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
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
| 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 |
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 Recommended Dose: 1.5 mg, 3 times / day Route: oral Route: multiple Dose: 1.5 mg, 3 times / day Sources: |
unhealthy, 61.6 |
Disc. AE: Hallucination, Hypotension... AEs leading to discontinuation/dose reduction: Hallucination (1.3%) Sources: Hypotension (0.5%) Peripheral edema (0.5%) |
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: |
unhealthy, 62.7 |
Disc. AE: Hallucinations, Sleepiness... AEs leading to discontinuation/dose reduction: Hallucinations (4.3%) Sources: Sleepiness (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: |
unhealthy, 62.8 |
DLT: Drowsiness, Muscle spasms... Dose limiting toxicities: Drowsiness (3.6%) Sources: Muscle 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 Recommended Dose: 1.5 mg, 3 times / day Route: oral Route: multiple Dose: 1.5 mg, 3 times / day Sources: |
unhealthy, 63 |
Disc. AE: Hallucination, Peripheral edema... AEs leading to discontinuation/dose reduction: Hallucination (1%) Sources: Peripheral edema (0.8%) Abdominal pain upper (0.6%) Myocardial infarction (0.6%) Nausea (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 Recommended Dose: 1.5 mg, 3 times / day Route: oral Route: multiple Dose: 1.5 mg, 3 times / day Sources: |
unhealthy, 61.6 |
| Peripheral edema | 0.5% Disc. AE |
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: |
unhealthy, 61.6 |
| Hallucination | 1.3% Disc. AE |
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: |
unhealthy, 61.6 |
| Paranoia | 0.6% Disc. AE |
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: |
unhealthy, 62.7 |
| Memory loss | 1.2% Disc. AE |
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: |
unhealthy, 62.7 |
| Dizziness | 2.5% Disc. AE |
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: |
unhealthy, 62.7 |
| Sleepiness | 3% Disc. AE |
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: |
unhealthy, 62.7 |
| Hallucinations | 4.3% Disc. AE |
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: |
unhealthy, 62.7 |
| 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: |
unhealthy, 62.8 |
| 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: |
unhealthy, 62.8 |
| 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: |
unhealthy, 62.8 |
| 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: |
unhealthy, 62.8 |
| 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: |
unhealthy, 62.8 |
| 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: |
unhealthy, 62.8 |
| 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: |
unhealthy, 62.8 |
| Abdominal pain upper | 0.6% Disc. AE |
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: |
unhealthy, 63 |
| Myocardial infarction | 0.6% Disc. AE |
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: |
unhealthy, 63 |
| Nausea | 0.6% Disc. AE |
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: |
unhealthy, 63 |
| Pneumonia | 0.6% Disc. AE |
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: |
unhealthy, 63 |
| Vomiting | 0.6% Disc. AE |
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: |
unhealthy, 63 |
| Peripheral edema | 0.8% Disc. AE |
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: |
unhealthy, 63 |
| Hallucination | 1% Disc. AE |
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: |
unhealthy, 63 |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Agonist-specific transactivation of phosphoinositide 3-kinase signaling pathway mediated by the dopamine D2 receptor. | 2003-11-21 |
|
| Potent activation of dopamine D3/D2 heterodimers by the antiparkinsonian agents, S32504, pramipexole and ropinirole. | 2003-11 |
|
| 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 |
|
| Randomized, double-blind study of pramipexole with placebo and bromocriptine in advanced Parkinson's disease. | 2003-10 |
|
| Dopamine receptor agonists in current clinical use: comparative dopamine receptor binding profiles defined in the human striatum. | 2003-10 |
|
| Current treatment options for restless legs syndrome. | 2003-10 |
|
| Clinical strategies to prevent and delay motor complications. | 2003-09-23 |
|
| Treatment effects on nigrostriatal projection integrity in partial 6-OHDA lesions: comparison of L-DOPA and pramipexole. | 2003-09 |
|
| Pramipexole inhibits MPTP toxicity in mice by dopamine D3 receptor dependent and independent mechanisms. | 2003-08-15 |
|
| Pramipexole increases vesicular dopamine uptake: implications for treatment of Parkinson's neurodegeneration. | 2003-08-08 |
|
| Current status of Parkinson's disease treatment in Korea. | 2003-08 |
|
| Assessment of sleepiness and unintended sleep in Parkinson's disease patients taking dopamine agonists. | 2003-07 |
|
| Parkinson's disease: is the initial treatment established? | 2003-07 |
|
| Dual dopamine agonist treatment in Parkinson's disease. | 2003-07 |
|
| Pramipexole and pergolide in the treatment of depression in Parkinson's disease: a national multicentre prospective randomized study. | 2003-07 |
|
| Neuroprotective mechanisms of antiparkinsonian dopamine D2-receptor subfamily agonists. | 2003-07 |
|
| Reduction of oxidative stress in amyotrophic lateral sclerosis following pramipexole treatment. | 2003-06 |
|
| [Treatment of restless legs syndrome in uremic patients undergoing dialysis with pramipexole: preliminary results]. | 2003-06 |
|
| Sleep attacks, daytime sleepiness, and dopamine agonists in Parkinson's disease. | 2003-06 |
|
| 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 |
|
| Efficacy, safety and cost of new drugs acting on the central nervous system. | 2003-05 |
|
| Dihydroergocriptine in Parkinson's disease: clinical efficacy and comparison with other dopamine agonists. | 2003-05 |
|
| Pramipexole in Parkinson's disease. A short-term study using the combined levodopa-dopamine agonist test. | 2003-04-05 |
|
| Pramipexole in comparison to l-dopa: a neuropsychological study. | 2003-04 |
|
| Slowing Parkinson's disease progression: recent dopamine agonist trials. | 2003-02-11 |
|
| Piribedil-induced sleep attacks in Parkinson's disease. | 2003-02 |
|
| 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 |
|
| Loss of color vision during long-term treatment with pramipexole. | 2003-01 |
|
| Sleepwalking and sleep terrors in prepubertal children: what triggers them? | 2003-01 |
|
| Pramipexole in routine clinical practice: a prospective observational trial in Parkinson's disease. | 2003 |
|
| 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 |
|
| Comparison of the risk of adverse events with pramipexole and ropinirole in patients with Parkinson's disease: a meta-analysis. | 2003 |
|
| Dopamine agonists induce episodes of irresistible daytime sleepiness. | 2003 |
|
| Gender and pramipexole effects on levodopa pharmacokinetics and pharmacodynamics. | 2002-12-24 |
|
| Dopamine agonist monotherapy in Parkinson's disease. | 2002-11-30 |
|
| Restless legs syndrome augmentation and pramipexole treatment. | 2002-11 |
|
| Do dopamine agonists or levodopa modify Parkinson's disease progression? | 2002-11 |
|
| Dopamine agonists and neuroprotection in Parkinson's disease. | 2002-11 |
|
| 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 |
|
| 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 |
|
| Neuroprotection in idiopathic Parkinson's disease. | 2002-10 |
|
| Pramipexole in treatment-resistant depression: a 16-week naturalistic study. | 2002-10 |
|
| An evidence-based review of dopamine receptor agonists in the treatment of Parkinson's disease. | 2002-10 |
|
| Potential antidepressant properties of pramipexole detected in locomotor and operant behavioral investigations in mice. | 2002-10 |
|
| Combination of two different dopamine agonists in the management of Parkinson's disease. | 2002-09 |
|
| [Pramipexole in Parkinson disease. Results of a treatment observation]. | 2002-08 |
|
| Restless legs syndrome in the older adult: diagnosis and management. | 2002 |
|
| Sleep disorders in Parkinson's disease: epidemiology and management. | 2002 |
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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Mon Mar 31 17:59:18 GMT 2025
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on
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| Record UNII |
3D867NP06J
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| Record Status |
Validated (UNII)
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| Record Version |
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| Classification Tree | Code System | Code | ||
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EMA ASSESSMENT REPORTS |
PRAMIPEXOLE ACCORD (AUTHORIZED: RESTLESS LEGS SYNDROME)
Created by
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EMA ASSESSMENT REPORTS |
MIRAPEXIN (AUTHORIZED: RESTLESS LEGS SYNDROME)
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EMA ASSESSMENT REPORTS |
PRAMIPEXOLE TEVA (AUTHORIZED: PARKINSON DISEASE)
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EMA ASSESSMENT REPORTS |
SIFROL (AUTHORIZED: RESTLESS LEGS SYNDROME)
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EMA ASSESSMENT REPORTS |
MIRAPEXIN (AUTHORIZED: PARKINSON DISEASE)
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EMA ASSESSMENT REPORTS |
PRAMIPEXOLE ACCORD (AUTHORIZED: PARKINSON DISEASE)
Created by
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NCI_THESAURUS |
C66884
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EMA ASSESSMENT REPORTS |
OPRYMEA (AUTHORIZED: PARKINSON DISEASE)
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EMA ASSESSMENT REPORTS |
DAQUIRAN (WITHDRAWN: PARKINSON DISEASE)
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EMA ASSESSMENT REPORTS |
SIFROL (AUTHORIZED: PARKINSON DISEASE)
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NCI_THESAURUS |
C38149
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DTXSID1044227
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1553859
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236747
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191217-81-9
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3D867NP06J
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CHEMBL301265
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51147
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SUB25197
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C29374
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100000091470
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KK-01
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SUB12563MIG
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166589
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m9095
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SUB04004MIG
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| Related Record | Type | Details | ||
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BASIS OF STRENGTH->SUBSTANCE |
ASSAY (HPLC)
USP
|
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|
|
PARENT -> SALT/SOLVATE | |||
|
BASIS OF STRENGTH->SUBSTANCE |
ASSAY (TITRATION)
EP
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||
|
ANHYDROUS->SOLVATE |
| Related Record | Type | Details | ||
|---|---|---|---|---|
|
IMPURITY -> PARENT |
|
||
|
IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
|
||
|
IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
|
||
|
IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
|
||
|
IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
|
||
|
IMPURITY -> PARENT |
|
||
|
IMPURITY -> PARENT |
UNSPECIFIED
EP
|
||
|
IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
|
||
|
IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
|
||
|
IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
|
||
|
IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
|
||
|
IMPURITY -> PARENT |
|
| Related Record | Type | Details | ||
|---|---|---|---|---|
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ACTIVE MOIETY |