Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C9H10BiNO5 |
| Molecular Weight | 421.1598 |
| 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[Bi]=O
InChI
InChIKey=JRJJYJNGHVWAOI-ILKKLZGPSA-M
InChI=1S/C9H11NO4.Bi.O/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);;/q;+1;/p-1/t6-;;/m0../s1
DescriptionCurator'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
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
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: CHEMBL2056 |
|||
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 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 |
|
| Persistent parkinsonism following neuroleptanalgesia. | 1975 May |
|
| Levodopa-induced myoclonus. | 1975 May |
|
| [Effects and side effects of levodopa in parkinsonism - results of a collaborative study. (4) Dyskinesia caused by levodopa]. | 1976 Dec |
|
| The anticataleptic effect of 7-OH-DPAT: are dopamine D3 receptors involved? | 1999 |
|
| A unified dyskinesias rating scale for L-dopa-induced dyskinesias? | 1999 |
|
| Comparative effects of unilateral and bilateral subthalamic nucleus deep brain stimulation. | 1999 Aug 11 |
|
| Risk factors for levodopa-induced dyskinesias in Parkinson's disease. | 1999 Dec |
|
| Striatal fosB expression is causally linked with l-DOPA-induced abnormal involuntary movements and the associated upregulation of striatal prodynorphin mRNA in a rat model of 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 |
|
| [Levodopa-induced psychosis in patients with idiopathic Parkinson disease]. | 1999 Feb 27 |
|
| Short-term effects of high-dose 17beta-estradiol in postmenopausal PD patients: a crossover study. | 1999 Jul 13 |
|
| Selective inhibition of cocaine-seeking behaviour by a partial dopamine D3 receptor agonist. | 1999 Jul 22 |
|
| Renal effects of L-DOPA in heart failure. | 1999 Jun |
|
| From off-period dystonia to peak-dose chorea. The clinical spectrum of varying subthalamic nucleus activity. | 1999 Jun |
|
| Modulation of gastrin processing by vesicular monoamine transporter type 1 (VMAT1) in rat gastrin cells. | 1999 Jun 1 |
|
| Worsening of levodopa-induced dyskinesias by motor and mental tasks. | 1999 Mar |
|
| Riluzole for levodopa-induced dyskinesias in advanced Parkinson's disease. | 1999 May 22 |
|
| Dopamine D2 receptor gene polymorphism and the risk of levodopa-induced dyskinesias in PD. | 1999 Oct 22 |
|
| Preventing levodopa-induced dyskinesias. | 2000 Apr |
|
| Sleep attacks and Parkinson's disease treatment. | 2000 Apr 15 |
|
| 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 |
|
| 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 |
|
| Detection and assessment of the severity of levodopa-induced dyskinesia in patients with Parkinson's disease by neural networks. | 2000 Nov |
|
| 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 |
|
| Pharmacokinetic-pharmacodynamic relationship of levodopa with and without tolcapone in patients with Parkinson's disease. | 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 |
|
| 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 |
|
| Dimeric L-dopa derivatives as potential prodrugs. | 2001 Apr 23 |
|
| Dopamine D(2) receptors regulate tyrosine hydroxylase activity and phosphorylation at Ser40 in rat striatum. | 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 |
|
| Enhanced abilities of highly swollen chitosan beads for color removal and tyrosinase immobilization. | 2001 Jan 29 |
|
| Resveratrol and a novel tyrosinase in Carignan grape juice. | 2001 Mar |
|
| Chromium(VI) reduction by catechol(amine)s results in DNA cleavage in vitro: relevance to chromium genotoxicity. | 2001 May |
|
| Coadministration of (-)-OSU6162 with l-DOPA normalizes preproenkephalin mRNA expression in the sensorimotor striatum of primates with unilateral 6-OHDA lesions. | 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
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G69RN28K8B
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138455038
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1374841-22-1
Created by
admin on Sat Dec 16 14:44:40 GMT 2023 , Edited by admin on Sat Dec 16 14:44:40 GMT 2023
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ACTIVE MOIETY
SUBSTANCE RECORD
