methylenetetrahydrofolate reductase gene modifies the effect of angiotensin-converting enzyme inhibitor on blood pressure in essential hypertension patients--a family-based association study. Clin Exp Hypertens. 2005 Aug;27(6):509-21. [16081343 ]
  3. Jiang S, Hsu YH, Xu X, Xing H, Chen C, Niu T, Zhang Y, Peng S, Xu X: The C677T polymorphism of the methylenetetrahydrofolate reductase gene is associated with the level of decrease on diastolic blood pressure in essential hypertension patients treated by angiotensin-converting enzyme inhibitor. Thromb Res. 2004;113(6):361-9. [15226090 ]
General function:
Involved in metallopeptidase activity
Specific function:
Converts angiotensin I to angiotensin II by release of the terminal His-Leu, this results in an increase of the vasoconstrictor activity of angiotensin. Also able to inactivate bradykinin, a potent vasodilator. Has also a glycosidase activity which releases GPI-anchored proteins from the membrane by cleaving the mannose linkage in the GPI moiety
Gene Name:
ACE
Uniprot ID:
P12821
Molecular weight:
149713.7
References
  1. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [11752352 ]
  2. Song JC, White CM: Clinical pharmacokinetics and selective pharmacodynamics of new angiotensin converting enzyme inhibitors: an update. Clin Pharmacokinet. 2002;41(3):207-24. [11929321 ]

Transporters

General function:
Involved in transporter activity
Specific function:
Proton-coupled intake of oligopeptides of 2 to 4 amino acids with a preference for dipeptides. May constitute a major route for the absorption of protein digestion end-products
Gene Name:
SLC15A1
Uniprot ID:
P46059
Molecular weight:
78805.3
References
  1. Knutter I, Wollesky C, Kottra G, Hahn MG, Fischer W, Zebisch K, Neubert RH, Daniel H, Brandsch M: Transport of angiotensin-converting enzyme inhibitors by H+/peptide transporters revisited. J Pharmacol Exp Ther. 2008 Nov;327(2):432-41. Epub 2008 Aug 19. [18713951 ]
General function:
Involved in transporter activity
Specific function:
Proton-coupled intake of oligopeptides of 2 to 4 amino acids with a preference for dipeptides
Gene Name:
SLC15A2
Uniprot ID:
Q16348
Molecular weight:
81782.8
References
  1. Knutter I, Wollesky C, Kottra G, Hahn MG, Fischer W, Zebisch K, Neubert RH, Daniel H, Brandsch M: Transport of angiotensin-converting enzyme inhibitors by H+/peptide transporters revisited. J Pharmacol Exp Ther. 2008 Nov;327(2):432-41. Epub 2008 Aug 19. [18713951 ]