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 Date1.0552032E12 |
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 n = 1 Health Status: unhealthy Condition: idiopathic Parkinson's disease Age Group: 54 years Sex: F Population Size: 1 Sources: |
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 n = 114 Health Status: unhealthy Condition: Parkinson’s disease Age Group: adult Population Size: 114 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 n = 15 Health Status: unhealthy Condition: Vision Impairment Age Group: child|adult Population Size: 15 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 n = 15 Health Status: unhealthy Condition: Vision Impairment Age Group: child|adult Population Size: 15 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 n = 1 Health Status: unhealthy Condition: idiopathic Parkinson's disease Age Group: 54 years Sex: F Population Size: 1 Sources: |
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 n = 114 Health Status: unhealthy Condition: Parkinson’s disease Age Group: adult Population Size: 114 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 n = 15 Health Status: unhealthy Condition: Vision Impairment Age Group: child|adult Population Size: 15 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 n = 15 Health Status: unhealthy Condition: Vision Impairment Age Group: child|adult Population Size: 15 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 n = 15 Health Status: unhealthy Condition: Vision Impairment Age Group: child|adult Population Size: 15 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 n = 15 Health Status: unhealthy Condition: Vision Impairment Age Group: child|adult Population Size: 15 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 n = 15 Health Status: unhealthy Condition: Vision Impairment Age Group: child|adult Population Size: 15 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 n = 15 Health Status: unhealthy Condition: Vision Impairment Age Group: child|adult Population Size: 15 Sources: |
PubMed
Title | Date | PubMed |
---|---|---|
The effects of combining carbidopa with levodopa for Parkinson's disease. | 1975 Dec |
|
Levodopa-induced postural hypotension. Treatment with fludrocortisone. | 1975 Jan |
|
[Abnormal movements induced by L-dopa. New therapeutic possibilities]. | 1975 Jan 25 |
|
[A case of primary brain-stem injury recovered from persistent vegetative state after L-dopa administration]. | 1999 Dec |
|
Functional mapping of the human globus pallidus: contrasting effect of stimulation in the internal and external pallidum in Parkinson's disease. | 2000 |
|
Effects of oligonucleotide antisense to dopamine D(1A) receptor messenger RNA in a rodent model of levodopa-induced dyskinesia. | 2000 |
|
Preventing levodopa-induced dyskinesias. | 2000 Apr |
|
Investigating levodopa-induced dyskinesias in the parkinsonian primate. | 2000 Apr |
|
Bilateral subthalamic stimulation for Parkinson's disease by using three-dimensional stereotactic magnetic resonance imaging and electrophysiological guidance. | 2000 Apr |
|
Sleep attacks and Parkinson's disease treatment. | 2000 Apr 15 |
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[Dopaminergic agonists in the treatment of Parkinson's disease]. | 2000 Dec |
|
Evidence of functional somatotopy in GPi from results of pallidotomy. | 2000 Dec |
|
Effect of subthalamic nucleus stimulation on levodopa-induced dyskinesia in Parkinson's disease. | 2000 Dec 26 |
|
Association study of dopamine receptor gene polymorphisms with drug-induced hallucinations in patients with idiopathic Parkinson's disease. | 2000 Feb |
|
Four novel mutations in the tyrosine hydroxylase gene in patients with infantile parkinsonism. | 2000 Jan |
|
Levodopa-induced dyskinesias in autopsy-proven cortical-basal ganglionic degeneration. | 2000 Mar |
|
Idazoxan is ineffective for levodopa-induced dyskinesias in Parkinson's disease. | 2000 Mar |
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Levodopa-induced dyskinesias in Parkinson's disease: is sensitization reversible? | 2000 May |
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Detection and assessment of the severity of levodopa-induced dyskinesia in patients with Parkinson's disease by neural networks. | 2000 Nov |
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Centrally initiated postural adjustments in parkinsonian patients on and off levodopa. | 2000 Nov |
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[Treatment of advanced Parkinson's disease]. | 2000 Oct |
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Expression of metallothionein-III mRNA and its regulation by levodopa in the basal ganglia of hemi-parkinsonian rats. | 2000 Oct 20 |
|
The 4F2hc/LAT1 complex transports L-DOPA across the blood-brain barrier. | 2000 Oct 6 |
|
Workshop IV: drug treatment guidelines for the long-term management of Parkinson's disease. | 2000 Sep |
|
Beneficial effects of amantadine on L-dopa-induced dyskinesias in Parkinson's disease. | 2000 Sep |
|
Pathologic gambling in Parkinson's disease: a behavioral manifestation of pharmacologic treatment? | 2000 Sep |
|
Adverse drug reactions to selegiline: a review of the French pharmacovigilance database. | 2000 Sep-Oct |
|
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 |
|
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 |
|
High dose naltrexone for dyskinesias induced by levodopa. | 2001 Apr |
|
Localization of a novel locus for autosomal recessive early-onset parkinsonism, PARK6, on human chromosome 1p35-p36. | 2001 Apr |
|
Selective dopaminergic vulnerability: 3,4-dihydroxyphenylacetaldehyde targets mitochondria. | 2001 Apr 15 |
|
SCH 58261, an A(2A) adenosine receptor antagonist, counteracts parkinsonian-like muscle rigidity in rats. | 2001 Aug |
|
Dopamine D(2) receptors regulate tyrosine hydroxylase activity and phosphorylation at Ser40 in rat striatum. | 2001 Feb |
|
Induction by dopamine D1 receptor agonist ABT-431 of dyskinesia similar to levodopa in patients with Parkinson disease. | 2001 Feb |
|
Molecular mechanisms controlling the rate and specificity of catechol O-methylation by human soluble catechol O-methyltransferase. | 2001 Feb |
|
Accelerometric assessment of levodopa-induced dyskinesias in Parkinson's disease. | 2001 Jan |
|
SPECT imaging of the dopamine transporter in juvenile-onset dystonia. | 2001 Jan 23 |
|
Biogenic aldehyde(s) derived from the action of monoamine oxidase may mediate the antidipsotropic effect of daidzin. | 2001 Jan 30 |
|
Resveratrol and a novel tyrosinase in Carignan grape juice. | 2001 Mar |
|
Does stimulation of the GPi control dyskinesia by activating inhibitory axons? | 2001 Mar |
|
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 Mar |
|
Event-related functional magnetic resonance imaging in Parkinson's disease before and after levodopa. | 2001 Mar |
|
Comparative analysis of the gait disorder of normal pressure hydrocephalus and Parkinson's disease. | 2001 Mar |
|
The effect of levodopa on vocal function in Parkinson's disease. | 2001 Mar-Apr |
|
Levodopa-induced drowsiness in healthy volunteers: results of a choice reaction time test combined with a subjective evaluation of sedation. | 2001 Mar-Apr |
|
Parkinsonism after glycine-derivate exposure. | 2001 May |
|
Speech dysfluency exacerbated by levodopa in Parkinson's disease. | 2001 May |
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
admin
on
Edited
Thu Jul 06 22:28:23 UTC 2023
by
admin
on
Thu Jul 06 22:28:23 UTC 2023
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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
Created by
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DSLD |
1198 (Number of products:24)
Created by
admin on Thu Jul 06 22:28:25 UTC 2023 , Edited by admin on Thu Jul 06 22:28:25 UTC 2023
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WHO-ESSENTIAL MEDICINES LIST |
09 (LEV/CAR)
Created by
admin on Thu Jul 06 22:28:26 UTC 2023 , Edited by admin on Thu Jul 06 22:28:26 UTC 2023
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EMA ASSESSMENT REPORTS |
CORBILTA (AUTHORIZED: PARKINSON DISEASE)
Created by
admin on Thu Jul 06 22:28:26 UTC 2023 , Edited by admin on Thu Jul 06 22:28:26 UTC 2023
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EU-Orphan Drug |
EU/3/01/035
Created by
admin on Thu Jul 06 22:28:26 UTC 2023 , Edited by admin on Thu Jul 06 22:28:26 UTC 2023
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EMA ASSESSMENT REPORTS |
STALEVO (AUTHORIZED: PARKINSON DISEASE)
Created by
admin on Thu Jul 06 22:28:26 UTC 2023 , Edited by admin on Thu Jul 06 22:28:26 UTC 2023
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WHO-ATC |
N04BA01
Created by
admin on Thu Jul 06 22:28:25 UTC 2023 , Edited by admin on Thu Jul 06 22:28:25 UTC 2023
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EMA ASSESSMENT REPORTS |
CORBILTA (AUTHORIZED: NEURODEGENERATIVE DISEASES)
Created by
admin on Thu Jul 06 22:28:26 UTC 2023 , Edited by admin on Thu Jul 06 22:28:26 UTC 2023
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WHO-VATC |
QN04BA02
Created by
admin on Thu Jul 06 22:28:26 UTC 2023 , Edited by admin on Thu Jul 06 22:28:26 UTC 2023
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WHO-ATC |
N04BA03
Created by
admin on Thu Jul 06 22:28:25 UTC 2023 , Edited by admin on Thu Jul 06 22:28:25 UTC 2023
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WHO-VATC |
QN04BA01
Created by
admin on Thu Jul 06 22:28:26 UTC 2023 , Edited by admin on Thu Jul 06 22:28:26 UTC 2023
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LOINC |
79577-3
Created by
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NDF-RT |
N0000193220
Created by
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LIVERTOX |
NBK548734
Created by
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FDA ORPHAN DRUG |
129499
Created by
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NDF-RT |
N0000175754
Created by
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WHO-ATC |
N04BA02
Created by
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NCI_THESAURUS |
C66884
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NDF-RT |
N0000175755
Created by
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EMA ASSESSMENT REPORTS |
LEVODOPA/CARBIDOPA/ENTACAPONE ORION (AUTHORIZED: PARKINSON DISEASE)
Created by
admin on Thu Jul 06 22:28:26 UTC 2023 , Edited by admin on Thu Jul 06 22:28:26 UTC 2023
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EMA ASSESSMENT REPORTS |
CORBILTA (AUTHORIZED: NERVOUS SYSTEM DISEASES)
Created by
admin on Thu Jul 06 22:28:26 UTC 2023 , Edited by admin on Thu Jul 06 22:28:26 UTC 2023
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Code System | Code | Type | Description | ||
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6047
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L-DOPA
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Levodopa
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LEVODOPA
Created by
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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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D007980
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1567
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118381
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C611
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SUB08468MIG
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DTXSID9023209
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46627O600J
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CHEMBL1009
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46627O600J
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57504
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3348
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100000085446
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15765
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M6786
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2651
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200-445-2
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59-92-7
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1361009
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DB01235
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6375
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METABOLIC ENZYME -> SUBSTRATE |
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PARENT -> CONSTITUENT ALWAYS PRESENT | |||
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ASSAY (HPLC)
USP
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BASIS OF STRENGTH->SUBSTANCE |
ASSAY (TITRATION)
EP
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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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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
|
||
|
IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
|
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|
PARENT -> IMPURITY |
|
||
|
IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
|
||
|
IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
|
||
|
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
|
||
|
IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
|
Related Record | Type | Details | ||
---|---|---|---|---|
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ACTIVE MOIETY |
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