Identification

Name
Levodopa
Accession Number
DB01235  (APRD00309, EXPT01107)
Type
Small Molecule
Groups
Approved
Description

The naturally occurring form of dihydroxyphenylalanine and the immediate precursor of dopamine. Unlike dopamine itself, it can be taken orally and crosses the blood-brain barrier. It is rapidly taken up by dopaminergic neurons and converted to dopamine. It is used for the treatment of parkinsonian disorders and is usually given with agents that inhibit its conversion to dopamine outside of the central nervous system.

Structure
Thumb
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
Product Images
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
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 CRLevodopa (200 mg) + Carbidopa (50 mg)Tablet, extended releaseOralApotex Corporation2003-11-13Not applicableCanada
Apo-levocarb CRLevodopa (100 mg) + Carbidopa (25 mg)Tablet, extended releaseOralApotex Corporation2009-02-04Not applicableCanada
Apo-levocarb-tab 25mg/100mgLevodopa (100 mg) + Carbidopa (25 mg)TabletOralApotex Corporation1995-12-31Not applicableCanada
Carbidopa and LevodopaLevodopa (100 mg/1) + Carbidopa hydrate (25 mg/1)Tablet, extended releaseOralApotex Corporation2004-06-162011-06-30Us
Carbidopa and levodopaLevodopa (250 mg/1) + Carbidopa hydrate (25 mg/1)TabletOralRemedy Repack2014-01-232015-01-23Us
Carbidopa and LevodopaLevodopa (250 mg/1) + Carbidopa hydrate (25 mg/1)Tablet, orally disintegratingOralMylan Pharmaceuticals Inc.2008-09-18Not applicableUs
Carbidopa and LevodopaLevodopa (100 mg/1) + Carbidopa hydrate (25 mg/1)TabletOralNucare Pharmaceuticals, Inc.2008-10-28Not applicableUs
Carbidopa and levodopaLevodopa (100 mg/1) + Carbidopa hydrate (10 mg/1)TabletOralActavis Pharma, Inc.1993-09-01Not applicableUs
International/Other Brands
Bidopal (GlaxoSmithKline) / Dopar / Doparl (Kyowa Hakko Kirin) / Dopasol (Daiichi Sankyo) / Dopaston (Ohara Yakuhin)
Categories
UNII
46627O600J
CAS number
59-92-7
Weight
Average: 197.1879
Monoisotopic: 197.068807845
Chemical Formula
C9H11NO4
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

Pharmacology

Indication

For the treatment of idiopathic Parkinson's disease (Paralysis Agitans), postencephalitic parkinsonism, symptomatic parkinsonism which may follow injury to the nervous system by carbon monoxide intoxication, and manganese intoxication.

Associated Conditions
Pharmacodynamics

Levodopa (L-dopa) is used to replace dopamine lost in Parkinson's disease because dopamine itself cannot cross the blood-brain barrier where its precursor can. However, L-DOPA is converted to dopamine in the periphery as well as in the CNS, so it is administered with a peripheral DDC (dopamine decarboxylase) inhibitor such as carbidopa, without which 90% is metabolised in the gut wall, and with a COMT inhibitor if possible; this prevents about a 5% loss. The form given therapeutically is therefore a prodrug which avoids decarboxylation in the stomach and periphery, can cross the blood-brain barrier, and once in the brain is converted to the neurotransmitter dopamine by the enzyme aromatic-L-amino-acid decarboxylase.

Mechanism of action

Striatal dopamine levels in symptomatic Parkinson's disease are decreased by 60 to 80%, striatal dopaminergic neurotransmission may be enhanced by exogenous supplementation of dopamine through administration of dopamine's precursor, levodopa. A small percentage of each levodopa dose crosses the blood-brain barrier and is decarboxylated to dopamine. This newly formed dopamine then is available to stimulate dopaminergic receptors, thus compensating for the depleted supply of endogenous dopamine.

TargetActionsOrganism
AD(1A) dopamine receptor
agonist
Human
AD(1B) dopamine receptor
agonist
Human
AD(2) dopamine receptor
agonist
Human
AD(3) dopamine receptor
agonist
Human
AD(4) dopamine receptor
agonist
Human
Absorption

Levodopa is rapidly absorbed from the proximal small intestine by the large neutral amino acid (LNAA) transport carrier system.

Volume of distribution
Not Available
Protein binding

High

Metabolism

95% of an administered oral dose of levodopa is pre-systemically decarboxylated to dopamine by the L-aromatic amino acid decarboxylase (AAAD) enzyme in the stomach, lumen of the intestine, kidney, and liver. Levodopa also may be methoxylated by the hepatic catechol-O-methyltransferase (COMT) enzyme system to 3-O-methyldopa (3-OMD), which cannot be converted to central dopamine.

Route of elimination
Not Available
Half life

50 to 90 minutes

Clearance
Not Available
Toxicity

Oral, mouse: LD50 = 2363 mg/kg; Oral, rabbit: LD50 = 609 mg/kg; Oral, rat: LD50 = 1780 mg/kg.

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

Interactions

Drug Interactions
DrugInteraction
2,5-Dimethoxy-4-ethylamphetamineThe risk or severity of serotonin syndrome can be increased when Levodopa is combined with 2,5-Dimethoxy-4-ethylamphetamine.
2,5-Dimethoxy-4-ethylthioamphetamineThe risk or severity of serotonin syndrome can be increased when Levodopa is combined with 2,5-Dimethoxy-4-ethylthioamphetamine.
3,4-MethylenedioxyamphetamineThe risk or severity of serotonin syndrome can be increased when Levodopa is combined with 3,4-Methylenedioxyamphetamine.
4-Bromo-2,5-dimethoxyamphetamineThe risk or severity of serotonin syndrome can be increased when Levodopa is combined with 4-Bromo-2,5-dimethoxyamphetamine.
4-MethoxyamphetamineThe risk or severity of adverse effects can be increased when Levodopa is combined with 4-Methoxyamphetamine.
5-methoxy-N,N-dimethyltryptamineThe risk or severity of serotonin syndrome can be increased when Levodopa is combined with 5-methoxy-N,N-dimethyltryptamine.
7-NitroindazoleThe risk or severity of adverse effects can be increased when Levodopa is combined with 7-Nitroindazole.
7,8-Dichloro-1,2,3,4-tetrahydroisoquinolineThe risk or severity of serotonin syndrome can be increased when Levodopa is combined with 7,8-Dichloro-1,2,3,4-tetrahydroisoquinoline.
AcebutololThe risk or severity of hypotension and orthostatic hypotension can be increased when Acebutolol is combined with Levodopa.
AcebutololThe risk or severity of adverse effects can be increased when Acebutolol is combined with Levodopa.
Food Interactions
Not Available

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. 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]
External Links
Human Metabolome Database
HMDB0000181
KEGG Drug
D00059
KEGG Compound
C00355
PubChem Compound
6047
PubChem Substance
46508120
ChemSpider
5824
BindingDB
50130192
ChEBI
15765
ChEMBL
CHEMBL1009
Therapeutic Targets Database
DAP000209
PharmGKB
PA450213
IUPHAR
3639
Guide to Pharmacology
GtP Drug Page
HET
DAH
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Levodopa
ATC Codes
N04BA03 — Levodopa, decarboxylase inhibitor and comt inhibitorN04BA02 — Levodopa and decarboxylase inhibitorN04BA01 — Levodopa
PDB Entries
1ivv / 1rnr / 2vh3 / 2zwe / 2zwf / 2zwg / 3teg / 3teh / 4eis / 4p6s
show 5 more
MSDS
Download (37.5 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
1Active Not RecruitingTreatmentParkinson's Disease (PD)1
1CompletedNot AvailableAutonomic Failure / Idiopathic orthostatic hypotension1
1CompletedNot AvailableHealthy Volunteers2
1CompletedNot AvailableParkinson's Disease (PD)1
1CompletedBasic ScienceCocaine Abuse1
1CompletedOtherGilles de la Tourette's Syndrome1
1CompletedTreatmentAngelman's syndrome1
1CompletedTreatmentHealthy Volunteers5
1CompletedTreatmentParkinson's Disease (PD)19
1CompletedTreatmentPharmacokinetics1
1Enrolling by InvitationTreatmentDiabetes Mellitus (DM)1
1RecruitingOtherParkinson's Disease (PD)1
1RecruitingSupportive CareParkinson's Disease (PD)1
1RecruitingTreatmentParkinson's Disease (PD)1
1, 2CompletedNot AvailableIdiopathic Parkinson's Disease1
1, 2CompletedTreatmentParkinson's Disease (PD)2
1, 2CompletedTreatmentSpinal Cord Injuries (SCI)1
1, 2Unknown StatusNot AvailableParkinson's Disease (PD)1
2Active Not RecruitingTreatmentParkinson's Disease (PD)1
2CompletedDiagnosticParkinson's Disease (PD) / Parkinsonian Syndromes1
2CompletedPreventionParkinson's Disease (PD)1
2CompletedTreatmentAdvanced Parkinson's Disease1
2CompletedTreatmentAlbinism1
2CompletedTreatmentAmblyopia1
2CompletedTreatmentBrain Diseases / Central Nervous System Diseases / Movement Disorders / Neurodegenerative Disorders / Parkinson's Disease (PD)2
2CompletedTreatmentCocaine Abuse / Cocaine-Related Disorders1
2CompletedTreatmentDependence, Cocaine3
2CompletedTreatmentDyskinesias / Parkinson's Disease (PD)2
2CompletedTreatmentIdiopathic Parkinson's Disease1
2CompletedTreatmentMotor Fluctuations / Parkinson's Disease (PD)1
2CompletedTreatmentParkinson's Disease (PD)17
2CompletedTreatmentSchizophrenic Disorders1
2Not Yet RecruitingTreatmentASD1
2Not Yet RecruitingTreatmentParkinson's Disease (PD)1
2RecruitingTreatmentAge-Related Macular Degeneration (ARMD)1
2RecruitingTreatmentAlbinism / Albinism, Oculocutaneous1
2RecruitingTreatmentIdiopathic Parkinson's Disease1
2RecruitingTreatmentParkinson's Disease (PD)2
2TerminatedTreatmentParkinson´s Disease1
2Unknown StatusTreatmentCocaine Abuse / Cocaine-Related Disorders1
2Unknown StatusTreatmentParkinson's Disease (PD)1
2WithdrawnTreatmentPain, Acute1
2WithdrawnTreatmentParkinson's Disease (PD)1
2, 3CompletedTreatmentAngelman's syndrome1
2, 3CompletedTreatmentNonfluent Aphasia / Strokes1
2, 3CompletedTreatmentParkinson's Disease (PD)1
2, 3RecruitingTreatmentParkinson's Disease (PD)1
3Active Not RecruitingTreatmentParkinson's Disease (PD)1
3CompletedNot AvailableParkinson's Disease (PD)2
3CompletedBasic ScienceParkinson's Disease (PD)1
3CompletedPreventionParkinson's Disease (PD)1
3CompletedTreatmentAdvanced Parkinson's Disease1
3CompletedTreatmentAdvanced Stage Parkinson's Disease1
3CompletedTreatmentAmblyopia1
3CompletedTreatmentIdiopathic Parkinson's Disease1
3CompletedTreatmentIschaemic Stroke1
3CompletedTreatmentParkinson's Disease (PD)5
3CompletedTreatmentRestless Legs Syndrome (RLS)1
3Enrolling by InvitationTreatmentAutonomic Nervous System Diseases / Dopamine Beta-Hydroxylase Deficiency / Idiopathic orthostatic hypotension / Orthostatic Intolerance1
3TerminatedTreatmentParkinson's Disease (PD)1
4CompletedNot AvailableHealthy Volunteers1
4CompletedTreatmentAdvanced Idiopathic Parkinson's Disease1
4CompletedTreatmentAkinesia / Delayed Levadopa Onset / Delayed Levodopa Onset / Mobility decreased / Motor Symptoms / Parkinson's Disease (PD)1
4CompletedTreatmentAphasia / Cerebrovascular Accidents1
4CompletedTreatmentDyskinesias / Parkinson's Disease (PD)1
4CompletedTreatmentHealthy Volunteers1
4CompletedTreatmentIdiopathic Parkinson's Disease1
4CompletedTreatmentImpulse Control Disorder1
4CompletedTreatmentParkinson's Disease (PD)9
4CompletedTreatmentParkinson's Disease With End of Dose "Wearing Off" / Parkinson's Disease With End of Dose Wearing Off1
4CompletedTreatmentParkinson's Disease With Wearing-off Motor Fluctuations1
4CompletedTreatmentRetinal Diseases1
4CompletedTreatmentSub-acute Back Pain1
4RecruitingOtherPost Traumatic Stress Disorder (PTSD)1
4RecruitingTreatmentDepression1
4RecruitingTreatmentObstructive Sleep Apnea (OSA) / Parkinson's Disease (PD)1
4RecruitingTreatmentParkinson's Disease (PD)2
4TerminatedTreatmentHealthy Volunteers1
4TerminatedTreatmentParkinson's Disease (PD)1
4Unknown StatusTreatmentAlzheimer's Disease (AD) / Healthy Volunteers / Mild Cognitive Impairment (MCI)1
4Unknown StatusTreatmentDyslexia1
4WithdrawnTreatmentParkinson's Disease (PD)1
4WithdrawnTreatmentStrokes1
Not AvailableCompletedNot AvailableCardiovascular Events / Parkinson's Disease (PD)1
Not AvailableCompletedNot AvailableDyskinesias / Movement Disorders / Parkinson's Disease (PD)1
Not AvailableCompletedNot AvailableParkinson's Disease (PD)1
Not AvailableCompletedBasic ScienceDopamine Activity / Episodic Memory Consolidation / Response Preparation1
Not AvailableCompletedBasic ScienceMultisystemic Atrophy1
Not AvailableCompletedDiagnosticParkinson's Disease (PD) / Parkinsonian Syndromes1
Not AvailableCompletedTreatmentAphasia1
Not AvailableCompletedTreatmentIdiopathic Parkinson's Disease1
Not AvailableCompletedTreatmentStrokes1
Not AvailableEnrolling by InvitationTreatmentAngelman's syndrome1
Not AvailableNot Yet RecruitingTreatmentDepression / Dysthymic Disorder / Major Depressive Disorder (MDD)1
Not AvailableRecruitingNot AvailableAlcohol Dependence / Cocaine Abuse / Dependence, Cocaine / Opiate Dependence / Substance Abuse1
Not AvailableRecruitingNot AvailableAtypical Parkinson Disease / Corticobasal Degeneration / Gait, Frontal / Multiple System Atrophy (MSA) / Parkinson's Disease (PD) / Parkinsonian Disorders / Progressive Supranuclear Palsy (PSP)1
Not AvailableRecruitingNot AvailableParkinson´s Disease1
Not AvailableRecruitingTreatmentDecreased Gait Speed / Decreased Processing Speed / Depression Not Otherwise Specified / Dysthymic Disorder / Major Depressive Disorder (MDD)1
Not AvailableRecruitingTreatmentParkinson's Disease (PD) / Sleep disorders and disturbances1
Not AvailableUnknown StatusTreatmentRestless Legs Syndrome (RLS)1
Not AvailableWithdrawnNot AvailableParkinson's Disease (PD)1

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
GelEnteral
SuspensionEnteral
Capsule, extended releaseOral
Tablet, orally disintegratingOral
CapsuleOral
Tablet, extended releaseOral
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)
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

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)284-285U.S. Patent 3,253,023.
water solubility5000 mg/L (at 20 °C)YALKOWSKY,SH & DANNENFELSER,RM (1992)
logP-2.39SANGSTER (1993)
logS-1.6ADME Research, USCD
pKa2.32 (at 25 °C)KORTUM,G ET AL (1961)
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

Taxonomy

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
Tyrosine or derivatives / Phenylalanine or derivatives / 3-phenylpropanoic-acid / Alpha-amino acid / Amphetamine or derivatives / L-alpha-amino acid / Catechol / 1-hydroxy-4-unsubstituted benzenoid / Aralkylamine / 1-hydroxy-2-unsubstituted 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)

Targets

Kind
Protein
Organism
Human
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. [PubMed:9633680]
Kind
Protein
Organism
Human
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. [PubMed:9633680]
Kind
Protein
Organism
Human
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. [PubMed:9633680]
Kind
Protein
Organism
Human
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. [PubMed:9633680]
Kind
Protein
Organism
Human
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. [PubMed:9633680]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
Unknown
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]

Transporters

Kind
Protein
Organism
Human
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
Human
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
Human
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
Human
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 December 14, 2018 17:09