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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
Structure of LEVODOPA

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

HIDE SMILES / InChI
Molecular Formula C9H11NO4
Molecular Weight 197.1879
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

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

Approval Year

1970
42
Targets

Targets

Primary TargetPharmacologyConditionPotency
Agonist
2361
Parkinson Disease
Agonist
2361
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Dopamine receptor
Approved
7883
Stalevo
PubMed

PubMed

TitleDatePubMed
The effects of combining carbidopa with levodopa for Parkinson's disease.
1975 Dec
Levodopa-induced postural hypotension. Treatment with fludrocortisone.
1975 Jan
[Abnormal movements induced by L-dopa. New therapeutic possibilities].
1975 Jan 25
Persistent parkinsonism following neuroleptanalgesia.
1975 May
Functional mapping of the human globus pallidus: contrasting effect of stimulation in the internal and external pallidum in Parkinson's disease.
2000
[Amantadine for the treatment of levodopa dyskinesias in Parkinson's disease].
2000
[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
Four novel mutations in the tyrosine hydroxylase gene in patients with infantile parkinsonism.
2000 Jan
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
[Treatment of advanced Parkinson's disease].
2000 Oct
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
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
Pathologic gambling in Parkinson's disease: a behavioral manifestation of pharmacologic treatment?
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
Inhibition of potato polyphenol oxidase by anions and activity in various carboxylate buffers (pH 4.8) at constant ionic strength.
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
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
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
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
Does stimulation of the GPi control dyskinesia by activating inhibitory axons?
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
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
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
Intravenous amantadine improves levadopa-induced dyskinesias: an acute double-blind placebo-controlled study.
2001 May
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
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

Patents

8440795
6
8575276
6
JP2002520362A
6
JP2003512428A
9
JP2003528136A
7
JP2004529175A
6
JP2005507400A
6
JP2005514382A
16
JP2006511558A
6
JP2010155828A
6
JP2010195730A
6
JP2012500221A
6
JP2012500283A
14
JP2013543482A
6
JP2013545745A
7
JP2738881B2
6
JP3542801B2
6
JP4722295B2
86
JP4801042B2
6
JPH00570345A
7
JPH01216940A
8
JPH01268633A
6
JPH0381258A
6
JPH05213741A
6
JPH06157251A
6
JPH0638749A
7
JPH07252118A
6
JPH08512055A
14
JPH0867657A
6
JPH09225019A
11
JPH09291033A
6
JPH0987977A
6
JPS5441329A
6
JPS5651991A
6
JPS59164783A
6
JPS61134397A
6
JPS6354319A
6
JPS6410995A
6

Sample Use Guides

In Vivo Use Guide
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
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 Mon Oct 21 20:45:45 UTC 2019
Edited
by admin
on Mon Oct 21 20:45:45 UTC 2019
Record UNII
46627O600J
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
LEVODOPA
EMA EPAR   EP   HSDB   INN   MART.   MI   ORANGE BOOK   USAN   USP   USP-RS   VANDF   WHO-DD   WHO-IP  
INN   USAN  
Official Name English
LEVODOPA [JAN]
Common Name English
RYTARY COMPONENT LEVODOPA
Brand Name English
CARBILEV COMPONENT LEVODOPA
Common Name English
LEVODOPA [INN]
Common Name English
LEVODOPA COMPONENT OF SINEMET
Common Name English
V-1512
Code English
LEVODOPA [USP]
Common Name English
LEVODOPA [WHO-IP]
Common Name English
LEVODOPA [ORANGE BOOK]
Common Name English
CORBILTA COMPONENT LEVODOPA
Brand Name English
LEVODOPA [EMA EPAR]
Common Name English
L-DOPA
Systematic Name English
LEVODOPA [USP-RS]
Common Name English
LEVODOPA COMPONENT OF DUOPA
Brand Name English
BENDOPA
Brand Name English
LEVODOPA COMPONENT OF STALEVO
Brand Name English
LEVODOPA [USAN]
Common Name English
LEVODOPA COMPONENT OF DOPASNAP
Common Name English
LEVODOPA/CARBIDOPA/ENTACAPONE ORION COMPONENT LEVODOPA
Brand Name English
LEVODOPA COMPONENT OF CORBILTA
Brand Name English
STALEVO COMPONENT LEVODOPA
Brand Name English
LEVODOPA COMPONENT OF PARCOPA
Common Name English
LARODOPA
Brand Name English
LEVODOPA [WHO-DD]
Common Name English
LEVODOPA COMPONENT OF LEVODOPA/CARBIDOPA/ENTACAPONE ORION
Brand Name English
IPX203 COMPONENT LEVODOPA
Common Name English
DOPAR
Brand Name English
DUOPA COMPONENT LEVODOPA
Brand Name English
PARCOPA COMPONENT LEVODOPA
Common Name English
LEVODOPA [EP]
Common Name English
LEVODOPA [HSDB]
Common Name English
IPX-203 COMPONENT LEVODOPA
Common Name English
LEVODOPA [MI]
Common Name English
LEVODOPA COMPONENT OF CARBILEV
Common Name English
SINEMET COMPONENT LEVODOPA
Common Name English
DIHYDROXYPHENYLALANINE
Systematic Name English
NSC-118381
Code English
(-)-3-(3,4-DIHYDROXYPHENYL)-L-ALANINE
Systematic Name English
LEVODOPUM [WHO-IP LATIN]
Common Name English
LEVODOPA COMPONENT OF RYTARY
Brand Name English
L-TYROSINE, 3-HYDROXY-
Systematic Name English
DOPASNAP COMPONENT LEVODOPA
Common Name English
DOPA, L-
Systematic Name English
CVT-301
Common Name English
LEVODOPA [MART.]
Common Name English
INBRIJA
Brand Name English
LEVODOPA [VANDF]
Common Name English
Classification Tree Code System Code
WHO-VATC QN04BA03
Created by admin on Mon Oct 21 20:45:45 UTC 2019 , Edited by admin on Mon Oct 21 20:45:45 UTC 2019
WHO-ESSENTIAL MEDICINES LIST 09 (LEV/CAR)
Created by admin on Mon Oct 21 20:45:45 UTC 2019 , Edited by admin on Mon Oct 21 20:45:45 UTC 2019
EMA ASSESSMENT REPORTS CORBILTA (AUTHORIZED: PARKINSON DISEASE)
Created by admin on Mon Oct 21 20:45:45 UTC 2019 , Edited by admin on Mon Oct 21 20:45:45 UTC 2019
EU-Orphan Drug EU/3/01/035
Created by admin on Mon Oct 21 20:45:45 UTC 2019 , Edited by admin on Mon Oct 21 20:45:45 UTC 2019
EMA ASSESSMENT REPORTS STALEVO (AUTHORIZED: PARKINSON DISEASE)
Created by admin on Mon Oct 21 20:45:45 UTC 2019 , Edited by admin on Mon Oct 21 20:45:45 UTC 2019
WHO-ATC N04BA01
Created by admin on Mon Oct 21 20:45:45 UTC 2019 , Edited by admin on Mon Oct 21 20:45:45 UTC 2019
EMA ASSESSMENT REPORTS CORBILTA (AUTHORIZED: NEURODEGENERATIVE DISEASES)
Created by admin on Mon Oct 21 20:45:45 UTC 2019 , Edited by admin on Mon Oct 21 20:45:45 UTC 2019
WHO-VATC QN04BA02
Created by admin on Mon Oct 21 20:45:45 UTC 2019 , Edited by admin on Mon Oct 21 20:45:45 UTC 2019
WHO-ATC N04BA03
Created by admin on Mon Oct 21 20:45:45 UTC 2019 , Edited by admin on Mon Oct 21 20:45:45 UTC 2019
WHO-VATC QN04BA01
Created by admin on Mon Oct 21 20:45:45 UTC 2019 , Edited by admin on Mon Oct 21 20:45:45 UTC 2019
NDF-RT N0000193220
Created by admin on Mon Oct 21 20:45:45 UTC 2019 , Edited by admin on Mon Oct 21 20:45:45 UTC 2019
LIVERTOX 552
Created by admin on Mon Oct 21 20:45:45 UTC 2019 , Edited by admin on Mon Oct 21 20:45:45 UTC 2019
FDA ORPHAN DRUG 129499
Created by admin on Mon Oct 21 20:45:45 UTC 2019 , Edited by admin on Mon Oct 21 20:45:45 UTC 2019
NDF-RT N0000175754
Created by admin on Mon Oct 21 20:45:45 UTC 2019 , Edited by admin on Mon Oct 21 20:45:45 UTC 2019
WHO-ATC N04BA02
Created by admin on Mon Oct 21 20:45:45 UTC 2019 , Edited by admin on Mon Oct 21 20:45:45 UTC 2019
NCI_THESAURUS C66884
Created by admin on Mon Oct 21 20:45:45 UTC 2019 , Edited by admin on Mon Oct 21 20:45:45 UTC 2019
NDF-RT N0000175755
Created by admin on Mon Oct 21 20:45:45 UTC 2019 , Edited by admin on Mon Oct 21 20:45:45 UTC 2019
EMA ASSESSMENT REPORTS LEVODOPA/CARBIDOPA/ENTACAPONE ORION (AUTHORIZED: PARKINSON DISEASE)
Created by admin on Mon Oct 21 20:45:45 UTC 2019 , Edited by admin on Mon Oct 21 20:45:45 UTC 2019
EMA ASSESSMENT REPORTS CORBILTA (AUTHORIZED: NERVOUS SYSTEM DISEASES)
Created by admin on Mon Oct 21 20:45:45 UTC 2019 , Edited by admin on Mon Oct 21 20:45:45 UTC 2019
Code System Code Type Description
WIKIPEDIA
L-DOPA
Created by admin on Mon Oct 21 20:45:45 UTC 2019 , Edited by admin on Mon Oct 21 20:45:45 UTC 2019
PRIMARY
WHO INTERNATIONAL PHARMACOPEIA
LEVODOPA
Created by admin on Mon Oct 21 20:45:45 UTC 2019 , Edited by admin on Mon Oct 21 20:45:45 UTC 2019
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.
MESH
D007980
Created by admin on Mon Oct 21 20:45:45 UTC 2019 , Edited by admin on Mon Oct 21 20:45:45 UTC 2019
PRIMARY
NCI_THESAURUS
C611
Created by admin on Mon Oct 21 20:45:45 UTC 2019 , Edited by admin on Mon Oct 21 20:45:45 UTC 2019
PRIMARY
EVMPD
SUB08468MIG
Created by admin on Mon Oct 21 20:45:45 UTC 2019 , Edited by admin on Mon Oct 21 20:45:45 UTC 2019
PRIMARY
EPA CompTox
59-92-7
Created by admin on Mon Oct 21 20:45:45 UTC 2019 , Edited by admin on Mon Oct 21 20:45:45 UTC 2019
PRIMARY
ChEMBL
CHEMBL1009
Created by admin on Mon Oct 21 20:45:45 UTC 2019 , Edited by admin on Mon Oct 21 20:45:45 UTC 2019
PRIMARY
HSDB
59-92-7
Created by admin on Mon Oct 21 20:45:45 UTC 2019 , Edited by admin on Mon Oct 21 20:45:45 UTC 2019
PRIMARY
IUPHAR
3639
Created by admin on Mon Oct 21 20:45:45 UTC 2019 , Edited by admin on Mon Oct 21 20:45:45 UTC 2019
PRIMARY
MERCK INDEX
M6786
Created by admin on Mon Oct 21 20:45:45 UTC 2019 , Edited by admin on Mon Oct 21 20:45:45 UTC 2019
PRIMARY Merck Index
INN
2651
Created by admin on Mon Oct 21 20:45:45 UTC 2019 , Edited by admin on Mon Oct 21 20:45:45 UTC 2019
PRIMARY
ECHA (EC/EINECS)
200-445-2
Created by admin on Mon Oct 21 20:45:45 UTC 2019 , Edited by admin on Mon Oct 21 20:45:45 UTC 2019
PRIMARY
LactMed
59-92-7
Created by admin on Mon Oct 21 20:45:45 UTC 2019 , Edited by admin on Mon Oct 21 20:45:45 UTC 2019
PRIMARY
CAS
59-92-7
Created by admin on Mon Oct 21 20:45:45 UTC 2019 , Edited by admin on Mon Oct 21 20:45:45 UTC 2019
PRIMARY
DRUG BANK
DB01235
Created by admin on Mon Oct 21 20:45:45 UTC 2019 , Edited by admin on Mon Oct 21 20:45:45 UTC 2019
PRIMARY
RXCUI
6375
Created by admin on Mon Oct 21 20:45:45 UTC 2019 , Edited by admin on Mon Oct 21 20:45:45 UTC 2019
PRIMARY RxNorm
Related Record Type Details
CATECHOL O-METHYLTRANSFERASE
METABOLIC ENZYME -> SUBSTRATE
MUCUNA PRURIENS SEED
PARENT -> CONSTITUENT ALWAYS PRESENT
Structure of LEVODOPA
BASIS OF STRENGTH->SUBSTANCE
ASSAY (HPLC)
USP
Structure of LEVODOPA
BASIS OF STRENGTH->SUBSTANCE
ASSAY (TITRATION)
EP
D(1A) DOPAMINE RECEPTOR
TARGET -> AGONIST
Related Record Type Details
Structure of FOSLEVODOPA
PRODRUG -> METABOLITE ACTIVE
Structure of BISMUTH SUBDOPATE
PRODRUG -> METABOLITE ACTIVE
Structure of DOPAMINE
METABOLITE ACTIVE -> PRODRUG
Structure of DOPAMINE
METABOLITE -> PARENT
by DOPA decarboxylase
Structure of 3-O-METHYLDOPA
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).
Related Record Type Details
Structure of 3-O-METHYLDOPA, DL-
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Structure of DOPA, D-
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Structure of 6-HYDROXYDOPA, L-
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
Structure of 6-HYDROXYDOPA, DL-
PARENT -> IMPURITY
Structure of 6-HYDROXYDOPA, L-
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Structure of TYROSINE
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
Structure of TYROSINE
IMPURITY -> PARENT
For the calculation of contents, multiply the peak areas by 2.2
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Structure of 3-O-METHYLDOPA, DL-
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
Structure of 3,4-DIMETHOXYPHENYLALANINE, L-
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
Related Record Type Details
Structure of LEVODOPA
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