Details
Stereochemistry | ACHIRAL |
Molecular Formula | C16H24N2O.ClH |
Molecular Weight | 296.836 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
Cl.CCCN(CCC)CCC1=C2CC(=O)NC2=CC=C1
InChI
InChIKey=XDXHAEQXIBQUEZ-UHFFFAOYSA-N
InChI=1S/C16H24N2O.ClH/c1-3-9-18(10-4-2)11-8-13-6-5-7-15-14(13)12-16(19)17-15;/h5-7H,3-4,8-12H2,1-2H3,(H,17,19);1H
Molecular Formula | C16H24N2O |
Molecular Weight | 260.3746 |
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 |
DescriptionCurator's Comment: description was created based on several sources, including
http://reference.medscape.com/drug/requip-xl-ropinirole-343051 | https://www.drugs.com/cdi/ropinirole.html | https://www.drugbank.ca/drugs/DB00268
Curator's Comment: description was created based on several sources, including
http://reference.medscape.com/drug/requip-xl-ropinirole-343051 | https://www.drugs.com/cdi/ropinirole.html | https://www.drugbank.ca/drugs/DB00268
Ropinirole (INN; trade names Requip, Repreve, Ronirol, Adartrel) is a dopamine agonist of the non-ergoline class of medications, used in the treatment of Parkinson's disease and restless legs syndrome. Although the precise mechanism of action of ropinirole as a treatment for Parkinson's disease is unknown, 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 ropinirole 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. Ropinirole 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 mechanism of ropinirole-induced postural hypotension is presumed to be due to a D2 -mediated blunting of the noradrenergic response to standing and subsequent decrease in peripheral vascular resistance. Ropinirole can cause nausea, dizziness, hallucinations, orthostatic hypotension, and sudden sleep attacks during the daytime. Unusual side effects specific to D3 agonists such as ropinirole and pramipexole can include hypersexuality, punding, and compulsive gambling, even in patients without a history of these behaviors.
CNS Activity
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL217 Sources: https://www.ncbi.nlm.nih.gov/pubmed/17976986 |
83.0 nM [EC50] | ||
Target ID: CHEMBL234 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20038106 |
19.2 nM [EC50] | ||
Target ID: CHEMBL2096905 Sources: https://www.ncbi.nlm.nih.gov/pubmed/4045928 |
100.0 nM [EC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | REQUIP Approved UseParkinson's Disease Ropinirole tablets are indicated for the treatment of the signs and symptoms of idiopathic Parkinson's disease. The effectiveness of ropinirole tablet was demonstrated in randomized, controlled trials in patients with early Parkinson's disease who were not receiving concomitant L-dopa therapy as well as in patients with advanced disease on concomitant L-dopa (see CLINICAL PHARMACOLOGY: Clinical Trials). Restless Legs Syndrome Ropinirole tablets are indicated for the treatment of moderate-to-severe primary Restless Legs Syndrome (RLS). Key diagnostic criteria for RLS are: an urge to move the legs usually accompanied or caused by uncomfortable and unpleasant leg sensations; symptoms begin or worsen during periods of rest or inactivity such as lying or sitting; symptoms are partially or totally relieved by movement such as walking or stretching at least as long as the activity continues; and symptoms are worse or occur only in the evening or night. Difficulty falling asleep may frequently be associated with moderate-to-severe RLS. Launch Date1997 |
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Primary | REQUIP Approved UseParkinson's Disease Ropinirole tablets are indicated for the treatment of the signs and symptoms of idiopathic Parkinson's disease. The effectiveness of ropinirole tablet was demonstrated in randomized, controlled trials in patients with early Parkinson's disease who were not receiving concomitant L-dopa therapy as well as in patients with advanced disease on concomitant L-dopa (see CLINICAL PHARMACOLOGY: Clinical Trials). Restless Legs Syndrome Ropinirole tablets are indicated for the treatment of moderate-to-severe primary Restless Legs Syndrome (RLS). Key diagnostic criteria for RLS are: an urge to move the legs usually accompanied or caused by uncomfortable and unpleasant leg sensations; symptoms begin or worsen during periods of rest or inactivity such as lying or sitting; symptoms are partially or totally relieved by movement such as walking or stretching at least as long as the activity continues; and symptoms are worse or occur only in the evening or night. Difficulty falling asleep may frequently be associated with moderate-to-severe RLS. Launch Date1997 |
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Primary | REQUIP Approved UseParkinson's Disease Ropinirole tablets are indicated for the treatment of the signs and symptoms of idiopathic Parkinson's disease. The effectiveness of ropinirole tablet was demonstrated in randomized, controlled trials in patients with early Parkinson's disease who were not receiving concomitant L-dopa therapy as well as in patients with advanced disease on concomitant L-dopa (see CLINICAL PHARMACOLOGY: Clinical Trials). Restless Legs Syndrome Ropinirole tablets are indicated for the treatment of moderate-to-severe primary Restless Legs Syndrome (RLS). Key diagnostic criteria for RLS are: an urge to move the legs usually accompanied or caused by uncomfortable and unpleasant leg sensations; symptoms begin or worsen during periods of rest or inactivity such as lying or sitting; symptoms are partially or totally relieved by movement such as walking or stretching at least as long as the activity continues; and symptoms are worse or occur only in the evening or night. Difficulty falling asleep may frequently be associated with moderate-to-severe RLS. Launch Date1997 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
6.53 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9578193 |
2 mg 3 times / day steady-state, oral dose: 2 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
ROPINIROLE HYDROCHLORIDE plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
5.01 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9578193 |
2 mg 3 times / day steady-state, oral dose: 2 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
ROPINIROLE HYDROCHLORIDE plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FED |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
29.1 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9578193 |
2 mg 3 times / day steady-state, oral dose: 2 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
ROPINIROLE HYDROCHLORIDE plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
25.9 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9578193 |
2 mg 3 times / day steady-state, oral dose: 2 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
ROPINIROLE HYDROCHLORIDE plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FED |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
6 h |
unknown, oral |
ROPINIROLE HYDROCHLORIDE plasma | Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
Funbound
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
60% |
unknown, oral |
ROPINIROLE HYDROCHLORIDE plasma | Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
Doses
Dose | Population | Adverse events |
---|---|---|
50 mg 1 times / day steady, oral Highest studied dose Dose: 50 mg, 1 times / day Route: oral Route: steady Dose: 50 mg, 1 times / day Sources: |
unhealthy |
|
435 mg 1 times / day multiple, oral Overdose Dose: 435 mg, 1 times / day Route: oral Route: multiple Dose: 435 mg, 1 times / day Sources: |
unhealthy Health Status: unhealthy Sources: |
Other AEs: Nausea, Dizziness... Other AEs: Nausea Sources: Dizziness Claustrophobia Chorea Palpitations Asthenia Nightmares Hyperhidrosis Visual hallucinations |
0.5 mg 2 times / day steady, oral Recommended Dose: 0.5 mg, 2 times / day Route: oral Route: steady Dose: 0.5 mg, 2 times / day Sources: |
unhealthy Health Status: unhealthy Sources: |
Disc. AE: Nausea, Dizziness... AEs leading to discontinuation/dose reduction: Nausea (2%) Sources: Dizziness (2%) |
24 mg 1 times / day steady, oral Recommended Dose: 24 mg, 1 times / day Route: oral Route: steady Dose: 24 mg, 1 times / day Sources: |
unhealthy |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Asthenia | 435 mg 1 times / day multiple, oral Overdose Dose: 435 mg, 1 times / day Route: oral Route: multiple Dose: 435 mg, 1 times / day Sources: |
unhealthy Health Status: unhealthy Sources: |
|
Chorea | 435 mg 1 times / day multiple, oral Overdose Dose: 435 mg, 1 times / day Route: oral Route: multiple Dose: 435 mg, 1 times / day Sources: |
unhealthy Health Status: unhealthy Sources: |
|
Claustrophobia | 435 mg 1 times / day multiple, oral Overdose Dose: 435 mg, 1 times / day Route: oral Route: multiple Dose: 435 mg, 1 times / day Sources: |
unhealthy Health Status: unhealthy Sources: |
|
Dizziness | 435 mg 1 times / day multiple, oral Overdose Dose: 435 mg, 1 times / day Route: oral Route: multiple Dose: 435 mg, 1 times / day Sources: |
unhealthy Health Status: unhealthy Sources: |
|
Hyperhidrosis | 435 mg 1 times / day multiple, oral Overdose Dose: 435 mg, 1 times / day Route: oral Route: multiple Dose: 435 mg, 1 times / day Sources: |
unhealthy Health Status: unhealthy Sources: |
|
Nausea | 435 mg 1 times / day multiple, oral Overdose Dose: 435 mg, 1 times / day Route: oral Route: multiple Dose: 435 mg, 1 times / day Sources: |
unhealthy Health Status: unhealthy Sources: |
|
Nightmares | 435 mg 1 times / day multiple, oral Overdose Dose: 435 mg, 1 times / day Route: oral Route: multiple Dose: 435 mg, 1 times / day Sources: |
unhealthy Health Status: unhealthy Sources: |
|
Palpitations | 435 mg 1 times / day multiple, oral Overdose Dose: 435 mg, 1 times / day Route: oral Route: multiple Dose: 435 mg, 1 times / day Sources: |
unhealthy Health Status: unhealthy Sources: |
|
Visual hallucinations | 435 mg 1 times / day multiple, oral Overdose Dose: 435 mg, 1 times / day Route: oral Route: multiple Dose: 435 mg, 1 times / day Sources: |
unhealthy Health Status: unhealthy Sources: |
|
Dizziness | 2% Disc. AE |
0.5 mg 2 times / day steady, oral Recommended Dose: 0.5 mg, 2 times / day Route: oral Route: steady Dose: 0.5 mg, 2 times / day Sources: |
unhealthy Health Status: unhealthy Sources: |
Nausea | 2% Disc. AE |
0.5 mg 2 times / day steady, oral Recommended Dose: 0.5 mg, 2 times / day Route: oral Route: steady Dose: 0.5 mg, 2 times / day Sources: |
unhealthy Health Status: unhealthy Sources: |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
---|---|---|
Drug as perpetrator
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
major | yes (co-administration study) Comment: Ciprofloxacin increased Ropinirole AUC by 84% and Cmax by 60%. Page: 58, (Label) 22 |
|||
minor | ||||
Page: 22.0 |
no |
PubMed
Title | Date | PubMed |
---|---|---|
Sleep disorders in patients with Parkinson's disease: epidemiology and management. | 2001 |
|
Neostriatal muscarinic receptor subtypes involved in the generation of tremulous jaw movements in rodents implications for cholinergic involvement in parkinsonism. | 2001 Apr 27 |
|
Efficacy and tolerability of dopamine agonists in a parkinsonian population. | 2001 Feb |
|
Molecular mechanism in activation of glutathione system by ropinirole, a selective dopamine D2 agonist. | 2001 Jan |
|
Adjunctive dopamine agonists in treatment-resistant bipolar II depression: an open case series. | 2001 Jul |
|
The frissonnant mutant mouse, a model of dopamino-sensitive, inherited motor syndrome. | 2001 Jun |
|
Warfarin and ropinirole interaction. | 2001 Oct |
|
Alterations in striatal neuropeptide mRNA produced by repeated administration of L-DOPA, ropinirole or bromocriptine correlate with dyskinesia induction in MPTP-treated common marmosets. | 2002 |
|
Restless legs syndrome in the older adult: diagnosis and management. | 2002 |
|
[Use of dopamine agonists in the treatment of Parkinson's disease]. | 2002 |
|
DA agonists -- non-ergot derivatives: ropinirole: management of Parkinson's disease. | 2002 |
|
Choosing the right dopamine agonist for patients with Parkinson's disease. | 2002 |
|
Two advances in the management of Parkinson disease. | 2002 Aug |
|
Effect of ropinirole on sleep onset: a randomized, placebo-controlled study in healthy volunteers. | 2002 Feb 12 |
|
Long-term studies of dopamine agonists. | 2002 Feb 26 |
|
Pergolide in the treatment of patients with early and advanced Parkinson's disease. | 2002 Jan-Feb |
|
GSK's Requip slow the loss of dopamine function in Parkinson's disease. | 2002 Jul |
|
Gateways to clinical trials. | 2002 Jul-Aug |
|
Effect of dopamine receptor agonists on sensory nerve activity: possible therapeutic targets for the treatment of asthma and COPD. | 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 |
|
Do dopamine agonists or levodopa modify Parkinson's disease progression? | 2002 Nov |
|
Ropinirole for antidepressant-induced sexual dysfunction. | 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 |
|
Practical importance of neuroprotection in Parkinson's disease. | 2002 Oct |
|
Dosing with ropinirole in a clinical setting. | 2002 Oct |
|
Do dopaminergic agents increase the daytime sleep propensity? Article reviewed: Effect of ropinirole on sleep onset. A randomized, placebo-controlled study in healthy volunteers. | 2002 Sep |
|
Combination of two different dopamine agonists in the management of Parkinson's disease. | 2002 Sep |
|
Gabapentin versus ropinirole in the treatment of idiopathic restless legs syndrome. | 2003 |
|
Cabergoline, pramipexole and ropinirole used as monotherapy in early Parkinson's disease: an evidence-based comparison. | 2003 |
|
Comparison of the risk of adverse events with pramipexole and ropinirole in patients with Parkinson's disease: a meta-analysis. | 2003 |
|
Cost analysis of ropinirole versus levodopa in the treatment of Parkinson's disease. | 2003 |
|
Sleep attacks--facts and fiction: a critical review. | 2003 |
|
[Sexual delinquency and Parkinson's disease]. | 2003 Apr |
|
Current status of Parkinson's disease treatment in Korea. | 2003 Aug |
|
Piribedil-induced sleep attacks in Parkinson's disease. | 2003 Feb |
|
Slowing Parkinson's disease progression: recent dopamine agonist trials. | 2003 Feb 11 |
|
Ropinirole as an adjunct to levodopa in the treatment of Parkinson's disease A short commentary. | 2003 Jan |
|
Ropinirole as an adjunct to levodopa in the treatment of Parkinson's disease: a 16-week bromocriptine controlled study. | 2003 Jan |
|
Parkinson's disease: is the initial treatment established? | 2003 Jul |
|
REAL and CALM: what have we learned? | 2003 Jul |
|
The increased utilisation of dopamine agonists and the introduction of COMT inhibitors have not reduced levodopa consumption--a nation-wide perspective in Sweden. | 2003 Jun |
|
[Pseudopheochromocytoma in Parkinson disease and depression]. | 2003 May |
|
The initial drug treatment of older patients with Parkinson's disease - consider an agonist, but don't demonise dopa. | 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 |
|
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 |
|
Clinical strategies to prevent and delay motor complications. | 2003 Sep 23 |
Patents
Sample Use Guides
Parkinson Disease: 0.25 mg PO q8hr for 1 week initially, then increased weekly by 0.25 mg q8hr; if necessary, after week 4, may be increased weekly by 1.5 mg/day up to 9 mg/day, then increased weekly by 3 mg/day up to 24 mg/day
Restless Leg Syndrome: 0.25 mg/day PO 1-3 hr before bedtime; after day 2, may be increased to 0.5 mg/day PO; at end of week 1, increased to 1 mg/day, then increased weekly by 0.5 mg/day up to 4 mg/day
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/14637109
Human SH-SY5Y neuroblastoma cells were grown to confluence in Dulbecco’s Modified Eagle’s media (DMEM) supplemented with 10% fetal calf serum, 100 mkg/mL penicillin, 100 mkg/mL streptomycin, 0.25 mkg/mL amphotericin B, and 0.01 mkM non-essential amino acids (Gibco Grand Island, NY, USA) and then sub-cultured for differentiation in 48 well Costar culture plates. For differentiation, the cells were grown in same media containing 10 mkM retinoic acid for 3 days; then the media was removed and replaced with media containing 160 nM of the phorbol ester 12-O-tetradecanoyl-phorbol-13-acetate (TPA) for 3 days of differentiation. The cells were then administered a range doses of pramipexole, ropinirole and S32504 (10 nM to 1 mM) in DMEM for three days prior to addition of 1 mM MPP+. Following transfer of MPP+ to the media cells were tested every 24 h for 72 h for the cytotoxicity of MPP+ as measured by the MTT and LDH assays which accurately measure different aspects of apoptosis. In addition, we tested for the neuroprotective effects of a fixed dose of each drug (50 mkM) and a range of doses of S32504 on MPP+ induced apoptosis, and the effects of ropinirole alone (1 mM) as measured by DNA laddering.
Substance Class |
Chemical
Created
by
admin
on
Edited
Mon Mar 31 18:11:06 GMT 2025
by
admin
on
Mon Mar 31 18:11:06 GMT 2025
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Record UNII |
D7ZD41RZI9
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Record Status |
Validated (UNII)
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C38149
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68727
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EE-30
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SUB15144MIG
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1605205
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CHEMBL589
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m9658
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C47710
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236553
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100000091467
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BASIS OF STRENGTH->SUBSTANCE |
ASSAY (HPLC)
USP
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PARENT -> SALT/SOLVATE |
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
Ph.Eur.; USP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
Ph.Eur.; USP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
Ph.Eur.; USP
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ACTIVE MOIETY |