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Details

Stereochemistry ABSOLUTE
Molecular Formula C17H28N2O5
Molecular Weight 340.4146
Optical Activity UNSPECIFIED
Defined Stereocenters 5 / 5
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PERINDOPRILAT

SMILES

[H][C@]12C[C@H](N(C(=O)[C@H](C)N[C@@H](CCC)C(O)=O)[C@@]1([H])CCCC2)C(O)=O

InChI

InChIKey=ODAIHABQVKJNIY-PEDHHIEDSA-N
InChI=1S/C17H28N2O5/c1-3-6-12(16(21)22)18-10(2)15(20)19-13-8-5-4-7-11(13)9-14(19)17(23)24/h10-14,18H,3-9H2,1-2H3,(H,21,22)(H,23,24)/t10-,11-,12-,13-,14-/m0/s1

HIDE SMILES / InChI

Description

Perindoprilat is a metabolite of perindopril. Perindopril is a long-acting angiotensin converting enzyme (ACE) inhibitor and it is used to treat high blood pressure, heart failure or stable coronary artery disease. Perindopril is designed to allow oral administration as perindoprilat is poorly absorbed from the gastrointestinal tract.

CNS Activity

Curator's Comment: Known to be CNS active in rats. Human data not available.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
1.05 nM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
ACEON

Approved Use

Perindopril erbumine tablets are indicated for treatment of patients with stable coronary artery disease to reduce the risk of cardiovascular mortality or nonfatal myocardial infarction. Perindopril erbumine tablets can be used with conventional treatment for management of coronary artery disease, such as antiplatelet, antihypertensive or lipid-lowering therapy.

Launch Date

1993
Primary
ACEON

Approved Use

Perindopril erbumine tablets are indicated for the treatment of patients with essential hypertension. Perindopril erbumine tablets may be used alone or given with other classes of antihypertensives, especially thiazide diuretics.

Launch Date

1993
Palliative
Unknown

Approved Use

Unknown
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
83.83 ng/mL
4 mg single, oral
dose: 4 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
PERINDOPRIL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
3.54 ng/mL
4 mg single, oral
dose: 4 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
PERINDOPRILAT plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
130 ng × h/mL
4 mg single, oral
dose: 4 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
PERINDOPRIL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
170.61 ng × h/mL
4 mg single, oral
dose: 4 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
PERINDOPRILAT plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
1.05 h
4 mg single, oral
dose: 4 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
PERINDOPRIL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
38.01 h
4 mg single, oral
dose: 4 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
PERINDOPRILAT plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
40%
4 mg single, oral
dose: 4 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
PERINDOPRIL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
80%
4 mg single, oral
dose: 4 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
PERINDOPRILAT plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
Doses

Doses

DosePopulationAdverse events​
4 mg 1 times / day steady, oral
Recommended
Dose: 4 mg, 1 times / day
Route: oral
Route: steady
Dose: 4 mg, 1 times / day
Sources:
unhealthy, adult
n = 320
Health Status: unhealthy
Condition: hypertension
Age Group: adult
Sex: unknown
Population Size: 320
Sources:
Disc. AE: Cough...
AEs leading to
discontinuation/dose reduction:
Cough (2.8%)
Sources:
AEs

AEs

AESignificanceDosePopulation
Cough 2.8%
Disc. AE
4 mg 1 times / day steady, oral
Recommended
Dose: 4 mg, 1 times / day
Route: oral
Route: steady
Dose: 4 mg, 1 times / day
Sources:
unhealthy, adult
n = 320
Health Status: unhealthy
Condition: hypertension
Age Group: adult
Sex: unknown
Population Size: 320
Sources:
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer




Drug as perpetrator​

Drug as perpetrator​

Drug as victim
PubMed

PubMed

TitleDatePubMed
Challenges for the prevention of primary and secondary stroke: the importance of lowering blood pressure and total cardiovascular risk.
2001
[Effects of angiotensin-converting enzyme inhibitors and cosaar on quality of life of patients with pulmonary tuberculosis and chronic heart failure].
2001
Interventions for deliberately altering blood pressure in acute stroke.
2001
[Hypotension followed the first dose of angiotensin-converting enzyme inhibitor in patients with heart failure (a multicenter clinical trial)].
2001
[Effects of perindopril and its combination with indapamide on risk stratification in patients with hypertension].
2001
[The comparison of clinical effectiveness of perindopril and acebutolol in the primary hypertension treatment].
2001
[Effects of perstarium on the systolic and diastolic functions of the myocardium in patients with chronic cardiac failure].
2001
Perindopril lowers blood pressure without reducing cerebral blood flow in stroke patients with carotid disease.
2001 Apr-May
Indapamide plus perindopril--simpler treatment, better compliance.
2001 Apr-May
Vasoactive peptides and procollagen propeptides in patients with hypertension in relation to cardiac hypertrophy and diastolic heart failure: design of the study and patient characteristics.
2001 Aug
Persistent cardiovascular effects of chronic renin-angiotensin system inhibition following withdrawal in adult spontaneously hypertensive rats.
2001 Aug
Ongoing trials of angiotensin-converting enzyme inhibition: what they can tell us.
2001 Aug
Effects of ACE inhibitor therapy on derived central arterial waveforms in hypertension.
2001 Aug
Academic support for combination therapy in hypertension.
2001 Aug-Sep
Comparison of endothelial pleiotropic actions of angiotensin converting enzyme inhibitors and statins.
2001 Dec
ACE inhibitors in vascular disease: some PROGRESS, more HOPE.
2001 Dec
Chronic ACE inhibition enhances the endothelial control of arterial mechanics and flow-dependent vasodilatation in heart failure.
2001 Dec 1
The lowering of blood pressure after stroke.
2001 Dec 8
Comparison of the effect of perindopril and acebutolol on cerebral hemodynamics in hypertensive patients.
2001 Jan
Assessment of perindopril's efficacy on arterial distensibility in mild to moderate hypertension.
2001 Jul
[PROGRESS Study examines transient cerebral ischemia and stroke patients. Future goal: attaining basic blood pressure control].
2001 Jul 5
Coversyl plus--when monotherapy is not enough.
2001 Jun-Jul
New benefits of blood pressure lowering treatments for millions of stroke sufferers.
2001 Jun-Jul
Clinical benefit of very-low-dose perindopril-indapamide combination in hypertension.
2001 Nov
[Clinical study of the month. Secondary prevention of cerebrovascular accident with perindopril: the PROGRESS study].
2001 Nov
Does ACE inhibition slow progression of glomerulopathy in patients with Type 2 diabetes mellitus?
2001 Nov
Angiotensin-converting enzyme gene insertion/deletion, not bradykinin B2 receptor -58T/C gene polymorphism, associated with angiotensin-converting enzyme inhibitor-related cough in Chinese female patients with non-insulin-dependent diabetes mellitus.
2001 Nov
[Efficacy of a converting enzyme inhibitor in the prevention of recurrence of stroke].
2001 Nov 24
A double-blind trial of perindopril and nitrendipine in incipient diabetic nephropathy.
2001 Oct
Angiotensin-II type 1 receptor interaction is a major regulator for liver fibrosis development in rats.
2001 Oct
Proangiogenic effect of angiotensin-converting enzyme inhibition is mediated by the bradykinin B(2) receptor pathway.
2001 Oct 12
Safety profile of perindopril.
2001 Oct 4
Perindopril treatment for congestive heart failure.
2001 Oct 4
Dosage considerations with perindopril for systemic hypertension.
2001 Oct 4
Efficacy of perindopril in the treatment of systemic hypertension.
2001 Oct 4
Dietary n-3 polyunsaturated fatty acids affect the development of renovascular hypertension in rats.
2001 Sep
Very-low-dose combination of perindopril and indapamide as a novel strategy in first-line management of hypertension.
2001 Sep
Study rationale and design of ADVANCE: action in diabetes and vascular disease--preterax and diamicron MR controlled evaluation.
2001 Sep
Effect of blood pressure reduction on abnormal left atrial appendage function in untreated systemic hypertensive patients with sinus rhythm.
2001 Sep
Restenotic process and DD genotype after angiotensin-converting enzyme inhibitor treatment.
2001 Sep 1
Blood-pressure lowering for the secondary prevention of stroke.
2001 Sep 29
Identification and determination of selected medicines reducing hypertension by densitometric and gas chromatographic methods.
2001 Sep-Oct
Detection of coronary microvascular disease by means of cardiac scintigraphy.
2002 Feb
Progress in secondary prevention of stroke with PROGRESS. The perindopril protection against recurrent stroke study.
2002 Feb
Long-term treatment with perindopril ameliorates dobutamine-induced myocardial ischemia in patients with coronary artery disease.
2002 Jan
Attenuation of tubular apoptosis by blockade of the renin-angiotensin system in diabetic Ren-2 rats.
2002 Jan
The PROGRESS Trial: preventing strokes by lowering blood pressure in patients with cerebral ischemia. Emerging therapies: critique of an important advance.
2002 Jan
Comparison of perindopril versus captopril for treatment of acute myocardial infarction.
2002 Jan 15
Effects of low-dose and early versus late perindopril treatment on the progression of severe diabetic nephropathy in (mREN-2)27 rats.
2002 Mar
Combined therapy with indapamide and perindopril but not perindopril alone reduced the risk for recurrent stroke.
2002 Mar-Apr
Patents

Sample Use Guides

In Vivo Use Guide
In patients with essential hypertension, the recommended initial dose is 4 mg once a day. The dose may be titrated, as needed to a maximum of 16 mg per day. The usual maintenance dose range is 4 mg to 8 mg administered as a single daily dose or in two divided doses. In patients with stable coronary artery disease, Perindopril erbumine tablets should be given at an initial dose of 4 mg once daily for 2 weeks, and then increased as tolerated, to a maintenance dose of 8 mg once daily. In elderly patients (greater than 70 years), Perindopril erbumine tablets should be given as a 2 mg dose once daily in the first week, followed by 4 mg once daily in the second week and 8 mg once daily for maintenance dose if tolerated.
Route of Administration: Oral
In Vitro Use Guide
Perindoprilat (S-9780), the major metabolite of perindopril, inhibited guinea pig plasma angiotensin-converting enzyme (ACE) by 50% (IC50) at a concentration of 2.4 +/- 0.1 nM. A Ki of 1.2 nM was obtained for S-9780 (Dixon-Webb plot) with angiotensin I as a substrate.
Name Type Language
PERINDOPRILAT
INN  
INN  
Official Name English
perindoprilat [INN]
Common Name English
PERINDOPRIL TERT-BUTYLAMINE IMPURITY B [EP IMPURITY]
Common Name English
(2S,3AS,7AS)-1-((S)-N-((S)-1-CARBOXYBUTYL)ALANYL)HEXAHYDRO-2-INDOLINECARBOXYLIC ACID
Common Name English
PERINDOPRIL RELATED COMPOUND B
USP-RS  
Common Name English
PERINDOPRIL RELATED COMPOUND B [USP-RS]
Common Name English
PERINDOPRIL DIACID FORM [MI]
Common Name English
PERINDOPRIL DIACID FORM
MI  
Common Name English
S-9780
Code English
Classification Tree Code System Code
NDF-RT N0000175562
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NCI_THESAURUS C247
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Code System Code Type Description
ChEMBL
CHEMBL1201368
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PRIMARY
DRUG BANK
DB14213
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PRIMARY
IUPHAR
6373
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PRIMARY
RS_ITEM_NUM
1510903
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PRIMARY
EVMPD
SUB09731MIG
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PRIMARY
CHEBI
132041
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PRIMARY
CAS
95153-31-4
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PRIMARY
EPA CompTox
DTXSID90869249
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PRIMARY
INN
5987
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PRIMARY
FDA UNII
2UV6ZNQ92K
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PRIMARY
RXCUI
1546400
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PRIMARY RxNorm
DAILYMED
2UV6ZNQ92K
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PRIMARY
SMS_ID
100000082774
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PRIMARY
PUBCHEM
72022
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PRIMARY
MERCK INDEX
m8555
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PRIMARY Merck Index
NCI_THESAURUS
C66357
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PRIMARY