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 |
---|---|---|
Metoclopramide and pimozide in Parkinson's disease and levodopa-induced dyskinesias. | 1975 Apr |
|
The effects of combining carbidopa with levodopa for Parkinson's disease. | 1975 Dec |
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A wide variety of mutations in the parkin gene are responsible for autosomal recessive parkinsonism in Europe. French Parkinson's Disease Genetics Study Group and the European Consortium on Genetic Susceptibility in Parkinson's Disease. | 1999 Apr |
|
[A case of primary brain-stem injury recovered from persistent vegetative state after L-dopa administration]. | 1999 Dec |
|
Risk factors for levodopa-induced dyskinesias in Parkinson's disease. | 1999 Dec |
|
Short-term effects of high-dose 17beta-estradiol in postmenopausal PD patients: a crossover study. | 1999 Jul 13 |
|
Drug-induced motor complications in dopa-responsive dystonia: implications for the pathogenesis of dyskinesias and motor fluctuations. | 1999 Jul-Aug |
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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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[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 |
|
Combined use of the adenosine A(2A) antagonist KW-6002 with L-DOPA or with selective D1 or D2 dopamine agonists increases antiparkinsonian activity but not dyskinesia in MPTP-treated monkeys. | 2000 Apr |
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L-Dopa uptake and dopamine production in proximal tubular cells are regulated by beta(2)-adrenergic receptors. | 2000 Jul |
|
The effect of amantadine on levodopa-induced dyskinesias in Parkinson's disease: a double-blind, placebo-controlled study. | 2000 Mar-Apr |
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Levodopa-induced dyskinesias in Parkinson's disease: is sensitization reversible? | 2000 May |
|
Detection and assessment of the severity of levodopa-induced dyskinesia in patients with Parkinson's disease by neural networks. | 2000 Nov |
|
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 |
|
Accelerometric assessment of levodopa-induced dyskinesias in Parkinson's disease. | 2001 Jan |
|
Enhanced abilities of highly swollen chitosan beads for color removal and tyrosinase immobilization. | 2001 Jan 29 |
|
Biogenic aldehyde(s) derived from the action of monoamine oxidase may mediate the antidipsotropic effect of daidzin. | 2001 Jan 30 |
|
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 |
|
Levodopa-induced drowsiness in healthy volunteers: results of a choice reaction time test combined with a subjective evaluation of sedation. | 2001 Mar-Apr |
|
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
Sun Dec 18 19:39:25 UTC 2022
by
admin
on
Sun Dec 18 19:39:25 UTC 2022
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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 Sun Dec 18 19:39:28 UTC 2022 , Edited by admin on Sun Dec 18 19:39:28 UTC 2022
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EMA ASSESSMENT REPORTS |
CORBILTA (AUTHORIZED: PARKINSON DISEASE)
Created by
admin on Sun Dec 18 19:39:28 UTC 2022 , Edited by admin on Sun Dec 18 19:39:28 UTC 2022
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EU-Orphan Drug |
EU/3/01/035
Created by
admin on Sun Dec 18 19:39:28 UTC 2022 , Edited by admin on Sun Dec 18 19:39:28 UTC 2022
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EMA ASSESSMENT REPORTS |
STALEVO (AUTHORIZED: PARKINSON DISEASE)
Created by
admin on Sun Dec 18 19:39:28 UTC 2022 , Edited by admin on Sun Dec 18 19:39:28 UTC 2022
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WHO-ATC |
N04BA01
Created by
admin on Sun Dec 18 19:39:28 UTC 2022 , Edited by admin on Sun Dec 18 19:39:28 UTC 2022
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EMA ASSESSMENT REPORTS |
CORBILTA (AUTHORIZED: NEURODEGENERATIVE DISEASES)
Created by
admin on Sun Dec 18 19:39:28 UTC 2022 , Edited by admin on Sun Dec 18 19:39:28 UTC 2022
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WHO-VATC |
QN04BA02
Created by
admin on Sun Dec 18 19:39:28 UTC 2022 , Edited by admin on Sun Dec 18 19:39:28 UTC 2022
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WHO-ATC |
N04BA03
Created by
admin on Sun Dec 18 19:39:28 UTC 2022 , Edited by admin on Sun Dec 18 19:39:28 UTC 2022
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WHO-VATC |
QN04BA01
Created by
admin on Sun Dec 18 19:39:28 UTC 2022 , Edited by admin on Sun Dec 18 19:39:28 UTC 2022
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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
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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 Sun Dec 18 19:39:28 UTC 2022 , Edited by admin on Sun Dec 18 19:39:28 UTC 2022
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EMA ASSESSMENT REPORTS |
CORBILTA (AUTHORIZED: NERVOUS SYSTEM DISEASES)
Created by
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Code System | Code | Type | Description | ||
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6047
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PRIMARY | |||
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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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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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15765
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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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1361009
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DB01235
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6375
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PRIMARY | RxNorm |
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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 |
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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 |