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Details

Stereochemistry RACEMIC
Molecular Formula C19H32N2O5
Molecular Weight 368.4678
Optical Activity ( + / - )
Defined Stereocenters 5 / 5
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of 2'-EPI-PERINDOPRIL, (±)-

SMILES

CCC[C@H](N[C@H](C)C(=O)N1[C@H]2CCCC[C@H]2C[C@H]1C(O)=O)C(=O)OCC

InChI

InChIKey=IPVQLZZIHOAWMC-YXMSTPNBSA-N
InChI=1S/C19H32N2O5/c1-4-8-14(19(25)26-5-2)20-12(3)17(22)21-15-10-7-6-9-13(15)11-16(21)18(23)24/h12-16,20H,4-11H2,1-3H3,(H,23,24)/t12-,13+,14+,15+,16+/m1/s1

HIDE SMILES / InChI
Molecular Formula C19H32N2O5
Molecular Weight 368.4678
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 5 / 5
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
Curator's Comment: description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/1718688

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

CNS Active
4002
Curator's Comment: Known to be CNS active in rats. Human data not available.

Originator

Approval Year

1993
138
Targets

Targets

Primary TargetPharmacologyConditionPotency
Inhibitor
8504
 1.05 nM [IC50]
Inhibitor
8504
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Approved
8583
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
Approved
8583
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
Not Provided
511
Unknown

Approved Use

Unknown
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
83.83 ng/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/21650082
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
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/21650082
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
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/21650082
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
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/21650082
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
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/21650082
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
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/21650082
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%
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/21650082
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%
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/21650082
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:
https://pubmed.ncbi.nlm.nih.gov/12076191/
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sex: unknown
Sources:
https://pubmed.ncbi.nlm.nih.gov/12076191/
Disc. AE: Cough...
AEs leading to
discontinuation/dose reduction:
Cough (2.8%)
Sources:
https://pubmed.ncbi.nlm.nih.gov/12076191/
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:
https://pubmed.ncbi.nlm.nih.gov/12076191/
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sex: unknown
Sources:
https://pubmed.ncbi.nlm.nih.gov/12076191/
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer
CYP2J2
33
UGT
219

CYP
303
CYP
74
Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
CYP
150
 no
CYP2J2
36
 no
Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
CYP
303
 no
UGT
219
 yes
Sourcing

Sourcing

Vendor/AggregatorIDURL
ChEBI
CHEBI:132041
https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:132041
ChemicalBook
CB0240343
https://www.chemicalbook.com/ChemicalProductProperty_EN_CB0240343
eMolecules
36754394
https://www.emolecules.com/cgi-bin/more?vid=36754394
MolPort
MolPort-006-395-652
https://www.molport.com/shop/molecule-link/MolPort-006-395-652
ZINC
ZINC000004217270
http://zinc15.docking.org/substances/ZINC000004217270
PubMed

PubMed

TitleDatePubMed
Identification and determination of selected medicines reducing hypertension by densitometric and gas chromatographic methods.
2002-03-06
Combined therapy with indapamide and perindopril but not perindopril alone reduced the risk for recurrent stroke.
2002-03-05
Effects of low-dose and early versus late perindopril treatment on the progression of severe diabetic nephropathy in (mREN-2)27 rats.
2002-03
[Antihypertensive agents after cerebral stroke are more effective than expected].
2002-02-16
Detection of coronary microvascular disease by means of cardiac scintigraphy.
2002-02
Progress in secondary prevention of stroke with PROGRESS. The perindopril protection against recurrent stroke study.
2002-02
Comparison of perindopril versus captopril for treatment of acute myocardial infarction.
2002-01-15
Academic support for combination therapy in hypertension.
2002-01-05
Long-term treatment with perindopril ameliorates dobutamine-induced myocardial ischemia in patients with coronary artery disease.
2002-01
Attenuation of tubular apoptosis by blockade of the renin-angiotensin system in diabetic Ren-2 rats.
2002-01
The PROGRESS Trial: preventing strokes by lowering blood pressure in patients with cerebral ischemia. Emerging therapies: critique of an important advance.
2002-01
The lowering of blood pressure after stroke.
2001-12-08
The lowering of blood pressure after stroke.
2001-12-08
The lowering of blood pressure after stroke.
2001-12-08
The lowering of blood pressure after stroke.
2001-12-08
The lowering of blood pressure after stroke.
2001-12-08
Chronic ACE inhibition enhances the endothelial control of arterial mechanics and flow-dependent vasodilatation in heart failure.
2001-12-01
Comparison of endothelial pleiotropic actions of angiotensin converting enzyme inhibitors and statins.
2001-12
ACE inhibitors in vascular disease: some PROGRESS, more HOPE.
2001-12
[Efficacy of a converting enzyme inhibitor in the prevention of recurrence of stroke].
2001-11-24
Coversyl plus--when monotherapy is not enough.
2001-11-17
New benefits of blood pressure lowering treatments for millions of stroke sufferers.
2001-11-17
Clinical benefit of very-low-dose perindopril-indapamide combination in hypertension.
2001-11
Amelioration of arterial properties with a perindopril-indapamide very-low-dose combination.
2001-11
[Clinical study of the month. Secondary prevention of cerebrovascular accident with perindopril: the PROGRESS study].
2001-11
[Early prevention of experimental left ventricular hypertrophy in experimental hypertension and angiotensin II levels].
2001-11
Effect of angiotensin-converting enzyme inhibition on renal filtration surface area in hypertensive rats.
2001-11
Does ACE inhibition slow progression of glomerulopathy in patients with Type 2 diabetes mellitus?
2001-11
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.
2001-11
Angiotensin-converting enzyme inhibition improves defective angiogenesis in the ischemic limb of spontaneously hypertensive rats.
2001-11
Effects of combined administration of ACE inhibitor and angiotensin II receptor antagonist are prevented by a high NaCl intake.
2001-11
Proangiogenic effect of angiotensin-converting enzyme inhibition is mediated by the bradykinin B(2) receptor pathway.
2001-10-12
Safety profile of perindopril.
2001-10-04
Effects of perindopril on cardiovascular remodeling.
2001-10-04
A double-blind trial of perindopril and nitrendipine in incipient diabetic nephropathy.
2001-10
Increased absorption of zinc from alimentary tract in primary arterial hypertension.
2001-10
Improvement in blood pressure, arterial stiffness and wave reflections with a very-low-dose perindopril/indapamide combination in hypertensive patient: a comparison with atenolol.
2001-10
Dietary n-3 polyunsaturated fatty acids affect the development of renovascular hypertension in rats.
2001-09
Very-low-dose combination of perindopril and indapamide as a novel strategy in first-line management of hypertension.
2001-09
Study rationale and design of ADVANCE: action in diabetes and vascular disease--preterax and diamicron MR controlled evaluation.
2001-09
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.
2001-08
Anglo-Scandinavian Cardiac Outcomes Trial: a brief history, rationale and outline protocol.
2001-08
Assessment of perindopril's efficacy on arterial distensibility in mild to moderate hypertension.
2001-07
The EUROPA trial: design, baseline demography and status of the substudies.
2001-03
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
Patents

Patents

07279595
6
08686161
7
20060063941
8
20070071838
8
20100298400
6
7351840
8
7858611
6
8470869
6
JP2002535367A
25
JP2002536332A
39
JP2008019214A
6
JP2011506455A
52
JP4705912B2
48
US4508729
6
WO2004046172A1
8
WO2007017893A2
6
WO2007017893A3
6
WO2007017893B1
6
WO2007017894A2
6
WO2007058634A1
6
WO2007058634B1
6
WO2007092758A2
6
WO2008114270A1
6
WO2008150245A2
6
WO2009000909A2
6
WO2012044189A1
6

Sample Use Guides

In Vivo Use Guide
Unknown
Route of Administration: Unknown
In Vitro Use Guide
Unknown
Substance Class Chemical
Created
by admin
on Mon Mar 31 21:52:17 GMT 2025
Edited
by admin
on Mon Mar 31 21:52:17 GMT 2025
Record UNII
LUF968K225
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
2'-EPI-PERINDOPRIL, (±)-
Common Name English
(±)-2'-EPI-PERINDOPRIL
Preferred Name English
PERINDOPRIL TERT-BUTYLAMINE IMPURITY P [EP IMPURITY]
Common Name English
(2RS,3ARS,7ARS)-1-((2SR)-2-(((1RS)-1-(ETHOXYCARBONYL)BUTYL)AMINO)PROPANOYL)OCTAHYDRO-1H-INDOLE-2-CARBOXYLIC ACID
Systematic Name English
Code System Code Type Description
FDA UNII
LUF968K225
Created by admin on Mon Mar 31 21:52:17 GMT 2025 , Edited by admin on Mon Mar 31 21:52:17 GMT 2025
PRIMARY
Related Record Type Details
Structure of PERINDOPRIL ERBUMINE
PARENT -> IMPURITY
NIH
NCATS
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