Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C9H11NO4 |
Molecular Weight | 197.1883 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 1 / 1 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
c1cc(c(cc1C[C@@]([H])(C(=O)O)N)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 | 197.1883 |
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 |
---|---|---|
[Abnormal movements induced by L-dopa. New therapeutic possibilities]. | 1975 Jan 25 |
|
The anticataleptic effect of 7-OH-DPAT: are dopamine D3 receptors involved? | 1999 |
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Levodopa-induced dyskinesias treated by pallidotomy. | 1999 Aug 1 |
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Risk factors for levodopa-induced dyskinesias in Parkinson's disease. | 1999 Dec |
|
Comparison of pallidal and subthalamic nucleus deep brain stimulation for advanced Parkinson's disease: results of a randomized, blinded pilot study. | 1999 Dec |
|
Pharmacokinetics and pharmacodynamics of L-Dopa after acute and 6-week tolcapone administration in patients with Parkinson's disease. | 1999 Jan-Feb |
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Selective inhibition of cocaine-seeking behaviour by a partial dopamine D3 receptor agonist. | 1999 Jul 22 |
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Worsening of levodopa-induced dyskinesias by motor and mental tasks. | 1999 Mar |
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Riluzole for levodopa-induced dyskinesias in advanced Parkinson's disease. | 1999 May 22 |
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Actions of adenosine A2A receptor antagonist KW-6002 on drug-induced catalepsy and hypokinesia caused by reserpine or MPTP. | 1999 Nov |
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Punding on L-dopa. | 1999 Sep |
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[Amantadine for the treatment of levodopa dyskinesias in Parkinson's disease]. | 2000 |
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Effects of oligonucleotide antisense to dopamine D(1A) receptor messenger RNA in a rodent model of levodopa-induced dyskinesia. | 2000 |
|
Quetiapine for l-dopa-induced psychosis in PD. | 2000 Apr 11 |
|
Sleep attacks and Parkinson's disease treatment. | 2000 Apr 15 |
|
[Dopaminergic agonists in the treatment of Parkinson's disease]. | 2000 Dec |
|
Effect of subthalamic nucleus stimulation on levodopa-induced dyskinesia in Parkinson's disease. | 2000 Dec 26 |
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Association study of dopamine receptor gene polymorphisms with drug-induced hallucinations in patients with idiopathic Parkinson's disease. | 2000 Feb |
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Embryonic ventral mesencephalic grafts improve levodopa-induced dyskinesia in a rat model of Parkinson's disease. | 2000 Jul |
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Levodopa-induced dyskinesias in autopsy-proven cortical-basal ganglionic degeneration. | 2000 Mar |
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[Treatment of advanced Parkinson's disease]. | 2000 Oct |
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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 |
|
Apomorphine: an underutilized therapy for Parkinson's disease. | 2000 Sep |
|
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 |
|
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 |
|
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 |
|
Parkinsonism after glycine-derivate exposure. | 2001 May |
|
Speech dysfluency exacerbated by levodopa in Parkinson's disease. | 2001 May |
|
Chromium(VI) reduction by catechol(amine)s results in DNA cleavage in vitro: relevance to chromium genotoxicity. | 2001 May |
|
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 Dec 3 |
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
Fri Jun 25 20:59:09 UTC 2021
by
admin
on
Fri Jun 25 20:59:09 UTC 2021
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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
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WHO-ESSENTIAL MEDICINES LIST |
09 (LEV/CAR)
Created by
admin on Fri Jun 25 20:59:09 UTC 2021 , Edited by admin on Fri Jun 25 20:59:09 UTC 2021
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EMA ASSESSMENT REPORTS |
CORBILTA (AUTHORIZED: PARKINSON DISEASE)
Created by
admin on Fri Jun 25 20:59:09 UTC 2021 , Edited by admin on Fri Jun 25 20:59:09 UTC 2021
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EU-Orphan Drug |
EU/3/01/035
Created by
admin on Fri Jun 25 20:59:09 UTC 2021 , Edited by admin on Fri Jun 25 20:59:09 UTC 2021
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EMA ASSESSMENT REPORTS |
STALEVO (AUTHORIZED: PARKINSON DISEASE)
Created by
admin on Fri Jun 25 20:59:09 UTC 2021 , Edited by admin on Fri Jun 25 20:59:09 UTC 2021
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WHO-ATC |
N04BA01
Created by
admin on Fri Jun 25 20:59:09 UTC 2021 , Edited by admin on Fri Jun 25 20:59:09 UTC 2021
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EMA ASSESSMENT REPORTS |
CORBILTA (AUTHORIZED: NEURODEGENERATIVE DISEASES)
Created by
admin on Fri Jun 25 20:59:09 UTC 2021 , Edited by admin on Fri Jun 25 20:59:09 UTC 2021
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WHO-VATC |
QN04BA02
Created by
admin on Fri Jun 25 20:59:09 UTC 2021 , Edited by admin on Fri Jun 25 20:59:09 UTC 2021
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WHO-ATC |
N04BA03
Created by
admin on Fri Jun 25 20:59:09 UTC 2021 , Edited by admin on Fri Jun 25 20:59:09 UTC 2021
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WHO-VATC |
QN04BA01
Created by
admin on Fri Jun 25 20:59:09 UTC 2021 , Edited by admin on Fri Jun 25 20:59:09 UTC 2021
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LOINC |
79577-3
Created by
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NDF-RT |
N0000193220
Created by
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LIVERTOX |
552
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
Created by
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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 Fri Jun 25 20:59:09 UTC 2021 , Edited by admin on Fri Jun 25 20:59:09 UTC 2021
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EMA ASSESSMENT REPORTS |
CORBILTA (AUTHORIZED: NERVOUS SYSTEM DISEASES)
Created by
admin on Fri Jun 25 20:59:09 UTC 2021 , Edited by admin on Fri Jun 25 20:59:09 UTC 2021
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Code System | Code | Type | Description | ||
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6047
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L-DOPA
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PRIMARY | |||
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Levodopa
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PRIMARY | |||
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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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C611
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SUB08468MIG
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59-92-7
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46627O600J
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CHEMBL1009
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3348
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1361009
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3639
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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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DB01235
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6375
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PRIMARY | RxNorm |
Related Record | Type | Details | ||
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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 |
Related Record | Type | Details | ||
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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 |
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 |