PRAMIPEXOLE DIHYDROCHLORIDE

First approved in 1997

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C10H17N3S.2ClH.H2O
Molecular Weight	302.264
Optical Activity	UNSPECIFIED
Defined Stereocenters	1 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure of PRAMIPEXOLE DIHYDROCHLORIDE

Structure Search

SMILES

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

InChI

InChIKey=APVQOOKHDZVJEX-QTPLPEIMSA-N

InChI=1S/C10H17N3S.2ClH.H2O/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;1H2/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	H2O
Molecular Weight	18.0153
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

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
Does combined treatment with novel antidepressants and a dopamine D3 receptor agonist reproduce cocaine discrimination in rats?	2001 Nov-Dec	11985331
Daytime sleepiness and other sleep disorders in Parkinson's disease.	2001 Oct 23	11673578
Locomotor hypoactivity and motor disturbances--behavioral effects induced by intracerebellar microinjections of dopaminergic DA-D2/D3 receptor agonists.	2001 Sep-Oct	11990070
Restless legs syndrome in the older adult: diagnosis and management.	2002	12390051
Sleep disorders in Parkinson's disease: epidemiology and management.	2002	12390050
Choosing the right dopamine agonist for patients with Parkinson's disease.	2002	12201621
Clinical pharmacokinetic and pharmacodynamic properties of drugs used in the treatment of Parkinson's disease.	2002	11978145
Dopamine transporter brain imaging to assess the effects of pramipexole vs levodopa on Parkinson disease progression.	2002 Apr 3	11926889
[Pramipexole in Parkinson disease. Results of a treatment observation].	2002 Aug	12242961
Two advances in the management of Parkinson disease.	2002 Aug	12184472
Gender and pramipexole effects on levodopa pharmacokinetics and pharmacodynamics.	2002 Dec 24	12499509
[Rapid-eye-movement sleep disorders in Parkinson's disease].	2002 Feb	11965170
Restless legs syndrome: treatment with dopaminergic agents.	2002 Feb 26	11909990
Long-term studies of dopamine agonists.	2002 Feb 26	11909984
Neuroprotection and dopamine agonists.	2002 Feb 26	11909981
[Rhabdomyolysis as a complication of Parkinson's disease].	2002 Jan-Feb	12165940
Pergolide in the treatment of patients with early and advanced Parkinson's disease.	2002 Jan-Feb	11852289
Pramipexole in patients with Parkinson's disease and marked drug resistant tremor: a randomised, double blind, placebo controlled multicentre study.	2002 Jun	12023411
Sleep attacks in patients taking dopamine agonists: review.	2002 Jun 22	12077032
Gender and pramipexole effects on levodopa pharmacokinetics and pharmacodynamics.	2002 May 14	12011296
Restless legs syndrome augmentation and pramipexole treatment.	2002 Nov	14592163
Do dopamine agonists or levodopa modify Parkinson's disease progression?	2002 Nov	12464117
Dopamine agonists and neuroprotection in Parkinson's disease.	2002 Nov	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 Nov	12388667
Neuroprotection in idiopathic Parkinson's disease.	2002 Oct	12522567
Potential antidepressant properties of pramipexole detected in locomotor and operant behavioral investigations in mice.	2002 Oct	12373450
Pramipexole in Parkinson's disease. A short-term study using the combined levodopa-dopamine agonist test.	2002 Oct-Dec	12675263
Review: selegiline improves symptoms and levodopa is better than pramipexole for motor function in untreated Parkinson disease.	2002 Sep-Oct	12207431
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
Dopamine agonists induce episodes of irresistible daytime sleepiness.	2003	12464715
Current status of Parkinson's disease treatment in Korea.	2003 Aug	12915074
Pramipexole inhibits MPTP toxicity in mice by dopamine D3 receptor dependent and independent mechanisms.	2003 Aug 15	12954356
Pramipexole increases vesicular dopamine uptake: implications for treatment of Parkinson's neurodegeneration.	2003 Aug 8	12921866
Loss of color vision during long-term treatment with pramipexole.	2003 Jan	12528002
Sleepwalking and sleep terrors in prepubertal children: what triggers them?	2003 Jan	12509590
Assessment of sleepiness and unintended sleep in Parkinson's disease patients taking dopamine agonists.	2003 Jul	14592299
Parkinson's disease: is the initial treatment established?	2003 Jul	12930698
Pramipexole and pergolide in the treatment of depression in Parkinson's disease: a national multicentre prospective randomized study.	2003 Jul	12823492
Reduction of oxidative stress in amyotrophic lateral sclerosis following pramipexole treatment.	2003 Jun	14506939
[Treatment of restless legs syndrome in uremic patients undergoing dialysis with pramipexole: preliminary results].	2003 Jun	12942600
Dihydroergocriptine in Parkinson's disease: clinical efficacy and comparison with other dopamine agonists.	2003 May	12713527
Potent activation of dopamine D3/D2 heterodimers by the antiparkinsonian agents, S32504, pramipexole and ropinirole.	2003 Nov	14535946
Agonist-specific transactivation of phosphoinositide 3-kinase signaling pathway mediated by the dopamine D2 receptor.	2003 Nov 21	12970364
Randomized, double-blind study of pramipexole with placebo and bromocriptine in advanced Parkinson's disease.	2003 Oct	14534919
Dopamine receptor agonists in current clinical use: comparative dopamine receptor binding profiles defined in the human striatum.	2003 Oct	14523624
Current treatment options for restless legs syndrome.	2003 Oct	14521483
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	14534244
Treatment effects on nigrostriatal projection integrity in partial 6-OHDA lesions: comparison of L-DOPA and pramipexole.	2003 Sep	12957491
Clinical strategies to prevent and delay motor complications.	2003 Sep 23	14504375

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 17:59:18 GMT 2025` Edited by `admin` on `Mon Mar 31 17:59:18 GMT 2025`
Record UNII	3D867NP06J
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

PRAMIPEXOLE DIHYDROCHLORIDE MONOHYDRATE

Preferred Name

English

PRAMIPEXOLE DIHYDROCHLORIDE

Official Name

English

SND-919CL2Y

Code

English

SND919CL2Y

Code

English

SIFROL

Brand Name

English

PRAMIPEXOLE HYDROCHLORIDE MONOHYDRATE

Common Name

English

PRAMIPEXOLE TEVA

Brand Name

English

PRAMIPEXOLE DIHYDROCHLORIDE MONOHYDRATE [EMA EPAR]

Common Name

English

PNU-98528E

Code

English

PRAMIPEXOLE DIHYDROCHLORIDE [USP MONOGRAPH]

Common Name

English

(S)-2-Amino-4,5,6,7-tetrahydro-6-(propylamino)benzothiazole dihydrochloride monohydrate

Systematic Name

English

MIRAPEX

Brand Name

English

PRAMIPEXOLE DIHYDROCHLORIDE [VANDF]

Common Name

English

PRAMIPEXOLE ACCORD

Brand Name

English

MIRAPEXIN

Brand Name

English

PRAMIPEXOLE DIHYDROCHLORIDE MONOHYDRATE [USP-RS]

Common Name

English

PRAMIPEXOLE HYDROCHLORIDE HYDRATE [JAN]

Common Name

English

PRAMIPEXOLE DIHYDROCHLORIDE [USAN]

Common Name

English

PRAMIPEXOLE HYDROCHLORIDE [MART.]

Common Name

English

PRAMIPEXOLE DIHYDROCHLORIDE MONOHYDRATE [EP MONOGRAPH]

Common Name

English

PRAMIPEXOLE HYDROCHLORIDE HYDRATE

Common Name

English

OPRYMEA

Brand Name

English

Pramipexole dihydrochloride monohydrate [WHO-DD]

Common Name

English

PRAMIPEXOLE DIHYDROCHLORIDE [ORANGE BOOK]

Common Name

English

PRAMIPEXOLE HYDROCHLORIDE

Common Name

English

DAQUIRAN

Brand Name

English

PRAMIPEXOLE DIHYDROCHLORIDE MONOHYDRATE [MI]

Common Name

English

Classification Tree Code System Code

EMA ASSESSMENT REPORTS

PRAMIPEXOLE ACCORD (AUTHORIZED: RESTLESS LEGS SYNDROME)