PIRIBEDIL

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 Search

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

Description
Sources: http://www.servier.com.ve/sites/default/files/spc-pil/spc-trivastal.pdf | https://www.ncbi.nlm.nih.gov/pubmed/11222455

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.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
D(3) dopamine receptor 16 Target ID: P35462 Gene ID: 1814.0 Gene Symbol: DRD3 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/11222455	Agonist 2678
D(2) dopamine receptor 58 Target ID: P14416 Gene ID: 1813.0 Gene Symbol: DRD2 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/8588823	Agonist 2678

Conditions

Condition	Modality	Highest Phase	Product
Chronic obliterating arteriopathy 2 Sources: http://www.servier.com.ve/sites/default/files/spc-pil/spc-trivastal.pdf	Primary	Approved 8429	TRIVASTAL Approved Use Adjunctive treatment of intermittent claudication in chronic obliterating arteriopathies of the lower limbs (in stage 2).
Cognitive impairment 15 Sources: http://www.servier.com.ve/sites/default/files/spc-pil/spc-trivastal.pdf	Palliative	Approved 8429	TRIVASTAL Approved Use Adjunctive symptomatic treatment of chronic pathological cognitive and neurosensorial deficit in elderly subjects (excluding Alzheimer's disease and other dementia).
Parkinson's disease 226 Sources: http://www.servier.com.ve/sites/default/files/spc-pil/spc-trivastal.pdf	Primary	Approved 8429	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

Title	Date	PubMed
Piribedil: its synergistic effect in multidrug regimens for parkinsonism.	1976 May	944394
Parkinsonism by haloperidol and piribedil.	1978 Oct 31	103114
Pharmacological treatment for aphasia following stroke.	2001	11687079
Dopamine agonist-induced dyskinesias are correlated to both firing pattern and frequency alterations of pallidal neurones in the MPTP-treated monkey.	2001 Mar	11222455
Formulation and in vitro-in vivo evaluation of piribedil solid lipid micro- and nanoparticles.	2001 May-Jun	11308226
[Use of dopamine analogs in Parkinson's disease treatment].	2002	12520782
[Use of dopamine agonists in the treatment of Parkinson's disease].	2002	12378886
Choosing the right dopamine agonist for patients with Parkinson's disease.	2002	12201621
Clinical pharmacokinetic and pharmacodynamic properties of drugs used in the treatment of Parkinson's disease.	2002	11978145
Psychomotor and cognitive effects of piribedil, a dopamine agonist, in young healthy volunteers.	2002 Feb	11903513
[Alpha-2 adrenergic receptors and Parkinson's disease].	2002 Jul 27	12192732
Sleep attacks in patients taking dopamine agonists: review.	2002 Jun 22	12077032
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	12388668
Differential actions of antiparkinson agents at multiple classes of monoaminergic receptor. I. A multivariate analysis of the binding profiles of 14 drugs at 21 native and cloned human receptor subtypes.	2002 Nov	12388666
Repeated administration of piribedil induces less dyskinesia than L-dopa in MPTP-treated common marmosets: a behavioural and biochemical investigation.	2002 Sep	12360537
Efficacy of piribedil as early combination to levodopa in patients with stable Parkinson's disease: a 6-month, randomized, placebo-controlled study.	2003 Apr	12671949
Quantitative determination of some pharmaceutical piperazine derivatives through complexation with iron(III) chloride.	2003 Aug	12875888
Piribedil-induced sleep attacks in Parkinson's disease.	2003 Feb	12588638
Age-related mild cognitive deficit: a ready-to-use concept?	2003 Mar	22033646
Piribedil and bromocriptine in Parkinson's disease: a single-blind crossover study.	2003 Mar	12614313
[Treatment of Parkinson's disease: use of piribedil].	2004	14870695
[The effectiveness and tolerance of piribedil as adjunct therapy to levodopa in patients with Parkinson's disease: a nine month follow up].	2004 Apr 16-30	15122540
Adsorptive stripping voltammetric behaviour of azomethine group in pyrimidine-containing drugs.	2004 Feb 18	15127806
Acute treatment of migraine. Breaking the paradigm of monotherapy.	2004 Jan 28	15005810
Drug treatment of Parkinson's disease.	2004 Sep	22033779
[Modern aproaches to the treatment of early stages of Parkinson disease].	2005	16329637
[Efficacy of pronoran in age-related memory impairment].	2005	15792142
[Dopaminergic and noradrenergic therapy of cognitive impairment].	2006	17069060
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	16267842
Pathophysiology and management of syncope in Kearns-Sayre syndrome.	2006 Fall	17086014
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	16772809
Antidepressant-like properties of the anti-Parkinson agent, piribedil, in rodents: mediation by dopamine D2 receptors.	2006 Nov	17021388
A reversed-phase high-performance liquid chromatographic method for the determination of zafirlukast in pharmaceutical formulations and human plasma.	2006 Nov-Dec	17225602
Effects of the dopamine agonist piribedil on prefrontal temporal cortical network function in normal aging as assessed by verbal fluency.	2007 Jan 30	16876301
[Implication of piribedil (pronoran) in the treatment of Parkinson's disease; a clinical and pharmacoeconomic analysis].	2008	18567194
Impact of newer pharmacological treatments on quality of life in patients with Parkinson's disease.	2008	18547126
Comparative effects of the dopaminergic agonists piribedil and bromocriptine in three different memory paradigms in rodents.	2008 Jul	18308794
Hallucinations: Etiology and clinical implications.	2009 Jul	21180490
Dopamine Agonists and their risk to induce psychotic episodes in Parkinson's disease: a case-control study.	2009 Jun 10	19515253
Orodispersible sublingual piribedil to abort OFF episodes: a single dose placebo-controlled, randomized, double-blind, cross-over study.	2010 Feb 15	20063435
Cognitive psychiatry in India.	2010 Jan	21836668
Pre-treatment with dopamine agonists influence L-dopa mediated rotations without affecting abnormal involuntary movements in the 6-OHDA lesioned rat.	2010 Nov 12	20434491

Patents

Sample Use Guides

In Vivo Use Guide

For the treatment of Parkinson's disease as a monotherapy, piribedil should be administered orally at 150 to 250 mg.

Route of Administration: Oral

In Vitro Use Guide

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

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