Identification

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Name
Pramipexole
Accession Number
DB00413  (APRD00156)
Type
Small Molecule
Groups
Approved, Investigational
Description

Pramipexole is a drug used to treat the symptoms of Parkinson's Disease (PD). It is a non-ergot dopamine agonist drug that is efficacious in treating various Parkinson's symptoms such as tremor, rigidity, and bradykinesia (slow movement) 6. It was first approved by the FDA in 1997 12. Parkinson's Disease is one of the most common neurodegenerative disorders and causes a high level of disability in patients 2, leading to increased difficulty in performing activities of daily living due to symptoms that progress over time 3. The prevalence of Parkinson's Disease worldwide has increased from approximately 2.5 million in 1990 to about 6.1 million in 2016 4. This increase may be attributed to an aging population along with other contributing factors 4.

In addition to the above FDA approval for Parkinson's Disease, pramipexole was also approved by the FDA in 2006 for the treatment of Restless Legs Syndrome (RLS) 8. RLS is a sleep-related disorder characterized by unpleasant sensations in the lower extremities, often accompanied by an uncontrollable urge to move the legs 9.

Structure
Thumb
Synonyms
  • (-)-Pramipexole
  • (S)-N  6-propyl-4,5,6,7-tetrahydro-1,3-benzothiazole-2,6-diamine
  • Pramipexol
  • Pramipexole
  • Pramipexolum
External IDs
PNU 98528 / SND 919 Cl 2Y / SUD 919 CL 24 / U 98528 E
Product Ingredients
IngredientUNIICASInChI Key
Pramipexole dihydrochloride monohydrate3D867NP06J191217-81-9APVQOOKHDZVJEX-QTPLPEIMSA-N
Pramipexole hydrochloride4R2HD0M28N104632-25-9QMNWXHSYPXQFSK-KLXURFKVSA-N
Product Images
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Act PramipexoleTablet1.5 mgOralActavis Pharma Company2009-04-15Not applicableCanada
Act PramipexoleTablet0.5 mgOralActavis Pharma Company2009-04-15Not applicableCanada
Act PramipexoleTablet1 mgOralActavis Pharma Company2009-04-15Not applicableCanada
Act PramipexoleTablet0.25 mgOralActavis Pharma Company2009-04-15Not applicableCanada
MirapexTablet1.5 mgOralBoehringer Ingelheim (Canada) Ltd Ltee1998-02-26Not applicableCanada
MirapexTablet1 mg/1OralBoehringer Ingelheim2004-01-01Not applicableUs
MirapexTablet0.125 mg/1OralLake Erie Medical Dba Quality Care Produts Llc2010-10-052014-12-31Us
MirapexTablet0.500 mg/1OralPhysicians Total Care, Inc.2005-09-12Not applicableUs
MirapexTablet1.0 mgOralBoehringer Ingelheim (Canada) Ltd Ltee1998-02-26Not applicableCanada
MirapexTablet.750 mg/1OralBoehringer Ingelheim2007-10-01Not applicableUs
Additional Data Available
  • Application Number
    Application Number

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

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  • Product Code
    Product Code

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Apo-pramipexoleTablet1.5 mgOralApotex Corporation2007-02-26Not applicableCanada
Apo-pramipexoleTablet1.0 mgOralApotex Corporation2007-02-26Not applicableCanada
Apo-pramipexoleTablet0.75 mgOralApotex CorporationNot applicableNot applicableCanada
Apo-pramipexoleTablet0.5 mgOralApotex Corporation2007-02-26Not applicableCanada
Apo-pramipexoleTablet0.125 mgOralApotex CorporationNot applicableNot applicableCanada
Apo-pramipexoleTablet0.25 mgOralApotex Corporation2007-02-26Not applicableCanada
Auro-pramipexoleTablet0.5 mgOralAuro Pharma Inc2014-04-29Not applicableCanada
Auro-pramipexoleTablet0.25 mgOralAuro Pharma Inc2014-04-29Not applicableCanada
Auro-pramipexoleTablet0.125 mgOralAuro Pharma Inc2014-04-29Not applicableCanada
Auro-pramipexoleTablet1 mgOralAuro Pharma Inc2014-04-29Not applicableCanada
Additional Data Available
  • Application Number
    Application Number

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

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  • Product Code
    Product Code

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
Mirapex ERPramipexole dihydrochloride monohydrate (0.375 mg/1) + Pramipexole dihydrochloride monohydrate (0.75 mg/1) + Pramipexole dihydrochloride monohydrate (1.5 mg/1)KitOralBoehringer Ingelheim Pharmaceuticals, Inc.2010-02-222010-11-03Us
Mirapex ERPramipexole dihydrochloride monohydrate (0.375 mg/1) + Pramipexole dihydrochloride monohydrate (0.75 mg/1) + Pramipexole dihydrochloride monohydrate (1.5 mg/1)KitOralBoehringer Ingelheim Pharmaceuticals, Inc.2010-02-222010-11-03Us
Mirapex ERPramipexole dihydrochloride monohydrate (0.375 mg/1) + Pramipexole dihydrochloride monohydrate (0.75 mg/1) + Pramipexole dihydrochloride monohydrate (1.5 mg/1)KitOralBoehringer Ingelheim Pharmaceuticals, Inc.2010-02-222010-11-03Us
International/Other Brands
Glepark (Glenmark) / Medopexol (Medochemie) / Miramel (Clonmel) / Miraper (Specifar) / Pexola (Boehringer Ingelheim) / Sifrol ER (Boehringer Ingelheim)
Categories
UNII
83619PEU5T
CAS number
104632-26-0
Weight
Average: 211.327
Monoisotopic: 211.114318249
Chemical Formula
C10H17N3S
InChI Key
FASDKYOPVNHBLU-ZETCQYMHSA-N
InChI
InChI=1S/C10H17N3S/c1-2-5-12-7-3-4-8-9(6-7)14-10(11)13-8/h7,12H,2-6H2,1H3,(H2,11,13)/t7-/m0/s1
IUPAC Name
(6S)-N6-propyl-4,5,6,7-tetrahydro-1,3-benzothiazole-2,6-diamine
SMILES
CCCN[C@H]1CCC2=C(C1)SC(N)=N2

Pharmacology

Indication

This drug is indicated for the symptomatic treatment of Parkinson’s disease Label. This drug can be administered as monotherapy or in conjunction with levodopa. It is also indicated for symptomatic treatment of moderate to severe primary Restless Legs Syndrome (RLS) Label.

Associated Conditions
Pharmacodynamics

Parkinson's Disease

Through the stimulation of dopamine receptors, pramipexole is thought to relieve the symptoms of Parkinson's Disease Label. The motor symptoms of Parkinson's disease occur partly due to a reduction of dopamine in the substantia nigra of the brain 11. Dopamine is an essential neurotransmitter that has major effects on motor movements in humans.

Restless Legs Syndrome

Pramipexole likely restores balance to the dopaminergic system, controlling the symptoms of this condition. Restless legs syndrome is thought to occur, in part, through dysfunction of the dopaminergic system, resulting in unpleasant lower extremity symptoms 9, 14.

Other effects

In addition to the abovementioned effects, animal studies demonstrate that pramipexole blocks dopamine synthesis, release, and turnover. Additionally, this drug is neuroprotective to dopamine neuron degeneration after ischemia or methamphetamine neurotoxicity 14.

Mechanism of action

The exact mechanism of action of pramipexole as a treatment for Parkinson's disease is unknown at this time. It is thought, however, that the ability of pramipexole to cause stimulation of the dopamine receptors in the striatum of the brain, a region that receives a vast array of neurological input and is responsible for a wide variety of functions, may be involved10. Studies performed in animals show that pramipexole influences striatal neuronal transmission rates following activation of dopamine receptors Label.

Pramipexole is considered a non-ergot dopamine agonist that shows specificity and strong activity at the D2 subfamily of dopamine receptors in vitro, binding selectively and dopamine D2 receptors and showing a preference for the dopamine D3 receptor subtype rather than other subtypes 8. The clinical significance of this binding specificity is unknown Label, 8.

TargetActionsOrganism
AD(3) dopamine receptor
agonist
Humans
AD(2) dopamine receptor
agonist
Humans
AD(4) dopamine receptor
agonist
Humans
U5-hydroxytryptamine receptor 1A
agonist
Humans
UAlpha-2A adrenergic receptor
agonist
Humans
Additional Data Available
Adverse Effects

Comprehensive structured data on known drug adverse effects with statistical prevalence. MedDRA and ICD10 ids are provided for adverse effect conditions and symptoms.

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Additional Data Available
Contraindications

Structured data covering drug contraindications. Each contraindication describes a scenario in which the drug is not to be used. Includes restrictions on co-administration, contraindicated populations, and more.

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Additional Data Available
Blackbox Warnings

Structured data representing warnings from the black box section of drug labels. These warnings cover important and dangerous risks, contraindications, or adverse effects.

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Absorption

The bioavailability of pramipexole is higher than 90%, indicating a high level of absorption Label.

Volume of distribution

This drug is extensively distributed in the body with a volume of distribution of approximately 500 L Label.

Protein binding

About 15% bound to plasma proteins Label.

Metabolism

This drug undergoes little metabolism in humans Label.

Route of elimination

The main route of pramipexole elimination, with 90% of a pramipexole dose found in the urine, almost entirely as unchanged drug Label.

Half life

About 8.5-12 hours Label.

Clearance

Renal clearance is about 400 mL/min, indicating heavy secretion by the renal tubules Label.

Toxicity

LD50

Rat Oral LD 50 >800 mg/kg 13.

Carcinogenicity, mutagenicity, impact on fertility

Pramipexole was not found to be carcinogenic in 2-year studies on mice and rats at 0.3, 2.2, and 11 times the maximum recommended human dose (MRHD). No increased incidence of tumors was observed Label. No mutagenicity was detected in various assays, including the Ames test. Finally, pramipexole given to rat models at a dose of 2.5 mg/kg/day (5 times the maximum recommended human dose), increased estrus cycles and inhibited implantation of a fertilized ovum. Decreased levels of prolactin, a hormone necessary for implantation and maintenance of early pregnancy, were measured Label. The significance of these findings in humans is unknown.

Pregnancy

This drug is considered a pregnancy category C drug, showing teratogenic effects in animals. Currently, there no studies of pramipexole in human pregnancy. Animal reproduction studies are not always predictive of human response. This drug should only be used in pregnancy if the potential benefit outweighs the possible fetal risks Label.

Nursing

Whether pramipexole is excreted in human milk is unknown. A decision should be made regarding the administration pramipexole during nursing, or whether to discontinue it during nursing, as many drugs are excreted in human milk. The potential exists for risk to the infant if pramipexole is, in fact, excreted in the milk Label.

Affected organisms
  • Humans and other mammals
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
2,5-Dimethoxy-4-ethylthioamphetamine2,5-Dimethoxy-4-ethylthioamphetamine may increase the sedative activities of Pramipexole.
4-Bromo-2,5-dimethoxyamphetamine4-Bromo-2,5-dimethoxyamphetamine may increase the sedative activities of Pramipexole.
4-Methoxyamphetamine4-Methoxyamphetamine may increase the sedative activities of Pramipexole.
5-methoxy-N,N-dimethyltryptamine5-methoxy-N,N-dimethyltryptamine may increase the sedative activities of Pramipexole.
7-Nitroindazole7-Nitroindazole may increase the sedative activities of Pramipexole.
7,8-Dichloro-1,2,3,4-tetrahydroisoquinoline7,8-Dichloro-1,2,3,4-tetrahydroisoquinoline may increase the sedative activities of Pramipexole.
AbacavirPramipexole may decrease the excretion rate of Abacavir which could result in a higher serum level.
AcarboseAcarbose may decrease the excretion rate of Pramipexole which could result in a higher serum level.
AcebutololThe therapeutic efficacy of Acebutolol can be increased when used in combination with Pramipexole.
AceclofenacAceclofenac may decrease the excretion rate of Pramipexole which could result in a higher serum level.
Additional Data Available
  • Extended Description
    Extended Description

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  • Severity
    Severity

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  • Evidence Level
    Evidence Level

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  • Action
    Action

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Food Interactions
  • Take without regard to meals, however if nausea is a problem, taking the product with food may reduce its incidence.

References

Synthesis Reference
US4886812
General References
  1. Mierau J, Schneider FJ, Ensinger HA, Chio CL, Lajiness ME, Huff RM: Pramipexole binding and activation of cloned and expressed dopamine D2, D3 and D4 receptors. Eur J Pharmacol. 1995 Jun 23;290(1):29-36. [PubMed:7664822]
  2. Massano J, Bhatia KP: Clinical approach to Parkinson's disease: features, diagnosis, and principles of management. Cold Spring Harb Perspect Med. 2012 Jun;2(6):a008870. doi: 10.1101/cshperspect.a008870. [PubMed:22675666]
  3. Poewe W, Mahlknecht P: The clinical progression of Parkinson's disease. Parkinsonism Relat Disord. 2009 Dec;15 Suppl 4:S28-32. doi: 10.1016/S1353-8020(09)70831-4. [PubMed:20123553]
  4. Authors unspecified: Global, regional, and national burden of Parkinson's disease, 1990-2016: a systematic analysis for the Global Burden of Disease Study 2016. Lancet Neurol. 2018 Nov;17(11):939-953. doi: 10.1016/S1474-4422(18)30295-3. Epub 2018 Oct 1. [PubMed:30287051]
  5. Aiken CB: Pramipexole in psychiatry: a systematic review of the literature. J Clin Psychiatry. 2007 Aug;68(8):1230-6. [PubMed:17854248]
  6. Constantinescu R: Update on the use of pramipexole in the treatment of Parkinson's disease. Neuropsychiatr Dis Treat. 2008 Apr;4(2):337-52. [PubMed:18728740]
  7. Antonini A, Calandrella D: Pharmacokinetic evaluation of pramipexole. Expert Opin Drug Metab Toxicol. 2011 Oct;7(10):1307-14. doi: 10.1517/17425255.2011.614232. Epub 2011 Sep 6. [PubMed:21892895]
  8. Merlino G, Serafini A, Robiony F, Valente M, Gigli GL: Clinical experience with pramipexole in the treatment of restless legs syndrome. Expert Opin Drug Metab Toxicol. 2008 Feb;4(2):225-35. doi: 10.1517/17425255.4.2.225. [PubMed:18248314]
  9. Guo S, Huang J, Jiang H, Han C, Li J, Xu X, Zhang G, Lin Z, Xiong N, Wang T: Restless Legs Syndrome: From Pathophysiology to Clinical Diagnosis and Management. Front Aging Neurosci. 2017 Jun 2;9:171. doi: 10.3389/fnagi.2017.00171. eCollection 2017. [PubMed:28626420]
  10. Rolls ET: Neurophysiology and cognitive functions of the striatum. Rev Neurol (Paris). 1994 Aug-Sep;150(8-9):648-60. [PubMed:7754303]
  11. Galvan A, Wichmann T: Pathophysiology of parkinsonism. Clin Neurophysiol. 2008 Jul;119(7):1459-74. doi: 10.1016/j.clinph.2008.03.017. Epub 2008 May 7. [PubMed:18467168]
  12. FDA Approval package, Mirapex [Link]
  13. Pramipexole hydrochloride tablets SDS [File]
  14. MedSafe NZ, Ramipex tablet information sheet [File]
External Links
Human Metabolome Database
HMDB0014557
KEGG Drug
D00559
PubChem Compound
119570
PubChem Substance
46505897
ChemSpider
106770
BindingDB
50116766
ChEBI
8356
ChEMBL
CHEMBL301265
Therapeutic Targets Database
DAP000019
PharmGKB
PA164742949
Guide to Pharmacology
GtP Drug Page
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
PDRhealth
PDRhealth Drug Page
Wikipedia
Pramipexole
ATC Codes
N04BC05 — Pramipexole
AHFS Codes
  • 28:36.20.08 — Nonergot-derivative Dopamine Receptor Agonists
FDA label
Download (353 KB)
MSDS
Download (25.4 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
0Not Yet RecruitingTreatmentExtrapyramidal Syndrome1
0RecruitingTreatmentPain, Chronic1
1CompletedNot AvailableCocaine Abuse / Dependence, Cocaine / Substance Abuse1
1CompletedNot AvailableHealthy Volunteers2
1CompletedTreatmentHealthy Volunteers5
1CompletedTreatmentObsessive Compulsive Disorder (OCD)1
1CompletedTreatmentParkinson's Disease (PD)1
2CompletedDiagnosticParkinson's Disease (PD) / Parkinsonian Syndromes1
2CompletedTreatmentBipolar Disorder (BD)1
2CompletedTreatmentDepression, Bipolar1
2CompletedTreatmentGilles de la Tourette's Syndrome1
2CompletedTreatmentMajor Depressive Disorder (MDD)1
2CompletedTreatmentRestless Legs Syndrome (RLS)2
2RecruitingTreatmentParkinson's Disease (PD)1
2TerminatedTreatmentAdvanced Stage Parkinson's Disease1
2TerminatedTreatmentFibromyalgia1
2Unknown StatusTreatmentParkinson's Disease (PD)1
2, 3CompletedTreatmentParkinson's Disease (PD)1
3CompletedTreatmentEarly Parkinson Disease (Early PD)1
3CompletedTreatmentEarly Stage Parkinson's Disease1
3CompletedTreatmentIdiopathic Parkinson's Disease1
3CompletedTreatmentIdiopathic Restless Legs Syndrome2
3CompletedTreatmentParkinson's Disease (PD)10
3CompletedTreatmentRestless Legs Syndrome (RLS)6
3Not Yet RecruitingTreatmentTremor, Essential1
3RecruitingTreatmentMajor Depressive Disorder (MDD) / Post Traumatic Stress Disorder (PTSD)1
3RecruitingTreatmentParkinson's Disease (PD)1
3Unknown StatusTreatmentSchizoaffective Disorders / Schizophrenic Disorders1
3WithdrawnTreatmentBinge Eating Disorder (BED)1
4CompletedNot AvailableDepression / Parkinson's Disease (PD)1
4CompletedNot AvailableParkinson's Disease (PD)1
4CompletedDiagnosticParkinson's Disease (PD)1
4CompletedOtherMajor Depressive Disorder (MDD)1
4CompletedOtherRestless Legs Syndrome (RLS)1
4CompletedTreatmentBipolar Disorder (BD)2
4CompletedTreatmentDepression2
4CompletedTreatmentDepression / Parkinson's Disease (PD)1
4CompletedTreatmentDepression / Restless Legs Syndrome (RLS)1
4CompletedTreatmentParkinson's Disease (PD)4
4CompletedTreatmentRestless Legs Syndrome (RLS)4
4Not Yet RecruitingTreatmentCircadian Rhythm Disorders / Depression / Parkinson's Disease (PD) / Sleep disorders and disturbances1
4Not Yet RecruitingTreatmentRestless Legs Syndrome (RLS)1
4RecruitingTreatmentParkinson's Disease (PD)1
4SuspendedTreatmentHealthy Volunteers1
4TerminatedTreatmentEarly-Stage Parkinson's Disease1
4Unknown StatusTreatmentParkinson's Disease (PD)1
Not AvailableCompletedNot AvailableHealthy Volunteers1
Not AvailableCompletedNot AvailableHeart Failure1
Not AvailableCompletedNot AvailableParkinson's Disease (PD)9
Not AvailableCompletedNot AvailableRestless Legs Syndrome (RLS)3
Not AvailableCompletedTreatmentIdiopathic Parkinson's Disease1
Not AvailableRecruitingNot AvailableAnxiety / Depression1
Not AvailableRecruitingNot AvailableAtypical Parkinson Disease / Corticobasal Degeneration / Gait, Frontal / Multiple System Atrophy (MSA) / Parkinson's Disease (PD) / Parkinsonian Disorders / Progressive Supranuclear Palsy (PSP)1
Not AvailableRecruitingBasic ScienceDopamine / Emotions / Motivation / Pramipexole / Reward1

Pharmacoeconomics

Manufacturers
  • Boehringer ingelheim
Packagers
  • Barr Pharmaceuticals
  • Boehringer Ingelheim Ltd.
  • Cardinal Health
  • Kaiser Foundation Hospital
  • Murfreesboro Pharmaceutical Nursing Supply
  • Pfizer Inc.
  • Pharmacia Inc.
  • Physicians Total Care Inc.
  • Rebel Distributors Corp.
  • Resource Optimization and Innovation LLC
  • Sandoz
  • Stat Rx Usa
  • Teva Pharmaceutical Industries Ltd.
  • Vangard Labs Inc.
  • Zydus Pharmaceuticals
Dosage forms
FormRouteStrength
TabletOral0.75 mg
TabletOral.250 mg/1
TabletOral.500 mg/1
TabletOral.750 mg/1
TabletOral0.125 mg
TabletOral0.25 mg
TabletOral0.250 mg/1
TabletOral0.5 mg
TabletOral0.500 mg/1
TabletOral1.0 mg
TabletOral1.5 mg
KitOral
TabletOral0.088 mg
TabletOral0.18 mg
TabletOral0.35 mg
TabletOral0.7 mg
TabletOral1.1 mg
Tablet, extended releaseOral0.26 mg
Tablet, extended releaseOral0.52 mg
Tablet, extended releaseOral1.05 mg
Tablet, extended releaseOral1.57 mg
Tablet, extended releaseOral2.1 mg
Tablet, extended releaseOral2.62 mg
Tablet, extended releaseOral3.15 mg
TabletOral0.50 mg
TabletOral1 mg
TabletOral0.125 mg/1
TabletOral0.25 mg/1
TabletOral0.5 mg/1
TabletOral0.75 mg/1
TabletOral1 mg/1
TabletOral1.5 mg/1
Tablet, extended releaseOral0.375 mg/1
Tablet, extended releaseOral0.75 mg/1
Tablet, extended releaseOral1.5 mg/1
Tablet, extended releaseOral2.25 mg/1
Tablet, extended releaseOral3 mg/1
Tablet, extended releaseOral3.75 mg/1
Tablet, extended releaseOral4.5 mg/1
Prices
Unit descriptionCostUnit
Mirapex er 0.375 mg tablet9.83USD tablet
Mirapex er 0.75 mg tablet9.83USD tablet
Mirapex er 1.5 mg tablet9.83USD tablet
Mirapex er 3 mg tablet9.83USD tablet
Mirapex er 4.5 mg tablet9.83USD tablet
Mirapex 0.125 mg tablet3.48USD tablet
Mirapex 0.25 mg tablet3.42USD tablet
Mirapex 0.5 mg tablet3.42USD tablet
Mirapex 1 mg tablet3.42USD tablet
Mirapex 1.5 mg tablet3.42USD tablet
Mirapex 0.75 mg tablet3.28USD tablet
Pramipexole Dihydrochloride 0.125 mg tablet3.07USD tablet
Pramipexole Dihydrochloride 0.25 mg tablet3.07USD tablet
Pramipexole Dihydrochloride 0.5 mg tablet3.07USD tablet
Pramipexole Dihydrochloride 1 mg tablet3.07USD tablet
Pramipexole Dihydrochloride 1.5 mg tablet3.07USD tablet
Pramipexole di-hcl 0.125 mg tablet2.95USD tablet
Pramipexole di-hcl 0.25 mg tablet2.95USD tablet
Pramipexole di-hcl 0.5 mg tablet2.95USD tablet
Pramipexole di-hcl 1 mg tablet2.95USD tablet
Pramipexole di-hcl 1.5 mg tablet2.95USD tablet
Mirapex 1 mg Tablet2.2USD tablet
Mirapex 1.5 mg Tablet2.2USD tablet
Apo-Pramipexole 1 mg Tablet1.23USD tablet
Apo-Pramipexole 1.5 mg Tablet1.23USD tablet
Co Pramipexole 1 mg Tablet1.23USD tablet
Co Pramipexole 1.5 mg Tablet1.23USD tablet
Novo-Pramipexole 1 mg Tablet1.23USD tablet
Novo-Pramipexole 1.5 mg Tablet1.23USD tablet
Pms-Pramipexole 1 mg Tablet1.23USD tablet
Pms-Pramipexole 1.5 mg Tablet1.23USD tablet
Sandoz Pramipexole 1 mg Tablet1.23USD tablet
Sandoz Pramipexole 1.5 mg Tablet1.23USD tablet
Mirapex 0.25 mg Tablet1.1USD tablet
Apo-Pramipexole 0.25 mg Tablet0.62USD tablet
Co Pramipexole 0.25 mg Tablet0.62USD tablet
Novo-Pramipexole 0.25 mg Tablet0.62USD tablet
Pms-Pramipexole 0.25 mg Tablet0.62USD tablet
Sandoz Pramipexole 0.25 mg Tablet0.62USD tablet
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
US4886812No1989-12-122010-10-08Us
CA2275379No2006-11-282018-01-16Canada
US6001861No1999-12-142018-01-16Us
US6194445No2001-02-272018-01-16Us
US8679533No2014-03-252029-09-08Us
US7695734No2010-04-132028-04-26Us
Additional Data Available
  • Filed On
    Filed On

    The date on which a patent was filed with the relevant government.

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Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)288-290https://www.chemicalbook.com/ChemicalProductProperty_US_CB0486178.aspx
boiling point (°C)378https://www.lookchem.com/Pramipexole/
water solubilityfreely soluble in waterhttps://www.accessdata.fda.gov/drugsatfda_docs/nda/2010/022421s000ChemR.pdf
logP1.42https://pdf.hres.ca/dpd_pm/00043389.PDF
logS-3.2http://www.t3db.ca/toxins/T3D2783
pKa5.6, 9.5https://pdf.hres.ca/dpd_pm/00043389.PDF
Predicted Properties
PropertyValueSource
Water Solubility0.14 mg/mLALOGPS
logP2.18ALOGPS
logP1.76ChemAxon
logS-3.2ALOGPS
pKa (Strongest Acidic)17.66ChemAxon
pKa (Strongest Basic)10.31ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area50.94 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity59.77 m3·mol-1ChemAxon
Polarizability24.47 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9967
Blood Brain Barrier+0.9631
Caco-2 permeable-0.6419
P-glycoprotein substrateSubstrate0.6384
P-glycoprotein inhibitor INon-inhibitor0.842
P-glycoprotein inhibitor IINon-inhibitor0.7464
Renal organic cation transporterNon-inhibitor0.6788
CYP450 2C9 substrateNon-substrate0.8524
CYP450 2D6 substrateNon-substrate0.9116
CYP450 3A4 substrateNon-substrate0.7558
CYP450 1A2 substrateInhibitor0.9179
CYP450 2C9 inhibitorNon-inhibitor0.7353
CYP450 2D6 inhibitorInhibitor0.5364
CYP450 2C19 inhibitorInhibitor0.586
CYP450 3A4 inhibitorNon-inhibitor0.6708
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.7797
Ames testNon AMES toxic0.8133
CarcinogenicityNon-carcinogens0.915
BiodegradationNot ready biodegradable0.9255
Rat acute toxicity2.8676 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8732
hERG inhibition (predictor II)Non-inhibitor0.8397
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

Description
This compound belongs to the class of organic compounds known as aralkylamines. These are alkylamines in which the alkyl group is substituted at one carbon atom by an aromatic hydrocarbyl group.
Kingdom
Organic compounds
Super Class
Organic nitrogen compounds
Class
Organonitrogen compounds
Sub Class
Amines
Direct Parent
Aralkylamines
Alternative Parents
Thiazoles / Heteroaromatic compounds / Isothioureas / Dialkylamines / Azacyclic compounds / Organopnictogen compounds / Hydrocarbon derivatives
Substituents
Aralkylamine / Heteroaromatic compound / Thiazole / Azole / Isothiourea / Azacycle / Organoheterocyclic compound / Secondary amine / Secondary aliphatic amine / Organopnictogen compound
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
benzothiazoles, diamine (CHEBI:8356)

Targets

Details
1. D(3) dopamine receptor
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Agonist
General Function
G-protein coupled amine receptor activity
Specific Function
Dopamine receptor whose activity is mediated by G proteins which inhibit adenylyl cyclase. Promotes cell proliferation.
Gene Name
DRD3
Uniprot ID
P35462
Uniprot Name
D(3) dopamine receptor
Molecular Weight
44224.335 Da
References
  1. Merlino G, Serafini A, Robiony F, Valente M, Gigli GL: Clinical experience with pramipexole in the treatment of restless legs syndrome. Expert Opin Drug Metab Toxicol. 2008 Feb;4(2):225-35. doi: 10.1517/17425255.4.2.225. [PubMed:18248314]
  2. Piercey MF: Pharmacology of pramipexole, a dopamine D3-preferring agonist useful in treating Parkinson's disease. Clin Neuropharmacol. 1998 May-Jun;21(3):141-51. [PubMed:9617505]
  3. Chernoloz O, El Mansari M, Blier P: Long-term administration of the dopamine D3/2 receptor agonist pramipexole increases dopamine and serotonin neurotransmission in the male rat forebrain. J Psychiatry Neurosci. 2012 Feb;37(2):113-21. doi: 10.1503/jpn.110038. [PubMed:22023785]
  4. Dooley M, Markham A: Pramipexole. A review of its use in the management of early and advanced Parkinson's disease. Drugs Aging. 1998 Jun;12(6):495-514. doi: 10.2165/00002512-199812060-00007. [PubMed:9638397]
Details
2. D(2) dopamine receptor
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Agonist
General Function
Potassium channel regulator activity
Specific Function
Dopamine receptor whose activity is mediated by G proteins which inhibit adenylyl cyclase.
Gene Name
DRD2
Uniprot ID
P14416
Uniprot Name
D(2) dopamine receptor
Molecular Weight
50618.91 Da
References
  1. Piercey MF: Pharmacology of pramipexole, a dopamine D3-preferring agonist useful in treating Parkinson's disease. Clin Neuropharmacol. 1998 May-Jun;21(3):141-51. [PubMed:9617505]
  2. Chernoloz O, El Mansari M, Blier P: Long-term administration of the dopamine D3/2 receptor agonist pramipexole increases dopamine and serotonin neurotransmission in the male rat forebrain. J Psychiatry Neurosci. 2012 Feb;37(2):113-21. doi: 10.1503/jpn.110038. [PubMed:22023785]
  3. Dooley M, Markham A: Pramipexole. A review of its use in the management of early and advanced Parkinson's disease. Drugs Aging. 1998 Jun;12(6):495-514. doi: 10.2165/00002512-199812060-00007. [PubMed:9638397]
Details
3. D(4) dopamine receptor
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Agonist
General Function
Sh3 domain binding
Specific Function
Dopamine receptor responsible for neuronal signaling in the mesolimbic system of the brain, an area of the brain that regulates emotion and complex behavior. Its activity is mediated by G proteins ...
Gene Name
DRD4
Uniprot ID
P21917
Uniprot Name
D(4) dopamine receptor
Molecular Weight
48359.86 Da
References
  1. Piercey MF: Pharmacology of pramipexole, a dopamine D3-preferring agonist useful in treating Parkinson's disease. Clin Neuropharmacol. 1998 May-Jun;21(3):141-51. [PubMed:9617505]
  2. Dooley M, Markham A: Pramipexole. A review of its use in the management of early and advanced Parkinson's disease. Drugs Aging. 1998 Jun;12(6):495-514. doi: 10.2165/00002512-199812060-00007. [PubMed:9638397]
  3. Mierau J, Schneider FJ, Ensinger HA, Chio CL, Lajiness ME, Huff RM: Pramipexole binding and activation of cloned and expressed dopamine D2, D3 and D4 receptors. Eur J Pharmacol. 1995 Jun 23;290(1):29-36. [PubMed:7664822]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Agonist
Curator comments
This is a potential target of Pramipexole.
General Function
Serotonin receptor activity
Specific Function
G-protein coupled receptor for 5-hydroxytryptamine (serotonin). Also functions as a receptor for various drugs and psychoactive substances. Ligand binding causes a conformation change that triggers...
Gene Name
HTR1A
Uniprot ID
P08908
Uniprot Name
5-hydroxytryptamine receptor 1A
Molecular Weight
46106.335 Da
References
  1. Chernoloz O, El Mansari M, Blier P: Long-term administration of the dopamine D3/2 receptor agonist pramipexole increases dopamine and serotonin neurotransmission in the male rat forebrain. J Psychiatry Neurosci. 2012 Feb;37(2):113-21. doi: 10.1503/jpn.110038. [PubMed:22023785]
  2. Chernoloz O, El Mansari M, Blier P: Sustained administration of pramipexole modifies the spontaneous firing of dopamine, norepinephrine, and serotonin neurons in the rat brain. Neuropsychopharmacology. 2009 Feb;34(3):651-61. doi: 10.1038/npp.2008.114. Epub 2008 Aug 6. [PubMed:18688211]
  3. Rogoz Z, Skuza G: Mechanism of synergistic action following co-treatment with pramipexole and fluoxetine or sertraline in the forced swimming test in rats. Pharmacol Rep. 2006 Jul-Aug;58(4):493-500. [PubMed:16963794]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Agonist
General Function
Thioesterase binding
Specific Function
Alpha-2 adrenergic receptors mediate the catecholamine-induced inhibition of adenylate cyclase through the action of G proteins. The rank order of potency for agonists of this receptor is oxymetazo...
Gene Name
ADRA2A
Uniprot ID
P08913
Uniprot Name
Alpha-2A adrenergic receptor
Molecular Weight
48956.275 Da
References
  1. Kvernmo T, Houben J, Sylte I: Receptor-binding and pharmacokinetic properties of dopaminergic agonists. Curr Top Med Chem. 2008;8(12):1049-67. [PubMed:18691132]
  2. Newman-Tancredi A, Cussac D, Audinot V, Nicolas JP, De Ceuninck F, Boutin JA, Millan MJ: 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. J Pharmacol Exp Ther. 2002 Nov;303(2):805-14. [PubMed:12388667]
  3. Apraxine M, Pasquet A, Jeanjean A: Pramipexole-Induced Reversible Heart Failure. Mov Disord Clin Pract. 2014 Oct 23;1(4):381-382. doi: 10.1002/mdc3.12096. eCollection 2014 Dec. [PubMed:30363854]
  4. McCormick PN, Fletcher PJ, Wilson VS, Remington GJ: The adrenergic alpha2 antagonist atipamezole alters the behavioural effects of pramipexole and increases pramipexole concentration in blood plasma. Life Sci. 2016 Apr 15;151:300-304. doi: 10.1016/j.lfs.2016.03.017. Epub 2016 Mar 11. [PubMed:26976325]
  5. Zhang Lab, University of Michigan document [Link]

Transporters

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Quaternary ammonium group transmembrane transporter activity
Specific Function
Mediates tubular uptake of organic compounds from circulation. Mediates the influx of agmatine, dopamine, noradrenaline (norepinephrine), serotonin, choline, famotidine, ranitidine, histamin, creat...
Gene Name
SLC22A2
Uniprot ID
O15244
Uniprot Name
Solute carrier family 22 member 2
Molecular Weight
62579.99 Da
References
  1. Ishiguro N, Saito A, Yokoyama K, Morikawa M, Igarashi T, Tamai I: Transport of the dopamine D2 agonist pramipexole by rat organic cation transporters OCT1 and OCT2 in kidney. Drug Metab Dispos. 2005 Apr;33(4):495-9. Epub 2005 Jan 7. [PubMed:15640376]
  2. Diao L, Shu Y, Polli JE: Uptake of pramipexole by human organic cation transporters. Mol Pharm. 2010 Aug 2;7(4):1342-7. doi: 10.1021/mp100036b. [PubMed:20496886]
  3. Knop J, Hoier E, Ebner T, Fromm MF, Muller F: Renal tubular secretion of pramipexole. Eur J Pharm Sci. 2015 Nov 15;79:73-8. doi: 10.1016/j.ejps.2015.09.004. Epub 2015 Sep 7. [PubMed:26360835]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Secondary active organic cation transmembrane transporter activity
Specific Function
Translocates a broad array of organic cations with various structures and molecular weights including the model compounds 1-methyl-4-phenylpyridinium (MPP), tetraethylammonium (TEA), N-1-methylnico...
Gene Name
SLC22A1
Uniprot ID
O15245
Uniprot Name
Solute carrier family 22 member 1
Molecular Weight
61153.345 Da
References
  1. Ishiguro N, Saito A, Yokoyama K, Morikawa M, Igarashi T, Tamai I: Transport of the dopamine D2 agonist pramipexole by rat organic cation transporters OCT1 and OCT2 in kidney. Drug Metab Dispos. 2005 Apr;33(4):495-9. Epub 2005 Jan 7. [PubMed:15640376]
  2. Diao L, Shu Y, Polli JE: Uptake of pramipexole by human organic cation transporters. Mol Pharm. 2010 Aug 2;7(4):1342-7. doi: 10.1021/mp100036b. [PubMed:20496886]
  3. Antonini A, Calandrella D: Once-daily pramipexole for the treatment of early and advanced idiopathic Parkinson's disease: implications for patients. Neuropsychiatr Dis Treat. 2011;7:297-302. doi: 10.2147/NDT.S10097. Epub 2011 May 15. [PubMed:21654875]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Toxin transporter activity
Specific Function
Mediates potential-dependent transport of a variety of organic cations. May play a significant role in the disposition of cationic neurotoxins and neurotransmitters in the brain.
Gene Name
SLC22A3
Uniprot ID
O75751
Uniprot Name
Solute carrier family 22 member 3
Molecular Weight
61279.485 Da
References
  1. Diao L, Shu Y, Polli JE: Uptake of pramipexole by human organic cation transporters. Mol Pharm. 2010 Aug 2;7(4):1342-7. doi: 10.1021/mp100036b. [PubMed:20496886]

Drug created on June 13, 2005 07:24 / Updated on August 19, 2019 05:48