BENAZEPRIL

Details

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

SHOW SMILES / InChI

Structure Search

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
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/019851s042lbl.pdfhttps://www.google.com/patents/WO2006084761A1 | https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/019851s042lbl.pdf | http://usp35.infostar.com.cn/uspnf/pub/data/v35300/usp35nf30s0_m7495.html
Curator's Comment: description was created based on several sources, including: https://www.drugs.com/pro/benazepril.html | DOI: 10.1111/j.1527-3466.1990.tb00432.x

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

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Angiotensin-converting enzyme 94 Target ID: CHEMBL1808 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/019851s042lbl.pdf	Inhibitor 8504		14.0 nM [IC50]
Angiotensin-converting enzyme 94 Target ID: CHEMBL1808 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/019851s042lbl.pdf \| https://www.ncbi.nlm.nih.gov/pubmed/2999394	Inhibitor 8504		0.1 µM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Hypertension 575 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/019851s042lbl.pdf	Primary		Approved 8583	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
Hypertension 575 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/019851s042lbl.pdf	Primary		Approved 8583	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

C_max

Value	Dose	Co-administered	Analyte	Population
437 pmol/g EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/2344861	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

Value	Dose	Co-administered	Analyte	Population
334 pmol × h/g EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/2344861	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

T_1/2

Value	Dose	Co-administered	Analyte	Population
0.6 h EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/2344861	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

Dose	Population	Adverse 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: https://pubmed.ncbi.nlm.nih.gov/11464260/	unhealthy, adult Health Status: unhealthy Age Group: adult Sources: https://pubmed.ncbi.nlm.nih.gov/11464260/	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: https://pubmed.ncbi.nlm.nih.gov/11464260/
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: https://pubmed.ncbi.nlm.nih.gov/1893640/	unhealthy Health Status: unhealthy Sources: https://pubmed.ncbi.nlm.nih.gov/1893640/	Other AEs: Headache, Fatigue... Other AEs: Headache (9%) Fatigue (2%) Nausea (2%) Dizziness (2%) Cough increased (2%) Sources: https://pubmed.ncbi.nlm.nih.gov/1893640/
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: https://pubmed.ncbi.nlm.nih.gov/1893640/	unhealthy Health Status: unhealthy Sources: https://pubmed.ncbi.nlm.nih.gov/1893640/	Other AEs: Headache, Fatigue... Other AEs: Headache (3%) Fatigue (2%) Nausea (1%) Dizziness (3%) Dizziness postural (1%) Cough increased (2%) Sources: https://pubmed.ncbi.nlm.nih.gov/1893640/
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: https://pubmed.ncbi.nlm.nih.gov/1893640/	unhealthy Health Status: unhealthy Sources: https://pubmed.ncbi.nlm.nih.gov/1893640/	Other AEs: Headache, Fatigue... Other AEs: Headache (3%) Fatigue (2%) Nausea (1%) Dizziness (2%) Dizziness postural (1%) Cough increased (1%) Sources: https://pubmed.ncbi.nlm.nih.gov/1893640/
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: https://pubmed.ncbi.nlm.nih.gov/1893640/	unhealthy Health Status: unhealthy Sources: https://pubmed.ncbi.nlm.nih.gov/1893640/	Other AEs: Headache, Dizziness... Other AEs: Headache (6%) Dizziness (2%) Dizziness postural (2%) Sources: https://pubmed.ncbi.nlm.nih.gov/1893640/
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: https://pubmed.ncbi.nlm.nih.gov/1893640/	unhealthy Health Status: unhealthy Sources: https://pubmed.ncbi.nlm.nih.gov/1893640/	Other AEs: Headache, Fatigue... Other AEs: Headache (2%) Fatigue (5%) Nausea (1%) Cough increased (1%) Sources: https://pubmed.ncbi.nlm.nih.gov/1893640/

AEs

Overview

CYP3A4	CYP2C9	CYP2D6	hERG

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
OATP1B1 1079	PEPT1 60 CES1 45

Drug as perpetrator

Target	Modality	Activity	Metabolite	Clinical evidence
OATP1B1 1095	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/22587986/	yes

Drug as victim

Target	Modality	Activity	Metabolite	Clinical evidence
CES1 45	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/23386599/	yes
PEPT1 60	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/18713951/	yes

PubMed

Title	Date	PubMed
Sympathomoderating influence of benazepril in essential hypertension.	1992 Apr	1316404
Benazepril versus felodipine as supplement to bendroflumethiazide: evaluation by office and ambulatory blood pressure.	1998 Apr	10212340
Antiatherogenic effect of angiotensin converting enzyme inhibitor (benazepril) and angiotensin II receptor antagonist (valsartan) in the cholesterol-fed rabbits.	1999 Apr	10217360
Low Dose Combination Therapy vs. High Dose Monotherapy in the Management of Hypertension.	1999 Nov	11416610
Renal protective effects of blocking the intrarenal renin-angiotensin system.	1999 Sep	10515446
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	10678548
Effect of combination of valsartan with benazepril on blood pressure and left ventricular hypertrophy in SHR.	2000 Nov	11501062
Renin-angiotensin system plays an important role in the regulation of water transport in the peritoneum.	2001	11510275
Angiotensin-converting enzyme inhibition potentiates angiotensin II type 1 receptor effects on renal bradykinin and cGMP.	2001 Aug	11509473
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	11494095
Significance of ACE genotypes and medical treatments in childhood focal glomerulosclerosis.	2001 Aug	11474225
Amlodipine/benazepril: fixed dose combination therapy for hypertension.	2001 Jan	11336577
Cilnidipine is as effective as benazepril for control of blood pressure and proteinuria in hypertensive patients with benign nephrosclerosis.	2001 Jul	11510750
Valsartan alone or with a diuretic or ACE inhibitor as treatment for African American hypertensives: relation to salt intake.	2001 Jul	11465651
Once-daily treatment of patients with hypertension: a placebo-controlled study of amlodipine and benazepril vs amlodipine or benazepril alone.	2001 Jul	11464260
The quantitative determination of several inhibitors of the angiotensin-converting enzyme by CE.	2001 Jul	11377060
Comparison of the effects of an ACE inhibitor and alphabeta blocker on the progression of renal failure with left ventricular hypertrophy: preliminary report.	2001 Mar	11325074
Effects of the angiotensin converting enzyme inhibitor benazepril in cats with induced renal insufficiency.	2001 Mar	11277203
Spectrophotometric determination of benazepril hydrochloride and hydrochlorothiazide in binary mixture using second derivative, second derivative of the ratio spectra and chemometric methods.	2001 May	11275437
Prescribing patterns and cost of antihypertensive drugs in an internal medicine clinic.	2001 May-Jun	11516032
Combination of hydrochlorothiazide or benazepril with valsartan in hypertensive patients unresponsive to valsartan alone.	2001 Nov	11677377
Treatment of IgA nephropathy with angiotensin converting enzyme inhibitors: design of a prospective randomized multicenter trial.	2001 Nov-Dec	11783600
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	11587165
Valsartan/hydrochlorothiazide: a review of its pharmacology, therapeutic efficacy and place in the management of hypertension.	2002	12215069
Using ACE inhibitors appropriately.	2002 Aug 1	12182524
Kinetics of the acidic and enzymatic hydrolysis of benazepril HCl studied by LC.	2002 Jan 1	11682216
Potentiometric and thermal studies of a coated-wire benazepril-selective electrode.	2002 Jan 1	11682207
[The effects of angiotensin-converting enzyme inhibitor on IgA nephropathy and the influencing factors].	2002 Jun	12137603
Comparison of benazepril-amlodipine and captopril-thiazide combinations in the management of mild-to-moderate hypertension.	2002 Jun	12078940
Combination therapy of amlodipine/benazepril versus monotherapy of amlodipine in a practice-based setting.	2002 Jun	12074358
Self-measured systolic blood pressure in the morning is a strong indicator of decline of renal function in hypertensive patients with non-diabetic chronic renal insufficiency.	2002 May	12069356
The effects of antihypertensive agents on the survival rate of polycystic kidney disease in Han:SPRD rats.	2002 Nov	12484519
Rhabdomyolysis with concurrent atorvastatin and diltiazem.	2002 Oct	12243603
Pregnancy with prolonged fetal exposure to an angiotensin-converting enzyme inhibitor.	2002 Oct-Nov	12368978
Fentanyl-associated syndrome of inappropriate antidiuretic hormone secretion.	2002 Sep	12222557
Effects of valsartan with or without benazepril on blood pressure, angiotensin II, and endoxin in patients with essential hypertension.	2003 Apr	12676074
Additive effect of ACE inhibition and angiotensin II receptor blockade in type I diabetic patients with diabetic nephropathy.	2003 Apr	12660333
[Effect of the compound of traditional Chinese drugs on gene expression of renal endothelin and its receptor of experimental diabetic nephropathy].	2003 Feb	15015294
Quantitative determination of benazepril and benazeprilat in human plasma by gas chromatography-mass spectrometry using automated 96-well disk plate solid-phase extraction for sample preparation.	2003 Jan 5	12450539
Rationale for combination therapy as initial treatment for hypertension.	2003 Jul-Aug	12941992
Combination is better than monotherapy with ACE inhibitor or angiotensin receptor antagonist at recommended doses.	2003 Mar	12692753
Correlation of Angiotensin-converting enzyme gene polymorphism with effect of antihypertensive therapy by Angiotensin-converting enzyme inhibitor.	2003 Mar	12652327
Effects of combined ACE inhibitor and angiotensin II antagonist treatment in human chronic nephropathies.	2003 Mar	12631093
Effect of benazepril addition to amlodipine on ankle oedema and subcutaneous tissue pressure in hypertensive patients.	2003 Mar	12624612
Systemic contact dermatitis due to captopril without cross-sensitivity to fosinopril, quinapril and benazepril.	2004	15040496
Effects of co-administration of urokinase and benazepril on severe IgA nephropathy.	2004 Apr	15031340
Hypertensive patients from two rural Chinese counties respond differently to benazepril: the Anhui Hypertension Health Care Study.	2004 Feb	15018885

Patents

Sample Use Guides

In Vivo Use Guide

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

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 18:29:36 GMT 2025` Edited by `admin` on `Mon Mar 31 18:29:36 GMT 2025`
Record UNII	UDM7Q7QWP8
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

BENAZEPRIL

Official Name

English

BENAZEPRIL SANDOZ

Preferred Name

English

benazepril [INN]

Common Name

English

CIBACEN WS

Common Name

English

BENAZEPRIL [MI]

Common Name

English

Benazepril [WHO-DD]

Common Name

English

1H-1-Benzazepine-1-acetic acid, 3-[[(1S)-1-(ethoxycarbonyl)-3-phenylpropyl]amino]-2,3,4,5-tetrahydro-2-oxo-, (3S)-

Systematic Name

English

C09AA07

Code

English

BENAZEPRIL [VANDF]

Common Name

English

BRIEM

Common Name

English

BENAZEPRIL [EMA EPAR VETERINARY]

Common Name

English

(3S)-3-[[(1S)-1-(Ethoxycarbonyl)-3-phenylpropyl]amino]-2,3,4,5-tetrahydro-2-oxo-1H-1-benzazepine-1-acetic acid

Systematic Name

English

CGS-14824A

Code

English

CIBACENE

Common Name

English

FORTEEKOR

Brand Name

English

Classification Tree Code System Code

NDF-RT

N0000175562