BENAZEPRIL, (±)-

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

SMILES

CCOC(=O)[C@@H](CCC1=CC=CC=C1)N[C@@H]2CCC3=C(C=CC=C3)N(CC(O)=O)C2=O

InChI

InChIKey=XPCFTKFZXHTYIP-WOJBJXKFSA-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-/m1/s1

HIDE SMILES / InChI

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

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Angiotensin-converting enzyme	Inhibitor		14.0 nM [IC50]
Angiotensin-converting enzyme	Inhibitor		0.1 µM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Hypertension	Primary		Approved	LOTENSIN
Hypertension	Primary		Approved	BENAZEPRIL HYDROCHLORIDE

C_max

Value	Dose	Co-administered	Analyte	Population
437 pmol/g	10 mg single, oral		BENAZEPRIL plasma	Homo sapiens

AUC

Value	Dose	Co-administered	Analyte	Population
334 pmol × h/g	10 mg single, oral		BENAZEPRIL plasma	Homo sapiens

T_1/2

Value	Dose	Co-administered	Analyte	Population
0.6 h	10 mg single, oral		BENAZEPRIL plasma	Homo sapiens

Doses

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Dose	Population	Adverse events
10 mg 1 times / day multiple, oral Recommended	unhealthy, adult	Other AEs: Headache, Back pain...
10 mg 1 times / day multiple, oral Recommended	unhealthy	Other AEs: Headache, Fatigue...
20 mg 1 times / day multiple, oral Recommended	unhealthy	Other AEs: Headache, Fatigue...
40 mg 1 times / day multiple, oral Recommended	unhealthy	Other AEs: Headache, Fatigue...
5 mg 1 times / day multiple, oral Recommended	unhealthy	Other AEs: Headache, Dizziness...

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AEs

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AE	Significance	Dose	Population
Arthralgia	0.9%	10 mg 1 times / day multiple, oral Recommended	unhealthy, adult
Diarrhoea	0.9%	10 mg 1 times / day multiple, oral Recommended	unhealthy, adult
Fatigue	0.9%	10 mg 1 times / day multiple, oral Recommended	unhealthy, adult
Cough	1.7%	10 mg 1 times / day multiple, oral Recommended	unhealthy, adult
Peripheral oedema	1.7%	10 mg 1 times / day multiple, oral Recommended	unhealthy, adult

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Overview

CYP3A4	CYP2C9	CYP2D6	hERG

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
OATP1B1	PEPT1 CES1

Drug as perpetrator

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Target	Modality	Activity	Metabolite	Clinical evidence
OATP1B1	inhibitor	yes

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Drug as victim

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Target	Modality	Activity	Metabolite	Clinical evidence
CES1	substrate	yes
PEPT1	substrate	yes

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PubMed

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Title	Date	PubMed
Short-term metabolic effects of the ACE-inhibitor benazepril in type 2 diabetes mellitus associated with arterial hypertension.	1992 Jul-Aug	1459316
Effects of combination of ACE inhibitor and angiotensin receptor blocker on cardiac remodeling, cardiac function, and survival in rat heart failure.	2001 Jan 2	11136700
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
Valsartan/hydrochlorothiazide: a review of its pharmacology, therapeutic efficacy and place in the management of hypertension.	2002	12215069
Effects of losartan and benazepril on abnormal circadian blood pressure rhythm and target organ damage in SHRSP.	2002 Apr	11883791

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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.

Show entries

Name

Type

Language

BENAZEPRIL, (±)-

Common Name

English

BENAZEPRIL HYDROCHLORIDE IMPURITY B [EP IMPURITY]

Common Name

English

((3RS)-3-(((1SR)-1-(ETHOXYCARBONYL)-3-PHENYLPROPYL)AMINO)-2-OXO-2,3,4,5-TETRAHYDRO-1H-1-BENZAZEPIN-1-YL)ACETIC ACID

Systematic Name

English

1H-1-BENZAZEPINE-1-ACETIC ACID, 3-((1-(ETHOXYCARBONYL)-3-PHENYLPROPYL)AMINO)-2,3,4,5-TETRAHYDRO-2-OXO-

Common Name

English

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Code System

Code

Type

Description

PUBCHEM

51698396

PRIMARY

FDA UNII

PX47FSF9B3

PRIMARY

CAS

98626-50-7

PRIMARY

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SUBSTANCE RECORD


					PX47FSF9B3

BENAZEPRIL, (±)-

SMILES

InChI

CNS Activity

Originator

Approval Year

Targets

Conditions

Cmax

AUC

T1/2

Doses

AEs

Overview

OverviewOther

Drug as perpetrator​

Drug as victim

PubMed

Patents

Sample Use Guides

C_max

T_1/2

Drug as perpetrator