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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

1997
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

1997
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
Pramipexole-induced somnolence and episodes of daytime sleep.
2000 Jul
Sleep disorders in patients with Parkinson's disease: epidemiology and management.
2001
Are dopamine receptor agonists neuroprotective in Parkinson's disease?
2001
Dopamine agonists.
2001
A study of excessive daytime sleepiness and its clinical significance in three groups of Parkinson's disease patients taking pramipexole, cabergoline and levodopa mono and combination therapy.
2001
Switching from pergolide to pramipexole in patients with Parkinson's disease.
2001
Release and aggregation of cytochrome c and alpha-synuclein are inhibited by the antiparkinsonian drugs, talipexole and pramipexole.
2001 Apr 6
Daytime sleepiness and other sleep disorders in Parkinson's disease.
2001 Oct 23
Locomotor hypoactivity and motor disturbances--behavioral effects induced by intracerebellar microinjections of dopaminergic DA-D2/D3 receptor agonists.
2001 Sep-Oct
Gender and pramipexole effects on levodopa pharmacokinetics and pharmacodynamics.
2002 Dec 24
A review of pramipexole and its clinical utility in Parkinson's disease.
2002 Feb
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
[Rhabdomyolysis as a complication of Parkinson's disease].
2002 Jan-Feb
A case of Parkinsonism due to lithium intoxication: treatment with Pramipexole.
2002 May
Restless legs syndrome augmentation and pramipexole treatment.
2002 Nov
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
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
Pramipexole in Parkinson's disease. A short-term study using the combined levodopa-dopamine agonist test.
2002 Oct-Dec
Combination of two different dopamine agonists in the management of Parkinson's disease.
2002 Sep
Comparison of the risk of adverse events with pramipexole and ropinirole in patients with Parkinson's disease: a meta-analysis.
2003
Pramipexole inhibits MPTP toxicity in mice by dopamine D3 receptor dependent and independent mechanisms.
2003 Aug 15
Piribedil-induced sleep attacks in Parkinson's disease.
2003 Feb
Double-blind, single-dose, cross-over study of the effects of pramipexole, pergolide, and placebo on rest tremor and UPDRS part III in Parkinson's disease.
2003 Feb
Slowing Parkinson's disease progression: recent dopamine agonist trials.
2003 Feb 11
Parkinson's disease: is the initial treatment established?
2003 Jul
Agonist-specific transactivation of phosphoinositide 3-kinase signaling pathway mediated by the dopamine D2 receptor.
2003 Nov 21
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 Fri Dec 15 19:39:53 GMT 2023
Edited
by admin
on Fri Dec 15 19:39:53 GMT 2023
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 Fri Dec 15 19:39:53 GMT 2023 , Edited by admin on Fri Dec 15 19:39:53 GMT 2023
PRIMARY
PUBCHEM
119569
Created by admin on Fri Dec 15 19:39:53 GMT 2023 , Edited by admin on Fri Dec 15 19:39:53 GMT 2023
PRIMARY
SMS_ID
100000089409
Created by admin on Fri Dec 15 19:39:53 GMT 2023 , Edited by admin on Fri Dec 15 19:39:53 GMT 2023
PRIMARY
EVMPD
SUB25210
Created by admin on Fri Dec 15 19:39:53 GMT 2023 , Edited by admin on Fri Dec 15 19:39:53 GMT 2023
PRIMARY
FDA UNII
4R2HD0M28N
Created by admin on Fri Dec 15 19:39:53 GMT 2023 , Edited by admin on Fri Dec 15 19:39:53 GMT 2023
PRIMARY
CAS
104632-25-9
Created by admin on Fri Dec 15 19:39:53 GMT 2023 , Edited by admin on Fri Dec 15 19:39:53 GMT 2023
PRIMARY
MERCK INDEX
m9095
Created by admin on Fri Dec 15 19:39:53 GMT 2023 , Edited by admin on Fri Dec 15 19:39:53 GMT 2023
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
SUBSTANCE->BASIS OF STRENGTH
SOLVATE->ANHYDROUS
Related Record Type Details
ACTIVE MOIETY