U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C11H15NO4
Molecular Weight 225.2411
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ETILEVODOPA

SMILES

CCOC(=O)[C@@H](N)CC1=CC=C(O)C(O)=C1

InChI

InChIKey=NULMGOSOSZBEQL-QMMMGPOBSA-N
InChI=1S/C11H15NO4/c1-2-16-11(15)8(12)5-7-3-4-9(13)10(14)6-7/h3-4,6,8,13-14H,2,5,12H2,1H3/t8-/m0/s1

HIDE SMILES / InChI

Molecular Formula C11H15NO4
Molecular Weight 225.2411
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
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.

Originator

Curator's Comment: # Hoffmann-La Roche

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Stalevo

Approved Use

Stalevo® (carbidopa, levodopa and entacapone) is indicated to treat patients with idiopathic Parkinson’s disease.

Launch Date

2003
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
0.946 μg/mL
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

AUC

ValueDoseCo-administeredAnalytePopulation
84.8 μg × min/mL
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

T1/2

ValueDoseCo-administeredAnalytePopulation
78.7 min
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

Funbound

ValueDoseCo-administeredAnalytePopulation
80%
LEVODOPA plasma
Homo sapiens
Doses

Doses

DosePopulationAdverse 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
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)
Nausea (below serious, 2 patients)
Sources:
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)
Dry mouth (below serious, 2 patients)
Nausea (below serious, 1 patient)
Fatigue (below serious, 2 patients)
Sources:
AEs

AEs

AESignificanceDosePopulation
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:
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
Levodopa-induced postural hypotension. Treatment with fludrocortisone.
1975 Jan
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
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
Riluzole for levodopa-induced dyskinesias in advanced Parkinson's disease.
1999 May 22
Actions of adenosine A2A receptor antagonist KW-6002 on drug-induced catalepsy and hypokinesia caused by reserpine or MPTP.
1999 Nov
Internal globus pallidus discharge is nearly suppressed during levodopa-induced dyskinesias.
1999 Nov
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
Four novel mutations in the tyrosine hydroxylase gene in patients with infantile parkinsonism.
2000 Jan
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
Centrally initiated postural adjustments in parkinsonian patients on and off levodopa.
2000 Nov
Inhibition of potato polyphenol oxidase by anions and activity in various carboxylate buffers (pH 4.8) at constant ionic strength.
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
Selective dopaminergic vulnerability: 3,4-dihydroxyphenylacetaldehyde targets mitochondria.
2001 Apr 15
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
Molecular mechanisms controlling the rate and specificity of catechol O-methylation by human soluble catechol O-methyltransferase.
2001 Feb
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
Parkinsonism after glycine-derivate exposure.
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
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 Fri Dec 15 15:43:03 GMT 2023
Edited
by admin
on Fri Dec 15 15:43:03 GMT 2023
Record UNII
895X917GYE
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ETILEVODOPA
INN   USAN   WHO-DD  
INN   USAN  
Official Name English
O-ETHYL-DOPA
Systematic Name English
TV-1203
Code English
(-)-3,4-DIHYDROXY-L-PHENYLALANINE, ETHYL ESTER
Common Name English
L-DOPA ETHYL ESTER
Common Name English
Etilevodopa [WHO-DD]
Common Name English
3-HYDROXY-TYROSINE ETHYL ESTER
Systematic Name English
L-TYROSINE, 3-HYDROXY-, ETHYL ESTER
Common Name English
3-HYDROXY-L-TYROSINE ETHYL ESTER
Systematic Name English
3,4-DIHYDROXY-L-PHENYLALANINE ETHYL ESTER
Systematic Name English
ETILEVODOPA [USAN]
Common Name English
etilevodopa [INN]
Common Name English
Classification Tree Code System Code
WHO-VATC QN04BA06
Created by admin on Fri Dec 15 15:43:03 GMT 2023 , Edited by admin on Fri Dec 15 15:43:03 GMT 2023
NCI_THESAURUS C38149
Created by admin on Fri Dec 15 15:43:03 GMT 2023 , Edited by admin on Fri Dec 15 15:43:03 GMT 2023
WHO-ATC N04BA06
Created by admin on Fri Dec 15 15:43:03 GMT 2023 , Edited by admin on Fri Dec 15 15:43:03 GMT 2023
Code System Code Type Description
SMS_ID
100000087477
Created by admin on Fri Dec 15 15:43:03 GMT 2023 , Edited by admin on Fri Dec 15 15:43:03 GMT 2023
PRIMARY
WIKIPEDIA
Etilevodopa
Created by admin on Fri Dec 15 15:43:03 GMT 2023 , Edited by admin on Fri Dec 15 15:43:03 GMT 2023
PRIMARY
DAILYMED
895X917GYE
Created by admin on Fri Dec 15 15:43:03 GMT 2023 , Edited by admin on Fri Dec 15 15:43:03 GMT 2023
PRIMARY
PUBCHEM
170345
Created by admin on Fri Dec 15 15:43:03 GMT 2023 , Edited by admin on Fri Dec 15 15:43:03 GMT 2023
PRIMARY
USAN
MM-88
Created by admin on Fri Dec 15 15:43:03 GMT 2023 , Edited by admin on Fri Dec 15 15:43:03 GMT 2023
PRIMARY
RXCUI
1421444
Created by admin on Fri Dec 15 15:43:03 GMT 2023 , Edited by admin on Fri Dec 15 15:43:03 GMT 2023
PRIMARY RxNorm
NCI_THESAURUS
C81562
Created by admin on Fri Dec 15 15:43:03 GMT 2023 , Edited by admin on Fri Dec 15 15:43:03 GMT 2023
PRIMARY
DRUG CENTRAL
4422
Created by admin on Fri Dec 15 15:43:03 GMT 2023 , Edited by admin on Fri Dec 15 15:43:03 GMT 2023
PRIMARY
FDA UNII
895X917GYE
Created by admin on Fri Dec 15 15:43:03 GMT 2023 , Edited by admin on Fri Dec 15 15:43:03 GMT 2023
PRIMARY
MESH
C481190
Created by admin on Fri Dec 15 15:43:03 GMT 2023 , Edited by admin on Fri Dec 15 15:43:03 GMT 2023
PRIMARY
EPA CompTox
DTXSID10905092
Created by admin on Fri Dec 15 15:43:03 GMT 2023 , Edited by admin on Fri Dec 15 15:43:03 GMT 2023
PRIMARY
CAS
37178-37-3
Created by admin on Fri Dec 15 15:43:03 GMT 2023 , Edited by admin on Fri Dec 15 15:43:03 GMT 2023
PRIMARY
INN
7818
Created by admin on Fri Dec 15 15:43:03 GMT 2023 , Edited by admin on Fri Dec 15 15:43:03 GMT 2023
PRIMARY
ChEMBL
CHEMBL1823681
Created by admin on Fri Dec 15 15:43:03 GMT 2023 , Edited by admin on Fri Dec 15 15:43:03 GMT 2023
PRIMARY
EVMPD
SUB02042MIG
Created by admin on Fri Dec 15 15:43:03 GMT 2023 , Edited by admin on Fri Dec 15 15:43:03 GMT 2023
PRIMARY
DRUG BANK
DB06535
Created by admin on Fri Dec 15 15:43:03 GMT 2023 , Edited by admin on Fri Dec 15 15:43:03 GMT 2023
PRIMARY
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