Identification

Name
Levodopa
Accession Number
DB01235
Description

Levodopa is a prodrug of dopamine that is administered to patients with Parkinson's due to its ability to cross the blood-brain barrierLabel. Levodopa can be metabolised to dopamine on either side of the blood-brain barrier and so it is generally administered with a dopa decarboxylase inhibitor like carbidopa to prevent metabolism until after it has crossed the blood-brain barrierLabel,1. Once past the blood-brain barrier, levodopa is metabolized to dopamine and supplements the low endogenous levels of dopamine to treat symptoms of Parkinson'sLabel. The first developed drug product that was approved by the FDA was a levodopa and carbidopa combined product called Sinemet that was approved on May 2, 19751,7.

Type
Small Molecule
Groups
Approved
Structure
Thumb
Weight
Average: 197.1879
Monoisotopic: 197.068807845
Chemical Formula
C9H11NO4
Synonyms
  • (−)-3-(3,4-dihydroxyphenyl)-L-alanine
  • (−)-dopa
  • 3-Hydroxy-L-tyrosine
  • 3,4-Dihydroxy-L-phenylalanine
  • Dihydroxy-L-phenylalanine
  • L-3,4-dihydroxyphenylalanine
  • L-beta-(3,4-Dihydroxyphenyl)alanine
  • L-DOPA
  • Levodopa
  • Levodopum
  • β-(3,4-dihydroxyphenyl)-L-alanine
  • β-(3,4-dihydroxyphenyl)alanine
External IDs
  • V-1512

Pharmacology

Indication

Levodopa on its own is formulated as an oral inhalation powder indicated for intermittent treatment of off episodes in Parkinson's patients who are already being treated with carbidopa and levodopaLabel. Levodopa is most commonly formulated as an oral tablet with a peripheral dopa decarboxylase inhibitor indicated for treatment of Parkinson's disease, post-encephalitic parkinsonism, and symptomatic parkinsonism following carbon monoxide intoxication or manganese intoxication8.

Associated Conditions
Contraindications & Blackbox Warnings
Learn about our commercial Contraindications & Blackbox Warnings data.
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Pharmacodynamics

Levodopa is able to cross the blood-brain barrier while dopamine is notLabel,8. The addition of a peripheral dopa decarboxylase inhibitor prevents the conversion of levodopa to dopamine in the periphery so that more levodopa can reach the blood-brain barrierLabel,8. Once past the blood-brain barrier, levodopa is converted to dopamine by aromatic-L-amino-acid decarboxylaseLabel,8.

Mechanism of action

Levodopa by various routes crosses the blood brain barrier, is decarboxylated to form dopamineLabel,8. This supplemental dopamine performs the role that endogenous dopamine cannot due to a decrease of natural concentrations and stimulates dopaminergic receptorsLabel,8.

TargetActionsOrganism
ADopamine D1 receptor
agonist
Humans
ADopamine D5 receptor
agonist
Humans
ADopamine D2 receptor
agonist
Humans
ADopamine D3 receptor
agonist
Humans
ADopamine D4 receptor
agonist
Humans
Absorption

Orally inhaled levodopa reaches a peak concentration in 0.5 hours with a bioavailability than is 70% that of the immediate release levodopa tablets with a peripheral dopa decarboxylase inhibitor like carbidopa or benserazideLabel,1.

Volume of distribution

168L for orally inhaled levodopaLabel.

Protein binding

Levodopa binding to plasma proteins is negligible6.

Metabolism

Levodopa is either converted to dopamine by aromatic-L-amino-acid decarboxylase or O-methylated to 3-O-methyldopa by catechol-O-methyltransferaseLabel,2,3. 3-O-methyldopa cannot be metabolized to dopamine3. Once levodopa is converted to dopamine, it is converted to sulfated or glucuronidated metabolites, epinephrine E, or homovanillic acid through various metabolic processes2. The primary metabolites are 3,4-dihydroxyphenylacetic acid (13-47%) and homovanillic acid (23-39%)3,5.

Hover over products below to view reaction partners

Route of elimination

After 48 hours, 0.17% of an orally administered dose is recovered in stool, 0.28% is exhaled, and 78.4% is recovered in urine5

Half-life

2.3 hours for orally inhaled levodopaLabel. Oral levodopa has a half life of 50 minutes but when combined with a peripheral dopa decarboxylase inhibitor, the half life is increased to 1.5 hours8.

Clearance

Intravenously administered levodopa is cleared at a rate of 14.2mL/min/kg in elderly patients and 23.4mL/min/kg in younger patients4. When given carbidopa, the clearance of levodopa was 5.8mL/min/kg in elderyly patients and 9.3mL/min/kg in younger patients4.

Adverse Effects
Learn about our commercial Adverse Effects data.
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Toxicity

There is no readily available data for the use of levodopa in pregnancyLabel. Rabbits treated with levodopa and carbidopa produced smaller litters and their offspring developed visceral and skeletal deformitiesLabel. Levodopa may lower prolactin and interfere with lactation but there is limited human data to demonstrate this effectLabel. Levodopa is present in human breast milk and so the potential effects of nursing while taking levodopa should be considered before prescribing levodopa to nursing mothersLabel. There is currently a lack of data on the safety and effectiveness of using levodopa in pediatric patientsLabel. Patients over 65 years of age are more likely to experience adverse effects associated with taking levodopa, however this generally is not sufficient to exclude this patient group from treatmentLabel.

Affected organisms
  • Humans and other mammals
Pathways
PathwayCategory
Aromatic L-Aminoacid Decarboxylase DeficiencyDisease
Tyrosine MetabolismMetabolic
Catecholamine BiosynthesisMetabolic
Tyrosinemia Type IDisease
Disulfiram Action PathwayDrug action
AlkaptonuriaDisease
HawkinsinuriaDisease
Tyrosinemia, Transient, of the NewbornDisease
Tyrosine Hydroxylase DeficiencyDisease
Dopamine beta-Hydroxylase DeficiencyDisease
Monoamine Oxidase-A Deficiency (MAO-A)Disease
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
AcebutololThe risk or severity of hypotension and orthostatic hypotension can be increased when Acebutolol is combined with Levodopa.
AcetazolamideThe risk or severity of adverse effects can be increased when Acetazolamide is combined with Levodopa.
AcetophenazineThe risk or severity of adverse effects can be increased when Acetophenazine is combined with Levodopa.
AclidiniumThe absorption of Levodopa can be decreased when combined with Aclidinium.
AgomelatineThe risk or severity of adverse effects can be increased when Levodopa is combined with Agomelatine.
AldesleukinThe risk or severity of hypotension and orthostatic hypotension can be increased when Aldesleukin is combined with Levodopa.
AlfentanilThe risk or severity of adverse effects can be increased when Alfentanil is combined with Levodopa.
AlimemazineThe risk or severity of adverse effects can be increased when Levodopa is combined with Alimemazine.
AliskirenThe risk or severity of hypotension and orthostatic hypotension can be increased when Aliskiren is combined with Levodopa.
AlmotriptanThe risk or severity of adverse effects can be increased when Almotriptan is combined with Levodopa.
Additional Data Available
  • Extended Description
    Extended Description

    Extended description of the mechanism of action and particular properties of each drug interaction.

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  • Severity
    Severity

    A severity rating for each drug interaction, from minor to major.

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  • Evidence Level
    Evidence Level

    A rating for the strength of the evidence supporting each drug interaction.

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  • Action
    Action

    An effect category for each drug interaction. Know how this interaction affects the subject drug.

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Food Interactions
  • Avoid multivalent ions. Iron salts may reduce levodopa absorption.
  • Take with or without food. A diet high in protein may delay absorption and AUC of levodopa.

Products

Product Images
International/Other Brands
Bidopal (GlaxoSmithKline) / Dopar / Doparl (Kyowa Hakko Kirin) / Dopasol (Daiichi Sankyo) / Dopaston (Ohara Yakuhin)
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
InbrijaCapsule42 mg/1Respiratory (inhalation)Acorda Therapeutics, Inc.2018-12-22Not applicableUs
Additional Data Available
  • Application Number
    Application Number

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

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  • Product Code
    Product Code

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
Aa-levocarb CRLevodopa (100 mg) + Carbidopa (25 mg)Tablet, extended releaseOralAa Pharma Inc2009-02-04Not applicableCanada
Aa-levocarb CRLevodopa (200 mg) + Carbidopa (50 mg)Tablet, extended releaseOralAa Pharma Inc2003-11-13Not applicableCanada
Apo-levocarb - Tab 10mg/100mgLevodopa (100 mg) + Carbidopa (10 mg)TabletOralApotex Corporation1995-12-31Not applicableCanada
Apo-levocarb - Tab 25mg/250mgLevodopa (250 mg) + Carbidopa (25 mg)TabletOralApotex Corporation1995-12-31Not applicableCanada
Apo-levocarb-tab 25mg/100mgLevodopa (100 mg) + Carbidopa (25 mg)TabletOralApotex Corporation1995-12-31Not applicableCanada
Carbidopa and LevodopaLevodopa (200 mg/1) + Carbidopa hydrate (50 mg/1)Tablet, extended releaseOralETHEX2007-08-15Not applicableUs
Carbidopa and LevodopaLevodopa (100 mg/1) + Carbidopa hydrate (25 mg/1)Tablet, extended releaseOralPhysicians Total Care, Inc.2006-08-18Not applicableUs
Carbidopa and LevodopaLevodopa (100 mg/1) + Carbidopa hydrate (25 mg/1)TabletOralAphena Pharma Solutions - Tennessee, LLC2018-07-16Not applicableUs
Carbidopa and LevodopaLevodopa (200 mg/1) + Carbidopa hydrate (50 mg/1)Tablet, extended releaseOralMylan Pharmaceuticals Inc.1999-10-06Not applicableUs0378 009420180907 15195 woun21
Carbidopa and LevodopaLevodopa (100 mg/1) + Carbidopa hydrate (25 mg/1)TabletOralMajor Pharmaceuticals2011-02-11Not applicableUs

Categories

ATC Codes
N04BA03 — Levodopa, decarboxylase inhibitor and comt inhibitorN04BA01 — LevodopaN04BA02 — Levodopa and decarboxylase inhibitor
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as tyrosine and derivatives. These are compounds containing tyrosine or a derivative thereof resulting from reaction of tyrosine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.
Kingdom
Organic compounds
Super Class
Organic acids and derivatives
Class
Carboxylic acids and derivatives
Sub Class
Amino acids, peptides, and analogues
Direct Parent
Tyrosine and derivatives
Alternative Parents
Phenylalanine and derivatives / Phenylpropanoic acids / L-alpha-amino acids / Amphetamines and derivatives / Catechols / 1-hydroxy-2-unsubstituted benzenoids / 1-hydroxy-4-unsubstituted benzenoids / Aralkylamines / Amino acids / Monocarboxylic acids and derivatives
show 6 more
Substituents
1-hydroxy-2-unsubstituted benzenoid / 1-hydroxy-4-unsubstituted benzenoid / 3-phenylpropanoic-acid / Alpha-amino acid / Amine / Amino acid / Amphetamine or derivatives / Aralkylamine / Aromatic homomonocyclic compound / Benzenoid
show 18 more
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
non-proteinogenic L-alpha-amino acid, L-tyrosine derivative, dopa (CHEBI:15765) / Other amino acids, Biogenic amines (C00355)

Chemical Identifiers

UNII
46627O600J
CAS number
59-92-7
InChI Key
WTDRDQBEARUVNC-LURJTMIESA-N
InChI
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
IUPAC Name
(2S)-2-amino-3-(3,4-dihydroxyphenyl)propanoic acid
SMILES
N[C@@H](CC1=CC(O)=C(O)C=C1)C(O)=O

References

Synthesis Reference

Vincenzo Cannata, Giancarlo Tamerlani, Mauro Morotti, "Process for the synthesis of the levodopa." U.S. Patent US4962223, issued December, 1986.

US4962223
General References
  1. Djamshidian A, Poewe W: Apomorphine and levodopa in Parkinson's disease: Two revolutionary drugs from the 1950's. Parkinsonism Relat Disord. 2016 Dec;33 Suppl 1:S9-S12. doi: 10.1016/j.parkreldis.2016.12.004. Epub 2016 Dec 22. [PubMed:28012951]
  2. Meiser J, Weindl D, Hiller K: Complexity of dopamine metabolism. Cell Commun Signal. 2013 May 17;11(1):34. doi: 10.1186/1478-811X-11-34. [PubMed:23683503]
  3. Elroby SA, Makki MS, Sobahi TR, Hilal RH: Toward the understanding of the metabolism of levodopa I. DFT investigation of the equilibrium geometries, acid-base properties and levodopa-water complexes. Int J Mol Sci. 2012;13(4):4321-39. doi: 10.3390/ijms13044321. Epub 2012 Apr 2. [PubMed:22605980]
  4. Robertson DR, Wood ND, Everest H, Monks K, Waller DG, Renwick AG, George CF: The effect of age on the pharmacokinetics of levodopa administered alone and in the presence of carbidopa. Br J Clin Pharmacol. 1989 Jul;28(1):61-9. [PubMed:2775615]
  5. Abrams WB, Coutinho CB, Leon AS, Spiegel HE: Absorption and metabolism of levodopa. JAMA. 1971 Dec 27;218(13):1912-4. [PubMed:5171067]
  6. Fanali G, Rampoldi V, di Masi A, Bolli A, Lopiano L, Ascenzi P, Fasano M: Binding of anti-Parkinson's disease drugs to human serum albumin is allosterically modulated. IUBMB Life. 2010 May;62(5):371-6. doi: 10.1002/iub.317. [PubMed:20225277]
  7. FDA Approved Drug Products: Sinemet [Link]
  8. Sinemet FDA Label [File]
Human Metabolome Database
HMDB0000181
KEGG Drug
D00059
KEGG Compound
C00355
PubChem Compound
6047
PubChem Substance
46508120
ChemSpider
5824
BindingDB
60928
RxNav
6375
ChEBI
15765
ChEMBL
CHEMBL1009
ZINC
ZINC000000895199
Therapeutic Targets Database
DAP000209
PharmGKB
PA450213
Guide to Pharmacology
GtP Drug Page
PDBe Ligand
DAH
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Levodopa
PDB Entries
1ivv / 1rnr / 2vh3 / 2zwe / 2zwf / 2zwg / 3teg / 3teh / 4eis / 4p6s
show 17 more
FDA label
Download (705 KB)
MSDS
Download (37.5 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4CompletedNot AvailableHealthy Volunteers1
4CompletedOtherPost Traumatic Stress Disorder (PTSD)1
4CompletedTreatmentAdvanced Idiopathic Parkinson's Disease1
4CompletedTreatmentAkinesia / Delayed Levadopa Onset / Delayed Levodopa Onset / Mobility decreased / Motor Symptoms / Parkinson's Disease (PD)1
4CompletedTreatmentAphasia / Cerebrovascular Accident1
4CompletedTreatmentDecreased Gait Speed / Decreased Processing Speed / Depression Not Otherwise Specified / Dysthymic Disorder / Major Depressive Disorder (MDD)1
4CompletedTreatmentDyskinesia / Parkinson's Disease (PD)1
4CompletedTreatmentHealthy Volunteers1
4CompletedTreatmentIdiopathic Parkinson's Disease1
4CompletedTreatmentImpulse-control disorder1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
  • Actavis Group
  • Amerisource Health Services Corp.
  • Apotex Inc.
  • Atlantic Biologicals Corporation
  • AzurPharma Inc.
  • Bristol-Myers Squibb Co.
  • Caraco Pharmaceutical Labs
  • Cardinal Health
  • Caremark LLC
  • Cima Laboratories Inc.
  • Direct Dispensing Inc.
  • Diversified Healthcare Services Inc.
  • Endo Pharmaceuticals Inc.
  • Global Pharmaceuticals
  • Heartland Repack Services LLC
  • Impax Laboratories Inc.
  • Ivax Pharmaceuticals
  • Major Pharmaceuticals
  • Mckesson Corp.
  • Medisca Inc.
  • Merck & Co.
  • Murfreesboro Pharmaceutical Nursing Supply
  • Mylan
  • Novartis AG
  • Nucare Pharmaceuticals Inc.
  • Orion Corporation
  • Pharmaceutical Utilization Management Program VA Inc.
  • Physicians Total Care Inc.
  • Prepak Systems Inc.
  • Remedy Repack
  • Resource Optimization and Innovation LLC
  • Sandhills Packaging Inc.
  • Schwarz Pharma Inc.
  • Southwood Pharmaceuticals
  • Spectrum Pharmaceuticals
  • Sun Pharmaceutical Industries Ltd.
  • Teva Pharmaceutical Industries Ltd.
  • Torpharm Inc.
  • UDL Laboratories
  • Vangard Labs Inc.
  • Watson Pharmaceuticals
Dosage Forms
FormRouteStrength
TabletOral
Tablet, extended releaseOral
GelEnteral
SuspensionEnteral
CapsuleRespiratory (inhalation)42 mg/1
Capsule, extended releaseOral
Tablet, orally disintegratingOral
CapsuleOral
Tablet, film coatedOral
Prices
Unit descriptionCostUnit
L-dopa powder15.19USD g
Levodopa powder7.31USD g
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)Region
US6500867No2002-12-312020-06-29Us
US6797732No2004-09-282020-06-29Us
US9089607No2015-07-282028-12-26Us
US8377474No2013-02-192028-12-26Us
US8454998No2013-06-042028-12-26Us
US7094427No2006-08-222022-05-29Us
US8557283No2013-10-152028-12-26Us
US9089608No2015-07-282028-12-26Us
US9463246No2016-10-112028-12-26Us
US9533046No2017-01-032028-12-26Us
US9901640No2018-02-272028-12-26Us
USRE43711No2012-10-022029-02-03Us
US8628754No2014-01-142020-06-19Us
US7556798No2009-07-072021-11-04Us
US8404276No2013-03-262023-03-19Us
US6921528No2005-07-262020-06-19Us
US6613308No2003-09-022020-09-19Us
US8586093No2013-11-192023-03-19Us
US6979437No2005-12-272020-09-19Us
US7146978No2006-12-122021-04-16Us
US6858199No2005-02-222021-11-04Us
US6514482No2003-02-042020-09-19Us
US8685442No2014-04-012032-11-16Us
US8545878No2013-10-012032-11-16Us
US9393210No2016-07-192032-11-16Us
US7182961No2007-02-272024-02-22Us
US7384649No2008-06-102022-11-20Us
US9155699No2015-10-132023-03-19Us
US8945612No2015-02-032032-11-16Us
Additional Data Available
  • Filed On
    Filed On

    The date on which a patent was filed with the relevant government.

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Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)295MSDS
boiling point (°C)448.4ChemSpider
water solubility5mMChemSpider
logP0.05https://www.chemeo.com/cid/46-030-7/Levodopa.pdf
Predicted Properties
PropertyValueSource
Water Solubility3.3 mg/mLALOGPS
logP-2.3ALOGPS
logP-1.8ChemAxon
logS-1.8ALOGPS
pKa (Strongest Acidic)1.65ChemAxon
pKa (Strongest Basic)9.06ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area103.78 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity49.08 m3·mol-1ChemAxon
Polarizability18.91 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.8715
Blood Brain Barrier-0.9264
Caco-2 permeable-0.8957
P-glycoprotein substrateNon-substrate0.5734
P-glycoprotein inhibitor INon-inhibitor0.989
P-glycoprotein inhibitor IINon-inhibitor0.988
Renal organic cation transporterNon-inhibitor0.9211
CYP450 2C9 substrateNon-substrate0.8236
CYP450 2D6 substrateNon-substrate0.8514
CYP450 3A4 substrateNon-substrate0.7117
CYP450 1A2 substrateNon-inhibitor0.9467
CYP450 2C9 inhibitorNon-inhibitor0.9765
CYP450 2D6 inhibitorNon-inhibitor0.9576
CYP450 2C19 inhibitorNon-inhibitor0.9504
CYP450 3A4 inhibitorNon-inhibitor0.914
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9713
Ames testAMES toxic0.9106
CarcinogenicityNon-carcinogens0.941
BiodegradationReady biodegradable0.7332
Rat acute toxicity2.0131 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9872
hERG inhibition (predictor II)Non-inhibitor0.9524
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Download (7.19 KB)
Spectra
SpectrumSpectrum TypeSplash Key
GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (4 TMS)GC-MSsplash10-014i-0790000000-b2f7f063a2c8197c7edd
GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)GC-MSsplash10-014i-0690000000-622497b3104c6082a45d
GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (4 TMS)GC-MSsplash10-00xr-9350000000-b0cc4636931d2de64d81
GC-MS Spectrum - GC-MS (4 TMS)GC-MSsplash10-014i-0590000000-4474e81e4226bb4e1d4c
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-014i-0790000000-b2f7f063a2c8197c7edd
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-014i-0690000000-622497b3104c6082a45d
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-00xr-9350000000-b0cc4636931d2de64d81
GC-MS Spectrum - GC-MSGC-MSsplash10-014i-0590000000-4474e81e4226bb4e1d4c
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-014i-1890000000-646d209fa1943582a336
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-014i-0690000000-720ed87e98a0d9f1721d
MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)LC-MS/MSsplash10-0uea-0900000000-8eb71aa0cc8622f097a2
MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)LC-MS/MSsplash10-0a59-2900000000-bf63b9b719959b82b543
MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)LC-MS/MSsplash10-056r-9300000000-a78b0b31dd33fe8479a7
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , PositiveLC-MS/MSsplash10-0f6t-0911000000-15affa616923dfb9c45a
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , PositiveLC-MS/MSsplash10-000i-0900000000-22d8267801d0eb0b73c2
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , PositiveLC-MS/MSsplash10-001i-0900000000-2c310034a1a871502b4c
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , PositiveLC-MS/MSsplash10-0udi-0900000000-5e6020c952f741531fcb
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , PositiveLC-MS/MSsplash10-0007-0970100000-49594dae82ce73e734e6
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , PositiveLC-MS/MSsplash10-001i-0900000000-2183a68f58b951f3f1c7
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , PositiveLC-MS/MSsplash10-03di-0900000000-0030db588fbd92c5b761
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , PositiveLC-MS/MSsplash10-0006-0090000000-544615463a975baae9e4
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , NegativeLC-MS/MSsplash10-0002-0729111000-0a20b01f58fff8ad7ef0
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , NegativeLC-MS/MSsplash10-004i-0900000000-c8095a31ed4b3dbbc646
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , NegativeLC-MS/MSsplash10-03di-0190000000-41515cba3a6929721859
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , NegativeLC-MS/MSsplash10-0002-0900000000-8074c509ef5bae1129fc
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , NegativeLC-MS/MSsplash10-0006-0502193020-497bfad7ba247159ca00
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , NegativeLC-MS/MSsplash10-004i-0900000000-0b0d4b6dcb7f1fa24e1a
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , NegativeLC-MS/MSsplash10-004i-0029800000-05f40324c8c1fec7963a
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , NegativeLC-MS/MSsplash10-0006-0000090000-c0cd80185ce47b30e5fe
LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , PositiveLC-MS/MSsplash10-0002-0900000000-df116b84981cf4a1371a
LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, PositiveLC-MS/MSsplash10-0f6t-0900000000-1c1c39a8880442ea18df
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-004i-0900000000-c8095a31ed4b3dbbc646
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-03di-0190000000-330b3c81e4279f2c12b0
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-0002-0900000000-efc5dfd988dedf39f4f8
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-004i-0900000000-0b0d4b6dcb7f1fa24e1a
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-001i-0900000000-2c310034a1a871502b4c
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-001i-0900000000-2183a68f58b951f3f1c7
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0002-0900000000-df116b84981cf4a1371a
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0f6t-0900000000-1c1c39a8880442ea18df
1H NMR Spectrum1D NMRNot Applicable
[1H,13C] 2D NMR Spectrum2D NMRNot Applicable

Targets

Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Agonist
General Function
G-protein coupled amine receptor activity
Specific Function
Dopamine receptor whose activity is mediated by G proteins which activate adenylyl cyclase.
Gene Name
DRD1
Uniprot ID
P21728
Uniprot Name
D(1A) dopamine receptor
Molecular Weight
49292.765 Da
References
  1. Onofrj M, Bonanni L, Thomas A: An expert opinion on safinamide in Parkinson's disease. Expert Opin Investig Drugs. 2008 Jul;17(7):1115-25. doi: 10.1517/13543784.17.7.1115 . [PubMed:18549347]
  2. Deleu D, Northway MG, Hanssens Y: Clinical pharmacokinetic and pharmacodynamic properties of drugs used in the treatment of Parkinson's disease. Clin Pharmacokinet. 2002;41(4):261-309. [PubMed:11978145]
  3. Koller WC, Rueda MG: Mechanism of action of dopaminergic agents in Parkinson's disease. Neurology. 1998 Jun;50(6 Suppl 6):S11-4; discussion S44-8. doi: 10.1212/wnl.50.6_suppl_6.s11. [PubMed:9633680]
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Agonist
General Function
G-protein coupled amine receptor activity
Specific Function
Dopamine receptor whose activity is mediated by G proteins which activate adenylyl cyclase.
Gene Name
DRD5
Uniprot ID
P21918
Uniprot Name
D(1B) dopamine receptor
Molecular Weight
52950.5 Da
References
  1. Onofrj M, Bonanni L, Thomas A: An expert opinion on safinamide in Parkinson's disease. Expert Opin Investig Drugs. 2008 Jul;17(7):1115-25. doi: 10.1517/13543784.17.7.1115 . [PubMed:18549347]
  2. Deleu D, Northway MG, Hanssens Y: Clinical pharmacokinetic and pharmacodynamic properties of drugs used in the treatment of Parkinson's disease. Clin Pharmacokinet. 2002;41(4):261-309. [PubMed:11978145]
  3. Koller WC, Rueda MG: Mechanism of action of dopaminergic agents in Parkinson's disease. Neurology. 1998 Jun;50(6 Suppl 6):S11-4; discussion S44-8. doi: 10.1212/wnl.50.6_suppl_6.s11. [PubMed:9633680]
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Agonist
General Function
Potassium channel regulator activity
Specific Function
Dopamine receptor whose activity is mediated by G proteins which inhibit adenylyl cyclase.
Gene Name
DRD2
Uniprot ID
P14416
Uniprot Name
D(2) dopamine receptor
Molecular Weight
50618.91 Da
References
  1. Dupre KB, Eskow KL, Negron G, Bishop C: The differential effects of 5-HT(1A) receptor stimulation on dopamine receptor-mediated abnormal involuntary movements and rotations in the primed hemiparkinsonian rat. Brain Res. 2007 Jul 16;1158:135-43. Epub 2007 May 8. [PubMed:17553470]
  2. Mori A, Ohashi S, Nakai M, Moriizumi T, Mitsumoto Y: Neural mechanisms underlying motor dysfunction as detected by the tail suspension test in MPTP-treated C57BL/6 mice. Neurosci Res. 2005 Mar;51(3):265-74. Epub 2005 Jan 8. [PubMed:15710490]
  3. Zappia M, Annesi G, Nicoletti G, Arabia G, Annesi F, Messina D, Pugliese P, Spadafora P, Tarantino P, Carrideo S, Civitelli D, De Marco EV, Ciro-Candiano IC, Gambardella A, Quattrone A: Sex differences in clinical and genetic determinants of levodopa peak-dose dyskinesias in Parkinson disease: an exploratory study. Arch Neurol. 2005 Apr;62(4):601-5. [PubMed:15824260]
  4. Kovoor A, Seyffarth P, Ebert J, Barghshoon S, Chen CK, Schwarz S, Axelrod JD, Cheyette BN, Simon MI, Lester HA, Schwarz J: D2 dopamine receptors colocalize regulator of G-protein signaling 9-2 (RGS9-2) via the RGS9 DEP domain, and RGS9 knock-out mice develop dyskinesias associated with dopamine pathways. J Neurosci. 2005 Feb 23;25(8):2157-65. [PubMed:15728856]
  5. Onofrj M, Bonanni L, Thomas A: An expert opinion on safinamide in Parkinson's disease. Expert Opin Investig Drugs. 2008 Jul;17(7):1115-25. doi: 10.1517/13543784.17.7.1115 . [PubMed:18549347]
  6. Deleu D, Northway MG, Hanssens Y: Clinical pharmacokinetic and pharmacodynamic properties of drugs used in the treatment of Parkinson's disease. Clin Pharmacokinet. 2002;41(4):261-309. [PubMed:11978145]
  7. Koller WC, Rueda MG: Mechanism of action of dopaminergic agents in Parkinson's disease. Neurology. 1998 Jun;50(6 Suppl 6):S11-4; discussion S44-8. doi: 10.1212/wnl.50.6_suppl_6.s11. [PubMed:9633680]
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Agonist
General Function
G-protein coupled amine receptor activity
Specific Function
Dopamine receptor whose activity is mediated by G proteins which inhibit adenylyl cyclase. Promotes cell proliferation.
Gene Name
DRD3
Uniprot ID
P35462
Uniprot Name
D(3) dopamine receptor
Molecular Weight
44224.335 Da
References
  1. Onofrj M, Bonanni L, Thomas A: An expert opinion on safinamide in Parkinson's disease. Expert Opin Investig Drugs. 2008 Jul;17(7):1115-25. doi: 10.1517/13543784.17.7.1115 . [PubMed:18549347]
  2. Deleu D, Northway MG, Hanssens Y: Clinical pharmacokinetic and pharmacodynamic properties of drugs used in the treatment of Parkinson's disease. Clin Pharmacokinet. 2002;41(4):261-309. [PubMed:11978145]
  3. Koller WC, Rueda MG: Mechanism of action of dopaminergic agents in Parkinson's disease. Neurology. 1998 Jun;50(6 Suppl 6):S11-4; discussion S44-8. doi: 10.1212/wnl.50.6_suppl_6.s11. [PubMed:9633680]
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Agonist
General Function
Sh3 domain binding
Specific Function
Dopamine receptor responsible for neuronal signaling in the mesolimbic system of the brain, an area of the brain that regulates emotion and complex behavior. Its activity is mediated by G proteins ...
Gene Name
DRD4
Uniprot ID
P21917
Uniprot Name
D(4) dopamine receptor
Molecular Weight
48359.86 Da
References
  1. Onofrj M, Bonanni L, Thomas A: An expert opinion on safinamide in Parkinson's disease. Expert Opin Investig Drugs. 2008 Jul;17(7):1115-25. doi: 10.1517/13543784.17.7.1115 . [PubMed:18549347]
  2. Deleu D, Northway MG, Hanssens Y: Clinical pharmacokinetic and pharmacodynamic properties of drugs used in the treatment of Parkinson's disease. Clin Pharmacokinet. 2002;41(4):261-309. [PubMed:11978145]
  3. Koller WC, Rueda MG: Mechanism of action of dopaminergic agents in Parkinson's disease. Neurology. 1998 Jun;50(6 Suppl 6):S11-4; discussion S44-8. doi: 10.1212/wnl.50.6_suppl_6.s11. [PubMed:9633680]

Enzymes

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Pyridoxal phosphate binding
Specific Function
Catalyzes the decarboxylation of L-3,4-dihydroxyphenylalanine (DOPA) to dopamine, L-5-hydroxytryptophan to serotonin and L-tryptophan to tryptamine.
Gene Name
DDC
Uniprot ID
P20711
Uniprot Name
Aromatic-L-amino-acid decarboxylase
Molecular Weight
53925.815 Da
References
  1. BIRKMAYER W, HORNYKIEWICZ O: [The L-3,4-dioxyphenylalanine (DOPA)-effect in Parkinson-akinesia]. Wien Klin Wochenschr. 1961 Nov 10;73:787-8. [PubMed:13869404]
  2. Elroby SA, Makki MS, Sobahi TR, Hilal RH: Toward the understanding of the metabolism of levodopa I. DFT investigation of the equilibrium geometries, acid-base properties and levodopa-water complexes. Int J Mol Sci. 2012;13(4):4321-39. doi: 10.3390/ijms13044321. Epub 2012 Apr 2. [PubMed:22605980]
  3. Goodall M, Alton H: Metabolism of 3,4-dihydroxyphenylalanine (L-dopa) in human subjects. Biochem Pharmacol. 1972 Sep 1;21(17):2401-8. [PubMed:4647074]
  4. Meiser J, Weindl D, Hiller K: Complexity of dopamine metabolism. Cell Commun Signal. 2013 May 17;11(1):34. doi: 10.1186/1478-811X-11-34. [PubMed:23683503]
  5. Hadjiconstantinou M, Neff NH: Enhancing aromatic L-amino acid decarboxylase activity: implications for L-DOPA treatment in Parkinson's disease. CNS Neurosci Ther. 2008 Winter;14(4):340-51. doi: 10.1111/j.1755-5949.2008.00058.x. [PubMed:19040557]

Carriers

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Binder
General Function
Toxic substance binding
Specific Function
Serum albumin, the main protein of plasma, has a good binding capacity for water, Ca(2+), Na(+), K(+), fatty acids, hormones, bilirubin and drugs. Its main function is the regulation of the colloid...
Gene Name
ALB
Uniprot ID
P02768
Uniprot Name
Serum albumin
Molecular Weight
69365.94 Da
References
  1. Yeggoni DP, Subramanyam R: Binding studies of L-3,4-dihydroxyphenylalanine with human serum albumin. Mol Biosyst. 2014 Dec;10(12):3101-10. doi: 10.1039/c4mb00408f. Epub 2014 Sep 11. [PubMed:25209359]

Transporters

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Proton-dependent oligopeptide secondary active transmembrane transporter activity
Specific Function
Proton-coupled intake of oligopeptides of 2 to 4 amino acids with a preference for dipeptides. May constitute a major route for the absorption of protein digestion end-products.
Gene Name
SLC15A1
Uniprot ID
P46059
Uniprot Name
Solute carrier family 15 member 1
Molecular Weight
78805.265 Da
References
  1. Han HK, Rhie JK, Oh DM, Saito G, Hsu CP, Stewart BH, Amidon GL: CHO/hPEPT1 cells overexpressing the human peptide transporter (hPEPT1) as an alternative in vitro model for peptidomimetic drugs. J Pharm Sci. 1999 Mar;88(3):347-50. [PubMed:10052994]
  2. Tamai I, Nakanishi T, Nakahara H, Sai Y, Ganapathy V, Leibach FH, Tsuji A: Improvement of L-dopa absorption by dipeptidyl derivation, utilizing peptide transporter PepT1. J Pharm Sci. 1998 Dec;87(12):1542-6. [PubMed:10189264]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Transporter activity
Specific Function
Sodium-independent transporter that mediates the update of aromatic acid. Can function as a net efflux pathway for aromatic amino acids in the basosolateral epithelial cells (By similarity).
Gene Name
SLC16A10
Uniprot ID
Q8TF71
Uniprot Name
Monocarboxylate transporter 10
Molecular Weight
55492.07 Da
References
  1. Kim DK, Kanai Y, Chairoungdua A, Matsuo H, Cha SH, Endou H: Expression cloning of a Na+-independent aromatic amino acid transporter with structural similarity to H+/monocarboxylate transporters. J Biol Chem. 2001 May 18;276(20):17221-8. Epub 2001 Feb 20. [PubMed:11278508]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Peptide antigen binding
Specific Function
Sodium-independent, high-affinity transport of large neutral amino acids such as phenylalanine, tyrosine, leucine, arginine and tryptophan, when associated with SLC3A2/4F2hc. Involved in cellular a...
Gene Name
SLC7A5
Uniprot ID
Q01650
Uniprot Name
Large neutral amino acids transporter small subunit 1
Molecular Weight
55009.62 Da
References
  1. Pinho MJ, Serrao MP, Gomes P, Hopfer U, Jose PA, Soares-da-Silva P: Over-expression of renal LAT1 and LAT2 and enhanced L-DOPA uptake in SHR immortalized renal proximal tubular cells. Kidney Int. 2004 Jul;66(1):216-26. [PubMed:15200428]
  2. Kageyama T, Nakamura M, Matsuo A, Yamasaki Y, Takakura Y, Hashida M, Kanai Y, Naito M, Tsuruo T, Minato N, Shimohama S: The 4F2hc/LAT1 complex transports L-DOPA across the blood-brain barrier. Brain Res. 2000 Oct 6;879(1-2):115-21. [PubMed:11011012]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Toxin transporter activity
Specific Function
Sodium-independent, high-affinity transport of small and large neutral amino acids such as alanine, serine, threonine, cysteine, phenylalanine, tyrosine, leucine, arginine and tryptophan, when asso...
Gene Name
SLC7A8
Uniprot ID
Q9UHI5
Uniprot Name
Large neutral amino acids transporter small subunit 2
Molecular Weight
58381.12 Da
References
  1. Pinho MJ, Serrao MP, Gomes P, Hopfer U, Jose PA, Soares-da-Silva P: Over-expression of renal LAT1 and LAT2 and enhanced L-DOPA uptake in SHR immortalized renal proximal tubular cells. Kidney Int. 2004 Jul;66(1):216-26. [PubMed:15200428]

Drug created on June 13, 2005 07:24 / Updated on June 12, 2020 11:41

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