PRAMIPEXOLE DIHYDROCHLORIDE ANHYDROUS

First approved in 1997

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

Structure Search

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
Sources: http://www.drugbank.ca/drugs/DB00413
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.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
Dopamine D3 receptor 97 Target ID: CHEMBL234 Sources: http://www.drugbank.ca/drugs/DB00413	Agonist 2752	1.5 nM [EC50]
Dopamine D2 receptor 311 Target ID: CHEMBL217 Sources: http://www.drugbank.ca/drugs/DB00413	Agonist 2752	27.0 nM [EC50]
Dopamine D4 receptor 76 Target ID: CHEMBL219 Sources: http://www.drugbank.ca/drugs/DB00413	Agonist 2752	15.0 nM [EC50]
Carbonic anhydrase II 88 Target ID: CHEMBL205 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24289818	Inhibitor 8504	4.81 µM [IC50]
Carbonic anhydrase I 62 Target ID: CHEMBL261 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24289818	Inhibitor 8504	5.37 µM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Idiopathic Parkinson's disease 19 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/020667s014s017s018lbl.pdf	Primary		Approved 8583	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
Restless legs syndrome 17 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/020667s014s017s018lbl.pdf	Primary		Approved 8583	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

C_max

Value	Dose	Co-administered	Analyte	Population
0.268 ng/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/20110012	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

Value	Dose	Co-administered	Analyte	Population
5.29 ng × h/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/20110012	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

T_1/2

Value	Dose	Co-administered	Analyte	Population
31.2 h EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/20110012	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

Dose	Population	Adverse events
1.5 mg 3 times / day multiple, oral Recommended Dose: 1.5 mg, 3 times / day Route: oral Route: multiple Dose: 1.5 mg, 3 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/24834511	unhealthy, 61.6 Health Status: unhealthy Age Group: 61.6 Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/24834511	Disc. AE: Hallucination, Hypotension... AEs leading to discontinuation/dose reduction: Hallucination (1.3%) Hypotension (0.5%) Peripheral edema (0.5%) Sources: https://pubmed.ncbi.nlm.nih.gov/24834511
1.5 mg 3 times / day multiple, oral Recommended Dose: 1.5 mg, 3 times / day Route: oral Route: multiple Dose: 1.5 mg, 3 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/9305331	unhealthy, 62.7 Health Status: unhealthy Age Group: 62.7 Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/9305331	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: https://pubmed.ncbi.nlm.nih.gov/9305331
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: https://pubmed.ncbi.nlm.nih.gov/9214527	unhealthy, 62.8 Health Status: unhealthy Age Group: 62.8 Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/9214527	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: https://pubmed.ncbi.nlm.nih.gov/9214527
1.5 mg 3 times / day multiple, oral Recommended Dose: 1.5 mg, 3 times / day Route: oral Route: multiple Dose: 1.5 mg, 3 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/24834511	unhealthy, 63 Health Status: unhealthy Age Group: 63 Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/24834511	Disc. AE: Hallucination, Peripheral edema... AEs leading to discontinuation/dose reduction: Hallucination (1%) Peripheral edema (0.8%) Abdominal pain upper (0.6%) Myocardial infarction (0.6%) Nausea (0.6%) Pneumonia (0.6%) Vomiting (0.6%) Sources: https://pubmed.ncbi.nlm.nih.gov/24834511

AEs

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:8356	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:8356
ChemicalBook	CB0486178	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB0486178
eMolecules	6843675	https://www.emolecules.com/cgi-bin/more?vid=6843675
MolPort	MolPort-003-849-957	https://www.molport.com/shop/molecule-link/MolPort-003-849-957
Selleck Chemicals	Pramipexole-Mirapex	http://www.selleckchem.com/products/Pramipexole-Mirapex.html
ZINC	ZINC000003781664	http://zinc15.docking.org/substances/ZINC000003781664

PubMed

Title	Date	PubMed
Agonist-specific transactivation of phosphoinositide 3-kinase signaling pathway mediated by the dopamine D2 receptor.	2003-11-21	12970364
Potent activation of dopamine D3/D2 heterodimers by the antiparkinsonian agents, S32504, pramipexole and ropinirole.	2003-11	14535946
3,4-methylenedioxymethamphetamine (ecstasy) inhibits dyskinesia expression and normalizes motor activity in 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine-treated primates.	2003-10-08	14534244
Randomized, double-blind study of pramipexole with placebo and bromocriptine in advanced Parkinson's disease.	2003-10	14534919
Dopamine receptor agonists in current clinical use: comparative dopamine receptor binding profiles defined in the human striatum.	2003-10	14523624
Current treatment options for restless legs syndrome.	2003-10	14521483
Clinical strategies to prevent and delay motor complications.	2003-09-23	14504375
Treatment effects on nigrostriatal projection integrity in partial 6-OHDA lesions: comparison of L-DOPA and pramipexole.	2003-09	12957491
Pramipexole inhibits MPTP toxicity in mice by dopamine D3 receptor dependent and independent mechanisms.	2003-08-15	12954356
Pramipexole increases vesicular dopamine uptake: implications for treatment of Parkinson's neurodegeneration.	2003-08-08	12921866
Current status of Parkinson's disease treatment in Korea.	2003-08	12915074
Assessment of sleepiness and unintended sleep in Parkinson's disease patients taking dopamine agonists.	2003-07	14592299
Parkinson's disease: is the initial treatment established?	2003-07	12930698
Dual dopamine agonist treatment in Parkinson's disease.	2003-07	12883924
Pramipexole and pergolide in the treatment of depression in Parkinson's disease: a national multicentre prospective randomized study.	2003-07	12823492
Neuroprotective mechanisms of antiparkinsonian dopamine D2-receptor subfamily agonists.	2003-07	12737528
Reduction of oxidative stress in amyotrophic lateral sclerosis following pramipexole treatment.	2003-06	14506939
[Treatment of restless legs syndrome in uremic patients undergoing dialysis with pramipexole: preliminary results].	2003-06	12942600
Sleep attacks, daytime sleepiness, and dopamine agonists in Parkinson's disease.	2003-06	12784269
The increased utilisation of dopamine agonists and the introduction of COMT inhibitors have not reduced levodopa consumption--a nation-wide perspective in Sweden.	2003-06	12781593
Efficacy, safety and cost of new drugs acting on the central nervous system.	2003-05	12743674
Dihydroergocriptine in Parkinson's disease: clinical efficacy and comparison with other dopamine agonists.	2003-05	12713527
Pramipexole in Parkinson's disease. A short-term study using the combined levodopa-dopamine agonist test.	2003-04-05	12675263
Pramipexole in comparison to l-dopa: a neuropsychological study.	2003-04	12658365
Slowing Parkinson's disease progression: recent dopamine agonist trials.	2003-02-11	12580184
Piribedil-induced sleep attacks in Parkinson's disease.	2003-02	12588638
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.	2003-02	12539211
Loss of color vision during long-term treatment with pramipexole.	2003-01	12528002
Sleepwalking and sleep terrors in prepubertal children: what triggers them?	2003-01	12509590
Pramipexole in routine clinical practice: a prospective observational trial in Parkinson's disease.	2003	14533946
Cabergoline, pramipexole and ropinirole used as monotherapy in early Parkinson's disease: an evidence-based comparison.	2003	12964891
Advances in the pharmacological management of Parkinson disease.	2003	12830929
Inhibitory effects of D2 agonists by striatal injection on excessive release of dopamine and hyperactivity induced by Bay K 8644 in rats.	2003	12732253
Comparison of the risk of adverse events with pramipexole and ropinirole in patients with Parkinson's disease: a meta-analysis.	2003	12688834
Dopamine agonists induce episodes of irresistible daytime sleepiness.	2003	12464715
Gender and pramipexole effects on levodopa pharmacokinetics and pharmacodynamics.	2002-12-24	12499509
Dopamine agonist monotherapy in Parkinson's disease.	2002-11-30	12480442
Restless legs syndrome augmentation and pramipexole treatment.	2002-11	14592163
Do dopamine agonists or levodopa modify Parkinson's disease progression?	2002-11	12464117
Dopamine agonists and neuroprotection in Parkinson's disease.	2002-11	12464116
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.	2002-11	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.	2002-11	12388666
Neuroprotection in idiopathic Parkinson's disease.	2002-10	12522567
Pramipexole in treatment-resistant depression: a 16-week naturalistic study.	2002-10	12479663
An evidence-based review of dopamine receptor agonists in the treatment of Parkinson's disease.	2002-10	12436117
Potential antidepressant properties of pramipexole detected in locomotor and operant behavioral investigations in mice.	2002-10	12373450
Combination of two different dopamine agonists in the management of Parkinson's disease.	2002-09	12548370
[Pramipexole in Parkinson disease. Results of a treatment observation].	2002-08	12242961
Restless legs syndrome in the older adult: diagnosis and management.	2002	12390051
Sleep disorders in Parkinson's disease: epidemiology and management.	2002	12390050

Patents

Sample Use Guides

In Vivo Use Guide

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

In Vitro Use Guide

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 `Mon Mar 31 19:52:43 GMT 2025` Edited by `admin` on `Mon Mar 31 19:52:43 GMT 2025`
Record UNII	4R2HD0M28N
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

PRAMIPEXOLE DIHYDROCHLORIDE ANHYDROUS

Common Name

English

2,6-BENZOTHIAZOLEDIAMINE, 4,5,6,7-TETRAHYDRO-N6-PROPYL-, HYDROCHLORIDE (1:2), (6S)-

Preferred Name

English

Pramipexole dihydrochloride [WHO-DD]

Common Name

English

ANHYDROUS PRAMIPEXOLE HYDROCHLORIDE

Common Name

English

PRAMIPEXOLE DIHYDROCHLORIDE ANHYDROUS [MI]

Common Name

English

Code System Code Type Description

EPA CompTox

DTXSID90146623