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Details

Stereochemistry ACHIRAL
Molecular Formula C16H18N4O2
Molecular Weight 298.3397
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PIRIBEDIL

SMILES

C(N1CCN(CC1)C2=NC=CC=N2)C3=CC4=C(OCO4)C=C3

InChI

InChIKey=OQDPVLVUJFGPGQ-UHFFFAOYSA-N
InChI=1S/C16H18N4O2/c1-4-17-16(18-5-1)20-8-6-19(7-9-20)11-13-2-3-14-15(10-13)22-12-21-14/h1-5,10H,6-9,11-12H2

HIDE SMILES / InChI
Piribedil is an antiparkinsonian agent which acts as D2 and D3 receptor agonist. In European countries and worldwide it is used as a monotherapy or in combination with dopatherapy for treatment of Parkinson's disease, cognitive impairment and obliterating arteriopathy.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: P35462
Gene ID: 1814.0
Gene Symbol: DRD3
Target Organism: Homo sapiens (Human)
Target ID: P14416
Gene ID: 1813.0
Gene Symbol: DRD2
Target Organism: Homo sapiens (Human)
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
TRIVASTAL

Approved Use

Adjunctive treatment of intermittent claudication in chronic obliterating arteriopathies of the lower limbs (in stage 2).
Palliative
TRIVASTAL

Approved Use

Adjunctive symptomatic treatment of chronic pathological cognitive and neurosensorial deficit in elderly subjects (excluding Alzheimer's disease and other dementia).
Primary
TRIVASTAL

Approved Use

Treatment of Parkinson's disease: either as monotherapy (treatment of forms with predominant tremor), or in association with dopatherapy from the outset, or secondarily, particularly in forms with tremor.
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
350.91 ng/mL
50 mg single, oral
dose: 50 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
PIRIBEDIL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
23.2 μg/L
2 mg single, intravenous
dose: 2 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
PIRIBEDIL plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
46.5 μg/L
4 mg single, intravenous
dose: 4 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
PIRIBEDIL plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
86 μg/L
8 mg single, intravenous
dose: 8 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
PIRIBEDIL plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
222.3 μg/L
16 mg single, intravenous
dose: 16 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
PIRIBEDIL plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
4080 pg × h/mL
50 mg single, oral
dose: 50 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
PIRIBEDIL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
23.9 μg × h/L
2 mg single, intravenous
dose: 2 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
PIRIBEDIL plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
47.1 μg × h/L
4 mg single, intravenous
dose: 4 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
PIRIBEDIL plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
96.7 μg × h/L
8 mg single, intravenous
dose: 8 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
PIRIBEDIL plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
253.4 μg × h/L
16 mg single, intravenous
dose: 16 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
PIRIBEDIL plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
11.9 h
2 mg single, intravenous
dose: 2 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
PIRIBEDIL plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
11.8 h
4 mg single, intravenous
dose: 4 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
PIRIBEDIL plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
11.8 h
8 mg single, intravenous
dose: 8 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
PIRIBEDIL plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
12.9 h
16 mg single, intravenous
dose: 16 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
PIRIBEDIL plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
Doses

Doses

DosePopulationAdverse events​
150 mg 2 times / day multiple, oral
Highest studied dose
Dose: 150 mg, 2 times / day
Route: oral
Route: multiple
Dose: 150 mg, 2 times / day
Sources:
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
Disc. AE: Gastrointestinal disorder, Psychiatric symptom...
AEs leading to
discontinuation/dose reduction:
Gastrointestinal disorder (2.5%)
Psychiatric symptom (1%)
Sources:
AEs

AEs

AESignificanceDosePopulation
Psychiatric symptom 1%
Disc. AE
150 mg 2 times / day multiple, oral
Highest studied dose
Dose: 150 mg, 2 times / day
Route: oral
Route: multiple
Dose: 150 mg, 2 times / day
Sources:
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
Gastrointestinal disorder 2.5%
Disc. AE
150 mg 2 times / day multiple, oral
Highest studied dose
Dose: 150 mg, 2 times / day
Route: oral
Route: multiple
Dose: 150 mg, 2 times / day
Sources:
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
Overview

Overview

OverviewOther

Other InhibitorOther SubstrateOther Inducer








Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
no [IC50 >133 uM]
no [IC50 >133 uM]
no [IC50 >133 uM]
no [IC50 >133 uM]
no
yes [IC50 0.1995 uM]
yes [IC50 0.631 uM]
yes [IC50 1.9953 uM]
yes [IC50 10.964 uM]
yes [IC50 2.4545 uM]
Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
no
Tox targets

Tox targets

TargetModalityActivityMetaboliteClinical evidence
PubMed

PubMed

TitleDatePubMed
Piribedil: its synergistic effect in multidrug regimens for parkinsonism.
1976 May
Dopamine receptor stimulation in the treatment of depression: piribedil (ET-495).
1978
DA agonists -- non-ergot derivatives: piribedil: management of Parkinson's disease.
2002
Choosing the right dopamine agonist for patients with Parkinson's disease.
2002
Sleep attacks in patients taking dopamine agonists: review.
2002 Jun 22
Differential actions of antiparkinson agents at multiple classes of monoaminergic receptor. III. Agonist and antagonist properties at serotonin, 5-HT(1) and 5-HT(2), receptor subtypes.
2002 Nov
Repeated administration of piribedil induces less dyskinesia than L-dopa in MPTP-treated common marmosets: a behavioural and biochemical investigation.
2002 Sep
[Use of pronoran (piribedil) in Parkinson's disease: the results of a multicenter study].
2003
Efficacy and safety of piribedil in early combination with L-dopa in the treatment of Parkinson's disease: a 6-month open study.
2004 Nov
[Modern aproaches to the treatment of early stages of Parkinson disease].
2005
Chemically modified carbon paste electrode for the potentiometric flow injection analysis of piribedil in pharmaceutical preparation and urine.
2005 Jul 15
[Dopaminergic and noradrenergic therapy of cognitive impairment].
2006
The Parkinson-Control study: a 1-year randomized, double-blind trial comparing piribedil (150 mg/day) with bromocriptine (25 mg/day) in early combination with levodopa in Parkinson's disease.
2006 Apr
Early piribedil monotherapy of Parkinson's disease: A planned seven-month report of the REGAIN study.
2006 Dec
Activation of D2-like receptors induces sympathetic climactic-like responses in male and female anaesthetised rats.
2006 Jun
Identification of amino acid determinants of dopamine 2 receptor synthetic agonist function.
2007 Apr
Blockage of dopaminergic D(2) receptors produces decrease of REM but not of slow wave sleep in rats after REM sleep deprivation.
2008 Apr 9
Tinnitus treatment with piribedil guided by electrocochleography and acoustic otoemissions.
2009 Aug
Parkinson's disease sleep scale, sleep logs, and actigraphy in the evaluation of sleep in parkinsonian patients.
2009 Sep
Patents

Patents

Sample Use Guides

For the treatment of Parkinson's disease as a monotherapy, piribedil should be administered orally at 150 to 250 mg.
Route of Administration: Oral
Binding of piribedil to D2, D3 and D4 receptors was measured using [3H]spiperone as a radiolabel. Coronal sections from rat brains were cut at the level of the anterior caudate-putame. The sections were thaw-mounted on gelatin-coated glass slides. Sections were incubated for 5 min in a 50mM Tris-HCl buffer, then were incubated for 30 min at room temperature in the incubation buffer. Piribedil was tested in vitro at 5 different concentrations, from 10 uM to 1 nM.
Name Type Language
TRIVASTAL
Preferred Name English
PIRIBEDIL
INN   MART.   MI   WHO-DD  
INN  
Official Name English
Piribedil [WHO-DD]
Common Name English
piribedil [INN]
Common Name English
EU-4200
Code English
2-(4-PIPERONYL-1-PIPERAZINYL)PYRIMIDINE
Systematic Name English
ET-495
Code English
PIRIBEDIL [MI]
Common Name English
PIRIBEDIL [MART.]
Common Name English
Classification Tree Code System Code
WHO-ATC N04BC08
Created by admin on Mon Mar 31 17:45:05 GMT 2025 , Edited by admin on Mon Mar 31 17:45:05 GMT 2025
WHO-VATC QN04BC08
Created by admin on Mon Mar 31 17:45:05 GMT 2025 , Edited by admin on Mon Mar 31 17:45:05 GMT 2025
NCI_THESAURUS C66884
Created by admin on Mon Mar 31 17:45:05 GMT 2025 , Edited by admin on Mon Mar 31 17:45:05 GMT 2025
Code System Code Type Description
DRUG BANK
DB12478
Created by admin on Mon Mar 31 17:45:05 GMT 2025 , Edited by admin on Mon Mar 31 17:45:05 GMT 2025
PRIMARY
MESH
D010891
Created by admin on Mon Mar 31 17:45:05 GMT 2025 , Edited by admin on Mon Mar 31 17:45:05 GMT 2025
PRIMARY
RXCUI
8353
Created by admin on Mon Mar 31 17:45:05 GMT 2025 , Edited by admin on Mon Mar 31 17:45:05 GMT 2025
PRIMARY RxNorm
FDA UNII
DO22K1PRDJ
Created by admin on Mon Mar 31 17:45:05 GMT 2025 , Edited by admin on Mon Mar 31 17:45:05 GMT 2025
PRIMARY
NCI_THESAURUS
C81082
Created by admin on Mon Mar 31 17:45:05 GMT 2025 , Edited by admin on Mon Mar 31 17:45:05 GMT 2025
PRIMARY
MERCK INDEX
m8877
Created by admin on Mon Mar 31 17:45:05 GMT 2025 , Edited by admin on Mon Mar 31 17:45:05 GMT 2025
PRIMARY Merck Index
ECHA (EC/EINECS)
222-764-6
Created by admin on Mon Mar 31 17:45:05 GMT 2025 , Edited by admin on Mon Mar 31 17:45:05 GMT 2025
PRIMARY
WIKIPEDIA
PIRIBEDIL
Created by admin on Mon Mar 31 17:45:05 GMT 2025 , Edited by admin on Mon Mar 31 17:45:05 GMT 2025
PRIMARY
ChEMBL
CHEMBL1371770
Created by admin on Mon Mar 31 17:45:05 GMT 2025 , Edited by admin on Mon Mar 31 17:45:05 GMT 2025
PRIMARY
CAS
3605-01-4
Created by admin on Mon Mar 31 17:45:05 GMT 2025 , Edited by admin on Mon Mar 31 17:45:05 GMT 2025
PRIMARY
INN
2569
Created by admin on Mon Mar 31 17:45:05 GMT 2025 , Edited by admin on Mon Mar 31 17:45:05 GMT 2025
PRIMARY
EPA CompTox
DTXSID9045188
Created by admin on Mon Mar 31 17:45:05 GMT 2025 , Edited by admin on Mon Mar 31 17:45:05 GMT 2025
PRIMARY
PUBCHEM
4850
Created by admin on Mon Mar 31 17:45:05 GMT 2025 , Edited by admin on Mon Mar 31 17:45:05 GMT 2025
PRIMARY
SMS_ID
100000081665
Created by admin on Mon Mar 31 17:45:05 GMT 2025 , Edited by admin on Mon Mar 31 17:45:05 GMT 2025
PRIMARY
DRUG CENTRAL
2202
Created by admin on Mon Mar 31 17:45:05 GMT 2025 , Edited by admin on Mon Mar 31 17:45:05 GMT 2025
PRIMARY
EVMPD
SUB09908MIG
Created by admin on Mon Mar 31 17:45:05 GMT 2025 , Edited by admin on Mon Mar 31 17:45:05 GMT 2025
PRIMARY