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
CNS Activity
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
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Target ID: P35462 Gene ID: 1814.0 Gene Symbol: DRD3 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/11222455 |
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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 |
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Primary | TRIVASTAL Approved UseAdjunctive treatment of intermittent claudication in chronic obliterating arteriopathies of the lower limbs (in stage 2). |
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Palliative | TRIVASTAL Approved UseAdjunctive symptomatic treatment of chronic pathological cognitive and neurosensorial deficit in elderly subjects (excluding Alzheimer's disease and other dementia). |
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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 |
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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 |
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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 |
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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 |
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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 |
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OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
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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 |
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Piribedil: its synergistic effect in multidrug regimens for parkinsonism. | 1976 May |
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Dopamine receptor stimulation in the treatment of depression: piribedil (ET-495). | 1978 |
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DA agonists -- non-ergot derivatives: piribedil: management of Parkinson's disease. | 2002 |
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Choosing the right dopamine agonist for patients with Parkinson's disease. | 2002 |
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Sleep attacks in patients taking dopamine agonists: review. | 2002 Jun 22 |
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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 |
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Repeated administration of piribedil induces less dyskinesia than L-dopa in MPTP-treated common marmosets: a behavioural and biochemical investigation. | 2002 Sep |
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[Use of pronoran (piribedil) in Parkinson's disease: the results of a multicenter study]. | 2003 |
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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 |
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[Modern aproaches to the treatment of early stages of Parkinson disease]. | 2005 |
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Chemically modified carbon paste electrode for the potentiometric flow injection analysis of piribedil in pharmaceutical preparation and urine. | 2005 Jul 15 |
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[Dopaminergic and noradrenergic therapy of cognitive impairment]. | 2006 |
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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 |
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Early piribedil monotherapy of Parkinson's disease: A planned seven-month report of the REGAIN study. | 2006 Dec |
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Activation of D2-like receptors induces sympathetic climactic-like responses in male and female anaesthetised rats. | 2006 Jun |
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Identification of amino acid determinants of dopamine 2 receptor synthetic agonist function. | 2007 Apr |
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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 |
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Tinnitus treatment with piribedil guided by electrocochleography and acoustic otoemissions. | 2009 Aug |
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Parkinson's disease sleep scale, sleep logs, and actigraphy in the evaluation of sleep in parkinsonian patients. | 2009 Sep |
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.
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WHO-ATC |
N04BC08
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WHO-VATC |
QN04BC08
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NCI_THESAURUS |
C66884
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DB12478
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D010891
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C81082
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m8877
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222-764-6
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PIRIBEDIL
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CHEMBL1371770
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2202
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SUB09908MIG
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ACTIVE MOIETY
SALT/SOLVATE (PARENT)