Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C9H11NO4 |
| Molecular Weight | 197.1879 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 1 / 1 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
N[C@@H](CC1=CC(O)=C(O)C=C1)C(O)=O
InChI
InChIKey=WTDRDQBEARUVNC-LURJTMIESA-N
InChI=1S/C9H11NO4/c10-6(9(13)14)3-5-1-2-7(11)8(12)4-5/h1-2,4,6,11-12H,3,10H2,(H,13,14)/t6-/m0/s1
| Molecular Formula | C9H11NO4 |
| Molecular Weight | 197.1879 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 1 / 1 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
DescriptionSources: https://www.ncbi.nlm.nih.gov/pubmed/21080185Curator's Comment: Description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/23948989
http://www.accessdata.fda.gov/drugsatfda_docs/label/2010/021485s20lbl.pdf
Sources: https://www.ncbi.nlm.nih.gov/pubmed/21080185
Curator's Comment: Description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/23948989
http://www.accessdata.fda.gov/drugsatfda_docs/label/2010/021485s20lbl.pdf
Levodopa (L-DOPA) was first isolated from seedlings of Vicia faba by Marcus Guggenheim in 1913. Levodopa, a dopamine precursor, is an effective and well-tolerated dopamine replacement agent used to treat Parkinson's disease. Oral levodopa has been widely used for over 40 years, often in combination with a dopa-decarboxylase inhibitor carbidopa, which reduces many treatment complications, extending its half-life and increasing levodopa availability to the brain. Entacapone, a catechol-O-methyltransferase inhibitor, can also be used to improve the bioavailability of levodopa, especially when used in conjunction with a carbidopa.
CNS Activity
Originator
Sources: https://newdrugapprovals.org/tag/levodopa/
Curator's Comment: # Hoffmann-La Roche
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: CHEMBL2056 Sources: https://www.ncbi.nlm.nih.gov/pubmed/18851961 |
|||
Target ID: CHEMBL2096905 |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Primary | Stalevo Approved UseStalevo® (carbidopa, levodopa and entacapone) is indicated to treat patients with idiopathic Parkinson’s disease. Launch Date2003 |
Cmax
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
0.946 μg/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/22549097 |
100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered: CARBIDOPA, DL- |
LEVODOPA plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
AUC
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
84.8 μg × min/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/22549097 |
100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered: CARBIDOPA, DL- |
LEVODOPA plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
T1/2
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
78.7 min EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/22549097 |
100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered: CARBIDOPA, DL- |
LEVODOPA plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
Funbound
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
80% |
LEVODOPA plasma | Homo sapiens |
Doses
| Dose | Population | Adverse events |
|---|---|---|
3 g 1 times / day multiple, oral Dose: 3 g, 1 times / day Route: oral Route: multiple Dose: 3 g, 1 times / day Sources: |
unhealthy, 54 years |
Disc. AE: Alopecia... AEs leading to discontinuation/dose reduction: Alopecia (1 patient) Sources: |
420 mg 1 times / day multiple, respiratory Recommended Dose: 420 mg, 1 times / day Route: respiratory Route: multiple Dose: 420 mg, 1 times / day Sources: |
unhealthy, adult Health Status: unhealthy Age Group: adult Sources: |
|
84 mg 2 times / day multiple, respiratory Recommended Dose: 84 mg, 2 times / day Route: respiratory Route: multiple Dose: 84 mg, 2 times / day Sources: |
unhealthy, adult Health Status: unhealthy Age Group: adult Sources: |
Disc. AE: Cough... AEs leading to discontinuation/dose reduction: Cough (2%) Sources: |
0.51 mg/kg 3 times / day steady, oral Dose: 0.51 mg/kg, 3 times / day Route: oral Route: steady Dose: 0.51 mg/kg, 3 times / day Sources: |
unhealthy, child|adult Health Status: unhealthy Age Group: child|adult Sources: |
Other AEs: Headache, Nausea... Other AEs: Headache (below serious, 2 patients) Sources: Nausea (below serious, 2 patients) |
0.76 mg/kg 3 times / day steady, oral Dose: 0.76 mg/kg, 3 times / day Route: oral Route: steady Dose: 0.76 mg/kg, 3 times / day Sources: |
unhealthy, child|adult Health Status: unhealthy Age Group: child|adult Sources: |
Other AEs: Headache, Dry mouth... Other AEs: Headache (below serious, 1 patient) Sources: Dry mouth (below serious, 2 patients) Nausea (below serious, 1 patient) Fatigue (below serious, 2 patients) |
AEs
| AE | Significance | Dose | Population |
|---|---|---|---|
| Alopecia | 1 patient Disc. AE |
3 g 1 times / day multiple, oral Dose: 3 g, 1 times / day Route: oral Route: multiple Dose: 3 g, 1 times / day Sources: |
unhealthy, 54 years |
| Cough | 2% Disc. AE |
84 mg 2 times / day multiple, respiratory Recommended Dose: 84 mg, 2 times / day Route: respiratory Route: multiple Dose: 84 mg, 2 times / day Sources: |
unhealthy, adult Health Status: unhealthy Age Group: adult Sources: |
| Headache | below serious, 2 patients | 0.51 mg/kg 3 times / day steady, oral Dose: 0.51 mg/kg, 3 times / day Route: oral Route: steady Dose: 0.51 mg/kg, 3 times / day Sources: |
unhealthy, child|adult Health Status: unhealthy Age Group: child|adult Sources: |
| Nausea | below serious, 2 patients | 0.51 mg/kg 3 times / day steady, oral Dose: 0.51 mg/kg, 3 times / day Route: oral Route: steady Dose: 0.51 mg/kg, 3 times / day Sources: |
unhealthy, child|adult Health Status: unhealthy Age Group: child|adult Sources: |
| Headache | below serious, 1 patient | 0.76 mg/kg 3 times / day steady, oral Dose: 0.76 mg/kg, 3 times / day Route: oral Route: steady Dose: 0.76 mg/kg, 3 times / day Sources: |
unhealthy, child|adult Health Status: unhealthy Age Group: child|adult Sources: |
| Nausea | below serious, 1 patient | 0.76 mg/kg 3 times / day steady, oral Dose: 0.76 mg/kg, 3 times / day Route: oral Route: steady Dose: 0.76 mg/kg, 3 times / day Sources: |
unhealthy, child|adult Health Status: unhealthy Age Group: child|adult Sources: |
| Dry mouth | below serious, 2 patients | 0.76 mg/kg 3 times / day steady, oral Dose: 0.76 mg/kg, 3 times / day Route: oral Route: steady Dose: 0.76 mg/kg, 3 times / day Sources: |
unhealthy, child|adult Health Status: unhealthy Age Group: child|adult Sources: |
| Fatigue | below serious, 2 patients | 0.76 mg/kg 3 times / day steady, oral Dose: 0.76 mg/kg, 3 times / day Route: oral Route: steady Dose: 0.76 mg/kg, 3 times / day Sources: |
unhealthy, child|adult Health Status: unhealthy Age Group: child|adult Sources: |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Biperiden enhances L-DOPA methyl ester and dopamine D(l) receptor agonist SKF-82958 but antagonizes D(2)/D(3) receptor agonist rotigotine antihemiparkinsonian actions. | 2008-12-03 |
|
| SCH 58261, an A(2A) adenosine receptor antagonist, counteracts parkinsonian-like muscle rigidity in rats. | 2001-08 |
|
| Role of peroxynitrite in macrophage microbicidal mechanisms in vivo revealed by protein nitration and hydroxylation. | 2001-06-01 |
|
| Parkinsonism after glycine-derivate exposure. | 2001-05 |
|
| Speech dysfluency exacerbated by levodopa in Parkinson's disease. | 2001-05 |
|
| Intravenous amantadine improves levadopa-induced dyskinesias: an acute double-blind placebo-controlled study. | 2001-05 |
|
| Chromium(VI) reduction by catechol(amine)s results in DNA cleavage in vitro: relevance to chromium genotoxicity. | 2001-05 |
|
| Coadministration of (-)-OSU6162 with l-DOPA normalizes preproenkephalin mRNA expression in the sensorimotor striatum of primates with unilateral 6-OHDA lesions. | 2001-05 |
|
| Dimeric L-dopa derivatives as potential prodrugs. | 2001-04-23 |
|
| The effect of levodopa on vocal function in Parkinson's disease. | 2001-04-18 |
|
| Levodopa-induced drowsiness in healthy volunteers: results of a choice reaction time test combined with a subjective evaluation of sedation. | 2001-04-18 |
|
| Selective dopaminergic vulnerability: 3,4-dihydroxyphenylacetaldehyde targets mitochondria. | 2001-04-15 |
|
| High dose naltrexone for dyskinesias induced by levodopa. | 2001-04 |
|
| Localization of a novel locus for autosomal recessive early-onset parkinsonism, PARK6, on human chromosome 1p35-p36. | 2001-04 |
|
| Resveratrol and a novel tyrosinase in Carignan grape juice. | 2001-03 |
|
| Does stimulation of the GPi control dyskinesia by activating inhibitory axons? | 2001-03 |
|
| Effects of N-(2-chloroethyl)-N-ethyl-2-bromobenzylamine (DSP4) on alpha2-adrenoceptors which regulate the synthesis and release of noradrenaline in the rat brain. | 2001-03 |
|
| Event-related functional magnetic resonance imaging in Parkinson's disease before and after levodopa. | 2001-03 |
|
| Comparative analysis of the gait disorder of normal pressure hydrocephalus and Parkinson's disease. | 2001-03 |
|
| Dopamine D(2) receptors regulate tyrosine hydroxylase activity and phosphorylation at Ser40 in rat striatum. | 2001-02 |
|
| Induction by dopamine D1 receptor agonist ABT-431 of dyskinesia similar to levodopa in patients with Parkinson disease. | 2001-02 |
|
| Molecular mechanisms controlling the rate and specificity of catechol O-methylation by human soluble catechol O-methyltransferase. | 2001-02 |
|
| Biogenic aldehyde(s) derived from the action of monoamine oxidase may mediate the antidipsotropic effect of daidzin. | 2001-01-30 |
|
| Enhanced abilities of highly swollen chitosan beads for color removal and tyrosinase immobilization. | 2001-01-29 |
|
| SPECT imaging of the dopamine transporter in juvenile-onset dystonia. | 2001-01-23 |
|
| Adverse drug reactions to selegiline: a review of the French pharmacovigilance database. | 2001-01-12 |
|
| Accelerometric assessment of levodopa-induced dyskinesias in Parkinson's disease. | 2001-01 |
|
| Pharmacokinetic-pharmacodynamic relationship of levodopa with and without tolcapone in patients with Parkinson's disease. | 2001 |
|
| Melanogenesis by tyrosinase action on 3,4-dihydroxyphenylalanine (DOPA) in the presence of polyethylene glycol: a matrix-assisted laser desorption/ionization mass spectrometric investigation. | 2001 |
|
| Inhibition of potato polyphenol oxidase by anions and activity in various carboxylate buffers (pH 4.8) at constant ionic strength. | 2001 |
|
| A study of excessive daytime sleepiness and its clinical significance in three groups of Parkinson's disease patients taking pramipexole, cabergoline and levodopa mono and combination therapy. | 2001 |
|
| Efficacy and tolerability of entacapone as adjunctive therapy to levodopa in patients with Parkinson's disease and end-of-dose deterioration in daily medical practice: an open, multicenter study. | 2001 |
|
| Effect of subthalamic nucleus stimulation on levodopa-induced dyskinesia in Parkinson's disease. | 2000-12-26 |
|
| [Dopaminergic agonists in the treatment of Parkinson's disease]. | 2000-12 |
|
| Evidence of functional somatotopy in GPi from results of pallidotomy. | 2000-12 |
|
| Detection and assessment of the severity of levodopa-induced dyskinesia in patients with Parkinson's disease by neural networks. | 2000-11 |
|
| Centrally initiated postural adjustments in parkinsonian patients on and off levodopa. | 2000-11 |
|
| Expression of metallothionein-III mRNA and its regulation by levodopa in the basal ganglia of hemi-parkinsonian rats. | 2000-10-20 |
|
| The 4F2hc/LAT1 complex transports L-DOPA across the blood-brain barrier. | 2000-10-06 |
|
| [Treatment of advanced Parkinson's disease]. | 2000-10 |
|
| Workshop IV: drug treatment guidelines for the long-term management of Parkinson's disease. | 2000-09 |
|
| Beneficial effects of amantadine on L-dopa-induced dyskinesias in Parkinson's disease. | 2000-09 |
|
| Pathologic gambling in Parkinson's disease: a behavioral manifestation of pharmacologic treatment? | 2000-09 |
|
| Four novel mutations in the tyrosine hydroxylase gene in patients with infantile parkinsonism. | 2000-01 |
|
| Functional mapping of the human globus pallidus: contrasting effect of stimulation in the internal and external pallidum in Parkinson's disease. | 2000 |
|
| [Amantadine for the treatment of levodopa dyskinesias in Parkinson's disease]. | 2000 |
|
| The effects of combining carbidopa with levodopa for Parkinson's disease. | 1975-12 |
|
| Persistent parkinsonism following neuroleptanalgesia. | 1975-05 |
|
| [Abnormal movements induced by L-dopa. New therapeutic possibilities]. | 1975-01-25 |
|
| Levodopa-induced postural hypotension. Treatment with fludrocortisone. | 1975-01 |
Patents
Sample Use Guides
Maximum dosage in a 24-hour period is eight tablets (Stalevo 50, containing 12.5 mg of carbidopa, 50 mg of levodopa and 200 mg of entacapone; Stalevo 75, containing 18.75 mg of carbidopa, 75 mg of levodopa and 200 mg of entacapone; Stalevo 100, containing 25 mg of carbidopa, 100 mg of levodopa and 200 mg of entacapone; Stalevo 125, containing 31.25 mg of carbidopa, 125 mg of levodopa and 200 mg of entacapone; Stalevo 150, containing 37.5 mg of carbidopa, 150 mg of levodopa and 200 mg of entacapone; Stalevo 200, containing 50 mg of carbidopa, 200 mg of levodopa and 200 mg of entacapone). The optimum daily dosage must be determined by careful titration in each patient.
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/24743653
Low dose (<30 uM) Levodopa protects PC12 cells against oxidative stress which might be related to the up-regulation of CD39 and pCREB expression.
| Substance Class |
Chemical
Created
by
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on
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Wed Apr 02 08:42:43 GMT 2025
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| Record UNII |
46627O600J
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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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WHO-VATC |
QN04BA03
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DSLD |
1198 (Number of products:24)
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WHO-ESSENTIAL MEDICINES LIST |
09 (LEV/CAR)
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EMA ASSESSMENT REPORTS |
CORBILTA (AUTHORIZED: PARKINSON DISEASE)
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EU-Orphan Drug |
EU/3/01/035
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EMA ASSESSMENT REPORTS |
STALEVO (AUTHORIZED: PARKINSON DISEASE)
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WHO-ATC |
N04BA01
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EMA ASSESSMENT REPORTS |
CORBILTA (AUTHORIZED: NEURODEGENERATIVE DISEASES)
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WHO-VATC |
QN04BA02
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WHO-ATC |
N04BA03
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WHO-VATC |
QN04BA01
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LOINC |
79577-3
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NDF-RT |
N0000193220
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LIVERTOX |
NBK548734
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FDA ORPHAN DRUG |
129499
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NDF-RT |
N0000175754
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WHO-ATC |
N04BA02
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NCI_THESAURUS |
C66884
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NDF-RT |
N0000175755
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EMA ASSESSMENT REPORTS |
LEVODOPA/CARBIDOPA/ENTACAPONE ORION (AUTHORIZED: PARKINSON DISEASE)
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EMA ASSESSMENT REPORTS |
CORBILTA (AUTHORIZED: NERVOUS SYSTEM DISEASES)
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6047
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L-DOPA
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Levodopa
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LEVODOPA
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PRIMARY | Description: A white or almost white, crystalline powder; odourless. Solubility: Soluble in 300 parts of water; practically insoluble in ethanol (~750 g/l) TS and ether R. Category: Antiparkinsonism drug. Storage: Levodopa should be kept in a tightly closed container.Definition: Levodopa contains not less than 98.5% and not more than 101.0% of C9H11NO4, calculated with reference to the dried substance. | ||
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118381
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2651
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200-445-2
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6375
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BINDING
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METABOLIC ENZYME -> SUBSTRATE |
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PARENT -> CONSTITUENT ALWAYS PRESENT | |||
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BASIS OF STRENGTH->SUBSTANCE |
ASSAY (HPLC)
USP
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BASIS OF STRENGTH->SUBSTANCE |
ASSAY (TITRATION)
EP
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TARGET -> AGONIST |
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PRODRUG -> METABOLITE ACTIVE |
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PARENT -> METABOLITE |
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PRODRUG -> METABOLITE ACTIVE |
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PRODRUG -> METABOLITE ACTIVE | |||
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PRODRUG -> METABOLITE ACTIVE |
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METABOLITE ACTIVE -> PRODRUG |
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METABOLITE ACTIVE -> PRODRUG |
MAJOR
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METABOLITE -> PARENT |
When decarboxylation of levodopa is prevented by carbidopa, COMT becomes the major metabolizing enzyme for levodopa, catalyzing its metabolism to 3-methoxy-4-hydroxy-L-phenylalanine (3-OMD).
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METABOLITE -> PARENT |
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| Related Record | Type | Details | ||
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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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PARENT -> IMPURITY |
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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 |
For the calculation of contents, multiply the peak areas by 2.2
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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| Related Record | Type | Details | ||
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ACTIVE MOIETY |
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