U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C19H32N2O5.C6H14N4O2
Molecular Weight 542.6687
Optical Activity UNSPECIFIED
Defined Stereocenters 6 / 6
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PERINDOPRIL ARGININE

SMILES

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

InChI

InChIKey=RYCSJJXKEWBUTI-YDYAIEMNSA-N
InChI=1S/C19H32N2O5.C6H14N4O2/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;7-4(5(11)12)2-1-3-10-6(8)9/h12-16,20H,4-11H2,1-3H3,(H,23,24);4H,1-3,7H2,(H,11,12)(H4,8,9,10)/t12-,13-,14-,15-,16-;4-/m00/s1

HIDE SMILES / InChI

Molecular Formula C6H14N4O2
Molecular Weight 174.201
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

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

Perindopril arginine is a stable L-arginine salt of perindopril. Perindopril, a pro-drug, is hydrolyzed to perindoprilat, which inhibits ACE in humans and in animals. It is indicated for the treatment of hypertension, heart failure and coronary artery disease. Perindopril arginine may be used in monotherapy or in combination with other classes of antihypertensive therapy.

CNS Activity

Curator's Comment: Perindopril arginine is CNS active in mice.

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
PRESTALIA

Approved Use

Prestalia is a combination of perindopril arginine, an angiotensin converting enzyme inhibitor, and amlodipine besylate, a dihydropyridine calcium channel blocker, indicated for the treatment of hypertension to lower blood pressure

Launch Date

2015
Primary
Coversyl Arginine

Approved Use

Hypertension: Treatment of hypertension. Heart failure: Treatment of symptomatic heart failure. Stable coronary artery disease: Reduction of risk of cardiac events in patients with a history of myocardial infarction and/or revascularisation.
Primary
Coversyl Arginine

Approved Use

Hypertension: Treatment of hypertension. Heart failure: Treatment of symptomatic heart failure. Stable coronary artery disease: Reduction of risk of cardiac events in patients with a history of myocardial infarction and/or revascularisation.
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
15 ng/mL
2.5 mg 1 times / day steady-state, oral
dose: 2.5 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
PERINDOPRIL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: FASTED
26 ng/mL
5 mg 1 times / day steady-state, oral
dose: 5 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
PERINDOPRIL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: FASTED
61 ng/mL
10 mg 1 times / day steady-state, oral
dose: 10 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
PERINDOPRIL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: FASTED
16 ng/mL
10 mg 1 times / day steady-state, oral
dose: 10 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
PERINDOPRILAT plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: FASTED
3.8 ng/mL
2.5 mg 1 times / day steady-state, oral
dose: 2.5 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
PERINDOPRILAT plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: FASTED
8.3 ng/mL
5 mg 1 times / day steady-state, oral
dose: 5 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
PERINDOPRILAT plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: FASTED
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
17 ng × h/mL
2.5 mg 1 times / day steady-state, oral
dose: 2.5 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
PERINDOPRIL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: FASTED
34 ng × h/mL
5 mg 1 times / day steady-state, oral
dose: 5 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
PERINDOPRIL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: FASTED
69 ng × h/mL
10 mg 1 times / day steady-state, oral
dose: 10 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
PERINDOPRIL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: FASTED
127 ng × h/mL
10 mg 1 times / day steady-state, oral
dose: 10 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
PERINDOPRILAT plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: FASTED
52 ng × h/mL
2.5 mg 1 times / day steady-state, oral
dose: 2.5 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
PERINDOPRILAT plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: FASTED
81 ng × h/mL
5 mg 1 times / day steady-state, oral
dose: 5 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
PERINDOPRILAT plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: FASTED
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
0.42 h
2.5 mg 1 times / day steady-state, oral
dose: 2.5 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
PERINDOPRIL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: FASTED
0.45 h
5 mg 1 times / day steady-state, oral
dose: 5 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
PERINDOPRIL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: FASTED
0.42 h
10 mg 1 times / day steady-state, oral
dose: 10 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
PERINDOPRIL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: FASTED
Doses

Doses

DosePopulationAdverse events​
14 mg 1 times / day multiple, oral
Dose: 14 mg, 1 times / day
Route: oral
Route: multiple
Dose: 14 mg, 1 times / day
Co-administed with::
amlodipine(10 mg QD; 6 weeks)
Sources: Page: 205003Orig1s000MedR.pdf p.85
unhealthy, 65-75 years
n = 279
Health Status: unhealthy
Condition: hypertension
Age Group: 65-75 years
Sex: M+F
Population Size: 279
Sources: Page: 205003Orig1s000MedR.pdf p.85
Disc. AE: Gravitational oedema, Cough...
AEs leading to
discontinuation/dose reduction:
Gravitational oedema (1.8%)
Cough (0.4%)
Dizziness (0.4%)
Fatigue (0.4%)
Irritability (0.4%)
Pulmonary embolism (0.4%)
Sources: Page: 205003Orig1s000MedR.pdf p.85
180 mg 1 times / day single, oral
Dose: 180 mg, 1 times / day
Route: oral
Route: single
Dose: 180 mg, 1 times / day
Sources:
unhealthy
n = 1
Health Status: unhealthy
Condition: hypertension
Population Size: 1
Sources:
Other AEs: Hypothermia, Circulatory failure...
Other AEs:
Hypothermia
Circulatory failure
Death
Sources:
AEs

AEs

AESignificanceDosePopulation
Cough 0.4%
Disc. AE
14 mg 1 times / day multiple, oral
Dose: 14 mg, 1 times / day
Route: oral
Route: multiple
Dose: 14 mg, 1 times / day
Co-administed with::
amlodipine(10 mg QD; 6 weeks)
Sources: Page: 205003Orig1s000MedR.pdf p.85
unhealthy, 65-75 years
n = 279
Health Status: unhealthy
Condition: hypertension
Age Group: 65-75 years
Sex: M+F
Population Size: 279
Sources: Page: 205003Orig1s000MedR.pdf p.85
Dizziness 0.4%
Disc. AE
14 mg 1 times / day multiple, oral
Dose: 14 mg, 1 times / day
Route: oral
Route: multiple
Dose: 14 mg, 1 times / day
Co-administed with::
amlodipine(10 mg QD; 6 weeks)
Sources: Page: 205003Orig1s000MedR.pdf p.85
unhealthy, 65-75 years
n = 279
Health Status: unhealthy
Condition: hypertension
Age Group: 65-75 years
Sex: M+F
Population Size: 279
Sources: Page: 205003Orig1s000MedR.pdf p.85
Fatigue 0.4%
Disc. AE
14 mg 1 times / day multiple, oral
Dose: 14 mg, 1 times / day
Route: oral
Route: multiple
Dose: 14 mg, 1 times / day
Co-administed with::
amlodipine(10 mg QD; 6 weeks)
Sources: Page: 205003Orig1s000MedR.pdf p.85
unhealthy, 65-75 years
n = 279
Health Status: unhealthy
Condition: hypertension
Age Group: 65-75 years
Sex: M+F
Population Size: 279
Sources: Page: 205003Orig1s000MedR.pdf p.85
Irritability 0.4%
Disc. AE
14 mg 1 times / day multiple, oral
Dose: 14 mg, 1 times / day
Route: oral
Route: multiple
Dose: 14 mg, 1 times / day
Co-administed with::
amlodipine(10 mg QD; 6 weeks)
Sources: Page: 205003Orig1s000MedR.pdf p.85
unhealthy, 65-75 years
n = 279
Health Status: unhealthy
Condition: hypertension
Age Group: 65-75 years
Sex: M+F
Population Size: 279
Sources: Page: 205003Orig1s000MedR.pdf p.85
Pulmonary embolism 0.4%
Disc. AE
14 mg 1 times / day multiple, oral
Dose: 14 mg, 1 times / day
Route: oral
Route: multiple
Dose: 14 mg, 1 times / day
Co-administed with::
amlodipine(10 mg QD; 6 weeks)
Sources: Page: 205003Orig1s000MedR.pdf p.85
unhealthy, 65-75 years
n = 279
Health Status: unhealthy
Condition: hypertension
Age Group: 65-75 years
Sex: M+F
Population Size: 279
Sources: Page: 205003Orig1s000MedR.pdf p.85
Gravitational oedema 1.8%
Disc. AE
14 mg 1 times / day multiple, oral
Dose: 14 mg, 1 times / day
Route: oral
Route: multiple
Dose: 14 mg, 1 times / day
Co-administed with::
amlodipine(10 mg QD; 6 weeks)
Sources: Page: 205003Orig1s000MedR.pdf p.85
unhealthy, 65-75 years
n = 279
Health Status: unhealthy
Condition: hypertension
Age Group: 65-75 years
Sex: M+F
Population Size: 279
Sources: Page: 205003Orig1s000MedR.pdf p.85
Circulatory failure
180 mg 1 times / day single, oral
Dose: 180 mg, 1 times / day
Route: oral
Route: single
Dose: 180 mg, 1 times / day
Sources:
unhealthy
n = 1
Health Status: unhealthy
Condition: hypertension
Population Size: 1
Sources:
Death
180 mg 1 times / day single, oral
Dose: 180 mg, 1 times / day
Route: oral
Route: single
Dose: 180 mg, 1 times / day
Sources:
unhealthy
n = 1
Health Status: unhealthy
Condition: hypertension
Population Size: 1
Sources:
Hypothermia
180 mg 1 times / day single, oral
Dose: 180 mg, 1 times / day
Route: oral
Route: single
Dose: 180 mg, 1 times / day
Sources:
unhealthy
n = 1
Health Status: unhealthy
Condition: hypertension
Population Size: 1
Sources:
PubMed

PubMed

TitleDatePubMed
Perindopril arginine: benefits of a new salt of the ACE inhibitor perindopril.
2007 May
Patents

Sample Use Guides

Hypertension: The recommended starting dose is 5 mg given once daily in the morning. Patients with a strongly activated renin-angiotensin-aldosterone system (in particular, renovascular hypertension, salt and/or volume depletion, cardiac decompensation or severe hypertension) may experience an excessive drop in blood pressure following the initial dose. A starting dose of 2.5 mg is recommended in such patients and the initiation of treatment should take place under medical supervision. The dose may be increased to 10 mg once daily after one month of treatment. Symptomatic heart failure: It is recommended that Coversyl Arginine, generally associated with a non-potassium-sparing diuretic and/or digoxin and/or a beta-blocker, be introduced under close medical supervision with a recommended starting dose of 2.5 mg taken in the morning. This dose may be increased after 2 weeks to 5 mg once daily if tolerated. The dose adjustment should be based on the clinical response of the individual patient. Stable coronary artery disease: Coversyl Arginine should be introduced at a dose of 5 mg once daily for two weeks, then increased to 10 mg once daily, depending on renal function and provided that the 5 mg dose is well tolerated.
Route of Administration: Oral
In Vitro Use Guide
Unknown
Substance Class Chemical
Created
by admin
on Sat Dec 16 01:47:38 GMT 2023
Edited
by admin
on Sat Dec 16 01:47:38 GMT 2023
Record UNII
TFT5IM1KGB
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
PERINDOPRIL ARGININE
WHO-DD  
Common Name English
Perindopril Arginine [WHO-DD]
Common Name English
L-ARGININE, (2S,3AS,7AS)-1-((2S)-2-(((1S)-1-(ETHOXYCARBONYL)BUTYL)AMINO)-1-OXOPROPYL)OCTAHYDRO-1H-INDOLE-2-CARBOXYLATE (1:1)
Common Name English
PERINDOPRIL ARGININE [ORANGE BOOK]
Common Name English
COVERSYL
Common Name English
Code System Code Type Description
DRUG BANK
DBSALT001144
Created by admin on Sat Dec 16 01:47:38 GMT 2023 , Edited by admin on Sat Dec 16 01:47:38 GMT 2023
PRIMARY
FDA UNII
TFT5IM1KGB
Created by admin on Sat Dec 16 01:47:38 GMT 2023 , Edited by admin on Sat Dec 16 01:47:38 GMT 2023
PRIMARY
SMS_ID
100000088816
Created by admin on Sat Dec 16 01:47:38 GMT 2023 , Edited by admin on Sat Dec 16 01:47:38 GMT 2023
PRIMARY
PUBCHEM
12068809
Created by admin on Sat Dec 16 01:47:38 GMT 2023 , Edited by admin on Sat Dec 16 01:47:38 GMT 2023
PRIMARY
EVMPD
SUB23191
Created by admin on Sat Dec 16 01:47:38 GMT 2023 , Edited by admin on Sat Dec 16 01:47:38 GMT 2023
PRIMARY
EPA CompTox
DTXSID70210159
Created by admin on Sat Dec 16 01:47:38 GMT 2023 , Edited by admin on Sat Dec 16 01:47:38 GMT 2023
PRIMARY
DAILYMED
TFT5IM1KGB
Created by admin on Sat Dec 16 01:47:38 GMT 2023 , Edited by admin on Sat Dec 16 01:47:38 GMT 2023
PRIMARY
ChEMBL
CHEMBL1581
Created by admin on Sat Dec 16 01:47:38 GMT 2023 , Edited by admin on Sat Dec 16 01:47:38 GMT 2023
PRIMARY
CAS
612548-45-5
Created by admin on Sat Dec 16 01:47:38 GMT 2023 , Edited by admin on Sat Dec 16 01:47:38 GMT 2023
PRIMARY
RXCUI
1600711
Created by admin on Sat Dec 16 01:47:38 GMT 2023 , Edited by admin on Sat Dec 16 01:47:38 GMT 2023
PRIMARY RxNorm
CHEBI
77655
Created by admin on Sat Dec 16 01:47:38 GMT 2023 , Edited by admin on Sat Dec 16 01:47:38 GMT 2023
PRIMARY
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ACTIVE MOIETY