U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C10H17N3S.2ClH
Molecular Weight 284.249
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PRAMIPEXOLE DIHYDROCHLORIDE ANHYDROUS

SMILES

Cl.Cl.CCCN[C@H]1CCC2=C(C1)SC(N)=N2

InChI

InChIKey=QMNWXHSYPXQFSK-KLXURFKVSA-N
InChI=1S/C10H17N3S.2ClH/c1-2-5-12-7-3-4-8-9(6-7)14-10(11)13-8;;/h7,12H,2-6H2,1H3,(H2,11,13);2*1H/t7-;;/m0../s1

HIDE SMILES / InChI

Molecular Formula C10H17N3S
Molecular Weight 211.327
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

Molecular Formula ClH
Molecular Weight 36.461
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description
Curator's Comment: Description was created based on several sources, including https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/020667s014s017s018lbl.pdf

Pramipexole is a nonergot dopamine agonist with high relative in vitro specificity and full intrinsic activity at the D2 subfamily of dopamine receptors, binding with higher affinity to D3 than to D2 or D4 receptor subtypes. The relevance of D3 receptor binding in Parkinson's disease is unknown. The precise mechanism of action of Pramipexole as a treatment for Parkinson's disease is unknown, although it is believed to be related to its ability to stimulate dopamine receptors in the striatum. This conclusion is supported by electrophysiologic studies in animals that have demonstrated that Pramipexole influences striatal neuronal firing rates via activation of dopamine receptors in the striatum and the substantia nigra, the site of neurons that send projections to the striatum. Pramipexole is used for the treatment of signs and symptoms of idiopathic Parkinson's disease.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
1.5 nM [EC50]
27.0 nM [EC50]
15.0 nM [EC50]
4.81 µM [IC50]
5.37 µM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
MIRAPEX

Approved Use

Mirapex® (pramipexole dihydrochloride) tablets are indicated for the treatment of the signs and symptoms of idiopathic Parkinson's disease. MIRAPEX tablets are indicated for the treatment of moderate-to-severe primary Restless Legs Syndrome (RLS).

Launch Date

8.6762881E11
Primary
MIRAPEX

Approved Use

Mirapex® (pramipexole dihydrochloride) tablets are indicated for the treatment of the signs and symptoms of idiopathic Parkinson's disease. MIRAPEX tablets are indicated for the treatment of moderate-to-severe primary Restless Legs Syndrome (RLS).

Launch Date

8.6762881E11
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
0.268 ng/mL
0.375 mg single, oral
dose: 0.375 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
PRAMIPEXOLE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
5.29 ng × h/mL
0.375 mg single, oral
dose: 0.375 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
PRAMIPEXOLE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
31.2 h
0.375 mg single, oral
dose: 0.375 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
PRAMIPEXOLE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
Doses

Doses

DosePopulationAdverse events​
1.5 mg 3 times / day multiple, oral (max)
Recommended
Dose: 1.5 mg, 3 times / day
Route: oral
Route: multiple
Dose: 1.5 mg, 3 times / day
Sources: Page: p.740
unhealthy, 61.6
n = 391
Health Status: unhealthy
Condition: Parkinson's disease
Age Group: 61.6
Sex: M+F
Population Size: 391
Sources: Page: p.740
Disc. AE: Hallucination, Hypotension...
AEs leading to
discontinuation/dose reduction:
Hallucination (1.3%)
Hypotension (0.5%)
Peripheral edema (0.5%)
Sources: Page: p.740
1.5 mg 3 times / day multiple, oral (max)
Recommended
Dose: 1.5 mg, 3 times / day
Route: oral
Route: multiple
Dose: 1.5 mg, 3 times / day
Sources: Page: p.727
unhealthy, 62.7
n = 163
Health Status: unhealthy
Condition: Parkinson's disease
Age Group: 62.7
Sex: M+F
Population Size: 163
Sources: Page: p.727
Disc. AE: Hallucinations, Sleepiness...
AEs leading to
discontinuation/dose reduction:
Hallucinations (4.3%)
Sleepiness (3%)
Dizziness (2.5%)
Memory loss (1.2%)
Paranoia (0.6%)
Sources: Page: p.727
2 mg 3 times / day multiple, oral
Highest studied dose
Dose: 2 mg, 3 times / day
Route: oral
Route: multiple
Dose: 2 mg, 3 times / day
Sources: Page: p.128
unhealthy, 62.8
n = 55
Health Status: unhealthy
Condition: Parkinson's disease
Age Group: 62.8
Sex: M+F
Population Size: 55
Sources: Page: p.128
DLT: Drowsiness, Muscle spasms...
Dose limiting toxicities:
Drowsiness (3.6%)
Muscle spasms (1.8%)
Insomnia (1.8%)
Vertigo (1.8%)
Ankle swelling (1.8%)
Hallucination (3.6%)
Nausea (1.8%)
Sources: Page: p.128
1.5 mg 3 times / day multiple, oral (max)
Recommended
Dose: 1.5 mg, 3 times / day
Route: oral
Route: multiple
Dose: 1.5 mg, 3 times / day
Sources: Page: p.740
unhealthy, 63
n = 511
Health Status: unhealthy
Condition: Parkinson's disease
Age Group: 63
Sex: M+F
Population Size: 511
Sources: Page: p.740
Disc. AE: Nausea, Hallucination...
AEs leading to
discontinuation/dose reduction:
Nausea (0.6%)
Hallucination (1%)
Peripheral edema (0.8%)
Abdominal pain upper (0.6%)
Myocardial infarction (0.6%)
Pneumonia (0.6%)
Vomiting (0.6%)
Sources: Page: p.740
AEs

AEs

AESignificanceDosePopulation
Hypotension 0.5%
Disc. AE
1.5 mg 3 times / day multiple, oral (max)
Recommended
Dose: 1.5 mg, 3 times / day
Route: oral
Route: multiple
Dose: 1.5 mg, 3 times / day
Sources: Page: p.740
unhealthy, 61.6
n = 391
Health Status: unhealthy
Condition: Parkinson's disease
Age Group: 61.6
Sex: M+F
Population Size: 391
Sources: Page: p.740
Peripheral edema 0.5%
Disc. AE
1.5 mg 3 times / day multiple, oral (max)
Recommended
Dose: 1.5 mg, 3 times / day
Route: oral
Route: multiple
Dose: 1.5 mg, 3 times / day
Sources: Page: p.740
unhealthy, 61.6
n = 391
Health Status: unhealthy
Condition: Parkinson's disease
Age Group: 61.6
Sex: M+F
Population Size: 391
Sources: Page: p.740
Hallucination 1.3%
Disc. AE
1.5 mg 3 times / day multiple, oral (max)
Recommended
Dose: 1.5 mg, 3 times / day
Route: oral
Route: multiple
Dose: 1.5 mg, 3 times / day
Sources: Page: p.740
unhealthy, 61.6
n = 391
Health Status: unhealthy
Condition: Parkinson's disease
Age Group: 61.6
Sex: M+F
Population Size: 391
Sources: Page: p.740
Paranoia 0.6%
Disc. AE
1.5 mg 3 times / day multiple, oral (max)
Recommended
Dose: 1.5 mg, 3 times / day
Route: oral
Route: multiple
Dose: 1.5 mg, 3 times / day
Sources: Page: p.727
unhealthy, 62.7
n = 163
Health Status: unhealthy
Condition: Parkinson's disease
Age Group: 62.7
Sex: M+F
Population Size: 163
Sources: Page: p.727
Memory loss 1.2%
Disc. AE
1.5 mg 3 times / day multiple, oral (max)
Recommended
Dose: 1.5 mg, 3 times / day
Route: oral
Route: multiple
Dose: 1.5 mg, 3 times / day
Sources: Page: p.727
unhealthy, 62.7
n = 163
Health Status: unhealthy
Condition: Parkinson's disease
Age Group: 62.7
Sex: M+F
Population Size: 163
Sources: Page: p.727
Dizziness 2.5%
Disc. AE
1.5 mg 3 times / day multiple, oral (max)
Recommended
Dose: 1.5 mg, 3 times / day
Route: oral
Route: multiple
Dose: 1.5 mg, 3 times / day
Sources: Page: p.727
unhealthy, 62.7
n = 163
Health Status: unhealthy
Condition: Parkinson's disease
Age Group: 62.7
Sex: M+F
Population Size: 163
Sources: Page: p.727
Sleepiness 3%
Disc. AE
1.5 mg 3 times / day multiple, oral (max)
Recommended
Dose: 1.5 mg, 3 times / day
Route: oral
Route: multiple
Dose: 1.5 mg, 3 times / day
Sources: Page: p.727
unhealthy, 62.7
n = 163
Health Status: unhealthy
Condition: Parkinson's disease
Age Group: 62.7
Sex: M+F
Population Size: 163
Sources: Page: p.727
Hallucinations 4.3%
Disc. AE
1.5 mg 3 times / day multiple, oral (max)
Recommended
Dose: 1.5 mg, 3 times / day
Route: oral
Route: multiple
Dose: 1.5 mg, 3 times / day
Sources: Page: p.727
unhealthy, 62.7
n = 163
Health Status: unhealthy
Condition: Parkinson's disease
Age Group: 62.7
Sex: M+F
Population Size: 163
Sources: Page: p.727
Ankle swelling 1.8%
DLT
2 mg 3 times / day multiple, oral
Highest studied dose
Dose: 2 mg, 3 times / day
Route: oral
Route: multiple
Dose: 2 mg, 3 times / day
Sources: Page: p.128
unhealthy, 62.8
n = 55
Health Status: unhealthy
Condition: Parkinson's disease
Age Group: 62.8
Sex: M+F
Population Size: 55
Sources: Page: p.128
Insomnia 1.8%
DLT
2 mg 3 times / day multiple, oral
Highest studied dose
Dose: 2 mg, 3 times / day
Route: oral
Route: multiple
Dose: 2 mg, 3 times / day
Sources: Page: p.128
unhealthy, 62.8
n = 55
Health Status: unhealthy
Condition: Parkinson's disease
Age Group: 62.8
Sex: M+F
Population Size: 55
Sources: Page: p.128
Muscle spasms 1.8%
DLT
2 mg 3 times / day multiple, oral
Highest studied dose
Dose: 2 mg, 3 times / day
Route: oral
Route: multiple
Dose: 2 mg, 3 times / day
Sources: Page: p.128
unhealthy, 62.8
n = 55
Health Status: unhealthy
Condition: Parkinson's disease
Age Group: 62.8
Sex: M+F
Population Size: 55
Sources: Page: p.128
Nausea 1.8%
DLT
2 mg 3 times / day multiple, oral
Highest studied dose
Dose: 2 mg, 3 times / day
Route: oral
Route: multiple
Dose: 2 mg, 3 times / day
Sources: Page: p.128
unhealthy, 62.8
n = 55
Health Status: unhealthy
Condition: Parkinson's disease
Age Group: 62.8
Sex: M+F
Population Size: 55
Sources: Page: p.128
Vertigo 1.8%
DLT
2 mg 3 times / day multiple, oral
Highest studied dose
Dose: 2 mg, 3 times / day
Route: oral
Route: multiple
Dose: 2 mg, 3 times / day
Sources: Page: p.128
unhealthy, 62.8
n = 55
Health Status: unhealthy
Condition: Parkinson's disease
Age Group: 62.8
Sex: M+F
Population Size: 55
Sources: Page: p.128
Drowsiness 3.6%
DLT
2 mg 3 times / day multiple, oral
Highest studied dose
Dose: 2 mg, 3 times / day
Route: oral
Route: multiple
Dose: 2 mg, 3 times / day
Sources: Page: p.128
unhealthy, 62.8
n = 55
Health Status: unhealthy
Condition: Parkinson's disease
Age Group: 62.8
Sex: M+F
Population Size: 55
Sources: Page: p.128
Hallucination 3.6%
DLT
2 mg 3 times / day multiple, oral
Highest studied dose
Dose: 2 mg, 3 times / day
Route: oral
Route: multiple
Dose: 2 mg, 3 times / day
Sources: Page: p.128
unhealthy, 62.8
n = 55
Health Status: unhealthy
Condition: Parkinson's disease
Age Group: 62.8
Sex: M+F
Population Size: 55
Sources: Page: p.128
Abdominal pain upper 0.6%
Disc. AE
1.5 mg 3 times / day multiple, oral (max)
Recommended
Dose: 1.5 mg, 3 times / day
Route: oral
Route: multiple
Dose: 1.5 mg, 3 times / day
Sources: Page: p.740
unhealthy, 63
n = 511
Health Status: unhealthy
Condition: Parkinson's disease
Age Group: 63
Sex: M+F
Population Size: 511
Sources: Page: p.740
Myocardial infarction 0.6%
Disc. AE
1.5 mg 3 times / day multiple, oral (max)
Recommended
Dose: 1.5 mg, 3 times / day
Route: oral
Route: multiple
Dose: 1.5 mg, 3 times / day
Sources: Page: p.740
unhealthy, 63
n = 511
Health Status: unhealthy
Condition: Parkinson's disease
Age Group: 63
Sex: M+F
Population Size: 511
Sources: Page: p.740
Nausea 0.6%
Disc. AE
1.5 mg 3 times / day multiple, oral (max)
Recommended
Dose: 1.5 mg, 3 times / day
Route: oral
Route: multiple
Dose: 1.5 mg, 3 times / day
Sources: Page: p.740
unhealthy, 63
n = 511
Health Status: unhealthy
Condition: Parkinson's disease
Age Group: 63
Sex: M+F
Population Size: 511
Sources: Page: p.740
Pneumonia 0.6%
Disc. AE
1.5 mg 3 times / day multiple, oral (max)
Recommended
Dose: 1.5 mg, 3 times / day
Route: oral
Route: multiple
Dose: 1.5 mg, 3 times / day
Sources: Page: p.740
unhealthy, 63
n = 511
Health Status: unhealthy
Condition: Parkinson's disease
Age Group: 63
Sex: M+F
Population Size: 511
Sources: Page: p.740
Vomiting 0.6%
Disc. AE
1.5 mg 3 times / day multiple, oral (max)
Recommended
Dose: 1.5 mg, 3 times / day
Route: oral
Route: multiple
Dose: 1.5 mg, 3 times / day
Sources: Page: p.740
unhealthy, 63
n = 511
Health Status: unhealthy
Condition: Parkinson's disease
Age Group: 63
Sex: M+F
Population Size: 511
Sources: Page: p.740
Peripheral edema 0.8%
Disc. AE
1.5 mg 3 times / day multiple, oral (max)
Recommended
Dose: 1.5 mg, 3 times / day
Route: oral
Route: multiple
Dose: 1.5 mg, 3 times / day
Sources: Page: p.740
unhealthy, 63
n = 511
Health Status: unhealthy
Condition: Parkinson's disease
Age Group: 63
Sex: M+F
Population Size: 511
Sources: Page: p.740
Hallucination 1%
Disc. AE
1.5 mg 3 times / day multiple, oral (max)
Recommended
Dose: 1.5 mg, 3 times / day
Route: oral
Route: multiple
Dose: 1.5 mg, 3 times / day
Sources: Page: p.740
unhealthy, 63
n = 511
Health Status: unhealthy
Condition: Parkinson's disease
Age Group: 63
Sex: M+F
Population Size: 511
Sources: Page: p.740
PubMed

PubMed

TitleDatePubMed
Pramipexole treatment for cocaine cravings.
1999 Nov
Efficacy of pramipexole, a new dopamine receptor agonist, to relieve the parkinsonian-like muscle rigidity in rats.
1999 Nov 26
[Dopaminergic agonists in the treatment of Parkinson's disease].
2000 Dec
Role of dopamine D3 receptors in thermoregulation: a reappraisal.
2000 Jan 17
Pramipexole-induced somnolence and episodes of daytime sleep.
2000 Jul
Dopamine agonists.
2001
Efficacy and tolerability of dopamine agonists in a parkinsonian population.
2001 Feb
Adjunctive dopamine agonists in treatment-resistant bipolar II depression: an open case series.
2001 Jul
Influence of L-dopa and pramipexole on striatal dopamine transporter in early PD.
2001 Jun 12
Newer dopamine agonists in the treatment of restless legs syndrome.
2001 May
Sleep disorders in Parkinson's disease: epidemiology and management.
2002
[Pramipexole in Parkinson disease. Results of a treatment observation].
2002 Aug
Acute placebo-controlled sleep laboratory studies and clinical follow-up with pramipexole in restless legs syndrome.
2002 Aug
Gender and pramipexole effects on levodopa pharmacokinetics and pharmacodynamics.
2002 Dec 24
Inhibition by R(+) or S(-) pramipexole of caspase activation and cell death induced by methylpyridinium ion or beta amyloid peptide in SH-SY5Y neuroblastoma.
2002 Feb 15
Restless legs syndrome: treatment with dopaminergic agents.
2002 Feb 26
Long-term studies of dopamine agonists.
2002 Feb 26
Neuroprotection and dopamine agonists.
2002 Feb 26
Pramipexole ameliorates neurologic and psychiatric symptoms in a Westphal variant of Huntington's disease.
2002 Jan-Feb
Pergolide in the treatment of patients with early and advanced Parkinson's disease.
2002 Jan-Feb
Restless legs syndrome augmentation and pramipexole treatment.
2002 Nov
Dopamine agonists and neuroprotection in Parkinson's disease.
2002 Nov
Dopamine agonist monotherapy in Parkinson's disease.
2002 Nov 30
Pramipexole in treatment-resistant depression: a 16-week naturalistic study.
2002 Oct
Pramipexole in Parkinson's disease. A short-term study using the combined levodopa-dopamine agonist test.
2002 Oct-Dec
Pramipexole in routine clinical practice: a prospective observational trial in Parkinson's disease.
2003
Advances in the pharmacological management of Parkinson disease.
2003
Dopamine agonists induce episodes of irresistible daytime sleepiness.
2003
Pramipexole in comparison to l-dopa: a neuropsychological study.
2003 Apr
Current status of Parkinson's disease treatment in Korea.
2003 Aug
Pramipexole increases vesicular dopamine uptake: implications for treatment of Parkinson's neurodegeneration.
2003 Aug 8
Slowing Parkinson's disease progression: recent dopamine agonist trials.
2003 Feb 11
Assessment of sleepiness and unintended sleep in Parkinson's disease patients taking dopamine agonists.
2003 Jul
Dual dopamine agonist treatment in Parkinson's disease.
2003 Jul
Pramipexole and pergolide in the treatment of depression in Parkinson's disease: a national multicentre prospective randomized study.
2003 Jul
Reduction of oxidative stress in amyotrophic lateral sclerosis following pramipexole treatment.
2003 Jun
Sleep attacks, daytime sleepiness, and dopamine agonists in Parkinson's disease.
2003 Jun
The increased utilisation of dopamine agonists and the introduction of COMT inhibitors have not reduced levodopa consumption--a nation-wide perspective in Sweden.
2003 Jun
Efficacy, safety and cost of new drugs acting on the central nervous system.
2003 May
Dihydroergocriptine in Parkinson's disease: clinical efficacy and comparison with other dopamine agonists.
2003 May
Potent activation of dopamine D3/D2 heterodimers by the antiparkinsonian agents, S32504, pramipexole and ropinirole.
2003 Nov
Randomized, double-blind study of pramipexole with placebo and bromocriptine in advanced Parkinson's disease.
2003 Oct
Dopamine receptor agonists in current clinical use: comparative dopamine receptor binding profiles defined in the human striatum.
2003 Oct
Current treatment options for restless legs syndrome.
2003 Oct
3,4-methylenedioxymethamphetamine (ecstasy) inhibits dyskinesia expression and normalizes motor activity in 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine-treated primates.
2003 Oct 8
Patents

Sample Use Guides

Dosages should be increased gradually from a starting dose of 0.375 mg/day given in three divided doses and should not be increased more frequently than every 5 to 7 days.
Route of Administration: Oral
Pramipexole suppressed H2O2-induced ARPE-19 cell death in vitro at concentrations of 10(-6) M or higher.
Substance Class Chemical
Created
by admin
on Sat Dec 17 03:17:17 UTC 2022
Edited
by admin
on Sat Dec 17 03:17:17 UTC 2022
Record UNII
4R2HD0M28N
Record Status Validated (UNII)
Record Version
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Name Type Language
PRAMIPEXOLE DIHYDROCHLORIDE ANHYDROUS
Common Name English
Pramipexole dihydrochloride [WHO-DD]
Common Name English
ANHYDROUS PRAMIPEXOLE HYDROCHLORIDE
Common Name English
2,6-BENZOTHIAZOLEDIAMINE, 4,5,6,7-TETRAHYDRO-N6-PROPYL-, HYDROCHLORIDE (1:2), (6S)-
Common Name English
PRAMIPEXOLE DIHYDROCHLORIDE ANHYDROUS [MI]
Common Name English
Code System Code Type Description
EPA CompTox
DTXSID90146623
Created by admin on Sat Dec 17 03:17:18 UTC 2022 , Edited by admin on Sat Dec 17 03:17:18 UTC 2022
PRIMARY
PUBCHEM
119569
Created by admin on Sat Dec 17 03:17:18 UTC 2022 , Edited by admin on Sat Dec 17 03:17:18 UTC 2022
PRIMARY
EVMPD
SUB25210
Created by admin on Sat Dec 17 03:17:18 UTC 2022 , Edited by admin on Sat Dec 17 03:17:18 UTC 2022
PRIMARY
FDA UNII
4R2HD0M28N
Created by admin on Sat Dec 17 03:17:18 UTC 2022 , Edited by admin on Sat Dec 17 03:17:18 UTC 2022
PRIMARY
CAS
104632-25-9
Created by admin on Sat Dec 17 03:17:18 UTC 2022 , Edited by admin on Sat Dec 17 03:17:18 UTC 2022
PRIMARY
MERCK INDEX
M9095
Created by admin on Sat Dec 17 03:17:18 UTC 2022 , Edited by admin on Sat Dec 17 03:17:18 UTC 2022
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
SUBSTANCE->BASIS OF STRENGTH
SOLVATE->ANHYDROUS
Related Record Type Details
ACTIVE MOIETY