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
Clinical and pharmacological evaluation of the effects of piribedil in patients with parkinsonism.	1975 Jan	1091122
Piribedil: its synergistic effect in multidrug regimens for parkinsonism.	1976 May	944394
Parkinsonism by haloperidol and piribedil.	1978 Oct 31	103114
Sleep attacks and Parkinson's disease treatment.	2000 Apr 15	10776750
Discriminative stimulus properties of the dopamine D3 receptor agonists, PD128,907 and 7-OH-DPAT: a comparative characterization with novel ligands at D3 versus D2 receptors.	2000 Feb 14	10728880
Antiparkinsonian agent piribedil displays antagonist properties at native, rat, and cloned, human alpha(2)-adrenoceptors: cellular and functional characterization.	2001 Jun	11356907
Randomized study of the dopamine receptor agonist piribedil in the treatment of mild cognitive impairment.	2001 Sep	11532743
[Use of dopamine agonists in the treatment of Parkinson's disease].	2002	12378886
Clinical pharmacokinetic and pharmacodynamic properties of drugs used in the treatment of Parkinson's disease.	2002	11978145
[Alpha-2 adrenergic receptors and Parkinson's disease].	2002 Jul 27	12192732
Gateways to clinical trials.	2002 Jul-Aug	12224444
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. II. Agonist and antagonist properties at subtypes of dopamine D(2)-like receptor and alpha(1)/alpha(2)-adrenoceptor.	2002 Nov	12388667
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
[Use of pronoran (piribedil) in Parkinson's disease: the results of a multicenter study].	2003	14681961
[The use of pronoran (piribedil) in Parkinson's disease].	2003	14571680
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
Piribedil enhances frontocortical and hippocampal release of acetylcholine in freely moving rats by blockade of alpha 2A-adrenoceptors: a dialysis comparison to talipexole and quinelorane in the absence of acetylcholinesterase inhibitors.	2003 Apr	12649387
Piribedil as an adjunct to levodopa in advanced Parkinson's disease: the Asian experience.	2003 Dec	14644004
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
[Clinical and stabilometric analysis of postural instability in Parkinson's disease].	2004	14870691
[An impact of pronoran on cognitive and affective disorders in Parkinson's disease].	2005	15875942
[Efficacy of pronoran in age-related memory impairment].	2005	15792142
Proposed dose equivalence for rapid switch between dopamine receptor agonists in Parkinson's disease: a review of the literature.	2006 Jan	16490575
Antidepressant-like properties of the anti-Parkinson agent, piribedil, in rodents: mediation by dopamine D2 receptors.	2006 Nov	17021388
[Cognitive disturbances and dysfunction of neuromediator systems in cerebral vascular insufficiency after treatment with pronoran].	2007	18689025
About the anti-Parkinson equivalency of levodopa and dopamine agonists.	2007 Jan-Feb	17272974
Impact of newer pharmacological treatments on quality of life in patients with Parkinson's disease.	2008	18547126
Current management of the cognitive dysfunction in Parkinson's disease: how far have we come?	2008 Aug	18535172
Ruthenium-catalyzed N-alkylation of amines and sulfonamides using borrowing hydrogen methodology.	2009 Feb 11	19191700
Parkinson's disease sleep scale, sleep logs, and actigraphy in the evaluation of sleep in parkinsonian patients.	2009 Sep	19404716
Cognitive psychiatry in India.	2010 Jan	21836668

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