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Details

Stereochemistry ABSOLUTE
Molecular Formula C24H28N2O5
Molecular Weight 424.4895
Optical Activity UNSPECIFIED
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=C(C=CC=C3)N(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
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 2 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

Benazepril is a prodrug which is metabolized by the liver into its active form benazeprilat via cleavage of the drug's ester group. Benazepril and Benazeprilat inhibit angiotensin-converting enzyme (ACE) in human subjects and animals. Benazeprilat has much greater ACE inhibitory activity than does Benazepril. It is indicated for the treatment of hypertension. It may be used alone or in combination with thiazide diuretics. Adverse reactions reported in controlled clinical trials and rarer events seen in post-marketing experience, include the following: Stevens-Johnson syndrome, pemphigus, apparent hypersensitivity reactions (manifested by dermatitis, pruritus, or rash), photosensitivity, and flushing, nausea, pancreatitis, constipation, gastritis, vomiting, and melena, thrombocytopenia and hemolytic anemia, anxiety, decreased libido, hypertonia, insomnia, nervousness, and paresthesia. Patients on diuretics, especially those in whom diuretic therapy was recently instituted, may occasionally experience an excessive reduction of blood pressure after initiation of therapy with Benazepril. Increased serum lithium levels and symptoms of lithium toxicity have been reported in patients receiving ACE inhibitors (including benazepril) during therapy with lithium.

CNS Activity

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
14.0 nM [IC50]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
LOTENSIN

Cmax

ValueDoseCo-administeredAnalytePopulation
437 pmol/g
10 mg single, oral
BENAZEPRIL plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
334 pmol × h/g
10 mg single, oral
BENAZEPRIL plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
0.6 h
10 mg single, oral
BENAZEPRIL plasma
Homo sapiens

Doses

AEs

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer



Drug as perpetrator​

Drug as victim

PubMed

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
Record UNII
UDM7Q7QWP8
Record Status Validated (UNII)
Record Version