Benazepril

Identification

Summary

Benazepril is an ACE inhibitor prodrug used to treat hypertension.

Brand Names
Amlobenz, Lotensin, Lotensin Hct, Lotrel
Generic Name
Benazepril
DrugBank Accession Number
DB00542
Background

Benazepril, brand name Lotensin, is a medication used to treat high blood pressure (hypertension), congestive heart failure, and chronic renal failure3,2. Upon cleavage of its ester group by the liver, benazepril is converted into its active form benazeprilat, a non-sulfhydryl angiotensin-converting enzyme (ACE) inhibitor1.

Type
Small Molecule
Groups
Approved, Investigational
Structure
Thumb
Weight
Average: 424.4895
Monoisotopic: 424.199822016
Chemical Formula
C24H28N2O5
Synonyms
  • Bénazépril
  • Benazepril
  • Benazeprilum
External IDs
  • CGS-14824A

Pharmacology

Indication

Benazepril is indicated for the treatment of hypertension5. It may be used alone or in combination with thiazide diureticsLabel.

Pharmacology
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Associated Conditions
Contraindications & Blackbox Warnings
Contraindications
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Pharmacodynamics

Benazepril, an angiotensin-converting enzyme (ACE) inhibitor, is a prodrug which, when hydrolyzed by esterases to its active Benazeprilat1, 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 patients5,3,2. Benazepril and Benazeprilat inhibit angiotensin-converting enzyme (ACE) in human subjects and animals5,1. ACE is a peptidyl dipeptidase that catalyzes the conversion of angiotensin I to the vasoconstrictor substance, angiotensin IILabel. Angiotensin II also stimulates aldosterone secretion by the adrenal cortexLabel.

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 IILabel. Inhibition of ACE results in decreased plasma angiotensin IILabel. 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 secretionLabel.

TargetActionsOrganism
AAngiotensin-converting enzyme
inhibitor
Humans
Absorption

Bioavailability of oral dosing is 3% to 4% in horses6. In humans at least 37% of oral benazepril is absorbed and reaches peak plasma concentration in 0.5 hours to 1 hour7. Other studies have shown a peak plasma concentration at a median of 1.5 hours1.

Volume of distribution

The final population pharmacokinetic model in one study estimated the volume of distribution to be 203±69.9L11.

Protein binding

Benazepril is 96.7% protein bound while benazeprilat is 95.3% protein boundLabel.

Metabolism

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

Hover over products below to view reaction partners

Route of elimination

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

Half-life

The half life of the prodrug benazepril is 2.7±8.5h1. The half life of the active metabolite benazeprilat is 22.3±9.2h1 The accumulation half life of benazepril is 10 to 11 hoursLabel1.

Clearance

The final population pharmacokinetic model of one study estimates the clearance to be 129±30.0L11.

Adverse Effects
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Toxicity

The most common adverse effects include headache, dizziness, fatigue, somnolence, postural dizziness, nausea, and coughLabel,4.

The most likely symptom of overdosage is severe hypotensionLabel.

Pathways
PathwayCategory
Benazepril Action PathwayDrug action
Benazepril Metabolism PathwayDrug metabolism
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
AcarboseThe risk or severity of hypoglycemia can be increased when Benazepril is combined with Acarbose.
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.
AcetohexamideThe risk or severity of hypoglycemia can be increased when Benazepril is combined with Acetohexamide.
Acetylsalicylic acidThe therapeutic efficacy of Benazepril can be decreased when used in combination with Acetylsalicylic acid.
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.
AlbiglutideThe risk or severity of hypoglycemia can be increased when Benazepril is combined with Albiglutide.
AlclofenacThe risk or severity of renal failure, hyperkalemia, and hypertension can be increased when Alclofenac is combined with Benazepril.
Interactions
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Food Interactions
  • Avoid potassium-containing products. Potassium products increase the risk of hyperkalemia.
  • Take with or without food. Food slows the rate of absorption but not the extent.

Products

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Product Ingredients
IngredientUNIICASInChI Key
Benazepril hydrochlorideN1SN99T69T86541-74-4VPSRQEHTHIMDQM-FKLPMGAJSA-N
Active Moieties
NameKindUNIICASInChI Key
BenazeprilatprodrugJRM708L70386541-78-8MADRIHWFJGRSBP-ROUUACIJSA-N
Product Images
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))
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
BenazeprilTablet5 mgOralAa Pharma Inc2007-05-15Not applicableCanada flag
BenazeprilTablet20 mgOralAa Pharma Inc2006-03-24Not applicableCanada flag
BenazeprilTablet10 mgOralAa Pharma Inc2007-05-15Not applicableCanada flag
Benazepril HydrochlorideTablet, film coated10 mg/1OralETHEX2007-03-28Not applicableUS flag
Benazepril HydrochlorideTablet, film coated40 mg/1OralETHEX2007-03-28Not applicableUS flag
Benazepril HydrochlorideTablet, film coated5 mg/1OralETHEX2007-03-28Not applicableUS flag
Benazepril HydrochlorideTablet, film coated20 mg/1OralETHEX2007-03-28Not applicableUS flag
LotensinTablet10 mg/1OralPhysicians Total Care, Inc.2003-11-04Not applicableUS flag
LotensinTablet20 mg/1OralNovartis1991-06-252016-02-01US flag
LotensinTablet10 mg/1OralValidus Pharmaceuticals LLC1991-06-21Not applicableUS flag
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
BenazeprilTablet, coated20 mg/1OralDirect_Rx2019-01-15Not applicableUS flag
BenazeprilTablet, coated40 mg/1OralInternational Laboratories, Llc2013-09-192018-05-31US flag00093 5127 01 nlmimage10 7c233e09
BenazeprilTablet20 mg/1OralStat Rx USA2010-02-02Not applicableUS flag65162 0753 10 nlmimage10 7a3a3d61
Benazepril HClTablet10 mg/1OralNorthwind Pharmaceuticals2016-06-23Not applicableUS flag
Benazepril HydrochlorideTablet, film coated40 mg/1OralActavis Pharma Company2004-02-112006-06-30US flag
Benazepril HydrochlorideTablet, film coated5 mg/1OralGolden State Medical Supply, Inc.2004-02-11Not applicableUS flag
Benazepril HydrochlorideTablet40 mg/1OralA-S Medication Solutions2010-02-022017-10-31US flag
Benazepril HydrochlorideTablet, film coated40 mg/1OralRanbaxy Inc.2004-02-11Not applicableUS flag
Benazepril HydrochlorideTablet5 mg/1OralAvKARE, Inc.2009-07-29Not applicableUS flag
Benazepril HydrochlorideTablet, film coated10 mg/1OralCardinal Health2004-05-212019-10-31US flag55154 567320180907 15195 18be0wh
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
AmlobenzBenazepril hydrochloride (20 mg/1) + Amlodipine besylate (10 mg/1)CapsuleOralRebel Distributors2010-04-19Not applicableUS flag55111 0341 01 nlmimage10 c238e107
AmlobenzBenazepril hydrochloride (10 mg/1) + Amlodipine besylate (5 mg/1)CapsuleOralRebel Distributors2010-04-19Not applicableUS flag55111 0339 01 nlmimage10 6d03b6bd
Amlodipine and Benazepril HydrochlorideBenazepril hydrochloride (10 mg/1) + Amlodipine besylate (5 mg/1)CapsuleOralMylan Pharmaceuticals2012-02-202019-01-31US flag0378 689620180913 8702 191l2f6
Amlodipine and Benazepril HydrochlorideBenazepril hydrochloride (20 mg/1) + Amlodipine besylate (10 mg/1)CapsuleOralREMEDYREPACK INC.2019-06-10Not applicableUS flag
Amlodipine and Benazepril HydrochlorideBenazepril hydrochloride (10 mg/1) + Amlodipine besylate (2.5 mg/1)CapsuleOralNucare Pharmaceuticals,inc.2007-05-18Not applicableUS flag
Amlodipine and Benazepril HydrochlorideBenazepril hydrochloride (40 mg/1) + Amlodipine besylate (10 mg/1)CapsuleOralTeva Pharmaceuticals USA, Inc.2011-07-202020-05-31US flag00093 7671 01 nlmimage10 fe26ff27
Amlodipine and Benazepril HydrochlorideBenazepril hydrochloride (40 mg/1) + Amlodipine besylate (5 mg/1)CapsuleOralAurobindo Pharma Limited2012-09-05Not applicableUS flag
Amlodipine and Benazepril HydrochlorideBenazepril hydrochloride (10 mg/1) + Amlodipine besylate (5 mg/1)CapsuleOralbryant ranch prepack2012-09-05Not applicableUS flag
Amlodipine and Benazepril HydrochlorideBenazepril hydrochloride (20 mg/1) + Amlodipine besylate (5 mg/1)CapsuleOralA-S Medication Solutions2012-09-052020-02-20US flag50090 104220180907 15195 1228t51
Amlodipine and Benazepril HydrochlorideBenazepril hydrochloride (20 mg/1) + Amlodipine besylate (10 mg/1)CapsuleOralApotex Corp.2018-11-212018-11-22US flag

Categories

ATC Codes
C09BA07 — Benazepril and diureticsC09AA07 — Benazepril
Drug Categories
Chemical TaxonomyProvided by Classyfire
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-amino acid ester / Alpha-amino acid or derivatives / Alpha-dipeptide / Amine / Amino acid / Amino acid or derivatives / Aralkylamine / Aromatic heteropolycyclic compound / Azacycle / Azepine
show 22 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
dicarboxylic acid monoester, ethyl ester, benzazepine (CHEBI:3011)
Affected organisms
  • Humans and other mammals

Chemical Identifiers

UNII
UDM7Q7QWP8
CAS number
86541-75-5
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

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. 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. [Article]
  2. 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. [Article]
  3. 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. [Article]
  4. MacNab M, Mallows S: Safety profile of benazepril in essential hypertension. Clin Cardiol. 1991 Aug;14(8 Suppl 4):IV33-7; discussion IV51-5. [Article]
  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. [Article]
  6. Serrano-Rodriguez JM, Gomez-Diez M, Esgueva M, Castejon-Riber C, Mena-Bravo A, Priego-Capote F, Ayala N, Caballero JMS, Munoz A: Pharmacokinetic/pharmacodynamic modeling of benazepril and benazeprilat after administration of intravenous and oral doses of benazepril in healthy horses. Res Vet Sci. 2017 Oct;114:117-122. doi: 10.1016/j.rvsc.2017.03.016. Epub 2017 Mar 28. [Article]
  7. Balfour JA, Goa KL: Benazepril. A review of its pharmacodynamic and pharmacokinetic properties, and therapeutic efficacy in hypertension and congestive heart failure. Drugs. 1991 Sep;42(3):511-39. doi: 10.2165/00003495-199142030-00008. [Article]
  8. FDA Approved Drug Products: Lotensin Benazepril Oral Tablets [Link]
  9. FDA Approved Drug Products: Lotensin HCT (lotensin hydrochloride/hydrochlorothiazide) tablets for oral use [Link]
  10. FDA Approved Drug Products: LOTREL (amlodipine and benazepril hydrochloride) capsules [Link]
  11. FDA Clinical Pharmacology and Biopharmaceutics Review: Lotensin [File]
Human Metabolome Database
HMDB0014682
KEGG Drug
D07499
KEGG Compound
C06843
PubChem Compound
5362124
PubChem Substance
46507884
ChemSpider
4514935
BindingDB
50021153
RxNav
18867
ChEBI
3011
ChEMBL
CHEMBL838
ZINC
ZINC000003781943
Therapeutic Targets Database
DAP000584
PharmGKB
PA448561
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
PDRhealth
PDRhealth Drug Page
Wikipedia
Benazepril
FDA label
Download (323 KB)
MSDS
Download (350 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4CompletedTreatmentAlbuminuria1
4CompletedTreatmentAlbuminuria / High Blood Pressure (Hypertension) / Type 2 Diabetes Mellitus1
4CompletedTreatmentDiabetes Mellitus / High Blood Pressure (Hypertension)1
4CompletedTreatmentDiabetes / High Blood Pressure (Hypertension) / Proteinuria1
4CompletedTreatmentDilated Cardiomyopathy (DCM)1
4CompletedTreatmentHigh Blood Pressure (Hypertension)3
4CompletedTreatmentHigh Blood Pressure (Hypertension) / Left Ventricular Hypertrophy1
4CompletedTreatmentInduction of Intraoperative Hypotension1
4SuspendedPreventionCoronavirus Disease 2019 (COVID‑19) / High Blood Pressure (Hypertension)1
3CompletedPreventionAtherosclerosis / Cardiovascular Disease (CVD) / Coronary Heart Disease (CHD) / Diabetes Mellitus / High Blood Pressure (Hypertension) / High Cholesterol / Type 2 Diabetes Mellitus1

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
Tablet
TabletOral10 mg
TabletOral20 mg/1
TabletOral20 mg
TabletOral5 mg
Tablet, film coatedOral20 MG
Tablet, film coatedOral
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
Tablet, coatedOral
Tablet, coatedOral500 mg
TabletOral
TabletOral
Tablet, film coatedOral250 mg
SolutionOphthalmic3 mg
Tablet, film coatedOral10 MG
Tablet, film coatedOral5 MG
SolutionConjunctival; Ophthalmic3 mg
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)Region
US6162802No2000-12-192017-12-19US flag

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)148.5http://www.chemspider.com/Chemical-Structure.4514935.html
boiling point (°C)691.2http://www.chemspider.com/Chemical-Structure.4514935.html
water solubility19mg/mLhttp://www.chemspider.com/Chemical-Structure.4514935.html
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

Targets

Drugtargets2
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Kind
Protein
Organism
Humans
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. [Article]
  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. [Article]

Enzymes

Kind
Protein
Organism
Humans
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. [Article]
  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. [Article]
  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. [Article]

Transporters

Kind
Protein
Organism
Humans
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. [Article]
  2. Kitagawa S, Takeda J, Sato S: pH-dependent inhibitory effects of angiotensin-converting enzyme inhibitors on cefroxadine uptake by rabbit small intestinal brush-border membrane vesicles and their relationship with hydrophobicity and the ratio of zwitterionic species. Biol Pharm Bull. 1999 Jul;22(7):721-4. [Article]
  3. Wang CY, Liu S, Xie XN, Tan ZR: Regulation profile of the intestinal peptide transporter 1 (PepT1). Drug Des Devel Ther. 2017 Dec 8;11:3511-3517. doi: 10.2147/DDDT.S151725. eCollection 2017. [Article]
Kind
Protein
Organism
Humans
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. [Article]
  2. Kitagawa S, Takeda J, Sato S: pH-dependent inhibitory effects of angiotensin-converting enzyme inhibitors on cefroxadine uptake by rabbit small intestinal brush-border membrane vesicles and their relationship with hydrophobicity and the ratio of zwitterionic species. Biol Pharm Bull. 1999 Jul;22(7):721-4. [Article]

Drug created on June 13, 2005 13:24 / Updated on October 26, 2021 21:40