Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C10H17N3S |
Molecular Weight | 211.327 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 1 / 1 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CCCN[C@H]1CCC2=C(C1)SC(N)=N2
InChI
InChIKey=FASDKYOPVNHBLU-ZETCQYMHSA-N
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
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 |
DescriptionSources: http://www.drugbank.ca/drugs/DB00413Curator's Comment: Description was created based on several sources, including
https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/020667s014s017s018lbl.pdf
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 | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL234 Sources: http://www.drugbank.ca/drugs/DB00413 |
1.5 nM [EC50] | ||
Target ID: CHEMBL217 Sources: http://www.drugbank.ca/drugs/DB00413 |
27.0 nM [EC50] | ||
Target ID: CHEMBL219 Sources: http://www.drugbank.ca/drugs/DB00413 |
15.0 nM [EC50] | ||
Target ID: CHEMBL205 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24289818 |
4.81 µM [IC50] | ||
Target ID: CHEMBL261 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24289818 |
5.37 µM [IC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | MIRAPEX Approved UseMirapex® (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 Date1997 |
|||
Primary | MIRAPEX Approved UseMirapex® (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 Date1997 |
Cmax
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 |
T1/2
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 (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%) Sources: Page: p.740Hypotension (0.5%) Peripheral edema (0.5%) |
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%) Sources: Page: p.727Sleepiness (3%) Dizziness (2.5%) Memory loss (1.2%) Paranoia (0.6%) |
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%) Sources: Page: p.128Muscle spasms (1.8%) Insomnia (1.8%) Vertigo (1.8%) Ankle swelling (1.8%) Hallucination (3.6%) Nausea (1.8%) |
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%) Sources: Page: p.740Hallucination (1%) Peripheral edema (0.8%) Abdominal pain upper (0.6%) Myocardial infarction (0.6%) Pneumonia (0.6%) Vomiting (0.6%) |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
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
Title | Date | PubMed |
---|---|---|
Does combined treatment with novel antidepressants and a dopamine D3 receptor agonist reproduce cocaine discrimination in rats? | 2001 Nov-Dec |
|
Locomotor hypoactivity and motor disturbances--behavioral effects induced by intracerebellar microinjections of dopaminergic DA-D2/D3 receptor agonists. | 2001 Sep-Oct |
|
DA agonists -- non-ergot derivatives: pramipexole: management of Parkinson's disease. | 2002 |
|
Choosing the right dopamine agonist for patients with Parkinson's disease. | 2002 |
|
'Sleep attacks' or 'unintended sleep episodes' occur with dopamine agonists: is this a class effect? | 2002 |
|
Clinical pharmacokinetic and pharmacodynamic properties of drugs used in the treatment of Parkinson's disease. | 2002 |
|
Dopamine transporter brain imaging to assess the effects of pramipexole vs levodopa on Parkinson disease progression. | 2002 Apr 3 |
|
Acute placebo-controlled sleep laboratory studies and clinical follow-up with pramipexole in restless legs syndrome. | 2002 Aug |
|
Two advances in the management of Parkinson disease. | 2002 Aug |
|
[Rapid-eye-movement sleep disorders in Parkinson's disease]. | 2002 Feb |
|
Pramipexole for depression. | 2002 Feb |
|
Restless legs syndrome: treatment with dopaminergic agents. | 2002 Feb 26 |
|
Long-term studies of dopamine agonists. | 2002 Feb 26 |
|
[Rhabdomyolysis as a complication of Parkinson's disease]. | 2002 Jan-Feb |
|
Pramipexole in patients with Parkinson's disease and marked drug resistant tremor: a randomised, double blind, placebo controlled multicentre study. | 2002 Jun |
|
[Multiple latency test in a patient with episodes of sleep induced by pergolide]. | 2002 Jun 16-30 |
|
Sleep attacks in patients taking dopamine agonists: review. | 2002 Jun 22 |
|
A case of Parkinsonism due to lithium intoxication: treatment with Pramipexole. | 2002 May |
|
Gender and pramipexole effects on levodopa pharmacokinetics and pharmacodynamics. | 2002 May 14 |
|
Do dopamine agonists or levodopa modify Parkinson's disease progression? | 2002 Nov |
|
Dopamine agonists and neuroprotection in Parkinson's disease. | 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 |
|
Dopamine agonist monotherapy in Parkinson's disease. | 2002 Nov 30 |
|
Neuroprotection in idiopathic Parkinson's disease. | 2002 Oct |
|
Pramipexole in treatment-resistant depression: a 16-week naturalistic study. | 2002 Oct |
|
An evidence-based review of dopamine receptor agonists in the treatment of Parkinson's disease. | 2002 Oct |
|
Potential antidepressant properties of pramipexole detected in locomotor and operant behavioral investigations in mice. | 2002 Oct |
|
Effect of daily dosing duration of direct and indirect dopamine receptor agonists: cocaine cross-tolerance following chronic regimens. | 2002 Oct |
|
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 |
|
Review: selegiline improves symptoms and levodopa is better than pramipexole for motor function in untreated Parkinson disease. | 2002 Sep-Oct |
|
Cabergoline, pramipexole and ropinirole used as monotherapy in early Parkinson's disease: an evidence-based comparison. | 2003 |
|
Advances in the pharmacological management of Parkinson disease. | 2003 |
|
Inhibitory effects of D2 agonists by striatal injection on excessive release of dopamine and hyperactivity induced by Bay K 8644 in rats. | 2003 |
|
Dopamine agonists induce episodes of irresistible daytime sleepiness. | 2003 |
|
Current status of Parkinson's disease treatment in Korea. | 2003 Aug |
|
Pramipexole inhibits MPTP toxicity in mice by dopamine D3 receptor dependent and independent mechanisms. | 2003 Aug 15 |
|
Pramipexole increases vesicular dopamine uptake: implications for treatment of Parkinson's neurodegeneration. | 2003 Aug 8 |
|
Piribedil-induced sleep attacks in Parkinson's disease. | 2003 Feb |
|
Slowing Parkinson's disease progression: recent dopamine agonist trials. | 2003 Feb 11 |
|
Loss of color vision during long-term treatment with pramipexole. | 2003 Jan |
|
Sleepwalking and sleep terrors in prepubertal children: what triggers them? | 2003 Jan |
|
Assessment of sleepiness and unintended sleep in Parkinson's disease patients taking dopamine agonists. | 2003 Jul |
|
Pramipexole and pergolide in the treatment of depression in Parkinson's disease: a national multicentre prospective randomized study. | 2003 Jul |
|
Neuroprotective mechanisms of antiparkinsonian dopamine D2-receptor subfamily agonists. | 2003 Jul |
|
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 |
|
Treatment effects on nigrostriatal projection integrity in partial 6-OHDA lesions: comparison of L-DOPA and pramipexole. | 2003 Sep |
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
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/26213307
Pramipexole suppressed H2O2-induced ARPE-19 cell death in vitro at concentrations of 10(-6) M or higher.
Substance Class |
Chemical
Created
by
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on
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Record UNII |
83619PEU5T
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Record Status |
Validated (UNII)
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WHO-VATC |
QN04BC05
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LIVERTOX |
NBK547968
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NDF-RT |
N0000000117
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FDA ORPHAN DRUG |
252007
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NCI_THESAURUS |
C265
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WHO-ATC |
N04BC05
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N0000175768
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100000085495
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119570
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760426
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DB00413
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104632-26-0
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PRAMIPEXOLE
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C66456
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746741
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Pramipexole
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m9095
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SUB09990MIG
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CHEMBL301265
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SALT/SOLVATE -> PARENT |
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SALT/SOLVATE -> PARENT |
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BINDER->LIGAND |
BINDING
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TARGET -> AGONIST |
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TRANSPORTER -> INHIBITOR | |||
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TARGET -> AGONIST | |||
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TRANSPORTER -> INHIBITOR |
Related Record | Type | Details | ||
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ACTIVE MOIETY |
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Name | Property Type | Amount | Referenced Substance | Defining | Parameters | References |
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Biological Half-life | PHARMACOKINETIC |
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Elimination PHARMACOKINETIC PHARMACOKINETIC |
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Volume of Distribution | PHARMACOKINETIC |
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Biological Half-life | PHARMACOKINETIC |
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