Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C9H12NO7P |
Molecular Weight | 277.1682 |
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)OP(=O)(O)O
InChI
InChIKey=YNDMEEULGSTYJT-LURJTMIESA-N
InChI=1S/C9H12NO7P/c10-6(9(12)13)3-5-1-2-8(7(11)4-5)17-18(14,15)16/h1-2,4,6,11H,3,10H2,(H,12,13)(H2,14,15,16)/t6-/m0/s1
Molecular Formula | C9H12NO7P |
Molecular Weight | 277.1682 |
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 |
---|---|---|
Levodopa-induced postural hypotension. Treatment with fludrocortisone. | 1975 Jan |
|
[Abnormal movements induced by L-dopa. New therapeutic possibilities]. | 1975 Jan 25 |
|
Reduction of dyskinesia and induction of akinesia induced by morphine in two parkinsonian patients with severe sciatica. | 1999 |
|
A unified dyskinesias rating scale for L-dopa-induced dyskinesias? | 1999 |
|
Levodopa-induced dyskinesias treated by pallidotomy. | 1999 Aug 1 |
|
Comparative effects of unilateral and bilateral subthalamic nucleus deep brain stimulation. | 1999 Aug 11 |
|
Comparison of pallidal and subthalamic nucleus deep brain stimulation for advanced Parkinson's disease: results of a randomized, blinded pilot study. | 1999 Dec |
|
Drug-induced motor complications in dopa-responsive dystonia: implications for the pathogenesis of dyskinesias and motor fluctuations. | 1999 Jul-Aug |
|
Internal globus pallidus discharge is nearly suppressed during levodopa-induced dyskinesias. | 1999 Nov |
|
Dopamine D2 receptor gene polymorphism and the risk of levodopa-induced dyskinesias in PD. | 1999 Oct 22 |
|
Functional mapping of the human globus pallidus: contrasting effect of stimulation in the internal and external pallidum in Parkinson's disease. | 2000 |
|
Tolcapone increases maximum concentration of levodopa. | 2000 |
|
Preventing levodopa-induced dyskinesias. | 2000 Apr |
|
Investigating levodopa-induced dyskinesias in the parkinsonian primate. | 2000 Apr |
|
Sleep attacks and Parkinson's disease treatment. | 2000 Apr 15 |
|
[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 |
|
Embryonic ventral mesencephalic grafts improve levodopa-induced dyskinesia in a rat model of Parkinson's disease. | 2000 Jul |
|
Population pharmacokinetics of levodopa in patients with Parkinson's disease treated with tolcapone. | 2000 Jun |
|
[Worsened orthostatic hypotension due to levodopa administration in a case of Parkinson's disease]. | 2000 Mar |
|
Levodopa-induced dyskinesias in autopsy-proven cortical-basal ganglionic degeneration. | 2000 Mar |
|
The effect of amantadine on levodopa-induced dyskinesias in Parkinson's disease: a double-blind, placebo-controlled study. | 2000 Mar-Apr |
|
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 |
|
Centrally initiated postural adjustments in parkinsonian patients on and off levodopa. | 2000 Nov |
|
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 |
|
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 |
|
Dimeric L-dopa derivatives as potential prodrugs. | 2001 Apr 23 |
|
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 |
|
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 |
|
Role of peroxynitrite in macrophage microbicidal mechanisms in vivo revealed by protein nitration and hydroxylation. | 2001 Jun 1 |
|
Resveratrol and a novel tyrosinase in Carignan grape juice. | 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 |
|
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 |
|
Chromium(VI) reduction by catechol(amine)s results in DNA cleavage in vitro: relevance to chromium genotoxicity. | 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
Fri Jun 25 21:43:29 UTC 2021
by
admin
on
Fri Jun 25 21:43:29 UTC 2021
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Record UNII |
37NQZ0J76I
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Record Status |
Validated (UNII)
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Record Version |
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127766
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C166651
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