Identification

Name
Benazepril
Accession Number
DB00542  (APRD00063)
Type
Small Molecule
Groups
Approved, Investigational
Description

Benazepril, 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
  • Bénazépril
  • Benazepril
  • Benazeprilum
External IDs
CGS-14824A
Product Ingredients
IngredientUNIICASInChI Key
Benazepril hydrochlorideN1SN99T69T86541-74-4VPSRQEHTHIMDQM-FKLPMGAJSA-N
Active Moieties
NameKindUNIICASInChI Key
BenazeprilatprodrugJRM708L70386541-78-8MADRIHWFJGRSBP-ROUUACIJSA-N
Product Images
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
BenazeprilTablet20 mgOralAa Pharma Inc2006-03-24Not applicableCanada
BenazeprilTablet10 mgOralAa Pharma Inc2007-05-15Not applicableCanada
BenazeprilTablet5 mgOralAa Pharma Inc2007-05-15Not applicableCanada
Benazepril HydrochlorideTablet, film coated40 mg/1OralETHEX2007-03-28Not applicableUs
Benazepril HydrochlorideTablet, film coated5 mg/1OralETHEX2007-03-28Not applicableUs
Benazepril HydrochlorideTablet, film coated20 mg/1OralETHEX2007-03-28Not applicableUs
Benazepril HydrochlorideTablet, film coated10 mg/1OralETHEX2007-03-28Not applicableUs
LotensinTablet40 mg/1OralValidus Pharmaceuticals1991-06-21Not applicableUs
LotensinTablet40 mg/1OralNovartis1991-06-252016-01-01Us
LotensinTablet10 mg/1OralNovartis1991-06-252012-12-01Us
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
BenazeprilTablet, coated40 mg/1OralInternational Laboratories, Llc2013-09-19Not applicableUs00093 5127 01 nlmimage10 7c233e09
BenazeprilTablet20 mg/1OralStat Rx USA2010-02-02Not applicableUs65162 0753 10 nlmimage10 7a3a3d61
Benazepril HClTablet10 mg/1OralNorthwind Pharmaceuticals2016-06-23Not applicableUs
Benazepril HydrochlorideTablet, coated40 mg/1Oralbryant ranch prepack2014-01-01Not applicableUs
Benazepril HydrochlorideTablet, film coated40 mg/1OralApotex Corporation2006-04-212012-06-30Us
Benazepril HydrochlorideTablet, coated20 mg/1OralInternational Laboratories, Llc2014-02-01Not applicableUs
Benazepril HydrochlorideTablet, film coated5.00 mg/1OralRanbaxy Inc.2010-09-06Not applicableUs
Benazepril HydrochlorideTablet, coated10 mg/1OralTeva Pharmaceuticals USA, Inc.2004-02-11Not applicableUs00093 5125 01 nlmimage10 342d9a0c
Benazepril HydrochlorideTablet10 mg/1OralBlenheim Pharmacal, Inc.2013-11-14Not applicableUs
Benazepril HydrochlorideTablet, coated20 mg/1OralA-S Medication Solutions2014-01-01Not applicableUs
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
AmlobenzBenazepril hydrochloride (20 mg/1) + Amlodipine besylate (10 mg/1)CapsuleOralRebel Distributors2010-04-19Not applicableUs55111 0341 01 nlmimage10 c238e107
AmlobenzBenazepril hydrochloride (10 mg/1) + Amlodipine besylate (5 mg/1)CapsuleOralRebel Distributors2010-04-19Not applicableUs55111 0339 01 nlmimage10 6d03b6bd
Amlodipine and Benazepril HydrochlorideBenazepril hydrochloride (40 mg/1) + Amlodipine besylate (5 mg/1)CapsuleOralTeva Pharmaceuticals USA, Inc.2011-07-20Not applicableUs00093 7670 01 nlmimage10 8327c19e
Amlodipine and Benazepril HydrochlorideBenazepril hydrochloride (20 mg/1) + Amlodipine besylate (10 mg/1)CapsuleOralAurobindo Pharma Limited2012-09-05Not applicableUs
Amlodipine and Benazepril HydrochlorideBenazepril hydrochloride (10 mg/1) + Amlodipine besylate (2.5 mg/1)CapsuleOralActavis Pharma Company2010-10-15Not applicableUs
Amlodipine and Benazepril HydrochlorideBenazepril hydrochloride (10 mg/1) + Amlodipine besylate (5 mg/1)CapsuleOralRising Health, Llc2012-09-05Not applicableUs
Amlodipine and Benazepril HydrochlorideBenazepril hydrochloride (10 mg/1) + Amlodipine besylate (5 mg/1)CapsuleOralbryant ranch prepack2010-10-15Not applicableUs
Amlodipine and Benazepril HydrochlorideBenazepril hydrochloride (10 mg/1) + Amlodipine besylate (5 mg/1)CapsuleOralActavis Pharma Company2010-10-15Not applicableUs
Amlodipine and Benazepril HydrochlorideBenazepril hydrochloride (20 mg/1) + Amlodipine besylate (5 mg/1)CapsuleOralA-S Medication Solutions2012-02-202018-02-28Us50090 200820180913 8702 85k5un
Amlodipine and Benazepril HydrochlorideBenazepril hydrochloride (40 mg/1) + Amlodipine besylate (5 mg/1)CapsuleOralApotex Corporation2013-12-30Not applicableUs
International/Other Brands
Briem (Pierre Fabre (France)) / Cibacen (Novartis (Belgium, Philippines, Switzerland, Turkey), Meda (Denmark, Germany, Greece, Ireland, Italy, Netherlands, Spain)) / Cibacen WS / Cibacene (Meda (France))
Categories
UNII
UDM7Q7QWP8
CAS number
86541-75-5
Weight
Average: 424.4895
Monoisotopic: 424.199822016
Chemical Formula
C24H28N2O5
InChI Key
XPCFTKFZXHTYIP-PMACEKPBSA-N
InChI
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
IUPAC Name
2-[(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
SMILES
[H][C@@]1(CCC2=CC=CC=C2N(CC(O)=O)C1=O)N[C@@H](CCC1=CC=CC=C1)C(=O)OCC

Pharmacology

Indication

For the treatment of hypertension. It may be used alone or in combination with thiazide diuretics.

Associated Conditions
Pharmacodynamics

Benazepril, an angiotensin-converting enzyme (ACE) inhibitor, is a prodrug which, when hydrolyzed by estarases to its active Benazeprilat, is used to treat hypertension and heart failure, to reduce proteinuria and renal disease in patients with nephropathies, and to prevent stroke, myocardial infarction, and cardiac death in high-risk patients. Benazepril and Benazeprilat inhibit angiotensin-converting enzyme (ACE) in human subjects and animals. ACE is a peptidyl dipeptidase that catalyzes the conversion of angiotensin I to the vasoconstrictor substance, angiotensin II. Angiotensin II also stimulates aldosterone secretion by the adrenal cortex.

Mechanism of action

Benazeprilat, the active metabolite of Benazepril, competes with angiotensin I for binding at the angiotensin-converting enzyme, blocking the conversion of angiotensin I to angiotensin II. Inhibition of ACE results in decreased plasma angiotensin II. As angiotensin II is a vasoconstrictor and a negative-feedback mediator for renin activity, lower concentrations result in a decrease in blood pressure and stimulation of baroreceptor reflex mechanisms, which leads to decreased vasopressor activity and to decreased aldosterone secretion. Benazeprilat may also act on kininase II, an enzyme identical to ACE that degrades the vasodilator bradykinin.

TargetActionsOrganism
AAngiotensin-converting enzyme
inhibitor
Human
Absorption

Peak in plasma within 0.5-1.0 hours. The extent of absorption is at least 37% as determined by urinary recovery and is not significantly influenced by the presence of food in the GI tract.

Volume of distribution
Not Available
Protein binding

benazepril, 97%; benazeprilat, 95%

Metabolism

Cleavage of the ester group (primarily in the liver) converts benazepril to its active metabolite, benazeprilat. Benazepril and benazeprilat may be conjugated to glucuronic acid prior to urinary excretion.

Route of elimination

Benazepril and benazeprilat are cleared predominantly by renal excretion in healthy subjects with normal renal function. Nonrenal (i.e., biliary) excretion accounts for approximately 11%-12% of benazeprilat excretion in healthy subjects.

Half life

10-11 hours

Clearance
  • 0.35 L/hr/kg [pediatric hypertensive patients receiving multiple daily doses of Benazepril hydrochloride 0.1 - 0.5 mg/kg]
  • 0.13 L/hr/kg [healthy adults receiving a single dose of 10 mg]
Toxicity

Most likely symptom of overdosage is severe hypotension. Most common adverse effects include headache, dizziness, fatigue, somnolence, postural dizziness, nausea, and cough.

Affected organisms
  • Humans and other mammals
Pathways
PathwayCategory
Benazepril Action PathwayDrug action
Benazepril Metabolism PathwayDrug metabolism
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
AcebutololBenazepril may increase the hypotensive activities of Acebutolol.
AceclofenacThe risk or severity of renal failure, hyperkalemia, and hypertension can be increased when Aceclofenac is combined with Benazepril.
AcemetacinThe risk or severity of renal failure, hyperkalemia, and hypertension can be increased when Acemetacin is combined with Benazepril.
Acetylsalicylic acidThe risk or severity of renal failure, hyperkalemia, and hypertension can be increased when Acetylsalicylic acid is combined with Benazepril.
AgmatineThe risk or severity of hyperkalemia can be increased when Benazepril is combined with Agmatine.
Agrostis gigantea pollenThe risk or severity of adverse effects can be increased when Benazepril is combined with Agrostis gigantea pollen.
Agrostis stolonifera pollenThe risk or severity of adverse effects can be increased when Benazepril is combined with Agrostis stolonifera pollen.
AlclofenacThe risk or severity of renal failure, hyperkalemia, and hypertension can be increased when Alclofenac is combined with Benazepril.
AldesleukinThe risk or severity of adverse effects can be increased when Aldesleukin is combined with Benazepril.
AlfuzosinAlfuzosin may increase the hypotensive activities of Benazepril.
Food Interactions
  • Benazepril may decrease the excretion of potassium. Salt um may increase the risk of hyperkalemia. substitutes containing potassi
  • Food slows absorption without decreasing the quantity absorbed.
  • Herbs that may attenuate the antihypertensive effect of benazepril include: bayberry, blue cohash, cayenne, ephedra, ginger, ginseng (American), kola and licorice.
  • High salt intake may attenuate the antihypertensive effect of benazepril.
  • Take without regard to meals.

References

Synthesis Reference

Wei-Hong Tseng, "ASYMMETRIC SYNTHESIS OF A KEY INTERMEDIATE FOR MAKING BENAZEPRIL AND ANALOGUES THEREOF." U.S. Patent US20020183515, issued December 05, 2002.

US20020183515
General References
  1. 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. [PubMed:8008712]
  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. [PubMed:1459316]
  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. [PubMed:1893642]
  4. 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. [PubMed:16407508]
  5. 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. [PubMed:17498126]
  6. MacNab M, Mallows S: Safety profile of benazepril in essential hypertension. Clin Cardiol. 1991 Aug;14(8 Suppl 4):IV33-7; discussion IV51-5. [PubMed:1893640]
  7. 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. [PubMed:9328608]
External Links
Human Metabolome Database
HMDB0014682
KEGG Drug
D07499
KEGG Compound
C06843
PubChem Compound
5362124
PubChem Substance
46507884
ChemSpider
4514935
BindingDB
50021153
ChEBI
3011
ChEMBL
CHEMBL838
Therapeutic Targets Database
DAP000584
PharmGKB
PA448561
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
PDRhealth
PDRhealth Drug Page
Wikipedia
Benazepril
ATC Codes
C09AA07 — BenazeprilC09BA07 — Benazepril and diuretics
AHFS Codes
  • 24:32.04 — Angiotensin-converting Enzyme Inhibitors
FDA label
Download (237 KB)
MSDS
Download (57.5 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
1CompletedNot AvailableHealhty1
1CompletedNot AvailableHealthy Volunteers7
1CompletedTreatmentFasting1
1CompletedTreatmentFed1
1, 2RecruitingTreatmentHenoch-Schönlein Purpura Nephritis1
2CompletedTreatmentAlport Syndrome1
2RecruitingTreatmentHenoch-Schoenlein Purpura Nephritis2
2TerminatedTreatmentHigh Blood Pressure (Hypertension) / Unspecified Adult Solid Tumor, Protocol Specific1
3CompletedPreventionAtherosclerosis / Cardiovascular Disease (CVD) / Coronary Heart Disease (CHD) / Diabetes Mellitus (DM) / High Blood Pressure (Hypertension) / High Cholesterol / Type 2 Diabetes Mellitus1
3CompletedTreatmentDiabetes Mellitus (DM)2
3CompletedTreatmentHigh Blood Pressure (Hypertension)1
3CompletedTreatmentRenal Alteration1
4CompletedTreatmentAlbuminuria1
4CompletedTreatmentAlbuminuria / High Blood Pressure (Hypertension) / Type 2 Diabetes Mellitus1
4CompletedTreatmentCongestive Cardiomyopathy1
4CompletedTreatmentDiabetes Mellitus (DM) / High Blood Pressure (Hypertension)1
4CompletedTreatmentDiabetes Mellitus (DM) / High Blood Pressure (Hypertension) / Proteinuria1
4CompletedTreatmentHigh Blood Pressure (Hypertension)2
4CompletedTreatmentHigh Blood Pressure (Hypertension) / Left Ventricular Hypertrophy1
4CompletedTreatmentHigh Blood Pressure (Hypertension) / Induction of intra-operative hypotension1
Not AvailableCompletedTreatmentMicroalbuminuria1
Not AvailableCompletedTreatmentRenal Function Disorder1
Not AvailableTerminatedTreatmentACE Inhibitor / Angiotensin II Type 1 Receptor Blockers / Dose-Response Relationship, Drug / Progression, Disease / Proteinuria / Renal Insufficiency,Chronic1
Not AvailableTerminatedTreatmentChronic Renal Failure (CRF)1
Not AvailableTerminatedTreatmentRenal Insufficiency,Chronic1

Pharmacoeconomics

Manufacturers
  • Apotex inc etobicoke site
  • Aurobindo pharma ltd
  • Biokey inc
  • Genpharm inc
  • Huahai us inc
  • Ivax pharmaceuticals inc sub teva pharmaceuticals usa
  • Mylan pharmaceuticals inc
  • Ranbaxy laboratories ltd
  • Sandoz inc
  • Teva pharmaceuticals usa inc
  • Watson laboratories inc florida
  • Zydus pharmaceuticals usa inc
  • Novartis pharmaceuticals corp
Packagers
  • Advanced Pharmaceutical Services Inc.
  • Amneal Pharmaceuticals
  • Apotex Inc.
  • Apotheca Inc.
  • A-S Medication Solutions LLC
  • Atlantic Biologicals Corporation
  • Aurobindo Pharma Ltd.
  • Bryant Ranch Prepack
  • Cardinal Health
  • Caremark LLC
  • Corepharma LLC
  • Direct Dispensing Inc.
  • Direct Pharmaceuticals Inc.
  • Dispensing Solutions
  • Diversified Healthcare Services Inc.
  • Doctor Reddys Laboratories Ltd.
  • Eon Labs
  • Ethex Corp.
  • Greenstone LLC
  • H.J. Harkins Co. Inc.
  • Heartland Repack Services LLC
  • International Laboratories Inc.
  • Ivax Pharmaceuticals
  • KV Pharmaceutical Co.
  • Lake Erie Medical and Surgical Supply
  • Liberty Pharmaceuticals
  • Lupin Pharmaceuticals Inc.
  • Murfreesboro Pharmaceutical Nursing Supply
  • Mylan
  • Novartis AG
  • Nucare Pharmaceuticals Inc.
  • Ohm Laboratories Inc.
  • Palmetto Pharmaceuticals Inc.
  • PCA LLC
  • PD-Rx Pharmaceuticals Inc.
  • Pharmaceutical Utilization Management Program VA Inc.
  • Physicians Total Care Inc.
  • Preferred Pharmaceuticals Inc.
  • Prepak Systems Inc.
  • Ranbaxy Laboratories
  • Rebel Distributors Corp.
  • Resource Optimization and Innovation LLC
  • Sandoz
  • Southwood Pharmaceuticals
  • Stat Rx Usa
  • Teva Pharmaceutical Industries Ltd.
  • UDL Laboratories
Dosage forms
FormRouteStrength
CapsuleOral
TabletOral10 mg
TabletOral20 mg
TabletOral20 mg/1
TabletOral5 mg
TabletOral10 mg/1
TabletOral40 mg/1
TabletOral5 mg/1
Tablet, coatedOral10 mg/1
Tablet, coatedOral20 mg/1
Tablet, coatedOral40 mg/1
Tablet, coatedOral5 mg/1
Tablet, film coatedOral10 mg/1
Tablet, film coatedOral20 mg/1
Tablet, film coatedOral40 mg/1
Tablet, film coatedOral5 mg/1
Tablet, film coatedOral5.00 mg/1
Tablet, coatedOral
Tablet, film coatedOral
TabletOral
Prices
Unit descriptionCostUnit
Lotensin 20 mg tablet2.08USD tablet
Lotensin 10 mg tablet2.0USD tablet
Lotensin 40 mg tablet2.0USD tablet
Lotensin 5 mg tablet2.0USD tablet
Lotensin HCT 20-12.5 mg tablet1.97USD tablet
Lotensin HCT 10-12.5 mg tablet1.95USD tablet
Lotensin HCT 20-25 mg tablet1.94USD tablet
Lotensin hct 10-12.5 tablet1.9USD tablet
Lotensin hct 20-12.5 tablet1.9USD tablet
Lotensin hct 20-25 tablet1.9USD tablet
Lotensin hct 5-6.25 tablet1.9USD tablet
Lotensin HCT 5-6.25 mg tablet1.31USD tablet
Lotensin 20 mg Tablet1.14USD tablet
Benazepril hcl 10 mg tablet1.07USD tablet
Benazepril hcl 20 mg tablet1.07USD tablet
Benazepril hcl 40 mg tablet1.07USD tablet
Benazepril hcl 5 mg tablet1.07USD tablet
Lotensin 10 mg Tablet0.99USD tablet
Lotensin 5 mg Tablet0.84USD tablet
Apo-Benazepril 20 mg Tablet0.79USD tablet
Apo-Benazepril 10 mg Tablet0.69USD tablet
Apo-Benazepril 5 mg Tablet0.58USD tablet
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
US6162802No1997-12-192017-12-19Us

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)148.5 °CPhysProp
water solubility2.229 mg/LNot Available
logP3.3Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.0105 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 RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.5732
Blood Brain Barrier-0.7082
Caco-2 permeable-0.7279
P-glycoprotein substrateSubstrate0.8466
P-glycoprotein inhibitor IInhibitor0.7426
P-glycoprotein inhibitor IINon-inhibitor0.7565
Renal organic cation transporterNon-inhibitor0.8239
CYP450 2C9 substrateNon-substrate0.7518
CYP450 2D6 substrateNon-substrate0.8563
CYP450 3A4 substrateSubstrate0.5632
CYP450 1A2 substrateNon-inhibitor0.8232
CYP450 2C9 inhibitorNon-inhibitor0.6875
CYP450 2D6 inhibitorNon-inhibitor0.8266
CYP450 2C19 inhibitorInhibitor0.5461
CYP450 3A4 inhibitorInhibitor0.5425
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.6038
Ames testNon AMES toxic0.8377
CarcinogenicityNon-carcinogens0.9435
BiodegradationNot ready biodegradable0.9713
Rat acute toxicity2.2082 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9787
hERG inhibition (predictor II)Inhibitor0.6696
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
MS/MS Spectrum - , positiveLC-MS/MSsplash10-0ufu-0917700000-5f1f2ae9b1d7afc6eee5

Taxonomy

Description
This compound 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.
Kingdom
Organic compounds
Super Class
Organic acids and derivatives
Class
Carboxylic acids and derivatives
Sub Class
Amino acids, peptides, and analogues
Direct Parent
Dipeptides
Alternative Parents
Alpha amino acid esters / Benzazepines / Aralkylamines / Fatty acid esters / Azepines / Dicarboxylic acids and derivatives / Benzene and substituted derivatives / Tertiary carboxylic acid amides / Amino acids / Lactams
show 8 more
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
show 22 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
dicarboxylic acid monoester, ethyl ester, benzazepine (CHEBI:3011)

Targets

Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Inhibitor
General Function
Zinc ion binding
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...
Gene Name
ACE
Uniprot ID
P12821
Uniprot Name
Angiotensin-converting enzyme
Molecular Weight
149713.675 Da
References
  1. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed: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. [PubMed:11929321]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Protein complex binding
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
Uniprot Name
Methylenetetrahydrofolate reductase
Molecular Weight
74595.895 Da
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. doi: 10.1038/jhh.2010.50. Epub 2010 May 6. [PubMed: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. [PubMed: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. [PubMed:15226090]

Transporters

Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Proton-dependent oligopeptide secondary active transmembrane 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
Uniprot Name
Solute carrier family 15 member 1
Molecular Weight
78805.265 Da
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. doi: 10.1124/jpet.108.143339. Epub 2008 Aug 19. [PubMed:18713951]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Peptide:proton symporter 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
Uniprot Name
Solute carrier family 15 member 2
Molecular Weight
81782.77 Da
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. doi: 10.1124/jpet.108.143339. Epub 2008 Aug 19. [PubMed:18713951]

Drug created on June 13, 2005 07:24 / Updated on October 16, 2018 08:27