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
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
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 |
CNS Activity
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: P35462 Gene ID: 1814.0 Gene Symbol: DRD3 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/11222455 |
|||
Target ID: P14416 Gene ID: 1813.0 Gene Symbol: DRD2 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/8588823 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | TRIVASTAL Approved UseAdjunctive treatment of intermittent claudication in chronic obliterating arteriopathies of the lower limbs (in stage 2). |
|||
Palliative | TRIVASTAL Approved UseAdjunctive symptomatic treatment of chronic pathological cognitive and neurosensorial deficit in elderly subjects (excluding Alzheimer's disease and other dementia). |
|||
Primary | TRIVASTAL Approved UseTreatment 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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/15726579/ |
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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/15726579/ |
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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/15726579/ |
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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/15726579/ |
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/15726579/ |
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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/15726579/ |
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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/15726579/ |
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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/15726579/ |
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
11.9 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/15726579/ |
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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/15726579/ |
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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/15726579/ |
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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/15726579/ |
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
Dose | Population | Adverse 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%) Sources: Psychiatric symptom (1%) |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
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
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
---|---|---|
Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
no [IC50 >133 uM] | ||||
no [IC50 >133 uM] | ||||
no [IC50 >133 uM] | ||||
no [IC50 >133 uM] | ||||
Page: 155.0 |
no | |||
yes [IC50 0.1995 uM] | ||||
yes [IC50 0.631 uM] | ||||
yes [IC50 1.9953 uM] | ||||
Page: 9.0 |
yes [IC50 10.964 uM] | |||
Page: 5.0 |
yes [IC50 2.4545 uM] |
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Page: 11 | 185 |
no |
Tox targets
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Page: 218.0 |
PubMed
Title | Date | PubMed |
---|---|---|
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 |
|
Sleep attacks and Parkinson's disease treatment. | 2000 Apr 15 |
|
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 |
|
Antiparkinsonian agent piribedil displays antagonist properties at native, rat, and cloned, human alpha(2)-adrenoceptors: cellular and functional characterization. | 2001 Jun |
|
Dopamine agonist-induced dyskinesias are correlated to both firing pattern and frequency alterations of pallidal neurones in the MPTP-treated monkey. | 2001 Mar |
|
Piribedil for restless legs syndrome: a pilot study. | 2001 May |
|
Formulation and in vitro-in vivo evaluation of piribedil solid lipid micro- and nanoparticles. | 2001 May-Jun |
|
[Use of dopamine agonists in the treatment of Parkinson's disease]. | 2002 |
|
[Alpha-2 adrenergic receptors and Parkinson's disease]. | 2002 Jul 27 |
|
Gateways to clinical trials. | 2002 Jul-Aug |
|
Repeated administration of piribedil induces less dyskinesia than L-dopa in MPTP-treated common marmosets: a behavioural and biochemical investigation. | 2002 Sep |
|
Efficacy of piribedil as early combination to levodopa in patients with stable Parkinson's disease: a 6-month, randomized, placebo-controlled study. | 2003 Apr |
|
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 |
|
Electroanalytical characteristics of piribedil and its differential pulse and square wave voltammetric determination in pharmaceuticals and human serum. | 2003 Mar 10 |
|
[Treatment of Parkinson's disease: use of piribedil]. | 2004 |
|
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 of pronoran in age-related memory impairment]. | 2005 |
|
Early piribedil monotherapy of Parkinson's disease: A planned seven-month report of the REGAIN study. | 2006 Dec |
|
Antidepressant-like properties of the anti-Parkinson agent, piribedil, in rodents: mediation by dopamine D2 receptors. | 2006 Nov |
|
The dopamine agonist piribedil with L-DOPA improves attentional dysfunction: relevance for Parkinson's disease. | 2006 Nov |
|
A reversed-phase high-performance liquid chromatographic method for the determination of zafirlukast in pharmaceutical formulations and human plasma. | 2006 Nov-Dec |
|
[Effect of dopamine deficiency on the preparation of visually guided saccadic eye movements]. | 2006 Sep-Oct |
|
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 |
|
Peripheral edema and dopamine agonists in Parkinson disease. | 2007 Oct |
|
Functional neuroanatomy of the noradrenergic locus coeruleus: its roles in the regulation of arousal and autonomic function part II: physiological and pharmacological manipulations and pathological alterations of locus coeruleus activity in humans. | 2008 Sep |
|
Mild cognitive impairment: The dilemma. | 2009 Jan |
|
Impulse control disorder and piribedil: report of 5 cases. | 2010 Jan-Feb |
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
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/11222455
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
Edited
Mon Mar 31 17:45:05 GMT 2025
by
admin
on
Mon Mar 31 17:45:05 GMT 2025
|
Record UNII |
DO22K1PRDJ
|
Record Status |
Validated (UNII)
|
Record Version |
|
-
Download
Name | Type | Language | ||
---|---|---|---|---|
|
Preferred Name | English | ||
|
Official Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Code | English | ||
|
Systematic Name | English | ||
|
Code | English | ||
|
Common Name | English | ||
|
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 | ||
---|---|---|---|---|---|
|
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 | |||
|
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 | |||
|
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 | ||
|
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 | |||
|
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 | |||
|
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 | ||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 |
Related Record | Type | Details | ||
---|---|---|---|---|
|
SALT/SOLVATE -> PARENT | |||
|
TARGET -> AGONIST |
|
Related Record | Type | Details | ||
---|---|---|---|---|
|
ACTIVE MOIETY |