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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=CC=C4OCOC4=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

Molecular Formula C16H18N4O2
Molecular Weight 298.3397
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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.
PubMed

PubMed

TitleDatePubMed
Piribedil: its synergistic effect in multidrug regimens for parkinsonism.
1976 May
A comparison of piribedil, procyclidine and placebo in the control of phenothiazine-induced parkinsonism.
1977 Jun
Dopamine receptor stimulation in the treatment of depression: piribedil (ET-495).
1978
Sleep attacks and Parkinson's disease treatment.
2000 Apr 15
Dopamine agonist-induced dyskinesias are correlated to both firing pattern and frequency alterations of pallidal neurones in the MPTP-treated monkey.
2001 Mar
[Parkinson disease: diagnostic and therapeutic criteria].
2001 Mar 3
Piribedil for restless legs syndrome: a pilot study.
2001 May
Clinical pharmacokinetic and pharmacodynamic properties of drugs used in the treatment of Parkinson's disease.
2002
[Alpha-2 adrenergic receptors and Parkinson's disease].
2002 Jul 27
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
Differential actions of antiparkinson agents at multiple classes of monoaminergic receptor. II. Agonist and antagonist properties at subtypes of dopamine D(2)-like receptor and alpha(1)/alpha(2)-adrenoceptor.
2002 Nov
[Use of pronoran (piribedil) in Parkinson's disease: the results of a multicenter study].
2003
Treatment of memory impairment, vertigo and tinnitus in the elderly with piribedil in an Indian general practice setting.
2003 Aug
Quantitative determination of some pharmaceutical piperazine derivatives through complexation with iron(III) chloride.
2003 Aug
Piribedil-induced sleep attacks in Parkinson's disease.
2003 Feb
Piribedil and bromocriptine in Parkinson's disease: a single-blind crossover study.
2003 Mar
Electroanalytical characteristics of piribedil and its differential pulse and square wave voltammetric determination in pharmaceuticals and human serum.
2003 Mar 10
[Clinical and stabilometric analysis of postural instability in Parkinson's disease].
2004
Adsorptive stripping voltammetric behaviour of azomethine group in pyrimidine-containing drugs.
2004 Feb 18
Acute treatment of migraine. Breaking the paradigm of monotherapy.
2004 Jan 28
Determination of piribedil in pharmaceutical formulations by micellar electrokinetic capillary chromatography.
2004 May
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
Cognitive skill learning in healthy older adults after 2 months of double-blind treatment with piribedil.
2004 Nov
Drug treatment of Parkinson's disease.
2004 Sep
[Efficacy of pronoran in age-related memory impairment].
2005
End-of-dose akinesia after a single intravenous infusion of the dopaminergic agonist piribedil in Parkinson's disease patients: a pharmacokinetic/pharmacodynamic, randomized, double-blind study.
2005 Jul
Chemically modified carbon paste electrode for the potentiometric flow injection analysis of piribedil in pharmaceutical preparation and urine.
2005 Jul 15
[The role of pronoran in the therapy of late stage of Parkinson's disease].
2006
Proposed dose equivalence for rapid switch between dopamine receptor agonists in Parkinson's disease: a review of the literature.
2006 Jan
Prevalence and costs of parkinsonian syndromes associated with orthostatic hypotension.
2006 Mar-Apr
Switching from levodopa to the long-acting dopamine D2/D3 agonist piribedil reduces the expression of dyskinesia while maintaining effective motor activity in MPTP-treated primates.
2006 May-Jun
The dopamine agonist piribedil with L-DOPA improves attentional dysfunction: relevance for Parkinson's disease.
2006 Nov
[Cognitive disturbances and dysfunction of neuromediator systems in cerebral vascular insufficiency after treatment with pronoran].
2007
Importance of solid lipid nanoparticles (SLN) in various administration routes and future perspectives.
2007
Effects of the dopamine agonist piribedil on prefrontal temporal cortical network function in normal aging as assessed by verbal fluency.
2007 Jan 30
About the anti-Parkinson equivalency of levodopa and dopamine agonists.
2007 Jan-Feb
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
Current management of the cognitive dysfunction in Parkinson's disease: how far have we come?
2008 Aug
Comparative effects of the dopaminergic agonists piribedil and bromocriptine in three different memory paradigms in rodents.
2008 Jul
Hallucinations: Etiology and clinical implications.
2009 Jul
Parkinson's disease sleep scale, sleep logs, and actigraphy in the evaluation of sleep in parkinsonian patients.
2009 Sep
Delusional infestation induced by piribedil add-on in Parkinson's disease.
2010 Aug
Orodispersible sublingual piribedil to abort OFF episodes: a single dose placebo-controlled, randomized, double-blind, cross-over study.
2010 Feb 15
Impulse control disorder and piribedil: report of 5 cases.
2010 Jan-Feb
From the cell to the clinic: a comparative review of the partial D₂/D₃receptor agonist and α2-adrenoceptor antagonist, piribedil, in the treatment of Parkinson's disease.
2010 Nov
Pre-treatment with dopamine agonists influence L-dopa mediated rotations without affecting abnormal involuntary movements in the 6-OHDA lesioned rat.
2010 Nov 12
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.
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:03:46 GMT 2023
Edited
by admin
on Fri Dec 15 15:03:46 GMT 2023
Record UNII
DO22K1PRDJ
Record Status Validated (UNII)
Record Version
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Name Type Language
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
TRIVASTAL
Brand 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 Fri Dec 15 15:03:46 GMT 2023 , Edited by admin on Fri Dec 15 15:03:46 GMT 2023
WHO-VATC QN04BC08
Created by admin on Fri Dec 15 15:03:46 GMT 2023 , Edited by admin on Fri Dec 15 15:03:46 GMT 2023
NCI_THESAURUS C66884
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Code System Code Type Description
DRUG BANK
DB12478
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PRIMARY
MESH
D010891
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PRIMARY
RXCUI
8353
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PRIMARY RxNorm
FDA UNII
DO22K1PRDJ
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PRIMARY
NCI_THESAURUS
C81082
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PRIMARY
MERCK INDEX
m8877
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PRIMARY Merck Index
ECHA (EC/EINECS)
222-764-6
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PRIMARY
WIKIPEDIA
PIRIBEDIL
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PRIMARY
ChEMBL
CHEMBL1371770
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PRIMARY
CAS
3605-01-4
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PRIMARY
INN
2569
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PRIMARY
EPA CompTox
DTXSID9045188
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PRIMARY
PUBCHEM
4850
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PRIMARY
SMS_ID
100000081665
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PRIMARY
DRUG CENTRAL
2202
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PRIMARY
EVMPD
SUB09908MIG
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PRIMARY
Related Record Type Details
SALT/SOLVATE -> PARENT
TARGET -> AGONIST
Related Record Type Details
ACTIVE MOIETY