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Details

Stereochemistry RACEMIC
Molecular Formula C24H28N2O5
Molecular Weight 424.4895
Optical Activity ( + / - )
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of BENAZEPRIL, (±)-

SMILES

CCOC(=O)[C@H](CCC1=CC=CC=C1)N[C@H]2CCC3=CC=CC=C3N(CC(O)=O)C2=O

InChI

InChIKey=XPCFTKFZXHTYIP-PMACEKPBSA-N
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

HIDE SMILES / InChI

Molecular Formula C24H28N2O5
Molecular Weight 424.4895
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 2 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

BENAZEPRIL, (±)- is an impurity referred to as Related Compound B, which is a diastereomer of benazepril, an ACE inhibitor, under the brand name Lotensin used primarily in treatment of hypertension, congestive heart failure, and heart attacks, and also in preventing the renal and retinal complications of diabetes. BENAZEPRIL, (±)- is used as USP Reference Standard.

CNS Activity

Curator's Comment: Benazepril crossed the blood-brain barrier only to an extremely low extent.

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
LOTENSIN

Approved Use

Amlodipine besylate and benazepril hydrochloride capsules is a combination capsule of amlodipine, a dihydropyridine calcium channel blocker (DHP CCB) and benazepril, an angiotensin converting enzyme (ACE) inhibitor. Amlodipine besylate and benazepril hydrochloride capsules are indicated for the treatment of hypertension in patients not adequately controlled on monotherapy with either agent (1) 1.1 Hypertension Amlodipine besylate and benazepril hydrochloride capsules are indicated for the treatment of hypertension in patients not adequately controlled on monotherapy with either agent.

Launch Date

1991
Primary
BENAZEPRIL HYDROCHLORIDE

Approved Use

Benazepril hydrochloride tablets are indicated for the treatment of hypertension. They may be used alone or in combination with thiazide diuretics.

Launch Date

1991
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
437 pmol/g
10 mg single, oral
dose: 10 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
BENAZEPRIL plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
334 pmol × h/g
10 mg single, oral
dose: 10 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
BENAZEPRIL plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
0.6 h
10 mg single, oral
dose: 10 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
BENAZEPRIL plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
10 mg 1 times / day multiple, oral
Recommended
Dose: 10 mg, 1 times / day
Route: oral
Route: multiple
Dose: 10 mg, 1 times / day
Sources:
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sources:
Other AEs: Headache, Back pain...
Other AEs:
Headache (8.6%)
Back pain (2.6%)
Diarrhoea (0.9%)
Upper respiratory tract infection (3.4%)
Peripheral oedema (1.7%)
Sinusitis (1.7%)
Fatigue (0.9%)
Cough (1.7%)
Arthralgia (0.9%)
Sources:
10 mg 1 times / day multiple, oral
Recommended
Dose: 10 mg, 1 times / day
Route: oral
Route: multiple
Dose: 10 mg, 1 times / day
Sources:
unhealthy
Health Status: unhealthy
Sources:
Other AEs: Headache, Fatigue...
Other AEs:
Headache (9%)
Fatigue (2%)
Nausea (2%)
Dizziness (2%)
Cough increased (2%)
Sources:
20 mg 1 times / day multiple, oral
Recommended
Dose: 20 mg, 1 times / day
Route: oral
Route: multiple
Dose: 20 mg, 1 times / day
Sources:
unhealthy
Health Status: unhealthy
Sources:
Other AEs: Headache, Fatigue...
Other AEs:
Headache (3%)
Fatigue (2%)
Nausea (1%)
Dizziness (3%)
Dizziness postural (1%)
Cough increased (2%)
Sources:
40 mg 1 times / day multiple, oral
Recommended
Dose: 40 mg, 1 times / day
Route: oral
Route: multiple
Dose: 40 mg, 1 times / day
Sources:
unhealthy
Health Status: unhealthy
Sources:
Other AEs: Headache, Fatigue...
Other AEs:
Headache (3%)
Fatigue (2%)
Nausea (1%)
Dizziness (2%)
Dizziness postural (1%)
Cough increased (1%)
Sources:
5 mg 1 times / day multiple, oral
Recommended
Dose: 5 mg, 1 times / day
Route: oral
Route: multiple
Dose: 5 mg, 1 times / day
Sources:
unhealthy
Health Status: unhealthy
Sources:
Other AEs: Headache, Dizziness...
Other AEs:
Headache (6%)
Dizziness (2%)
Dizziness postural (2%)
Sources:
80 mg 1 times / day multiple, oral
Recommended
Dose: 80 mg, 1 times / day
Route: oral
Route: multiple
Dose: 80 mg, 1 times / day
Sources:
unhealthy
Health Status: unhealthy
Sources:
Other AEs: Headache, Fatigue...
Other AEs:
Headache (2%)
Fatigue (5%)
Nausea (1%)
Cough increased (1%)
Sources:
AEs

AEs

AESignificanceDosePopulation
Arthralgia 0.9%
10 mg 1 times / day multiple, oral
Recommended
Dose: 10 mg, 1 times / day
Route: oral
Route: multiple
Dose: 10 mg, 1 times / day
Sources:
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sources:
Diarrhoea 0.9%
10 mg 1 times / day multiple, oral
Recommended
Dose: 10 mg, 1 times / day
Route: oral
Route: multiple
Dose: 10 mg, 1 times / day
Sources:
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sources:
Fatigue 0.9%
10 mg 1 times / day multiple, oral
Recommended
Dose: 10 mg, 1 times / day
Route: oral
Route: multiple
Dose: 10 mg, 1 times / day
Sources:
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sources:
Cough 1.7%
10 mg 1 times / day multiple, oral
Recommended
Dose: 10 mg, 1 times / day
Route: oral
Route: multiple
Dose: 10 mg, 1 times / day
Sources:
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sources:
Peripheral oedema 1.7%
10 mg 1 times / day multiple, oral
Recommended
Dose: 10 mg, 1 times / day
Route: oral
Route: multiple
Dose: 10 mg, 1 times / day
Sources:
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sources:
Sinusitis 1.7%
10 mg 1 times / day multiple, oral
Recommended
Dose: 10 mg, 1 times / day
Route: oral
Route: multiple
Dose: 10 mg, 1 times / day
Sources:
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sources:
Back pain 2.6%
10 mg 1 times / day multiple, oral
Recommended
Dose: 10 mg, 1 times / day
Route: oral
Route: multiple
Dose: 10 mg, 1 times / day
Sources:
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sources:
Upper respiratory tract infection 3.4%
10 mg 1 times / day multiple, oral
Recommended
Dose: 10 mg, 1 times / day
Route: oral
Route: multiple
Dose: 10 mg, 1 times / day
Sources:
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sources:
Headache 8.6%
10 mg 1 times / day multiple, oral
Recommended
Dose: 10 mg, 1 times / day
Route: oral
Route: multiple
Dose: 10 mg, 1 times / day
Sources:
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sources:
Cough increased 2%
10 mg 1 times / day multiple, oral
Recommended
Dose: 10 mg, 1 times / day
Route: oral
Route: multiple
Dose: 10 mg, 1 times / day
Sources:
unhealthy
Health Status: unhealthy
Sources:
Dizziness 2%
10 mg 1 times / day multiple, oral
Recommended
Dose: 10 mg, 1 times / day
Route: oral
Route: multiple
Dose: 10 mg, 1 times / day
Sources:
unhealthy
Health Status: unhealthy
Sources:
Fatigue 2%
10 mg 1 times / day multiple, oral
Recommended
Dose: 10 mg, 1 times / day
Route: oral
Route: multiple
Dose: 10 mg, 1 times / day
Sources:
unhealthy
Health Status: unhealthy
Sources:
Nausea 2%
10 mg 1 times / day multiple, oral
Recommended
Dose: 10 mg, 1 times / day
Route: oral
Route: multiple
Dose: 10 mg, 1 times / day
Sources:
unhealthy
Health Status: unhealthy
Sources:
Headache 9%
10 mg 1 times / day multiple, oral
Recommended
Dose: 10 mg, 1 times / day
Route: oral
Route: multiple
Dose: 10 mg, 1 times / day
Sources:
unhealthy
Health Status: unhealthy
Sources:
Dizziness postural 1%
20 mg 1 times / day multiple, oral
Recommended
Dose: 20 mg, 1 times / day
Route: oral
Route: multiple
Dose: 20 mg, 1 times / day
Sources:
unhealthy
Health Status: unhealthy
Sources:
Nausea 1%
20 mg 1 times / day multiple, oral
Recommended
Dose: 20 mg, 1 times / day
Route: oral
Route: multiple
Dose: 20 mg, 1 times / day
Sources:
unhealthy
Health Status: unhealthy
Sources:
Cough increased 2%
20 mg 1 times / day multiple, oral
Recommended
Dose: 20 mg, 1 times / day
Route: oral
Route: multiple
Dose: 20 mg, 1 times / day
Sources:
unhealthy
Health Status: unhealthy
Sources:
Fatigue 2%
20 mg 1 times / day multiple, oral
Recommended
Dose: 20 mg, 1 times / day
Route: oral
Route: multiple
Dose: 20 mg, 1 times / day
Sources:
unhealthy
Health Status: unhealthy
Sources:
Dizziness 3%
20 mg 1 times / day multiple, oral
Recommended
Dose: 20 mg, 1 times / day
Route: oral
Route: multiple
Dose: 20 mg, 1 times / day
Sources:
unhealthy
Health Status: unhealthy
Sources:
Headache 3%
20 mg 1 times / day multiple, oral
Recommended
Dose: 20 mg, 1 times / day
Route: oral
Route: multiple
Dose: 20 mg, 1 times / day
Sources:
unhealthy
Health Status: unhealthy
Sources:
Cough increased 1%
40 mg 1 times / day multiple, oral
Recommended
Dose: 40 mg, 1 times / day
Route: oral
Route: multiple
Dose: 40 mg, 1 times / day
Sources:
unhealthy
Health Status: unhealthy
Sources:
Dizziness postural 1%
40 mg 1 times / day multiple, oral
Recommended
Dose: 40 mg, 1 times / day
Route: oral
Route: multiple
Dose: 40 mg, 1 times / day
Sources:
unhealthy
Health Status: unhealthy
Sources:
Nausea 1%
40 mg 1 times / day multiple, oral
Recommended
Dose: 40 mg, 1 times / day
Route: oral
Route: multiple
Dose: 40 mg, 1 times / day
Sources:
unhealthy
Health Status: unhealthy
Sources:
Dizziness 2%
40 mg 1 times / day multiple, oral
Recommended
Dose: 40 mg, 1 times / day
Route: oral
Route: multiple
Dose: 40 mg, 1 times / day
Sources:
unhealthy
Health Status: unhealthy
Sources:
Fatigue 2%
40 mg 1 times / day multiple, oral
Recommended
Dose: 40 mg, 1 times / day
Route: oral
Route: multiple
Dose: 40 mg, 1 times / day
Sources:
unhealthy
Health Status: unhealthy
Sources:
Headache 3%
40 mg 1 times / day multiple, oral
Recommended
Dose: 40 mg, 1 times / day
Route: oral
Route: multiple
Dose: 40 mg, 1 times / day
Sources:
unhealthy
Health Status: unhealthy
Sources:
Dizziness postural 2%
5 mg 1 times / day multiple, oral
Recommended
Dose: 5 mg, 1 times / day
Route: oral
Route: multiple
Dose: 5 mg, 1 times / day
Sources:
unhealthy
Health Status: unhealthy
Sources:
Dizziness 2%
5 mg 1 times / day multiple, oral
Recommended
Dose: 5 mg, 1 times / day
Route: oral
Route: multiple
Dose: 5 mg, 1 times / day
Sources:
unhealthy
Health Status: unhealthy
Sources:
Headache 6%
5 mg 1 times / day multiple, oral
Recommended
Dose: 5 mg, 1 times / day
Route: oral
Route: multiple
Dose: 5 mg, 1 times / day
Sources:
unhealthy
Health Status: unhealthy
Sources:
Cough increased 1%
80 mg 1 times / day multiple, oral
Recommended
Dose: 80 mg, 1 times / day
Route: oral
Route: multiple
Dose: 80 mg, 1 times / day
Sources:
unhealthy
Health Status: unhealthy
Sources:
Nausea 1%
80 mg 1 times / day multiple, oral
Recommended
Dose: 80 mg, 1 times / day
Route: oral
Route: multiple
Dose: 80 mg, 1 times / day
Sources:
unhealthy
Health Status: unhealthy
Sources:
Headache 2%
80 mg 1 times / day multiple, oral
Recommended
Dose: 80 mg, 1 times / day
Route: oral
Route: multiple
Dose: 80 mg, 1 times / day
Sources:
unhealthy
Health Status: unhealthy
Sources:
Fatigue 5%
80 mg 1 times / day multiple, oral
Recommended
Dose: 80 mg, 1 times / day
Route: oral
Route: multiple
Dose: 80 mg, 1 times / day
Sources:
unhealthy
Health Status: unhealthy
Sources:
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer



Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
yes
Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
yes
yes
PubMed

PubMed

TitleDatePubMed
[The effects of blocking intrarenal renin-angiotensin system on the expression of transforming growth factor-beta1 mRNA and extracellular matrix components].
1999 Jan
[Expression of type I transforming growth factor beta receptor in renal cortex in streptozotocin-induced diabetic rats and the regulation of benazepril].
1999 Jan
Low Dose Combination Therapy vs. High Dose Monotherapy in the Management of Hypertension.
1999 Nov
Renal protective effects of blocking the intrarenal renin-angiotensin system.
1999 Sep
Lack of evidence of blood pressure-independent protection by renin-angiotensin system blockade after renal ablation.
2000 Apr
Safety of the combination of valsartan and benazepril in patients with chronic renal disease. European Group for the Investigation of Valsartan in Chronic Renal Disease.
2000 Jan
Effect of combination of valsartan with benazepril on blood pressure and left ventricular hypertrophy in SHR.
2000 Nov
Renin-angiotensin system plays an important role in the regulation of water transport in the peritoneum.
2001
Angiotensin-converting enzyme inhibition potentiates angiotensin II type 1 receptor effects on renal bradykinin and cGMP.
2001 Aug
Efficacy and safety of a therapeutic interchange from high-dose calcium channel blockers to a fixed-dose combination of amlodipine/benazepril in patients with moderate-to-severe hypertension.
2001 Aug
Significance of ACE genotypes and medical treatments in childhood focal glomerulosclerosis.
2001 Aug
Amlodipine/benazepril: fixed dose combination therapy for hypertension.
2001 Jan
Effects of combination of ACE inhibitor and angiotensin receptor blocker on cardiac remodeling, cardiac function, and survival in rat heart failure.
2001 Jan 2
Voltammetric determination of benazepril and ramipril in dosage forms and biological fluids through nitrosation.
2001 Jan-Feb
Cilnidipine is as effective as benazepril for control of blood pressure and proteinuria in hypertensive patients with benign nephrosclerosis.
2001 Jul
Valsartan alone or with a diuretic or ACE inhibitor as treatment for African American hypertensives: relation to salt intake.
2001 Jul
Once-daily treatment of patients with hypertension: a placebo-controlled study of amlodipine and benazepril vs amlodipine or benazepril alone.
2001 Jul
The quantitative determination of several inhibitors of the angiotensin-converting enzyme by CE.
2001 Jul
Effects of the angiotensin converting enzyme inhibitor benazepril in cats with induced renal insufficiency.
2001 Mar
Spectrophotometric determination of benazepril hydrochloride and hydrochlorothiazide in binary mixture using second derivative, second derivative of the ratio spectra and chemometric methods.
2001 May
Application of LC and HPTLC-densitometry for the simultaneous determination of benazepril hydrochloride and hydrochlorothiazide.
2001 May
Prescribing patterns and cost of antihypertensive drugs in an internal medicine clinic.
2001 May-Jun
Combination of hydrochlorothiazide or benazepril with valsartan in hypertensive patients unresponsive to valsartan alone.
2001 Nov
Treatment of IgA nephropathy with angiotensin converting enzyme inhibitors: design of a prospective randomized multicenter trial.
2001 Nov-Dec
Pilot study to evaluate a water displacement technique to compare effects of diuretics and ACE inhibitors to alleviate lower extremity edema due to dihydropyridine calcium antagonists.
2001 Sep
Effects of losartan and benazepril on abnormal circadian blood pressure rhythm and target organ damage in SHRSP.
2002 Apr
Effects of benazepril, an angiotensin-converting enzyme inhibitor, combined with CGS 35066, a selective endothelin-converting enzyme inhibitor, on arterial blood pressure in normotensive and spontaneously hypertensive rats.
2002 Aug
Using ACE inhibitors appropriately.
2002 Aug 1
Kinetics of the acidic and enzymatic hydrolysis of benazepril HCl studied by LC.
2002 Jan 1
Potentiometric and thermal studies of a coated-wire benazepril-selective electrode.
2002 Jan 1
Combination therapy with benazepril and oral adsorbent ameliorates progressive renal fibrosis in uremic rats.
2002 Mar
Selection of the dose of angiotensin converting enzyme inhibitor for patients with diabetic nephropathy depends on the presence or absence of left ventricular hypertrophy.
2002 Nov
Effect of benazepril amlodipine combination on fibrinolysis in hypertensive diabetic patients.
2003 Aug
[Effect of the compound of traditional Chinese drugs on gene expression of renal endothelin and its receptor of experimental diabetic nephropathy].
2003 Feb
Pharmacokinetic/pharmacodynamic modelling of the disposition and effect of benazepril and benazeprilat in cats.
2003 Jun
Combination is better than monotherapy with ACE inhibitor or angiotensin receptor antagonist at recommended doses.
2003 Mar
Effects of combined ACE inhibitor and angiotensin II antagonist treatment in human chronic nephropathies.
2003 Mar
Adherence to antihypertensive therapy with fixed-dose amlodipine besylate/benazepril HCl versus comparable component-based therapy.
2003 Nov-Dec
Investigation of pimobendan versus benazepril in canine myxomatous valvular disease.
2003 Oct 4
Hypertensive patients from two rural Chinese counties respond differently to benazepril: the Anhui Hypertension Health Care Study.
2004 Feb
Patents

Sample Use Guides

The recommended initial dose for patients not receiving a diuretic is 10 mg once a day. The usual maintenance dosage range is 20-40 mg per day administered as a single dose or in two equally divided doses. A dose of 80 mg gives an increased response, but experience with this dose is limited.
Route of Administration: Oral
In Vitro Use Guide
Curator's Comment: In the isolated rabbit aorta the vasocontraction induced by PGF2 alpha was competitively antagonized at 10(-5)-10(-4) mol/l, while vascular responses induced by PGE1, PGE2 or PGI2 was inhibited at 3 x 10(-4) mol/l of benazepril. https://www.ncbi.nlm.nih.gov/pubmed/2080946
Benazepril inhibited both adrenaline-stimulated aortic PGI2 synthesis (25 pg mg -1 min-1) and carbachol-stimulated urinary bladder PGI2 synthesis (20 pg mg -1 min-1) in dose-dependent manners. IC50 (concentrations of antagonist at which agonist-stimulated PGI2 synthesis was inhibited by 50%) was 8 x 10-5.
Substance Class Chemical
Created
by admin
on Mon Mar 31 21:39:25 GMT 2025
Edited
by admin
on Mon Mar 31 21:39:25 GMT 2025
Record UNII
PX47FSF9B3
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
BENAZEPRIL, (±)-
Common Name English
1H-1-Benzazepine-1-acetic acid, 3-[[(1R)-1-(ethoxycarbonyl)-3-phenylpropyl]amino]-2,3,4,5-tetrahydro-2-oxo-, (3R)-rel-
Preferred Name English
1H-1-Benzazepine-1-acetic acid, 3-[[1-(ethoxycarbonyl)-3-phenylpropyl]amino]-2,3,4,5-tetrahydro-2-oxo-, (R*,R*)-
Systematic Name English
rel-(3R)-3-[[(1R)-1-(Ethoxycarbonyl)-3-phenylpropyl]amino]-2,3,4,5-tetrahydro-2-oxo-1H-1-benzazepine-1-acetic acid
Systematic Name English
1H-1-Benzazepine-1-acetic acid, 3-[[1-(ethoxycarbonyl)-3-phenylpropyl]amino]-2,3,4,5-tetrahydro-2-oxo-, (R*,R*)-(±)-
Systematic Name English
Code System Code Type Description
FDA UNII
PX47FSF9B3
Created by admin on Mon Mar 31 21:39:25 GMT 2025 , Edited by admin on Mon Mar 31 21:39:25 GMT 2025
PRIMARY
CAS
86499-21-0
Created by admin on Mon Mar 31 21:39:25 GMT 2025 , Edited by admin on Mon Mar 31 21:39:25 GMT 2025
PRIMARY
CAS
98626-50-7
Created by admin on Mon Mar 31 21:39:25 GMT 2025 , Edited by admin on Mon Mar 31 21:39:25 GMT 2025
NON-SPECIFIC STEREOCHEMISTRY