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 |
---|---|---|
Does combined treatment with novel antidepressants and a dopamine D3 receptor agonist reproduce cocaine discrimination in rats? | 2001 Nov-Dec |
|
Daytime sleepiness and other sleep disorders in Parkinson's disease. | 2001 Oct 23 |
|
Locomotor hypoactivity and motor disturbances--behavioral effects induced by intracerebellar microinjections of dopaminergic DA-D2/D3 receptor agonists. | 2001 Sep-Oct |
|
Restless legs syndrome in the older adult: diagnosis and management. | 2002 |
|
Sleep disorders in Parkinson's disease: epidemiology and management. | 2002 |
|
Choosing the right dopamine agonist for patients with Parkinson's disease. | 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 |
|
[Pramipexole in Parkinson disease. Results of a treatment observation]. | 2002 Aug |
|
Two advances in the management of Parkinson disease. | 2002 Aug |
|
Gender and pramipexole effects on levodopa pharmacokinetics and pharmacodynamics. | 2002 Dec 24 |
|
[Rapid-eye-movement sleep disorders in Parkinson's disease]. | 2002 Feb |
|
Restless legs syndrome: treatment with dopaminergic agents. | 2002 Feb 26 |
|
Long-term studies of dopamine agonists. | 2002 Feb 26 |
|
Neuroprotection and dopamine agonists. | 2002 Feb 26 |
|
[Rhabdomyolysis as a complication of Parkinson's disease]. | 2002 Jan-Feb |
|
Pergolide in the treatment of patients with early and advanced 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 |
|
Sleep attacks in patients taking dopamine agonists: review. | 2002 Jun 22 |
|
Gender and pramipexole effects on levodopa pharmacokinetics and pharmacodynamics. | 2002 May 14 |
|
Restless legs syndrome augmentation and pramipexole treatment. | 2002 Nov |
|
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 |
|
Neuroprotection in idiopathic Parkinson's disease. | 2002 Oct |
|
Potential antidepressant properties of pramipexole detected in locomotor and operant behavioral investigations in mice. | 2002 Oct |
|
Pramipexole in Parkinson's disease. A short-term study using the combined levodopa-dopamine agonist test. | 2002 Oct-Dec |
|
Review: selegiline improves symptoms and levodopa is better than pramipexole for motor function in untreated Parkinson disease. | 2002 Sep-Oct |
|
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 |
|
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 |
|
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 |
|
Parkinson's disease: is the initial treatment established? | 2003 Jul |
|
Pramipexole and pergolide in the treatment of depression in Parkinson's disease: a national multicentre prospective randomized study. | 2003 Jul |
|
Reduction of oxidative stress in amyotrophic lateral sclerosis following pramipexole treatment. | 2003 Jun |
|
[Treatment of restless legs syndrome in uremic patients undergoing dialysis with pramipexole: preliminary results]. | 2003 Jun |
|
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 |
|
Agonist-specific transactivation of phosphoinositide 3-kinase signaling pathway mediated by the dopamine D2 receptor. | 2003 Nov 21 |
|
Randomized, double-blind study of pramipexole with placebo and bromocriptine in advanced Parkinson's disease. | 2003 Oct |
|
Dopamine receptor agonists in current clinical use: comparative dopamine receptor binding profiles defined in the human striatum. | 2003 Oct |
|
Current treatment options for restless legs syndrome. | 2003 Oct |
|
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 |
|
Treatment effects on nigrostriatal projection integrity in partial 6-OHDA lesions: comparison of L-DOPA and pramipexole. | 2003 Sep |
|
Clinical strategies to prevent and delay motor complications. | 2003 Sep 23 |
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
admin
on
Edited
Mon Mar 31 17:59:18 GMT 2025
by
admin
on
Mon Mar 31 17:59:18 GMT 2025
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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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51148
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DBSALT001198
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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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3D867NP06J
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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 | |||
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BASIS OF STRENGTH->SUBSTANCE |
ASSAY (TITRATION)
EP
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ANHYDROUS->SOLVATE |
Related Record | Type | Details | ||
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IMPURITY -> PARENT |
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
|
||
|
IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
|
||
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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IMPURITY -> PARENT |
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IMPURITY -> PARENT |
UNSPECIFIED
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
|
||
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
|
||
|
IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
|
||
|
IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
|
||
|
IMPURITY -> PARENT |
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Related Record | Type | Details | ||
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ACTIVE MOIETY |